Midway Airport (MDW) Car & Van Rentals – Compare Suppliers

Welcome to Chicago Midway, the city’s convenient second airport and a perfect starting point for your Windy City travels. Renting a car at MDW unlocks all of Chicago and the greater Midwest for you to explore. Midway is just 10 miles from downtown Chicago picking up a car here means you can be cruising the shores of Lake Michigan or hitting the open road on historic Route 66 in no time. This page is your all-in-one guide to securing an affordable Midway Airport car rental. We’ve combined AirportVanRental’s best deals with insider local tips so you can book with confidence and drive Chicago’s roads like a pro. Whether you’re a visitor flying into MDW, a business traveler headed to meetings in the Loop, or a local starting a road trip from the city’s South Side, we’re here to get you behind the wheel quickly, easily, and at a great price all with that friendly Midwest hospitality. (Proudly serving Chicago! And if you happen to need a car at O’Hare or downtown, we cover those locations too but let’s focus on Midway for now.)

Chicago Midway’s rental car facility is located just a few minutes from the terminal via a free shuttle it’s an off-site facility but very accessible. Here’s how it works: After you land and grab your luggage, follow signs for “Rental Cars / Shuttles” at the lower level of the terminal. At Door #2 (Lower Level arrivals), you’ll find the pickup point for rental car shuttles. These dedicated shuttles run 24/7, approximately every 10-15 minutes (more frequently during peak hours). Look for the shuttle marked for your rental company or simply one that says “Rental Car Center” at Midway, all rental agencies are consolidated in one building at 5150 W. 55th Street, a short ride away. The shuttle will typically stop at a designated curb check for signs that list Rental Car Shuttles and wait in that area. Once on board, it’s about a 5-minute drive to the facility. The buses are equipped to handle luggage and are wheelchair accessible. When you arrive at the rental center, you’ll be dropped off right by the entrance where all the rental counters are located on the first floor. From there, you’ll check in at your rental company’s counter (have your license, credit card, and reservation info ready). Then you’ll head to the garage area to pick up your car. It’s a smooth, well-organized process Midway is smaller than O’Hare, and many travelers find it quicker and less overwhelming.

Pro Tip: Because Midway is closer to Chicago’s downtown than O’Hare, renting here can be a smart choice if Chicago is your main destination. The drive into the city from MDW is typically 20-30 minutes (outside of rush hour). Midway is also right near major highways like I-55, which is historic Route 66 perfect for a head start if you’re planning a road trip south or west. If you’re comparing airports, keep in mind Midway’s smaller size can mean faster baggage claim and car pick-up, meaning you start your adventure sooner. And don’t worry even though Midway is not as huge as O’Hare, it has plenty of rental car inventory and the same big brands, often at comparable or even better prices.

• No Pre-Payment Required: Reserve now, pay later. Our bookings at MDW typically don’t require any payment upfront. You can lock in a great rate in advance and keep flexibility if your plans aren’t 100% set.
• Free Cancellation: Plans change meetings get rescheduled, weather shifts we get it. That’s why you can cancel most Midway bookings free of charge up to 48 hours before pick-up. So go ahead and snag that low rate early, worry-free.
• Fast Confirmation: Our system is lightning fast. As soon as you find the car you want and confirm, you’ll receive your reservation details by email. All the info for pick-up (rental company, address, etc.) will be there, so you can arrive at Midway and know exactly where to go. No waiting in long lines for booking you’ll be in the express lane to pick up your car.
• All-Inclusive Pricing: The price we display for Midway rentals includes all mandatory taxes and fees (yes, even Chicago’s somewhat notorious rental taxes). Midway rentals do have some surcharges (like a concession fee for airport facility use, and the city’s rental car tax ~8% plus flat fees), but we show them upfront in your quote. The price you see is the price you pay at the counter no hidden surprises when you arrive. Transparency is our promise.
• Multiple Trusted Brands, One Search: AirportVanRental lets you compare rates from multiple companies in one go. We often have exclusive discounts or added perks (like a free additional driver or unlimited mileage though unlimited miles are standard at MDW for most rentals).

With those benefits, you can book your Midway car with confidence and maybe even a bit of excitement your Chicago adventure is just a few clicks away!

Why Rent a Car at Midway?

