Epic Road Trips Starting From Chicago

Driving in Chicago: Tips for Safe & Easy Navigation

Driving in Chicago offers the freedom to explore the city and its surroundings at your own pace. However, like any major metropolitan area, it has its quirks. Below are essential Chicago driving tips and local insights to help you navigate confidently.

Traffic & Rush Hours

Chicago is the third-largest city in the U.S., and traffic congestion is a part of life. Weekday rush hours typically peak around 7:00–9:30 AM and 4:00–6:30 PM. The downtown area (the Loop) and major expressways such as I-90/94 (Kennedy and Dan Ryan Expressways), I-290 (Eisenhower), and I-55 (Stevenson) often become stop-and-go during these times. For example, if you’re driving from O’Hare International Airport into the city via I-90 in the evening rush, be prepared for heavy traffic; a 30-minute trip can turn into a two-hour crawl at peak time. To have a smoother trip, plan extra travel time or consider driving during off-peak hours (midday or later in the evening).

Use a GPS or map app for real-time traffic routing. Chicago navigation apps may guide you along alternate routes like using LSD (Lake Shore Drive) or city surface streets if the interstates are jammed. Always stay alert: Chicago drivers can be a bit aggressive but generally follow the rules. Use your turn signals and keep a safe following distance in stop-and-go traffic.

Toll Roads (Illinois Tollways)

Many highways around Chicago (especially in the suburbs) are toll roads. Interstates like I-90 (toward Rockford), I-294 (Tri-State Tollway), I-88 (Reagan Tollway), and I-355 all require toll payments. Illinois has fully cashless tolling there are no toll booths to pay cash. Tolls are collected via I-PASS or E-ZPass transponders or by photographing license plates. If your rental car has a toll transponder (or if the rental company offers a toll payment program), it can automatically pay your tolls (often for a small daily fee plus the toll costs). If not, don’t worry you can still use the toll roads. The system will record your license plate, and you have a limited time (about 14 days) to pay your tolls online via the Illinois Tollway’s Pay By Plate system. In fact, customers without an I-PASS/EZ-Pass can enter their plate and travel dates online within 14 days to avoid fines.

Tip: Ask your rental provider about their toll policy. Some rental car companies offer toll programs but charge a hefty daily “convenience” fee (often around $3–$15 per day plus the tolls). This can end up costing more than the tolls themselves. Many savvy travelers prefer to decline the rental car’s toll program and either use their own I-PASS transponder or pay the tolls online afterward. In fact, most major rental companies charge a daily fee (sometimes ~$10) on top of the tolls for their pass “a total rip off,” as one frequent renter put it. Instead, you can simply note the rental car’s license plate and pay any tolls online within the 14-day window, avoiding those extra fees. If you know you’), consider these options to avoid surprise charges.

City Driving & Parking

Navigating Downtown: Downtown Chicago’s streets are laid out in a grid, which makes navigation straightforward. Do be mindful of one-way streets in the Loop and downtown. Traffic lights are well-marked. There are also dedicated bike lanes in some areas watch for cyclists, especially in neighborhoods like Wicker Park or near the lakefront where biking is popular.

Street Parking: Parking in Chicago ranges from plentiful to challenging depending on where you are. In downtown and popular districts (e.g. River North, Magnificent Mile, Wrigleyville), street parking is limited and often metered. Always read parking signs carefully Chicago strictly enforces street cleaning schedules and residential permit zones. (For example, street cleaning occurs April 1–November, and if you don’t move your car during the posted times you risk a $50 ticket or even towing.) Meters in busy areas typically cost about $2–$7 per hour, depending on the neighborhood (closer to $6–7 in the central Loop, and a bit less in outlying areas). You can pay by credit card or with a phone app (the official ParkChicago app) at most meters. Note that metered spaces often have time limits (commonly 2 hours); if you hit the max, your car can be ticketed for overstaying even if you feed the meter, so sometimes it’s not possible to park all day on the street.

For longer stays or if you’re making multiple stops, it’s usually easier to use a parking garage or lot. Expect typical garage rates around $15–$20 for a few hours downtown, and around $30–$50 per day for downtown hotel or public garages. If you’re planning to visit multiple sights in one day, you might choose to park once and then use public transit or ride-shares to hop around the core, to avoid paying multiple parking fees.

