How to make the most out of your layover in Chicago

With one of the most iconic skylines in the world, Chicago brings in millions of travelers each year. Navy Pier, Millennium Park, and the Art Institute are just a few of the country’s most popular tourist attractions located in downtown Chicago.  

Culturally, Chicago is second to none. Chicago-style hot dogs and deep-dish pizza are obvious draws for foodies, but the Windy City is home to some of the best restaurants in the world. The arts and music scenes are incredible, with major festivals like Lollapalooza being just a short walk from Chicago's downtown Loop. 

There are two major airports serving the city. The southwest side’s Chicago Midway International Airport (MDW) is primarily a domestic hub for carriers like Delta and Southwest. Chicago O'Hare International Airport (ORD) was once the busiest in the world and is still a busy airport and a major hub for United and other airlines. 

Chicago provides connections to destinations around the world for millions of American travelers, especially O’Hare. Because of this, a layover in Chicago is a common occurrence. Here's everything you need to know:

Things to keep in mind before leaving the airport

Visa requirements in the US

Domestic visitors with a valid state-issued ID or passport won’t have any trouble leaving the airport during a layover, but all international travelers will need to apply and be approved for visa-free entry to the U.S. or already have a valid visa. 

Minimum layover times at a Chicago airport

You’ll need about 5-6 hours at a minimum to get through customs, take the train or navigate traffic, and get back to the airport and through security. 

What to do in Chicago during a layover

While Chicago O'Hare Airport and Midway Airport are equipped with comfy lounges, above-average dining options, and even amenities like a yoga room, it makes sense to utilize a long layover and hit the city. The CTA Blue Line (serving O’Hare Airport) and Orange Line (serving Midway Airport) trains can help you skip traffic and reach downtown or other neighborhoods within 40 minutes. 

Bounce has dozens of locations near the airports along with the Loop (Chicago’s downtown) and its many neighborhoods. You can do a little bit of research ahead of time and book luggage storage in Chicago based on where your itinerary leads you. This makes the mobile app all the more useful! 

Morning layover in Chicago

If you're planning on heading into the city from either airport, taking the train is the best way to go as rush hour can be a challenge. Still, it's absolutely worth popping into downtown as opposed to sitting around the airport staring at your phone for five hours. 

• The most popular brunch place in downtown Chicago is the iconic Eleven City Diner, which will be crowded at any time of day, but is worth the short wait.   
• For something hearty, Manny’s Deli near downtown serves up Jewish deli classics and rivals even its New York counterparts in terms of authenticity and quality. There's a reason every celebrity and politician pops in here while in Chicago.  
• You can take the train downtown and explore Millennium Park to stretch your legs. You'll even get to pop over to see the famous “Bean” for a selfie. 
• If you're with the kids, head over to the Lincoln Park Zoo To admire the animals and enjoy the leafy surroundings for free. 

Afternoon Chicago layover 

If you're in Chicago during the summer, there's no better place to be than the city's lakefront or a neighborhood patio on a sunny afternoon. Taking the train into the city is simple, and you'll be able to reach desirable neighborhoods in as little as 20 minutes. 

• For newbies, the Architecture River Cruise through downtown is an absolute must. You can take an hour-long tour through one of the country’s best skylines and learn about how this city was built (and by whom). 
• The best way to see the Chicago skyline is to either take a boat tour out on Lake Michigan or to catch epic views from up close at the Skydeck at the Willis Tower. 
• For something trendy, head to Wicker Park or Logan Square for hipster-friendly dining and shopping. These are widely considered some of the most appealing neighborhoods in the country, and they're both right off the Blue Line for access from O'Hare. 
• For tacos and margaritas, head to Big Star in Wicker Park for a fun afternoon on the patio. 
• Chicago offers a taste of Nashville at Parson’s, which serves up the best hot chicken in the city in Logan Square. The trendy vibe and friendly atmosphere make for perfect patio afternoons, after a few of their signature Negroni slushies.

Evening layover in Chicago

As the sun sets over the Windy City, the bars and restaurants will fill up and Chicaho’s culture will be at its best. 

• Fulton Market is one of the country’s top culinary destinations, so stopping by Publican Quality Meats, Green Street Smoked Meats, or Trivoli Tavern is a must.
• If your layover is at Midway, you can head to Marz Community Brewing, which is the Southwest side’s top brewery destination. O’Hare is equally well-served by the north side’s Half Acre and Hopewell taprooms.

Overnight layover in Chicago

Depending on how long your layover is, you'll want to arrange accommodations either near the airport or downtown. While there are plenty of fun activities late into the evening, staying out all night and avoiding a hotel might be difficult. 

• For an overnight stay near O’Hare, the Hilton, Hyatt, and Comfort Suites are common options. For Midway, the Best Western and Double Tree are perfectly serviceable options. 
• For clubbing, head to the River North neighborhood to find the busiest and most luxurious nightclubs in the city. This neighborhood is easy to reach from downtown as it's right across the Chicago River, and both Blue and Orange Lines will have stops within a short walk. 
• If you have time for a ball game or an event, Wrigley Field has something going on almost every night of the summer. The lesser-appreciated (but convenient ballpark for Midway) is Guaranteed Rate Field. It’s known locally as either Comisky or “Sox Park,” depending on the age of the person you ask. 
• The music scene in Chicago is nothing short of epic, and iconic venues like the Metro near Wrigley Field or the shiny new Salt Shed are the top places to see a show. 

Tips to make the most out of your time in Chicago

• The US dollar is Chicago’s currency, but you'll be able to use a credit card basically anywhere in the city as cash-only businesses are exceedingly rare. For a full day, you'll want to budget at least $100 for dining and sightseeing. For a few hours, you can use public transportation and poke around for as little as $30.  
• Weekend days like Saturday and Sunday will have the largest crowds at attractions like Navy Pier or the Art Institute, but even weekdays can get busy during the summer. 
• Most of Chicago, especially downtown and central neighborhoods like Lincoln Park or Wicker Park, will be safe to explore. Still, it's advisable that you're familiar with your surroundings and not venture into certain neighborhoods on the south or west side.
• English is the primary language in Chicago, but there will be plenty of locals who speak Spanish as a first language. Polish is also widely spoken in many neighborhoods. 

Regardless of how long you have as a layover, you'll be back because Chicago is absolutely worthy of a full trip. Start planning a weekend in the Windy City for a music festival, a Cubs game, or simply to visit Chicago's world-class museums. Just remember that you can rely on secure and convenient luggage storage through Bounce!