Some travelers to Chicago wonder if they need a car after all, the city has the “L” trains, buses, and plenty of rideshares. Here’s the deal: if you’re sticking strictly to downtown/the Loop and immediate neighborhoods, you can get by without a car. But if you want to truly explore Chicago and its surroundings, or if convenience is a priority, a rental car is invaluable. A few reasons:

• Freedom to Explore Chicagoland: Chicago’s must-see spots aren’t just downtown. Want to visit the Frank Lloyd Wright houses in Oak Park? Drive out to Brookfield Zoo or the Chicago Botanic Garden in Glencoe? How about a food pilgrimage to far-flung legendary pizza joints or hot dog stands only accessible by car? With your own wheels, the whole metro area (and its suburbs) opens up. You’re not limited to train schedules especially helpful at night when some suburban trains stop running frequently.
• Ease for Multiple Meetings or Stops: If you’re a business traveler flying into Midway, having a car can be much more efficient if you have meetings spread across different parts of the city (say Downtown in the morning, Oak Brook in the afternoon). Chicago traffic can be heavy, but driving often still beats coordinating multiple rideshares or navigating transfers on transit with time constraints. Throw your briefcase in the trunk and go from point A to B to C on your schedule.
• Gateway to Road Trips: Midway’s location by I-55 literally puts you on the Mother Road Route 66 within minutes of leaving the airport. Many people start epic road trips here. Even if you’re not doing the full Route 66 to California, you might drive part of it to see charming towns in Illinois. Or head north after your Chicago visit to Wisconsin (cheese country and beautiful lakes), east to Indiana (Indiana Dunes National Park on Lake Michigan’s shore is just a 1.5-hour drive), or further to Michigan, Iowa, you name it. A car from Midway is your ticket to see the greater Midwest beyond the city.
• Family Convenience: Traveling with kids? Renting a car makes life much easier. You can install your car seats (we offer them if you can’t bring yours), keep snacks and strollers handy, and have a “home base” on wheels. Chicago’s museums, for instance, are spread out Field Museum/Shedd Aquarium on the lakefront, Museum of Science & Industry on the South Side, etc. Public transit with little ones and all their gear can be a challenge. A car simplifies those logistics (plus, you can easily do a nap drive if the little ones fall asleep between activities!).
• Cost for Groups: If you have a group of 3, 4, or more, renting a single vehicle can be more economical than buying multiple transit passes or ride-shares for each transfer. Chicago’s CTA train from Midway to downtown is $2.50 per person for a family of 5, that’s $12.50 one-way, which might be similar to what you’d pay in gas/parking driving in, without the walking and waiting. And if you plan any day trips, a single car rental definitely beats the sum of individual tickets or tours.

In short, renting at Midway is a popular choice for those who value flexibility and regional exploration. Chicago is a very drivable city outside of the core downtown congestion, and with a car you can craft your own itinerary with ease.

(Of course, if your trip is literally just downtown Chicago, you might rent for only part of your stay or not at all we’re honest about that. But many of our customers do a bit of both: spend a couple of car-free days in the heart of the city, then pick up a rental from a downtown location or swing back to Midway to get a car for the remainder to explore further. AirportVanRental gives you that flexibility!)

Our Chicago Midway Car Rental Advantages

When you book through AirportVanRental at Midway, you’re tapping into a host of advantages that make your experience smoother and more affordable than going it alone. Here’s why savvy travelers choose us for Chicago rentals:

• Best Rates in Town: We work closely with the rental companies at Midway to secure exclusive deals and discounts. Chicago can be an expensive city, but your car rental doesn’t have to break the bank. By comparing all offers, we ensure you’ll get the cheapest rate for the class you want. Found a lower price elsewhere for the same booking? Let us know we’ll do our best to match or beat it. We’re committed to saving you money.
• Multiple Pick-Up Options: While this page is about Midway Airport, maybe you’re staying downtown first or your plans change no problem. AirportVanRental has you covered with many Chicago area locations (including O’Hare Airport and various neighborhood branches). You can book at Midway to start, or easily arrange to drop off at a different Chicago location if that’s convenient (one-way within the metro area is typically free or minimal cost). We want you to have a seamless rental network at your disposal.
• Customer Service with Midwest Heart: Our support team knows Chicago and cares about your trip. If you have questions whether it’s extending your rental, adding a driver last-minute, or asking “hey, what’s the best route to avoid traffic at 5 PM out of downtown?” we’re here 24/7 to help. We often send a pre-trip email with Midway-specific tips (like exactly where the shuttle pickup is, or reminding you of Chicago’s quirky parking rules) so you feel prepared. And if an issue arises on the road, we’re a phone call away to assist. We pride ourselves on friendly, reliable service consider us your travel partner, not just a booking site.
• Safe, Sanitized Vehicles: All of our partner agencies have upped their cleaning game (especially since 2020). Your rental car will be thoroughly cleaned and disinfected from the steering wheel to the door handles before you pick it up. We know peace of mind is important, and we only work with companies that meet high safety and cleanliness standards. Need a contactless pick-up? Many brands offer curbside or fast-track services ask us and we’ll guide you to options like skipping the counter via app or pre-registration.
• Extras and Upgrades: Through AirportVanRental, you often get little extras that improve your rental experience. Unlimited mileage is standard (so drive as far as you want). Many of our deals allow free additional drivers so your travel buddy can share driving duties without paying $15/day extra (just make sure they meet age/license requirements and are listed on the contract). We also frequently have promotions for things like a free GPS unit or a child seat discount. And with our site, you can easily add any extras you do need (GPS, child seats, ski rack if you’re heading to Wisconsin slopes in winter, etc.) during booking so everything is ready at pick-up.