Pro tips for parking: Some attractions offer parking validations or discounts (for example, certain museums or restaurants will validate garage parking). Also consider using apps like SpotHero or Parkwhiz to find and reserve discounted parking spots in advance parking in Chicago typically averages ~$30, but those apps can secure rates much lower in many cases. Lastly, never leave valuables in plain sight inside your car. Chicago is generally safe, but an empty-looking car (or at least one with items tucked away) is less tempting for break-ins. Out of sight, out of mind if thieves don’t see anything worth stealing, they’re far less likely to target your car.

Seasonal Considerations

Chicago’s weather changes dramatically with the seasons, and your driving strategies should adapt accordingly:

• Winter (Dec–Feb): Winter brings snow, ice, and cold temperatures. The city and state do an excellent job plowing main roads, but after a heavy snowfall, side streets may stay snowy or slushy for a while. If you’re not used to winter driving, take it slow and increase your following distance stopping on icy roads takes much longer. Most rental cars in Chicago will have all-season tires (sufficient for city driving), but if you plan trips to snowier rural regions or are visiting in deep winter, consider renting an AWD vehicle for extra confidence. Keep an ice scraper/brush in the car (many rentals provide this) to clear off snow. Before driving, clear all windows and mirrors of ice and snow for full visibility it’s the law in Illinois that you cannot drive with snow or ice obstructing your windows. (Police can pull you over and ticket you for an obscured windshield or windows.) Also, watch for “black ice” on bridges and shaded roadways when temperatures dip below freezing this thin, invisible layer of ice can be very slippery.
• Summer (Jun–Aug): In Chicago, summer is often jokingly called “construction season.” Expect some detours or lane closures as the city takes advantage of warm weather to repair roads. Also be prepared for heavy thunderstorms summer storms can bring torrential rain that causes temporary street flooding. If rain is pounding, drive with headlights on and slow down, being cautious of pooled water on roads. On the flip side, summer is a fantastic time to drive with the windows down or to enjoy the breeze along Lake Shore Drive. Just be prepared for more pedestrians and cyclists out and about enjoying the weather too. Bonus: Summer Fridays, especially in the afternoon, can see an early mini-rush hour as people head to festivals or the lakefront, so traffic may start building earlier than usual on those days.
• Spring (Mar–May) and Fall (Sep–Nov): These seasons are relatively mild and can be the most pleasant for driving. In spring, rain is common April showers, etc. so maintain good wiper blades and be ready for slick roads. Fall brings beautiful foliage, but wet leaves on pavement can be surprisingly slippery, so take care on leaf-covered streets after rain. In late fall, early snow or frost can occur, so be mindful as temperatures drop toward freezing.

One more winter note: parking after snowstorms. Chicago has a winter overnight parking ban on many arterial streets (3am–7am) from Dec 1 to Apr 1, regardless of snowfall plus an additional ban on any street if snow on the ground exceeds 2 inches. In practical terms, if a big snow hits, check the city’s alerts or avoid parking on main routes so you don’t get towed for snow clearance. And if you do park on a street, shovel out a spot and don’t toss snow back into the street (that’s illegal and inconsiderate).

Navigating the City & Neighborhoods

Chicago is often called a “city of neighborhoods,” and having a car makes it easier to explore places beyond the downtown Loop. Some tips for getting around various parts of the city:

