Lollapalooza 2026 Chicago Travel & Rental Guide
TL;DR: Fly into Chicago via either O’Hare or Midway (Midway is closer, but both work) and reserve your rental car early a van or SUV is ideal if you’re coming with a group of friends. Grant Park (the Lollapalooza venue) is in downtown Chicago, so you can often skip the car and take the CTA trains from the airport (Blue Line from O’Hare, Orange Line from Midway) or use rideshares. If you do drive, plan for parking in advance (Millennium Garages offers pre-booked festival parking). Stay in the Loop or South Loop so you can walk to Lolla, and take some time to enjoy iconic Chicago attractions (from the Bean to deep-dish pizza) during your trip.
Crowds fill Grant Park as a performer takes the stage at Lollapalooza in downtown Chicago. The four-day festival draws hundreds of thousands of fans each summer. Grant Park spans 319 acres, so planning your transportation and stay ahead of time will make your Lolla experience much smoother.
Flying into Chicago: O’Hare vs. Midway Airport Tips
Chicago is served by O’Hare International Airport (ORD) on the northwest side and Midway International Airport (MDW) on the southwest side. If you have a choice, know that Midway is smaller and closer to downtown (about 12–13 miles away) whereas O’Hare is a major global airport about 17–18 miles out. In normal traffic, driving from O’Hare to downtown Chicago takes ~40–60 minutes, versus ~30–40 minutes from Midway. Midway often means a shorter, cheaper ride into the city (an Uber from MDW runs around $30 vs. $45 from ORD). However, O’Hare handles most international and cross-country flights, so many Lollapalooza travelers will end up there by default.
Transit from the Airport: Both airports have direct Chicago Transit Authority (CTA) train service into the city, a budget-friendly option. From O’Hare, you can hop on the CTA Blue Line train, which runs 24/7 and takes about 45–50 minutes to reach downtown (trains depart right from ORD’s terminals). From Midway, the CTA Orange Line gets you to the Loop in roughly 25–30 minutes (operating from early morning until late night). The trains are convenient and avoid traffic perfect if you’re packing light. If you have lots of luggage or gear, a taxi or rideshare might be more comfortable (just budget extra time and money for traffic). Both airports also have rental car centers: at O’Hare you’ll take a quick shuttle to the consolidated rental facility, and at Midway an airport shuttle or walkway connects to the rental center. If you’re renting a car, book ahead summer is peak travel season, and large vehicles like vans can sell out fast during big events.
Airport Tips: Aim to arrive in Chicago early if you can. Lollapalooza typically runs Thursday through Sunday in late July/early August, so consider flying in by Wednesday or early Thursday. This gives you time to get settled and pick up your rental before the festival gates open (usually around 11am each day). It also means you beat the last-minute rush O’Hare and Midway get very busy as festival-goers pour in, so give yourself extra time for everything from baggage claim to the car rental counter. If you land at O’Hare during rush hour, taking the Blue Line train can actually be faster than sitting in traffic on I-90/94. And if you land at Midway, be aware that a big weekend (or a Bears game at nearby Soldier Field) can still cause traffic on I-55 into downtown, so plan accordingly.
Best Rental Car Options: Solo Travelers vs. Groups
What’s the best ride for Lolla? It depends on your crew. Here are some tips for rental car options based on your traveler type:
- Solo or Couple: If you’re flying in alone or as a pair, you might not even need a car once you’re downtown the festival and city attractions are accessible by transit and walking. But if you plan to explore beyond downtown or prefer the flexibility, a compact or economy car will be cheapest and easiest to park. For a bit more comfort (and if you have luggage), consider a midsize sedan or small SUV. Driving in Chicago can be hectic, so a smaller vehicle makes navigating city streets and parking garages simpler.
- Group of Friends (3–5 people): For a small group, a standard SUV or minivan can be a great choice. An SUV (like a 7-passenger vehicle) gives you plenty of room for friends and stuff, without being too bulky for city driving. A minivan offers even more space and sliding doors (handy for piling in gear or pizza runs after the show). These vehicles let your group stay together rather than splitting into multiple cars or rideshares. Splitting the rental cost and gas a few ways also makes it quite economical per person. Plus, you’ll appreciate the extra trunk space for things like folding chairs, backpacks with festival essentials, or merch you pick up at Lolla.