Top Car Deals at Midway Today

• Economy Car, from $30/day.Example: Kia Rio or Chevrolet Spark. Ideal for solo travelers or couples, these compact cars are superb for Chicago’s city driving easy to maneuver and easy to park on those city streets. Despite their small size, they’re comfortable for around-town trips or even a highway jaunt to the outlets. Why so affordable? High competition and lots of these in the fleet at Midway keep prices low, especially on weekends. Plus, you’ll save on gas with 30+ MPG, perfect for hopping between Chicago’s neighborhoods on the cheap.
• Full-Size Sedan, from $38/day.Example: Toyota Camry or Nissan Altima. Need a bit more legroom or luggage space? A full-size sedan offers a smooth ride on the interstate and plenty of trunk room (think 2-3 suitcases). At under $40 a day in off-peak periods, it’s a great value for family or business travel alike. These cars are road-trip ready great for a drive to Milwaukee or Springfield to see Lincoln’s home. Many come with modern features like adaptive cruise and smartphone connectivity, making your drives safer and easier.
• Midsize SUV, from $45/day.Example: Ford Escape or Hyundai Santa Fe. Chicagoland weather can vary if you’re here in winter or just want a higher driving position, a midsize SUV is a popular pick. From Midway, a lot of renters snag SUVs to drive to ski resorts in Wisconsin or to have confidence if snow is in the forecast. At around $45/day, you get versatility: seating for 5, ample cargo space (strollers, shopping bags, you name it), and often all-wheel drive. Take an SUV for a spin along Lake Shore Drive or venture to Starved Rock State Park it can handle city potholes and country roads alike.
• Minivan, from $55/day.Example: Chrysler Pacifica or Dodge Grand Caravan (7-passenger). Got a bigger group or extra gear? Minivans are the unsung heroes of road trips. For around $55/day (often less when split among everyone), you get seating for 7 or 8 and a ton of cargo room. This is perfect for families hitting Chicago’s sights everyone gets a comfy seat and you can pack the day’s supplies easily. Planning an outing to Six Flags Great America or a weekend in the Wisconsin Dells? The DVD player (in some models) will keep kids entertained and the space means no one is squished after a long day at the amusement park. Pro tip: book minivans early for summer, as they tend to sell out during peak vacation season due to high demand from families visiting Chicago.

Note: “From” rates are based on current promotions for rentals picked up at Midway during off-peak dates (non-holiday, generally mid-week). Prices can fluctuate with season and demand for instance, summer and holiday periods might be a bit higher, and booking early can lock in lower rates. Always enter your specific dates in our search to see the most accurate price for your timeframe. We update deals often, so check back if you’re shopping around or better yet, book now with free cancellation to secure a good rate, and you have the flexibility to modify if needed!

Driving in Chicago: What to Know

Driving in Chicago and its surrounding areas is generally straightforward, but as with any big city, there are some local quirks and tips that can help you navigate like a native. Here’s a rundown on Chicago driving essentials:

• Traffic & Rush Hours: Chicago is known for heavy traffic during peak times. Weekday rush hours typically run 7–9 AM inbound (toward downtown) and 4–7 PM outbound. Highways like the Dan Ryan (I-90/94) on the South Side, the Kennedy (I-90/94) on the North Side, Eisenhower (I-290) coming in from the west, and Stevenson (I-55) which runs right by Midway, can get very congested. If you’re driving from Midway into the city on I-55, morning traffic can back up starting around 6:30 AM. If possible, plan your driving outside these windows you’ll enjoy a much quicker trip. On weekends, traffic is generally lighter, but be aware of sporting events: when the Cubs (Wrigley Field on the North Side) or White Sox (Guaranteed Rate Field, just off the Dan Ryan) have home games, or the Bears at Soldier Field, expect increased traffic before and after the games. Major events or festivals (Lollapalooza, Chicago Marathon, etc.) can also cause localized jams. Keep an ear on local traffic radio (WBBM 780 AM is a go-to for updates every 10 minutes) or use a navigation app to reroute around bad snarls. Chicagoans lovingly (or not) refer to certain bottlenecks by name the “Hillside Strangler” (where I-290 narrows near I-88) or the “Jane Byrne Interchange” downtown (where I-90/94 meets I-290) these are notorious slow points. Patience and leaving some buffer time in your schedule will serve you well.
• City Driving & Parking: The downtown “Loop” area is laid out in a grid with streets following a logical pattern (eight streets to a mile). It’s relatively easy to navigate, but it’s busy. Watch out for plenty of pedestrians, bicyclists, and buses in the city. Chicago drivers are generally assertive but polite use your turn signals, don’t block intersections, and you’ll fit right in. When making right turns, be mindful of pedestrians and cyclists (many main streets have bike lanes). Parking in downtown Chicago: There are lots of parking garages and surface lots. Rates can range from $15 to $40+ for a few hours, depending on location (closer to Michigan Ave or the heart of the Loop tends to be pricier). Street parking is available on many streets with pay-at-the-box meters (look for the central pay station on the block). Rates vary by area; downtown is around $4-7 per hour and often there’s a 2-hour limit until 10pm. You pay at the machine and put the printed ticket on your dashboard, or some areas now have pay-by-app (ParkChicago app) where you just enter your license plate. Read signs carefully there are rush hour parking restrictions on some streets (e.g., no parking 4-6pm to keep lanes clear) and street cleaning or snow route restrictions on certain days. In residential neighborhoods, you might see permit parking zones avoid those as a visitor, as you’ll get ticketed without a resident permit. Pro Tip: If you’re staying at a hotel downtown, valet parking can be $50-75 a night. You can often save by using a nearby self-park garage (some apps like SpotHero allow you to reserve a space in advance at a discount). Also, if you don’t need the car while in the core of the city, consider returning it for those days and picking up again when you’re ready to roam we can accommodate split rentals like that with a downtown location. That said, plenty of people keep their rental and find the convenience outweighs the parking cost. It’s all about your plans and budget.
• Tolls (Illinois Tollways): Many highways in the Chicago suburbs are toll roads. If you venture on I-90 northwest past O’Hare, I-294 (Tri-State Tollway around the city), I-88 west towards Aurora, I-355, or I-94 north of the city (toward Wisconsin), you’ll encounter toll plazas. Illinois has fully cashless tolling as of recent years they no longer staff most booths with attendants. Instead, you either pay via I-PASS (Illinois’ electronic transponder, compatible with E-ZPass) or you drive through and the system takes a photo of your license plate. As a rental driver, here’s what you need to know: most rental cars in this region will have an I-PASS/E-ZPass device or option. The rental company may offer it for a daily fee (e.g., ~$3.95 per day you use it, plus the tolls). If you opt in, you can breeze through the I-PASS lanes and not worry. If you don’t opt for a transponder, you can still use the toll roads; you just won’t stop (there are no toll booths to hand cash, except a couple legacy coin baskets on some exits). Instead, the toll authority will look up the plate and, since it’s a rental, send the bill to the rental company, who will then charge your card with the tolls plus an admin fee. To avoid the rental company’s admin fee, another option: pay the tolls online yourself. Illinois Tollway allows you to “Pay By Plate” within 14 days of using the road. You can go to illinoistollway.com, enter the rental car’s license plate and date range, and it’ll calculate any tolls due then you pay with a credit card. If you do this promptly, the rental company might never even get involved. Just ensure you include all days you had the car and all possible toll roads you used. If it sounds like a hassle, using the rental’s built-in program is easier just know it costs a bit extra. Alternatively, if you have your own E-ZPass from another state, you can bring it; it will work on Illinois tollways (just make sure it’s properly mounted and linked to the payment). Note: Driving into downtown Chicago via the Kennedy, Eisenhower, Stevenson, etc., has no tolls tolls are mostly on suburban stretches. Also, if you go out to the suburbs frequently, tolls can add up (though they’re usually $0.50 to $1.50 each). Budget a few bucks for tolls if your plans include them or use maps to find a “no toll” route (often side roads, slower but toll-free).