• Use major arterial roads to traverse long distances across town. For example, North Avenue (east-west), Western Avenue (north-south), or Roosevelt Road (east-west) are large streets that run through many neighborhoods. They’re often a better choice than smaller residential streets when covering miles. Avoid driving fast through narrow neighborhood streets many have speed humps and frequent stop signs.
• Be aware of some of Chicago’s quirky intersections. In certain spots (like the “Six Corners” intersections common on the northwest side, where three streets meet at odd angles), the layout can be confusing. Just stay calm, follow the traffic lights and posted signs, and remember that standard right-of-way rules still apply. If it’s confusing, yield cautiously and make eye contact with other drivers or pedestrians as needed.
• Right turn on red is allowed in Illinois (after a full stop), unless a sign explicitly says “No Turn on Red.” This can help traffic flow at big junctions. Just remember to always stop fully first and yield to any pedestrians in the crosswalk before turning.
• Heading to a big event? If you’re going to a Cubs game at Wrigley Field, a concert at Soldier Field, or any major event in the city, anticipate heavy traffic and limited parking near the venue. Often, it’s easiest to park a bit farther away and either walk or take public transit for the last part of the trip. For example, many locals will park along the CTA “L” train lines or at a park-and-ride, then take the train in for a Bears or Cubs game to avoid the traffic crunch right around the stadium.
• Downtown tip: Lower Wacker Drive. This is an underground expressway-ish road that runs below the downtown streets. Locals use it to avoid surface traffic (and as a famous set-piece in Batman movies), but it can be very confusing for newcomers. GPS signals often cut out down there, and entrances/exits are easy to miss. Unless you’re confident or feeling adventurous, it’s perfectly okay to avoid Lower Wacker and stay on the upper streets. (If you do find yourself on it, don’t panic it eventually pops back up. Just avoid sudden lane changes and follow the signs to an exit if you need to get back to ground level.)
• Chicago drivers, while sometimes aggressive, do generally follow the “rules of the road.” Use your turn signals, don’t block intersections, and when in doubt, a friendly wave goes a long way if someone lets you merge. The city has a grid system, so it’s hard to get truly lost if you miss a turn, you can often go around the block or turn at the next major street and navigate back.

Fueling Up

Gas prices in the Chicago area tend to be around or slightly above the national average, primarily due to higher taxes. As of mid-2025, expect roughly $3.50–$4.00 per gallon for regular unleaded in the Chicago region the average in the metro area was about $3.65 in summer 2025. Prices are generally higher in the city than in the suburbs (Chicago adds city and county fuel taxes on top of state tax). In fact, Illinois has some of the highest gas taxes in the country, making its gas prices among the most expensive in the Midwest. If you need to refuel and want a better price, you’ll find plenty of gas stations in the city, but note that downtown stations (for example, in River North or Streeterville) often charge a premium. It can pay off to drive a mile or two away from tourist areas or into neighborhoods outside the core to find cheaper gas.

When returning a rental car, if you picked up at an airport, remember to refuel nearby before you get to the airport area to avoid the rental company’s sky-high refueling fees. For example, near O’Hare Airport, there are several gas stations along Mannheim Road and on Cumberland Ave a few miles from the rental car center these are convenient last stops to top off the tank. At Midway Airport, look along S. Cicero Avenue or W. 55th Street for fuel before you drop the car.

Payment tip for international visitors: Illinois gas pumps will ask for your ZIP code if you pay by credit card at the pump. If you don’t have a U.S. ZIP (for example, visitors from abroad), one trick is to enter the digits of your postal code plus zeroes to make 5 digits (this works for some Canadian cards). If that fails, you will need to pay inside the station. You can usually prepay inside (say a dollar amount or ask to fill the tank, leaving a card imprint) and then pump gas. Don’t be surprised by this extra step it’s a fraud-prevention measure U.S. gas stations use.

Oh, and one more regional quirk: in Chicago (city proper) you may notice the pump price includes a few cents for an “underground storage tank” fee, etc. all part of the taxes mentioned earlier. Just know that gas will be a bit cheaper if your road trip takes you into Indiana, Wisconsin, or downstate Illinois.

By following these tips and staying alert, you’ll find that driving in Chicago is very manageable and it opens up a world of opportunities beyond the beaten path. From spontaneous drives up the coast of Lake Michigan to discovering a new favorite pizza joint in the suburbs, a car gives you the keys to a true Chicago experience. Buckle up, enjoy the ride, and welcome to driving in the Windy City!