- Large Group (6–15 people): Coming with a big crew or planning a road trip to Lollapalooza? Passenger vans are the way to go. Renting a 12-passenger or 15-passenger van keeps your whole squad in one vehicle, which is both cost-effective and logistically simpler for group travel. Instead of coordinating multiple cars, you have one set of keys, one parking spot, and everyone arrives together. Airport Van Rental specializes in larger vehicles you can compare deals on big vans easily. Vans not only allow room for everyone to ride together, but also for everyone’s luggage, coolers, and festival gear in one place. If you plan on tailgating or hanging out before/after the festival (some people gather at their vehicles to recharge), a van can serve as a convenient home base. Just remember that Chicago’s downtown streets can be tight for oversized vans drive cautiously and mind those clearances in parking garages. And importantly, designate a sober driver if your group will be partying safety first.
Why we emphasize vans/SUVs: Lollapalooza is a young and energetic crowd groups of college friends, recent grads, and music fans often road-trip together. A single large vehicle like an SUV or van keeps the fun going by keeping everyone together. You’ll save on gas and rental fees by splitting one vehicle, and it beats paying surge prices for multiple Ubers each night. Also, if you’re picking friends up from different airports or locations, it’s handy to have one roomy vehicle. Just be sure the driver is comfortable driving a larger car in city traffic and that you arrange parking in advance (large vehicles should fit in most downtown garages, but it’s worth checking height restrictions if you rent a tall van).
Getting to Grant Park (Lollapalooza Venue)
Grant Park is centrally located in downtown Chicago, along Michigan Avenue and the lakefront. If you’re staying downtown, walking is by far the easiest way to get to the festival gates you’ll avoid traffic and transit crowds. Many hotels in the Loop or South Loop are within a 10-15 minute walk of Grant Park. If you’re a bit farther out (or just saving your energy for dancing), here are the best ways to reach Grant Park:
- CTA “L” Trains: Chicago’s elevated/subway trains (the CTA) are very handy. The Red Line has multiple stops along State Street just a couple blocks west of Grant Park (exit at Monroe, Jackson, or Roosevelt and walk east). The Blue Line (from O’Hare) connects to the Red Line downtown, and the Orange Line (from Midway) stops in the Loop as well you can transfer or walk from its Harold Washington Library terminal (~15 min walk to the park). The Green Line and Brown Line also have Loop stops a short walk away. Basically, any train to the Loop will get you within walking distance. Pro Tip: buy a CTA pass or Ventra card at the airport or stations it’s cheaper than multiple single rides if you plan to use transit often. After the festival each night, expect trains to be busy; you might have to let a packed train pass and catch the next, but they run frequently and late.
- Buses: Several CTA bus routes run near Grant Park, including the #3 King Drive, #4 Cottage Grove, #20 Madison, #60 Blue Island, and others that circulate downtown. Buses can be a good option if you’re coming from neighborhoods not directly on a train line. However, keep in mind that buses will be affected by Lolla-related street closures and traffic. The #146 Inner Drive/Michigan Express is one bus that normally services the museum campus area (south end of Grant Park) check the CTA advisories, as routes may detour during the festival. If using a bus, plan extra travel time.
- Metra Commuter Trains: If you’re coming in from a Chicago suburb, Metra trains are a convenient choice. Millennium Station (at Randolph Street) and Van Buren Street Station are literally adjacent to Grant Park’s north and central sections. These stations serve the Metra Electric District and South Shore Line (from South Chicago and Indiana). Union Station and Ogilvie Station (from western suburbs) are about 1.5 miles away you can walk or take a short bus/ride share. Metra trains don’t run as late as CTA trains, so for the return trip, double-check the last evening departure if you’re not staying in the city.