• Rules of the Road: In Illinois, like everywhere in the USA, drive on the right side and pass on the left. Seat belts are required for all occupants. Right on red is allowed after a full stop, unless a sign says “No Turn on Red” (some busy city intersections have these signs obey them to avoid a ticket or risk of collision with pedestrians). Left on red from a one-way street to another one-way street is legal in Illinois (and Chicago) after a stop for example, if you’re on a one-way and turning left onto another one-way, you can do it on red unless signed otherwise (this scenario happens downtown occasionally). Not everyone knows this rule, so don’t be surprised if some locals hesitate or honk if you do it but it is lawful. Cell phone use: Handheld phone use while driving is illegal in Illinois. Use a hands-free device or speakerphone if you must make a call, or better yet, pull over. Texting/emailing while driving is absolutely illegal and enforced. Basically, keep off the phone when driving Chicago police do issue tickets for this (and state troopers on tollways too). Speed limits: On city streets, it’s generally 30 mph unless posted otherwise. In alleys or around parks/schools, often 20 mph. On highways, it ranges from 55 mph in the city/interstates to 65-70 in the suburbs/rural. Keep an eye on signs; speeding cameras exist in some school zones and park zones (you’ll see signs for “Photo Enforced” if you speed 6+ mph over in those zones at certain times, you might get a notice in the mail via the rental company). Red-light cameras are also present at many city intersections always stop at red lights completely before turning right, and don’t try to beat the light late. Chicago’s fines for those camera tickets are ~$100, and the rental co. will charge an admin fee on top if one arrives. Drive defensively but not fearfully just follow the rules and you’ll be fine.
• Winter Driving: Chicago winters are famous (infamous?) for cold and snow. If you’re renting in the winter months (December through March, roughly), here’s what to expect: The city is very effective at plowing main roads quickly when snow hits. The vast grid system means there are plenty of alternate routes if one is slow. Still, after a heavy snowfall, side streets can be messy for a day or two. Our rental partners equip vehicles with all-season tires, which are usually fine for moderate snow. If a blizzard hits and you don’t feel comfortable driving, don’t risk it wait for plows to do their job. MDW itself is good at clearing their lots and runways, but sometimes flights get delayed, which could affect car availability we and our partners will communicate with you if that happens. A few winter tips: Keep the gas tank at least half full (to prevent fuel line freeze and in case you get stuck in traffic you’ll want the heater). Allow extra time to scrape/defrost the car your rental should have an ice scraper/snow brush (if not, ask for one at pick-up!). Before a snowstorm, Chicago may declare a “Snow Route” parking ban on main arterial streets if you happen to park on one overnight, you could be towed. Generally, as a visitor, use garages or lots after heavy snowfalls to avoid street parking complications. Also note, Chicago has an odd tradition called “Dibs” locals put chairs or cones to save shoveled street parking spots after big snows. It’s not strictly legal, but it’s culturally observed in many neighborhoods. As a visitor, it’s best to not move someone’s “dibs” markers to take that spot it can cause confrontation. Find another spot. Finally, black ice can occur when temps drop bridges and shaded areas freeze first, so take it slow if it’s below freezing and things look wet (they could be icy). On the flip side, Chicago winters also have many clear, sunny days beautiful for a drive along the lake with snowy scenery, as long as roads are clear.
• Summer Driving & Construction: They joke Chicago has two seasons: winter and construction. In warmer months, you will encounter road work. Watch for orange signs and cones; speeding in work zones carries doubled fines. Major projects like highway bridge repairs can cause lane closures. We recommend checking travel apps or IDOT’s website for construction alerts if you’re heading on a long drive for instance, portions of I-90 or I-290 seem perpetually being improved. Summer also brings lots of events keep an eye out for signs announcing street closures for festivals in neighborhoods. If you plan to drive downtown during big summer festivals (Taste of Chicago, Air & Water Show), expect heavier traffic and limited parking near event sites. Consider using your rental to drive to a park & ride or closer neighborhood, then transit in for the event, to avoid the thick of it.
• Pedestrians & Cyclists: Chicago is a very walkable city, and it’s making strides (pun intended) in cycling infrastructure. By law, cars must yield to pedestrians in crosswalks, even if there are no traffic lights. In practice, downtown, you’ll see people crossing even when they shouldn’t be vigilant and courteous. Near tourist spots like Michigan Avenue or the Museum Campus, expect pedestrians everywhere. For cyclists: many streets have designated bike lanes (some protected by barriers, some just painted lines). When turning right, always check your passenger-side mirror for a cyclist coming up the bike lane. “Dooring” a cyclist (opening your car door on a parked street into a cyclist) is a common hazard always do the “Dutch reach” (open your door with your far hand so you naturally look back for bikes). Give bikes at least 3 feet when passing (it’s the law). There are also Divvy bike-share cycles all over riders can pop up anywhere. Essentially, assume in the city that any given second, someone on foot or two wheels could be in your path. Drive with that mindset and you’ll be good.
• Unique Chicago Things: If you drive in the downtown “Loop” area, note that some streets go under others (Lower Wacker Drive being the famous example as seen in Batman movies!). Don’t panic if your GPS signal gets weak under there. It’s actually a useful shortcut to avoid surface traffic, but first-timers might find it confusing. Also, Chicago has many one-way streets pay attention to signs so you don’t accidentally go the wrong way. If you’re headed to Navy Pier, note that on busy days they may direct cars to off-site lots once the main lot fills follow the signs or staff directions. If you’re venturing onto Lake Shore Drive (LSD, now officially Jean Baptiste Point du Sable Lake Shore Drive), enjoy the views but watch your speed the limit is 40 mph and is camera enforced in spots. Lastly, Chicago has some peculiar intersection layouts (six-corner intersections where three streets meet, for example). Just stay alert, yield appropriately, and you’ll get through fine.