Road Trip Ideas from Chicago, IL

One of the best parts about renting a car in Chicago is the ability to embark on some fantastic road trips. The city’s central location means you can drive off in almost any direction and hit interesting destinations from small Midwestern towns to other major cities and natural wonders. Here are three road trip itineraries from Chicago to spark your wanderlust:

1. Historic Route 66: Chicago to Santa Monica (Cross-Country Adventure)

Distance: ~2,400 miles one-way (plan 2 weeks or more for a comfortable, scenic trip). Route 66 was one of the original highways in the U.S., stretching over 2,400 miles from Chicago, Illinois to Santa Monica, California.

Route: Begin at Chicago’s “Route 66 Begin” sign on Adams Street (in the Loop, near the Art Institute) the historic starting point of Route 66, known as “America’s Mother Road.” From Chicago, the old Route 66 path roughly follows I-55 south through Illinois (passing Springfield), then I-44 through Missouri and Oklahoma, continuing on I-40 across Texas, New Mexico, and Arizona, and finally joins I-10 into California. You’ll wind your way through 8 states, ending at the Santa Monica Pier in Los Angeles, California, where Route 66 traditionally concludes at the Pacific Ocean.

Highlights: This is the ultimate American road trip, filled with nostalgia and quirky Americana. From Chicago, head south to see the Gateway Arch in St. Louis (a slight detour off the old route, but worth it for the iconic monument on the Mississippi River). Cruise through small Illinois towns like Pontiac or Bloomington to visit classic Route 66 museums and murals. In Missouri, stop in Springfield or at Meramec Caverns (a famous outlaw Jesse James hideout in the caves). Oklahoma offers the kitschy Blue Whale of Catoosa, a giant smiling blue whale sculpture by a pond that has become a beloved Route 66 roadside landmark. In Texas, don’t miss Cadillac Ranch in Amarillo where brightly painted cars are half-buried nose-down in a field; bring some spray paint so you can leave your mark on the cars (it’s encouraged spray cans litter the site as an open invitation to visitors to add their own artwork).

New Mexico’s stretch includes the high desert around Albuquerque (look for the neon signs on old Route 66 through town, or take a side trip to Santa Fe for a different vibe). Arizona will wow you with Petrified Forest National Park and the otherworldly Meteor Crater near Winslow. Plus, towns like Flagstaff, Williams, and Kingman still retain that mid-century Route 66 atmosphere (diners, motels with neon signs, etc.). Finally, in California, you’ll traverse the Mojave Desert consider a stop at the ghost town of Calico and then on to the Los Angeles area. Your finale: reaching the Santa Monica Pier, where you can literally dip your toes in the Pacific after an epic journey. Don’t forget to take a photo with the “End of the Trail Route 66” sign on the pier (a sign at the pier marks the traditional end of the highway).

Tips: Much of historic Route 66 has been bypassed by modern interstates, but you can often drive on the signposted historic segments of the old road, which parallel the highway, for a more scenic and nostalgic experience. Allow extra time to explore small towns half the fun is dining at vintage mom-and-pop diners and staying at retro motels with neon marquees. Summers can be extremely hot in parts of the Southwest (100°F+ common in Arizona and California deserts), so ensure your car’s A/C is working well and carry plenty of water. Thunderstorms can pop up in the Midwest during summer too be prepared to slow down or pull over in heavy rain if needed.

Because of the distance, an unlimited mileage rental is ideal for this trip. One-way rentals from Chicago to Los Angeles are possible many travelers do this classic journey. (Rental companies sometimes offer specials to waive the one-way drop fee on popular cross-country routes it’s worth checking with us when booking.) Lastly, embrace the spirit of Route 66: it’s not about getting there fast on the interstate; it’s about the journey. So take the scenic detours, snap photos of the funky roadside attractions, and enjoy every mile of Americana on this classic road trip.

2. Great Lakes Circle Tour: Lake Michigan Loop

Distance: ~1,100 miles round-trip loop (suggest 5–7 days to fully enjoy).

Route: This scenic loop circles Lake Michigan, one of the Great Lakes, through four states. Start in Chicago and head north into Wisconsin via I-94. You’ll follow Lake Michigan’s western shore through Milwaukee and up to Green Bay. From the top of Wisconsin, cross into Michigan’s Upper Peninsula (UP) near Menominee or via Marinette, WI. Continue east across the UP, then turn south over the Mackinac Bridge (a highlight itself!) into Michigan’s Lower Peninsula. Drive down Michigan’s west coast along routes like US-31, passing through lakeshore beach towns, then through a corner of Indiana and back to Chicago. This entire Lake Michigan Circle Tour spans roughly 1,100 miles of shoreline driving.