- Rideshare or Taxi: Uber, Lyft, and taxis will be plentiful, but know that you can’t get dropped off right at the entrance due to road closures. The city typically designates specific pickup/drop-off zones a few blocks from Grant Park. For example, in past years rideshare drop-offs were restricted west of State Street you’d be directed there and then walk the remaining few blocks. Follow the directions in your rideshare app, and consider arranging to be picked up at a convenient corner away from the heaviest foot traffic. A smart tip is to arrive and leave a bit early if you can beat the main crowds by even 30 minutes, your car will have a much easier time navigating. Expect surge pricing and some gridlock right when the festival ends each night (around 10pm). Sometimes hanging out at a nearby café or late-night eatery for an hour before calling a ride can save you both money and stress.
- Driving Yourself: Unless you absolutely need to, driving to Grant Park is not recommended during Lollapalooza. Many streets around the park (such as Columbus Dr., Balbo, Jackson) are closed off, and downtown traffic will be heavy with festival-goers and normal summer tourists. If you do drive, parking is the big challenge. Street parking is virtually nonexistent near Grant Park during the event if not closed off, it will be full or time-limited. Your best bet is to park in a downtown garage. The official partner is Millennium Garages, a network of large underground garages directly beneath Grant Park. Booking a space there in advance is highly advised they even offer multi-day “Unlimited In & Out” passes for Lolla attendees. With a multi-day pass, you can leave your car parked all weekend and come and go on foot. (Pro tip: Lakeside Garage at 5 S. Columbus Drive is recommended for easy access to Lake Shore Drive, avoiding some of the closed streets.) Expect to pay a premium for parking (festival rates can be $30–$50+ per day), but it’s secure and convenient. Other nearby parking options include the Grant Park North garage or private lots in the Loop use apps like SpotHero or Parkwhiz to compare prices and reserve a spot ahead of time.
- Biking: Cycling to Lolla is a great option for locals or even visitors staying a bit farther out. Chicago has a popular bike-share program called Divvy, and you can rent bikes at stations all over the city. During Lolla, there is usually a free bike valet offered (in 2025 it was in partnership with a group called Reverb). This is basically a secure, staffed area where you can drop your bicycle near the festival entrance and retrieve it later a nice perk if you don’t want to fuss with finding a lock spot. If using your own bike, bring a strong lock and note that you won’t be allowed to ride on the festival grounds. Always ride safely (use bike lanes, watch for heavy car/pedestrian traffic near the park) and bring front and rear lights if you’ll be biking back after dark.
Parking & Rideshare Tips for Lolla
To recap and emphasize: parking and pickup require some strategy during Lollapalooza. If you have a hotel with parking, it might be easiest to leave your car at the hotel and walk or transit to Grant Park. Many downtown hotels charge for parking but at least you know your car is in a garage you can treat it as home base. If you’re using rideshares, remember that thousands of others are too. The city will likely have Uber/Lyft staging areas a few blocks west of the park (often near Wabash or State Street). When you request a pickup, the app will direct you to a specific corner or zone to meet your driver. It helps to coordinate with your driver by text or call because it can be chaotic e.g. “We’re at State and Adams, southwest corner, wearing red shirts.” Also, be prepared to walk a bit your ride may not be able to get super close. For drop-offs, you can usually get within a block or two of the park if you go early in the day before roads close or crowds build.
Chicago police often implement temporary no-parking zones in the vicinity of Lolla heed those signs if you’re parking on the street (towing is strictly enforced). If you find a metered spot, double-check the hours, because some may turn into tow zones in the evening. A safer bet is to use one of the Millennium Park garages or another Loop garage as mentioned. One parking tip from locals: park slightly outside the immediate downtown area near a CTA station (for example, a garage in the West Loop or Near North) and take a short train ride in. This can sometimes be cheaper and avoid the worst traffic. Just ensure the garage allows overnight parking if needed and that it’s in a safe area.
Lastly, patience is key. Whether you drive or rideshare, expect delays when Lolla lets out. With ~100,000 people leaving at the same time, the first hour after the festival is peak congestion. You might find it’s faster to grab a bite or hang in Grant Park for a bit (there are often aftershow concerts at nearby venues if you’re going to one, you’ll stagger your travel times). If you do stick around the festival grounds, keep in mind the area will be cleared eventually by security, so you can’t loiter indefinitely. But the longer you wait, the easier your trip out will be.