By and large, driving in Chicago is manageable and often enjoyable (LSD on a sunny day is gorgeous!). Millions of residents do it every day. With these tips in mind, you’ll handle it like a local. And remember, if you have any questions on the road like “Is there a toll on this route?” or “Where’s a good place to park near X?” you can always call our support for some friendly advice.

Road Trip Ideas from Chicago Midway (MDW)

One of the best things about renting a car at Midway is your proximity to a wealth of road trip destinations. Chicago sits at a crossroads of interstate highways that can take you to scenic, historic, and fun spots in every direction. Here are three road trip ideas to spark your wanderlust:

• Lake Michigan Shoreline Adventure (Indiana & Michigan)Route: Chicago ➜ Indiana Dunes National Park (IN) ➜ Harbor Country (New Buffalo, MI)

Highlights: Head about 1 hour east of Midway on I-94 and you’ll reach Indiana Dunes National Park and State Park. These parks hug the southern shore of Lake Michigan and offer surprisingly beautiful sand dunes and beaches (yes, with real sand it’s like an ocean coastline!). Climb Mount Baldy (a big dune) or stroll the beach at West Beach with Chicago’s skyline faintly visible on the horizon. After some beach time or hiking in the dunes, continue into Michigan’s southwest corner often called Harbor Country. Towns like New Buffalo, Union Pier, and St. Joseph are charming lakefront escapes. Stop at New Buffalo (just 15 minutes past the Indiana border) for boutique shops, eateries, and the beach at New Buffalo Public Park. If you’re a wine lover or craft beer enthusiast, this region is dotted with wineries and breweries thanks to the fertile land slightly inland. You can easily make this a day trip (about 70 miles one-way to New Buffalo) or extend it overnight at a cozy B&B. In summer, the traffic to Indiana Dunes can spike on weekends, so leave early to beat the crowds.

Pro Tip: If you have more time, drive a bit further into Michigan to Saugatuck (about 2.5 hours from Chicago) a lovely artsy village on the water with dune rides and great galleries. And if you’re doing this trip in the autumn, you’re in for a treat: the fall foliage against the blue lake is stunning, and many wineries offer harvest-time events and tastings.

• Historic Route 66 to St. LouisRoute: Chicago ➜ Springfield, IL ➜ St. Louis, MO (via I-55 with Route 66 historic alignments)

Highlights: Get your kicks on Route 66! The famous Mother Road begins (or ends) in Chicago, and Midway is conveniently right by its path (I-55 largely parallels or covers old 66). You don’t have to drive all the way to California a great section to experience is the stretch from Chicago to Springfield, Illinois (the capital city) and onward to St. Louis, Missouri. Start by seeking out some Route 66 nostalgia in the Chicago suburbs: for example, you could grab a classic drive-in meal at Dell Rhea’s Chicken Basket in Willowbrook (a legendary 66 roadhouse) on your way out. As you drive south (~200 miles to Springfield), you’ll find numerous roadside attractions: Pontiac, IL has a wonderful Route 66 Museum and murals downtown, Atlanta, IL boasts the Bunyon Giant (a muffler man statue holding a hot dog!), and Litchfield, IL has the 66-era Ariston Café. In Springfield, visit sites connected to Abraham Lincoln his home, tomb, and the fantastic Lincoln Presidential Library and Museum. Springfield is also known for the cozy Cozy Dog Drive-In, home of the corn dog on a stick, a Route 66 icon. If you press on to St. Louis (another 100 miles from Springfield), you’ll be greeted by the famous Gateway Arch. St. Louis offers a lot: tour the Anheuser-Busch Brewery (with the Clydesdale horses), try some St. Louis-style BBQ ribs, and don’t miss the quirky City Museum (an adult/kid playground made from reclaimed materials indescribably fun).

Pro Tip: This trip is about the journey, so allow extra time to drive on the Historic Route 66 alignments when possible instead of the interstate. Many are marked with brown “Historic 66” signs off I-55. They lead you through small towns with vintage gas station museums (like Dwight, IL’s Texaco station) and old diners. Pick up a Route 66 guide pamphlet (often available at rest stops or museums) to know where to hop on and off the interstate for the best sights. It’s a perfect trip for history buffs and nostalgia lovers and yes, you can do it round-trip in a long weekend.

• Wisconsin Weekend Milwaukee & The DellsRoute: Chicago ➜ Milwaukee, WI ➜ Wisconsin Dells, WI (via I-94 and I-90)