Highlights: This trip is all about lakefront beauty, charming small towns, and the diverse regional culture around Lake Michigan.

• First leg, Chicago to Milwaukee, WI (about 1.5 hours): In Milwaukee, enjoy a brewery tour (it’s known for its beer heritage) or visit the Harley-Davidson Museum. Milwaukee is a city on the lake with a cool blend of industrial and modern vibes.
• Continuing north, consider a side trip to the Door County peninsula in Wisconsin (east of Green Bay) if time permits. Door County is full of quaint villages, cherry orchards, and beautiful shoreline it’s sometimes called the “Cape Cod of the Midwest.”
• Crossing into Michigan’s Upper Peninsula, you’ll find more rugged natural beauty. A detour alert: From the UP town of Munising, you could take a side trip to Pictured Rocks National Lakeshore on Lake Superior (about a 2-hour drive one-way from the Mackinac Bridge area, but unforgettable if you have a day to spare). Pictured Rocks features multicolored cliffs and rock formations along Lake Superior truly stunning on a boat tour or hike.
• Back on our main loop, crossing the Mackinac Bridge is a thrill. The “Mighty Mac” is one of the longest suspension bridges in the world (5 miles long!) and the longest in the Western Hemisphere. It connects the Upper and Lower Peninsulas of Michigan and offers sweeping views of Lake Michigan and Lake Huron. On the south side of the bridge is Mackinaw City, where you can catch a ferry to Mackinac Island. Mackinac Island is a gem no cars are allowed on the island (transport is by horse, bike, or foot), and it’s famous for its historic fort and delicious fudge. A side excursion to Mackinac Island is well worth it if time allows (even if just for a day trip to bike around the island and sample some fudge).
• Continuing down the eastern shore of Lake Michigan’s Lower Peninsula: Don’t miss Sleeping Bear Dunes National Lakeshore near Empire/Traverse City, Michigan. Here, towering sand dunes (up to 450 feet high) offer incredible vistas over Lake Michigan. You can even climb the dunes at the Dune Climb or drive the Pierce Stocking Scenic Drive for panoramic overlooks. (The dunes were once voted “America’s Most Beautiful Place.” Bring your camera and maybe your leg muscles, if you attempt the dune climb!)
• Traverse City, MI is a fantastic stop: it’s known for wineries (the surrounding peninsulas produce excellent rieslings and cherry wines) and has a lovely small-town vibe with great food and shops. In summer, the area’s cherry orchards are in season (Traverse City is nicknamed the Cherry Capital). This “Napa of the Midwest” region combines striking water views, rolling vineyards, and a friendly small-town feel.
• Further south, you’ll pass through charming beach towns in West Michigan like Holland, Grand Haven, or Saugatuck. Holland, MI proudly showcases its Dutch heritage complete with an authentic Dutch windmill and millions of tulips that bloom each spring during the Tulip Time festival. It’s a great stop in April/May to see tulip gardens and even wooden shoe dancing. Grand Haven and South Haven have picturesque lighthouses and piers, plus beautiful sandy beaches (yes, Lake Michigan beaches have golden sand and dune grass you might forget you’re in the Midwest!).
• As you loop back toward Chicago, you’ll pass the Indiana Dunes National Park and Indiana Dunes State Park at the southern tip of Lake Michigan (in Indiana). This area features big sand dunes right along the lake with the Chicago skyline visible in the distance on clear days. It’s a popular spot for hiking or a last beach stop before returning to the city.

Tips: This loop crosses four states (Illinois, Wisconsin, Michigan, Indiana). Keep some change or an IPass handy for a few toll roads (there are tolls on some Chicago-area segments and the Mackinac Bridge has a toll). Weather can vary by region: summers are delightful for swimming in Lake Michigan (water is warmest by late July), while fall offers stunning foliage especially in northern Michigan and Wisconsin. Winter driving in the northern sections can be challenging due to lake-effect snow if you attempt this loop in winter, ensure you have a suitable vehicle and check road conditions frequently (some smaller tourist businesses will also be seasonal or closed in winter).