Where to Stay: Best Lodging Areas for Lollapalooza
When it comes to accommodations, you’ll want to stay as close to Grant Park as your budget allows. The good news is Chicago has tons of hotels in the downtown area, plus hostels and vacation rentals. Here are the prime zones to consider:
- Loop & South Loop: These neighborhoods are top choice for Lolla attendees. The Loop (Chicago’s downtown business district) borders Grant Park to the west and north, and the South Loop is just below the park. You can’t beat the convenience many hotels here are within easy walking distance of the festival. For example, places like the Congress Plaza Hotel, The Blackstone, Hilton Chicago, Best Western Grant Park, etc., literally face the park. Staying in this area means you can quickly pop back to your room if you need a rest, a change of clothes, or to drop off merch. It also spares you from worrying about late-night transportation you can walk back safely with the crowds or a friend. Tip: Book early! These hotels fill up fast for Lollapalooza weekend and prices will spike as the festival approaches (expect many require 4-night minimum stays for the whole festival).
- River North & Magnificent Mile: Just north of the Loop across the Chicago River, the River North area (and the Mag Mile part of Streeterville) has a high concentration of hotels, restaurants, and nightlife. It’s a bit further (2+ miles from Grant Park), but still accessible a quick rideshare or a 5-10 minute Red Line train ride will get you near the festival. If you’re looking to enjoy Chicago’s famous bars and clubs after the festival ends each night, this area might appeal to you. Hotels here range from upscale chains to smaller boutiques. You’ll likely pay a premium compared to the Loop, but the benefit is being in the heart of the dining/entertainment district. Just factor in a daily commute to Lolla (which isn’t bad many Lolla-goers stay up here and have no issues).
- West Loop & Fulton Market: About 2–3 miles west of Grant Park, the West Loop is a trendy neighborhood known for its restaurant row on Randolph Street. There are a few hotels and a lot of cool eateries/breweries. While not walking distance, the #20 Madison bus or a short Uber can get you to the park. This could be a good option if you’re combining Lolla with exploring Chicago’s foodie scene. Lodging is more limited here (a few boutique hotels) so again, early booking is key.
- Lincoln Park/Lakeview: These are vibrant neighborhoods a bit farther north (3–5 miles from downtown). You likely wouldn’t stay here unless other areas are sold out or you have friends to stay with, but they do offer a different vibe (more residential, lots of bars by Wrigley Field in Lakeview, etc.). If you do, the CTA Red Line will be your friend for getting downtown. Keep in mind after a long day at the festival, a 30-minute train ride home can feel extra tiring but plenty of people do it to save money on lodging. These areas have some smaller hotels, B&Bs, or hostels.
- Budget Options (Hostels & Beyond): Chicago has a few hostels that are great for young travelers on a budget. The HI Chicago Hostel is actually in the South Loop, just blocks from Grant Park a perfect location for Lolla, with dorm beds much cheaper than any hotel (book super early, it sells out fast). Another option is the Freehand Chicago (a hybrid hostel/hotel in River North) which offers both bunk rooms and private rooms at lower rates than big hotels. If you’re coming with a group of friends, an Airbnb or vacation rental in downtown or nearby could be cost-effective just ensure it’s a legally registered rental if in the city. Some groups even stay further out by O’Hare or in suburbs to save money, but we’d only recommend that if you have a van/car and don’t mind commuting 45+ minutes each way. For the full Lolla experience, staying downtown is worth the cost if you can swing it you’ll be immersed in the festival buzz all around.
Parking at Hotels: One thing to note if you rent a car, check your hotel’s parking situation. Many downtown hotels charge ~$50–$75 per night for valet parking. Some have self-park garages for a bit less. And a few budget hotels or hostels might not have dedicated parking at all (you’d need to find a nearby public lot). Plan for this cost or strategy in your budget. During Lollapalooza weekend, it’s often a smart move to park your car and leave it for the duration of the festival, as we mentioned. If your hotel offers in/out privileges, great if not, consider whether you really need to use the car each day or if it can stay put. The city is very walkable and well-served by transit and cabs in the downtown area, so you might only use your vehicle for any non-Lolla excursions (like a trip to a neighborhood or suburbs).