Highlights: Head north from Chicago about 90 minutes and you’ll hit Milwaukee, Chicago’s smaller (and some say friendlier) neighbor city in Wisconsin. Milwaukee has a ton to offer: tour the Miller Brewery or the newer microbreweries that have popped up, stroll along the Milwaukee RiverWalk, and check out the stunning Milwaukee Art Museum (its architecture features a “brise soleil” that opens like wings). Don’t forget to grab some local cheese curds or a bratwurst you’re in the heart of German-American food country. After enjoying Milwaukee’s blend of industrial heritage and vibrant new life, continue another 2 hours northwest to the Wisconsin Dells. The Dells is known as the “Waterpark Capital of the World” it’s a major family-fun destination with numerous indoor and outdoor waterparks, amusement parks, mini-golf, go-karts you name it. Even if waterparks aren’t your thing, the area’s natural beauty is worth the trip: take a Duck Boat tour on the Wisconsin River to see the sandstone cliffs and rock formations that gave the Dells its name, or go hiking in nearby Devil’s Lake State Park for gorgeous vistas. The drive from Milwaukee to the Dells will take you through some pleasant Wisconsin farmland; consider a quick stop in Madison, the state capital, which lies roughly on the way. Madison is a lovely college town set between two lakes even an hour stop to see the State Capitol building (and maybe grab some famous chocolate shop ice cream at the Memorial Union terrace on UW campus) is worthwhile.

Pro Tip: If visiting the Dells in summer, weekdays are far less crowded than weekends. If you must go on a weekend, start your drive early to beat the rush on I-90 northbound (traffic can slow down around Madison). Also, keep an eye out for Wisconsin supper clubs classic eateries often outside town which offer hearty meals (think prime rib, fried fish, old fashioneds to drink). They’re a Wisconsin tradition and you’ll pass a few along the highways. One more tip: The Wisconsin Dells area has several indoor waterparks (like Kalahari, Great Wolf Lodge). So even if the weather is cold or rainy, you can still enjoy a 84-degree waterpark day. This trip showcases a mix of urban culture, small-town charm, and kid-friendly adventure all within about 3 hours’ drive of Chicago.

Each of these road trips can be adjusted to your time and interests. Whether you’re craving nature, Americana roadside kitsch, or just exploring Midwestern cities, a rental car from Midway is your passport to discovery. And remember, unlimited miles means you can roam as far as you want so who knows, maybe you’ll extend that Route 66 trip all the way to the Pacific! Whatever your journey, we’re excited to be part of it.

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Frequently Asked Questions

How do I get to the rental car facility at Midway Airport?

It’s easy! Midway’s rental car facility is a short shuttle ride from the main terminal. After you land and collect any checked bags, follow the signs in the terminal for “Rental Cars / Shuttles.” You’ll head to the Lower Level (Baggage Claim area) near Door #2 (also near Door #3, as shuttles pick up between those in the inner lane). Look for signs or overhead announcements directing you to the Rental Car Shuttle pick-up. At the curb, you’ll see blue signs and likely some branded signs for various rental companies. Midway runs dedicated shuttle buses labeled for rental cars some are general and stop at the consolidated facility for all companies, and others might be specific to a brand (though at MDW now they mostly all go to the same building). The shuttles come frequently, typically every 10–15 minutes, 24 hours a day. Climb aboard (there’s luggage racks for your suitcases). The ride to the rental center is only about 5 minutes (the facility is at 55th St and Cicero Ave). Once you arrive, the bus will drop you off right at the entrance where all the rental counters are located. From there, check in with your specific rental agency, and they’ll direct you to your car in the adjacent garage. If you have mobility issues or a ton of luggage, there are usually luggage carts at the rental center and the shuttles are wheelchair accessible. Also, if you arrive in the deep night, don’t worry the shuttles run 24/7, though you might wait 15 minutes or so in off-hours. Overall, it’s a very straightforward process, and the signage at Midway is clear. If in doubt, any airport staff can point you toward the rental shuttle stop. One nice thing: because Midway is smaller than other airports, everything (baggage claim, shuttle stop, etc.) is pretty close together, making the whole rental pick-up process quicker.

What if my flight is delayed or arrives after the rental counter closing time?

Many rental counters at Midway operate from early morning until late night (some until 11 PM or midnight). If you have a reservation and your flight is delayed beyond closing time, don’t panic there’s usually a procedure. First, if possible, call the rental location’s phone number (or AirportVanRental’s 24/7 support) to inform them of your delay. Often, for known incoming customers, they will either stay open a bit later or make arrangements (like leaving keys with an on-site security or at an adjacent company’s counter that is open 24h). Some brands at Midway might have 24-hour service or at least an after-hours pick-up process. In the worst case scenario, if you arrive and all counters are closed: check your rental confirmation or the signage at the counter for an emergency number. Sometimes a staff member is on-call and can come out to assist. If that fails, AirportVanRental’s support can help re-book you with another company that is open (for example, one or two might be open 24h, such as Enterprise or Alamo, etc., depending on day and demand). Generally, though, if your reservation had your flight info, rental staff will track it. They understand airline delays happen. They typically honor your reservation and will not give your car away as long as you pick up within a reasonable timeframe or communicate with them. If a delay pushes you to the next day entirely, then it becomes a new rental day we or the rental company can adjust the reservation date. If you’re stuck at an odd hour with no immediate rental car, one option is to take a taxi/Uber to your hotel and come back to Midway in the morning to get the car but usually we can avoid that hassle by coordinating with the rental agency. Bottom line: we’ve got your back if delays occur. Just keep us in the loop if you can (using airport Wi-Fi to shoot us an email or call if your phone works) and we’ll do everything to ensure a car is ready when you land.

