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Ultimate Chicago Layover Guide: Itineraries & Things to Do


A spacious, brightly lit airport terminal in Chicago with check-in counters and digital screens displaying flight information. The ceiling is adorned with international flags and illuminated in red and blue. Two travellers, one wearing a green shirt, are seen walking through the area.
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Welcome to Chicago! Known as the Windy City, this is a place where towering skyscrapers meet the shoreline of Lake Michigan, and deep-dish pizza is practically a way of life. You’re going to love it.

If you have a few hours to kill on a layover in Chicago O Hare airport, you’d be crazy not to venture into the city for an adventure around its top landmarks before hopping on your next flight.

But how do you start planning your layover? And is it even possible to see much if you’re on a tight schedule without delays or missing your connecting flight?

In this guide, we’ll answer all these questions and more, sharing our favourite Chicago layover itineraries so that you can have a great time no matter how many hours you have.

Things to Do in Chicago Airport

First things first, there are actually two international airports in Chicago: O’Hare and Midway. In this article, we’ll cover O’Hare airport, since it’s much, much busier. The good news is, if you’re looking to do a Chicago Midway layover, this airport is actually closer to the city centre!

Chicago O'Hare is notorious for its unpredictable wait times, so you may decide it's not worth the risk of leaving the airport without a long layover. No worries! The good news is, there are plenty of things to do on a Chicago airport layover to keep you entertained.

Admittedly, Terminal 3 is the best place to spend a Chicago layover, since it’s home to the Aeroponic Garden. Here, you can see how various herbs and vegetables are grown in a sustainable environment right in the airport! Terminal 3 also has its very own yoga room, perfect if you need to stretch out after a long flight.

If you feel like being pampered, O’Hare has got you covered, with Getaway Spa locations in both Terminal 1 and Terminal 3.

If you can’t leave the airport during your layover but want to experience a taste of the city, you’re in luck - you’ll find classic Chicago deep-dish pizza on the menus of many of the airport’s restaurants!

Best Chicago Layover Itineraries

Two cyclists ride along a waterfront path with the Chicago skyline in the background. The water reflects the iconic skyscrapers, including the John Hancock Center, under a clear, bright sky. Boats are visible on the water.

Your Chicago layover itinerary will vary greatly depending on how much time you have and what top attractions you want to hit.

Luckily, getting to downtown Chicago from O'Hare Airport is a breeze. That’s all thanks to the Blue Line train, which gets you downtown in around 45 minutes. Trains run frequently and 24/7, meaning that you can head into the city on a layover regardless of what time you land.

So, now that you’ve touched down in Chicago, what’s on the agenda? Below are our tailored layover itineraries to help you make the most out of your visit - even if it’s only for a few hours.

4 hours layover in Chicago

Wondering what to do with a 4 hour layover in Chicago? Go back and read our recommendations of things to do inside Chicago airport! With only four hours, it's best to spend your layover at Chicago O'Hare. Venturing into Chicago would put you at high risk of missing your next flight due to the unpredictable security lines. Plus, it takes at least 45 minutes to travel to and from downtown from O’Hare.

5 hours layover in Chicago

The iconic Chicago Theatre sign illuminated on a busy city street, with surrounding tall buildings reflecting the city's nightlife. This is one of the top places to visit on a Chicago overnight layover. The marquee advertises a performance by Brian Regan on April 1st. Traffic blurs by, highlighting the city's energetic pace.
The Chicago Theatre

A five-hour layover is the absolute minimum you might consider to briefly leave the airport, but it's a tight squeeze, and you’ll still be at serious risk of missing your connecting flight. The best way to decide is by seeing how long deplaning and navigating through the airport after your first flight takes you.

If you get through quickly, head straight for the Blue Line train to downtown, getting off at Clark/Lake for a quick glimpse of the city and perhaps picking up a Chicago hot dog before hustling back to the airport.

6 hours layover in Chicago

A six-hour layover offers a more realistic timeframe for a dash into Chicago. Start by taking the Blue Line to Clark/Lake, which will put you in the heart of the Loop, perfect for a quick photo at Willis Tower or a brisk walk along the Riverwalk.

Another option is to take the Blue Line to Washington/Wells and stroll over to see the famous Cloud Gate sculpture ("The Bean"), snapping the pretty-much-mandatory selfie before heading back to the airport. This short trip will give you a taste of Chicago without the stress of rushing too much, but keep your visit brief to ensure you have enough time for airport security.

7 hours layover in Chicago

A panoramic view of the Chicago skyline at sunset, with the sky transitioning from warm oranges to cool blues. The city's distinctive skyscrapers, including the Willis Tower, stand prominently against the horizon.

Seven hours in Chicago gives you enough time to actually explore one of the city’s most famous attractions. Start by taking the Blue Line to Monroe station. From here, it's just a short walk to the Art Institute of Chicago, known for its jaw-dropping selection of  Impressionist and Post-Impressionist paintings.

After you've got your art fill, head over to a nearby restaurant for a quick meal (Chicago deep-dish pizza is always a good idea!) before returning to the airport.

8 hours layover in Chicago

Cloud Gate sculpture, also known as "The Bean," in Chicago's Millennium Park reflects the surrounding skyline in its polished, mirror-like surface. This is one of the top things to do on a layover in Chicago.
"The Bean" Millennium Park

With eight hours, you have time to sample a few of Chicago's iconic attractions. Start by catching the Blue Line to Washington/Wells and walk a few blocks to Millennium Park, where you'll find the famous sculpture known as "The Bean". Snap some selfies before taking the short walk to the Chicago River.

