Layover in Chicago – the ultimate guide 2024

Chicago’s biggest airport, O’Hare International, is a truly massive facility that serves more than just the Windy City itself. Sprawling over more than 7000 acres, O’Hare is a hub for the entire Midwest, and a place from which it’s possible to reach almost anywhere in the world.

If you find yourself with some time to kill between flights at O’Hare International, a great way to pass the time is to take a trip into the city and explore some of what it has to offer. Make sure to leave yourself enough time, though. It takes around 30 minutes by car to go from the airport to downtown Chicago, depending on what part of the airport you leave from. You can also take the Blue Line L train which leaves from terminals 1, 2, and 3 of O’Hare International, taking around 45 minutes to reach downtown.

One thing is for certain: you won’t be short of things to do on your Chicago layover. Make sure to drop off your unneeded bags at a Chicago luggage storage to make it easier to get around, and get ready to explore this major US city.

6 hour layover in Chicago

With only six hours on your O’Hare international layover, you’ll have to be selective with what you do. Fortunately, it’s only a short walk from baggage claim to the Blue Line station, and the trains run 24 hours a day, so once you’ve cleared customs and drop off your bags at a Chicago luggage locker, you should still have an hour or two to spend downtown. The Blue Line stops downtown at Washington, Monroe, Jackson, and other subway stations, so you’ll have a few options as to where to enter downtown. Ride the train all the way to Jackson, and you’ll have a walk of just a few blocks to Skydeck Chicago. This observation deck is on the 103rd floor of Willis Tower, and offers incredible views of the towering Chicago skyline and beyond. By your tickets in advance so you can bypass line and make the most of your short stopover.

• Make sure you give yourself enough time to clear customs at this busy airport.
• Take the Blue Line from O’Hare International to downtown Chicago.
• Enjoy incredible views of the city from Skydeck Chicago, but don’t forget to book your tickets in advance.

8 hour layover in Chicago

If you have a little longer to make your connection in Chicago, you’ll be able to enjoy more of what the city has to offer. Once you’ve taken unforgettable photos from the Skydeck, it’s just a short walk or subway ride to the Museum of Illusions. This quirky activity will blow your mind with a variety of illusions and optical tricks that will make you question your perspective. Plus, it’s a great place to get unique photos. This fun attraction can be fully explored in around an hour, so you may still have time to grab a bite to eat in Chicago’s downtown. Check out Remington’s for a classic Chicago steakhouse that just around the corner from the Museum. There are also plenty of Bounce luggage storage locations in downtown Chicago, so you won’t struggle to find a place to leave your belongings.

• Walk or take the subway to the Museum of Illusions and spend an hour or so enjoying the optical illusions.
• Downtown Chicago has tons of places to eat, and Remington’s is a classic for steak and other satisfying meals.

10 hour layover in Chicago

A longer layover in Chicago gives you more time to see what makes the city so special. Maggie Daley Park offers incredible views of the city and is where the locals come to pass time on a sunny day. This large downtown park offers a children’s playground, a climbing wall, plenty of walking trails and picnic spots, and ice-skating in the winter. It’s a great place to spend an hour or two watching the world go by and gives you a chance to stretch your legs and get some exercise on your Chicago layover. It’s also free, making it a good option if you’re on a budget.

• Take a walk around Maggie Daley Park for stunning views of the Chicago skyline and a chance to get some exercise.
• The park is free to enter, making it great for travelers on a budget.

12 hour layover in Chicago

If you have a little longer to spend in Chicago, or if the weather makes the park unappealing, you could instead visit the Art Institute of Chicago. This is one of the biggest and best art museums in the entire country, so you’ll want to give yourself enough time to explore. You could easily spend at least three or four hours admiring this collection, so plan accordingly.

The Art Institute is home to works of art from around the world and through the centuries, but it’s especially known for having one of the finest collections of Impressionist art anywhere outside of France. You’ll see work by Cézanne, Monet, van Gogh, and other legendary artists. The museum also has an impressive collection of more modern artists including Jackson Pollock and Andy Warhol. It’s a truly incredible collection of artistic treasures you shouldn’t miss while in the city. Who knows? Maybe you’ll come away with a new favorite.

• Visit the Art Institute of Chicago to see some of the world’s best art works in downtown Chicago.
• Allow yourself at least three or four hours to see everything the museum has to offer.
• The museum is a great activity for rainy days.

24 hour layover in Chicago

On a long layover, you can really get to grips with the city. An overnight layover means a hotel stay, but it also means you can experience the city’s nightlife and dining scene. For instance, if your budget allows, you could enjoy an exquisite dinner at Alinea, Chicago’s only Michelin three star restaurant and one of only 14 in the United States. Alternatively, you could visit one of Chicago’s legendary speakeasies, such as the Ladies Room. Or you could enjoy the city’s world-class comedy scene at The Second City, one of the world’s top comedy clubs.

The next day, take a visit to one of Chicago’s top attractions, Navy Pier. Home to an iconic Ferris wheel, an amusement park, arcades, shops, and restaurants, you could easily spend the whole day exploring what the pier has to offer. It may be a bit of a tourist trap, but it’s also a really fun place, and somewhere you just have to visit while in Chicago.

• Enjoy a night out at a Michelin–starred restaurant or a comedy club in downtown Chicago.
• Visit Navy Pier for a fun time, whether by day or by night.