Can I rent at Midway and drop off at O’Hare, or vice versa?

Yes! Intra-city one-way rentals (picking up at MDW, returning at ORD or another Chicago location) are generally allowed and often carry no drop-off fee or just a minimal one, since it’s within the same metro area. This is convenient if, say, you fly into Midway but out of O’Hare, or you start with a car from Midway and later want to return it downtown to spend a car-free day in the city. When booking, just select different pick-up and drop-off locations (e.g., Midway Airport to O’Hare Airport). Our system will show you available cars and any fee. Most of the time, between Chicago’s airports, the rental companies treat it as a normal return (they shuffle cars between locations regularly). Do try to specify it at booking if you spontaneously decide to drop at O’Hare without prior notice, they’ll still check it in, but the paperwork not reflecting it could confuse things or incur an improper fee. Better to have it on the contract. Other common one-ways: Midway to downtown (no fee, usually) or Midway to an out-of-state location. If you’re returning in another city (say, drive to Detroit or Minneapolis and drop there), there will likely be a one-way fee depending on distance. Our booking engine shows that before you commit. It can be totally worth it for big trips (like the Route 66 journey ending in LA bucket list alert!). But within Illinois or neighboring states, fees are sometimes very reasonable or waived during certain promotions. We’ll always be transparent about it. Summing up:

I’ve never driven in snow before what should I do if it snows while I have my rental?

First, don’t worry too much thousands of folks in Chicago had a “first snow drive” at some point and managed fine by taking it slow and being cautious. If it does snow during your rental period, here are some tips: • Clear the car completely: Before driving, brush all snow off the windows, roof, hood, and lights. Flying snow from your car can endanger others, and you need full visibility. Your rental should have an ice scraper/snow brush (if not, many gas stations sell them cheap). Also, ensure your windshield wipers are not stuck to the glass (free them gently to avoid tearing the blade). • Give yourself extra time: Both for prepping the car and for driving to your destination. Everything goes slower in snow. • Slow and steady: Accelerate gently to avoid wheel spin. Increase your following distance on slick roads you want 8-10 seconds gap (as opposed to 3-4 in dry). Brake softly and early slamming brakes can cause a skid (if your car has ABS, you’ll feel pulses if you do have to brake hard that’s normal, don’t pump the brakes, just press and let ABS work). • Use lower gears on slick hills: If your car is a manual (unlikely, most rentals are automatic) use 2nd gear to start moving to avoid spin. In an automatic, you can often select “L” or “2” to keep speeds low on downhill slopes, which helps. • Don’t use cruise control: You want full control of acceleration in slippery conditions. • Bridges and ramps freeze first: Even if main roads are just wet, assume bridges could be icy. Approach them with caution. • Stay in plowed lanes: Chicago and Illinois DOT plows freeways pretty quickly. On surface streets, if there’s a visible tire path or plowed lane, stick to it. Avoid changing lanes through deep snow if you can those windrows between lanes can tug your wheels. • If you skid: Don’t panic. Most skids are rear-wheel slides or front-wheel plow. If the back end slides out, gently steer into the skid (toward where the back is sliding) and ease off the gas this helps straighten the car. If the front wheels lose grip and you go straight instead of turning, ease off the accelerator and maybe feather the brake weight shifts to front may help regain steering. • Be visible: In heavy snowfall or after dark, drive with headlights on (low beams). If visibility is really bad (e.g., near white-out), hazard lights can help others see you. • Know when not to go: If there’s a big blizzard, city authorities might ask people to stay off roads. Heed those warnings for your safety and to let plows work. Our rental partners often allow an extra grace in such events (you won’t be penalized for returning a bit late due to a major storm, typically). If needed, hunker down and drive once roads are cleared. • Emergency kit: It’s not a bad idea to keep an extra coat, some gloves, maybe a blanket and small shovel in the trunk in winter. Rental cars won’t automatically have those, but if you’re extra concerned, grabbing a $10 shovel could bring peace of mind (chances are you won’t need it unless parking in unplowed areas). • Fuel up: Try to keep at least half a tank in winter. Not only does it help prevent condensation, but if you did get stuck in traffic or snow, you have fuel to run the heater. The good news is Chicago (and interstates in the Midwest) have vast resources for snow clearing. Main roads get back to normal usually within hours of snow ending. And many winter days the sun comes out and melts a lot. So, while you might see some snow, odds are your whole trip won’t be a snowpocalypse (and hey, it can be quite pretty!). When in doubt, take it slow. You’ll get the hang of it. And of course, you can always ask us or locals for road condition updates. Drive safe and you’ll be fine.