Many lakeshore towns are seasonal bustling in summer, quieter in the winter off-season. If traveling in the summer, weekdays will be less crowded than peak weekends. If you want to shorten the loop, there are car ferries that cross Lake Michigan (for instance, the S.S. Badger from Ludington, MI to Manitowoc, WI) which can save driving time and provide a unique mini-cruise experience across the lake.

Plan for extra driving time on scenic coastal byways. While interstates might be faster, the shoreline routes (like M-22 in Michigan or Highway 42 in Wisconsin’s Door County) are far more rewarding, with lake views and charming pit stops take them when you can. And bring a cooler: you’ll encounter farm stands selling Wisconsin cheeses, Michigan cherries and apples, fresh blueberries, etc. perfect snacks for the road. This Great Lakes road trip will show you a quieter, nature-rich side of the Midwest far from Chicago’s big-city bustle.

3. Blues & BBQ Road Trip: Chicago to New Orleans (The Heart of America’s Music Highway)

Distance: ~950 miles one-way (technically about a 14-hour drive nonstop, but 5–7 days is recommended to fully enjoy the journey).

Route: Head south from Chicago through the heart of the Mississippi Delta region all the way to New Orleans, tracing the roots of blues, rock ’n’ roll, and jazz. The straightforward path is to take I-57 south from Chicago (through Illinois) to I-55, which leads through Missouri, down the length of Arkansas and Mississippi, and eventually into Louisiana. Major waypoints include St. Louis, Memphis, Clarksdale (Mississippi), Jackson (Mississippi), and then New Orleans. An alternate route variation is to swing east through Nashville (via I-65 and I-40) and then down to Memphis, if you want to add some country music into the mix but that adds mileage. For a pure blues trail, sticking to the Mississippi River corridor is fantastic.

Highlights: This drive takes you through the cradle of American music the lands of blues, soul, rock, and jazz as well as through some of the country’s best barbecue and Southern food regions.

• St. Louis, Missouri (about 5 hours from Chicago): In St. Louis, you can’t miss the Gateway Arch, the 630-foot stainless steel monument on the Mississippi River. It’s worth riding the tram to the top for the view if you have time. St. Louis also has its own barbecue style try some ribs or pork steaks with the tangy tomato-based sauce. The city has live blues clubs as well, especially around the Soulard district. (If you’re a baseball fan, Busch Stadium is right downtown too.)
• Memphis, Tennessee: Roughly another 4–5 hours south of St. Louis on I-55 brings you to Memphis, which is an absolute must-stop. Memphis is the Home of the Blues and Birthplace of Rock ’n’ Roll. Key stops: Graceland, the home of Elvis Presley (touring this mansion-turned-museum gives a deep dive into rock history), and Beale Street, the historic street lined with blues clubs and BBQ joints. On Beale Street you can catch live blues almost any night of the week and enjoy Memphis-style barbecue think dry-rubbed ribs and pulled pork. (As one magazine put it, “Blues and barbeque, smoke and sauce... in Memphis, they all meld beautifully just like heaven.”) Also highly recommended in Memphis: the National Civil Rights Museum, located at the Lorraine Motel where Dr. Martin Luther King Jr. was assassinated. It’s a powerful museum tracing the history of the Civil Rights Movement a stop that adds important context and depth to your trip through the South.
• Clarksdale, Mississippi: Heading south from Memphis, US-61 (the legendary “Blues Highway”) takes you into the Mississippi Delta. Clarksdale is a small city that looms large in blues lore it’s one of the places that claims to be the location of the famous “Crossroads” where, according to legend, bluesman Robert Johnson sold his soul to the devil in exchange for his guitar skills. At the intersection of Highways 61 and 49 in Clarksdale, you’ll even find a big decorative crossroads sign with guitars. Clarksdale has several stops for blues fans: the Delta Blues Museum, Morgan Freeman’s Ground Zero Blues Club (with live music in an authentic juke joint atmosphere), and Red’s Lounge (a very raw, beloved hole-in-the-wall blues bar). Even if you’re not a blues aficionado, the sense of history here is palpable. You can feel the roots of much modern music in these dusty Delta towns.
• Jackson, Mississippi: Continuing down US-61/I-55, you’ll pass through Jackson (the state capital). Jackson has civil rights history to explore (e.g., the Mississippi Civil Rights Museum) and some great soul food. It’s also referenced in plenty of blues/country songs. As a city, it’s a bit quieter tourist-wise than others on this route, but it could be a good rest stop for a night.
• New Orleans, Louisiana: The final leg is about 3 hours from Jackson to New Orleans. As you approach Louisiana, the landscape changes to bayous and marshes, and you’ll cross the massive Lake Pontchartrain via a causeway or bridge. New Orleans is your terminus, and what a finale it is! In New Orleans, music is everywhere from the jazz clubs of Frenchmen Street to the brass bands on street corners in the French Quarter. Enjoy some Creole cuisine: gumbo, jambalaya, beignets and café au lait at Café du Monde, po’boys, and more. Take a stroll down Bourbon Street for the spectacle (though it’s quite touristy/raucous at night), but also wander the historic French Quarter by day to appreciate the architecture and ambiance. A jazz brunch or an evening at a classic jazz club (like Preservation Hall) is a perfect capstone to this music-filled journey.