From here, you can join an Architecture River Cruise, which lasts 60-90 minutes depending on which one you join. This is the best way to get a whistle-stop tour of the city's skyscrapers and historic buildings!

Post-cruise, enjoy a quick lunch at one of the riverside cafes before heading to Willis Tower. Here, you can head up to the Skydeck on the 103rd floor for knockout views of the city. To return to the airport, catch the Blue Line from either Clark/Lake or Washington/Wells stations.

10 hours layover in Chicago

Famous landmarks standing tall in Chicago against a blue sky, this skyline includes the famous Willis Tower
Willis Tower

A ten-hour layover opens up even more possibilities. Start by taking the Blue Line to Monroe and visiting the Art Institute of Chicago. Spend a few hours exploring its vast collections before strolling over to Millennium Park to snap a selfie with The Bean. In the afternoon, shop 'til you drop along North Michigan Avenue, more famously known as “Magnificent Mile”.

From here, it’s just a 7-minute walk to 360 Chicago, where you can head up to the 94th floor for epic views of the city skyline and Lake Michigan. That’s not even the best bit, though - the tilt attraction is the star of the show here. It’s a glass enclosure that tilts you out over the city, 1,030 feet up!

From 360 Chicago, take the Red Line (from Chicago Station) to Jackson or Monroe, then transfer to the Blue Line towards the airport.

12 hours layover in Chicago

Twelve hours gives you a full day to delve into the best of what Chicago offers, and this itinerary for a long layover in Chicago covers it all! Kick off your day by taking the Blue Line to Addison and visiting Wrigley Field for a tour of this world-famous baseball stadium. Then, hop back on the train to Monroe and explore Millennium Park and the Art Institute of Chicago.

In the afternoon, head over to the Magnificent Mile for some shopping and sightseeing along this famous street, or, if shopping’s not your thing, an Architecture River Cruise for a guided tour of the city's impressive skyline. Finish your day by returning to O'Hare from Clark/Lake. It’s been an absolute whirlwind of a layover, but you’ve ticked off most of the city’s top attractions!

Overnight layover in Chicago

A glowing marquee at the famous theatre in Chicago, with illuminated signs spelling out the word Chicago, a cinema at night in Chicago, This venue is a must-see on any long layover in Chicago.
The Chicago Theatre (at night)

An overnight layover in Chicago is a great opportunity, since it’ll allow you to experience the city’s buzzing nightlife. After checking into a hotel (preferably near the Blue Line for easy airport access), you have two options: Navy Pier, or the theatre!

If you opt for Navy Pier, head out around dusk to enjoy dinner at one of the many restaurants, catch a live performance if available, and ride the Centennial Wheel for stunning night views of the city and Lake Michigan. Fancy catching one of the many performances touring from Broadway instead? Then be sure to book your tickets in advance at one of the numerous downtown theatres.

Bright and early the next morning, visit Millennium Park for an early walk around The Bean and the surrounding art installations. Grab breakfast downtown, then make your way to Willis Tower to experience Skydeck Chicago before heading back to the airport.

Until next time, Chicago!

Best Chicago Layover Tours You Can Book

Not up for planning your own Chicago layover itinerary? We get that! By opting for a layover tour, you’ll get to enjoy a stress-free experience that ticks off the city’s top spots. Here are our favourites:

This private Chicago layover tour is the golden standard. You’ll need a layover of at least 8 hours to book it, but, from there, Chicago is your oyster! The tour includes your airport pick-up and drop-off and a local guide to share all of the city’s most fascinating facts with you. What’s more, the tour is totally customisable, so you can tailor it to the things you’re most excited to see and do whilst in the Windy City.

This Chicago in a day tour is the perfect option if you’re looking to put the planning in someone else’s hands and still experience the best of Chicago’s history, food and architecture. This walking tour takes five hours, with plenty of stops for photos, and includes five food tastings to sample Chicago delights like deep dish pizza and classic Chicago Italian beef sandwiches.

Unusual Things to Do in Chicago

Unites States of America flags in red white and blue lined along a walkway at Chicago O'Hare International Airport in Chicago
Chicago O'Hare International Airport

Whilst Chicago is famous for The Bean and deep-dish pizza, there are plenty of other, more unusual, things to do in Chicago.

For a thrill, check out the Tilt at 360 Chicago. Here, you lean out over the city from the 94th floor for dizzying views. To check out Chicago’s lesser-broadcasted history, hop on the Chicago Crime and Mob Tour, where you’ll get to visit infamous mobster haunts and the site of the St. Valentine's Day Massacre.

For our favourite nerdy thing to do in Chicago, get a quick financial education at The Money Museum at the Federal Reserve, where you can snap a selfie with one million dollars in notes!

FAQs About Layovers in Chicago

Can you leave Chicago airport during a layover?

Yes, you can leave the airport during a layover in Chicago. However, whether you should or not depends on how long your layover is and whether you’re on domestic or international flights. Leaving the airport requires you to go through security screening again with your luggage upon your return, so plan accordingly.

How long of a layover do I need in Chicago?

If you plan to leave the airport to explore Chicago, you’ll need a layover of at least 5 to 6 hours. For those staying within the airport, a minimum layover of about 2 hours for domestic flights and 3 hours for international connections is more realistic, giving you time to deplane, possibly change terminals, and undergo any additional immigration checks or customs.

Do I have to go through immigration if I have a layover in Chicago?

If you are on an international flight that lands in Chicago and you are continuing on to another US destination, you will need to go through U.S. Customs and Border Protection. However, if you are in Chicago to connect from one US destination to another, you won’t have to go through immigration.

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