Things to Do in Chicago During Your Lolla Trip
Lollapalooza will keep you busy from late morning to night, but if you’re spending extra time in Chicago (or have some downtime before the music starts), definitely check out some of the city’s famous attractions. Whether you want to play tourist or just relax, here are a few must-do Chicago activities to consider:
- Millennium Park & The Bean: Since you’ll be right there, take a stroll through Millennium Park to see Cloud Gate, aka “The Bean,” and snap the requisite selfie with its shiny reflection of the skyline. The park also features the Crown Fountain (those big video-faced fountains) and is adjacent to Buckingham Fountain in Grant Park an iconic 1920s fountain that’s spectacular, especially when lit up at night.
- Skydeck at Willis Tower: Get a breathtaking view of Chicago from the Skydeck at Willis Tower (formerly Sears Tower). It’s an all-glass observation ledge on the 103rd floor step out if you dare for a photo as if you’re floating above the city. Another great viewpoint is 360 CHICAGO at the John Hancock Center, which even has a tilting glass thrill ride. Either way, on a clear day you can see several states and all of Chicagoland spread out below.
- Navy Pier & Lakefront: Head over to Navy Pier for classic summer fun: ride the giant Ferris wheel, grab a Chicago-style hot dog or some Garrett’s popcorn, and enjoy the lake breeze. Navy Pier often has fireworks on summer weekend nights (usually Wednesdays and Saturdays) you might catch them after Lolla. From the Pier or nearby beaches, you’ll also get a beautiful view of the skyline along Lake Michigan.
- Architecture Boat Tour: Chicago’s architecture is world-famous. One of the best ways to appreciate it is an architecture boat cruise on the Chicago River. These 90-minute tours are super informative and fun you’ll glide under the skyscrapers and learn a bit of history. It’s a relaxing daytime activity (and trust us, sitting on a boat is nice rest for your legs between festival days). If boats aren’t your thing, you can also walk the Chicago Riverwalk, a lively promenade along the water with restaurants and public art.
- Museums at Museum Campus: Just south of Grant Park is Chicago’s Museum Campus, home to the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. If you’re into dinosaurs, fish, or stars, respectively, these are top-notch institutions (Field Museum’s T. rex “Sue” is a star attraction). The Planetarium also offers one of the best skyline photo ops behind it. Note: Lolla attendees sometimes spend a recovery morning at the aquarium or laying on the grass behind the Planetarium it’s peaceful by the lake.
- Explore Neighborhoods & Food: Chicago is a city of neighborhoods, each with its own vibe. If you have time, explore beyond downtown: Lincoln Park has a free zoo, Chinatown offers amazing dim sum, Wicker Park and Logan Square have trendy shops and street art, Pilsen is known for vibrant Mexican culture and murals. And of course, eat your way through Chicago’s iconic foods try deep-dish pizza (Lou Malnati’s or Giordano’s are classic picks), a Chicago-style hot dog (no ketchup, all the veggies on top, Portillo’s is a solid choice for first-timers), and an Italian beef sandwich (Al’s Beef or Portillo’s). If you’re a foodie, the West Loop’s Randolph Street will blow your mind with dining options from upscale to taco joints.
- Aftershows & Nightlife: Lollapalooza official aftershows take place at venues around the city each night of the festival. If you still have energy, catching an aftershow at a place like Metro, House of Blues, or The Vic can be an unforgettable bonus performance (just buy tickets in advance, they sell out). For general nightlife, the Rush & Division area and River North have many bars and clubs catering to the 20s crowd. If you prefer a chill brewery vibe, check out districts like Fulton Market or breweries in Logan Square. And if you love blues or jazz, you’re in the right city Buddy Guy’s Legends (in South Loop) or Green Mill (Uptown) can give you a taste of Chicago’s music heritage.
In summary, make the most of your Lollapalooza 2026 trip by planning ahead. Arrange your transport (flight, rental, or transit) wisely, stay close to the action if you can, and don’t forget to experience a bit of Chicago while you’re here. With the right prep, you and your crew can focus on rocking out to your favorite bands and enjoying the festival, knowing that logistics are handled. Lolla is as much about the city as it is about the music so travel smart, stay safe, and get ready for an epic time in the heart of Chicago!
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