Tips: One-way rental from Chicago to New Orleans is very feasible many travelers use a road trip like this to experience a north-to-south slice of the U.S. (Then sometimes they’ll fly back from NOLA to avoid backtracking.) Check with the rental company about one-way drop fees; occasionally there are promotions or negotiations to reduce those.

The best time for this trip is spring or fall. Spring (March–May) in the South is warm and full of blooming flowers (azaleas, etc.), and you avoid Chicago’s winter cold. Fall (October) brings cooler temperatures and things like harvest festivals. Summer is doable but be prepared for hot, humid weather in the Deep South (July/August can see 90°F+ with high humidity in Mississippi and Louisiana). If traveling in summer, ensure your car’s A/C is in top shape and stay hydrated. Also note, hurricane season runs June–Nov, so keep an eye on weather forecasts if traveling late summer; storms can affect the Gulf Coast (including New Orleans).

When driving through rural stretches of Arkansas, Mississippi, or Louisiana, keep your gas tank above half full. Services (gas stations, rest stops) can be 30–40 miles apart in the more remote areas. At night, some small-town gas stations may be closed. So plan fuel stops ahead of time, especially at night or on Sundays when rural stations might have limited hours.

Speed limits on the interstates down south are typically 70 mph (and drivers do go fast), but always watch for sudden slowdowns near towns or construction zones. State troopers (highway police) are quite active on some stretches (particularly in Mississippi). Adhere to the limits and you’ll be fine.

Culturally, this is a diverse and enriching trip. In a matter of days, you’ll go from the urban Midwest through the rural Bible Belt to the jazz-filled streets of New Orleans. You can stop at roadside stands for sweet tea and boiled peanuts in the Deep South, hear gospel music or Delta blues on the radio, and see the landscape change from Illinois cornfields to Mississippi cotton fields to Louisiana swamps. Embrace it! There’s a famous Southern hospitality people along the way are generally friendly and love to share their local stories or recommendations.

A fun way to kick it off: grab some Chicago snacks for the road (Garrett’s popcorn, perhaps?). By the end, you can reward yourself with beignets and café au lait in New Orleans, having traded the deep-dish pizza for gumbo along the way. This journey is as much about the people and places as the miles traveled. Roll down your windows, turn up some blues or jazz on the radio, and enjoy the sounds of America on this road trip from the Great Lakes to the Gulf of Mexico.

Safe travels and happy driving! Whether you’re maneuvering through Chicago’s city streets or cruising down a scenic highway, the freedom of the open road is yours to enjoy. Chicago and its surroundings have so much to offer drivers willing to explore from urban adventures to road trips that create lifelong memories. Drive safely and have a wonderful journey.