Chicago's 5 Best Things To Do During Your Layover

When traveling by air, most people prefer taking a direct flight rather than plane-hopping through multiple cities to reach their destination. Unfortunately, connecting flights aren't always avoidable, and finding ways to effectively use long layover times can be a struggle. It is part of the modern world of travel.

Serviced by two major airports, Chicago is a common layover hub. If you're only grounded for an hour or two, staying in the terminal is the safest option to avoid missing your next flight. However, if you have the better part of a day to kill — and don't want to spend it sitting at Chicago Midway International Airport (MDW) or Chicago O'Hare International Airport (ORD), the latter of which is often cited as one of the worst airports for long layovers — it may be worth getting out, stretching your legs, and taking a quick spin through the Windy City.

Though there's certainly a fair share of tourist traps to avoid in Chicago, you'll also find plenty of can't-miss attractions and activities within reach of both airports. Whether you have just enough time for tracking down an iconic deep-dish pizza or a full day to spend touring the sights around the city, here are the five best things to do during a long layover in Chicago.

If it's your first time in Chicago, you'll likely want to check a few classic sights off your bucket list by heading downtown. From Midway, one of America's worst yet most convenient airports, you can take a half-hour ride on the Chicago Transit Authority's (CTA) Orange Line and get off at the Harold Washington Library stop in the heart of downtown. If you're traveling from O'Hare, it will take you a bit longer. The Blue Line reaches downtown in about an hour, where you can exit at the Jackson stop.

Whichever airport you're coming from, you'll find plenty of well-known attractions within walking distance once you arrive. Snapping an obligatory selfie with "The Bean" (officially Cloud Gate) in Millennium Park is practically a rite of passage, but take some time to wander the park itself, too. The lakeside oasis is filled with peaceful paths, trickling fountains, and gorgeous gardens, offering a perfect escape from the bustling airport.

Covering 1.25 miles between Lake Shore Drive and Lake Street, the Chicago Riverwalk provides another opportunity for a leisurely stroll, with sweeping views and waterside eateries along the way. If you have the time to indulge in some retail therapy, walk the Magnificent Mile. Running along Michigan Avenue, the renowned retail mecca is lined with upscale shops, swanky restaurants, and dazzling skyscrapers that add a bit of luxury to your layover.

One of Chicago's most illustrious traits is its architecture. From Art Deco skyscrapers to classic greystones and postmodern gems, the city's building styles are best appreciated on an architectural tour. The highly rated Chicago Architecture Center (CAC) offers an array of guided tours on both land and water.

If you choose a walking tour, you'll have your pick of areas and architectural eras to explore. The Roaring Twenties come to life on the Art Deco Skyscrapers Tour, during which you can step inside some of the most opulent buildings in the Loop district. Meanwhile, a walking tour of Chicago's Beverly neighborhood will expose you to mansions, castles, and Frank Lloyd Wright wonders. To give your feet a rest, you can hop on a bus tour to explore bungalows in Berwyn and Brutalist buildings or even the exact route of the Great Chicago Fire circa 1871.

All these options are worthwhile, but few hold a candle to the CAC River Cruise. Dubbed America's top boat tour by USA Today's 10 Best in 2025, this beloved Chicago excursion showcases the stunning skyline and iconic architecture. It also includes a historical rundown of the architects who built the city. Tours depart every two hours from 10 a.m. to 6 p.m. and run for 90 minutes, an ideal length for a long layover activity.

Next to its architecture, Chicago is famous for its food, covering everything from mustard-topped Chicago-style hot dogs to indulgent deep-dish pizzas. Instead of paying sky-high airport prices for a mediocre meal between flights, take your taste buds on a tour of the beloved city by biting into its signature menu items.

Built with an all-beef sausage topped with yellow mustard, relish, onions, peppers, tomato, celery salt, and a pickle spear on a poppy seed bun, the Chicago-style hot dog is more than a hot dog — it's an icon. From vintage diners to classic hot dog stands, you'll find plenty of places to sink your teeth into one throughout the city. Serving Chicago since 1946, Gene and Jude's remains a fan favorite, famed for serving Depression-style dogs made with Vienna beef. Located in the River Grove neighborhood, the beloved spot is just 5 miles south of Chicago O'Hare Airport, making it an easy stop for a layover bite. Situated about halfway between O'Hare and Midway, The Weiners Circle is Chicago's "most notorious hot dog stand," serving unbelievably tasty street food and lots of profanity. If you get cussed out while placing your order, don't panic — it's all part of the schtick.

Another star of the city's cuisine scene is deep-dish pizza. Just choose your restaurant wisely, as trying to eat the famous Chicago food could be an instant ticket to a total tourist trap. If your layover is at Midway, you have a couple of nearby options, including Giordano's, which is about a 15-minute walk from the airport. If you decide to travel farther, keep in mind that authentic deep-dish typically takes 40 to 50 minutes to bake, so factor that into your layover timing.

Chicago's arts and culture scene is vibrant, and its museums are among the city's biggest draws. Depending on the length of your layover, you may even be able to visit a few (just beware of the one considered the most disappointing tourist trap in Chicago). The Loop has a generous collection of museums, many within walking distance of one another, so you can make the most of your time.

One of the city's top attractions is the Art Institute of Chicago. Home to thousands of works, the museum features some of the most famous pieces in history, including Grant Wood's "American Gothic" and several of Claude Monet's "Water Lilies" paintings. As the second-largest museum in the country, it's a place where you could easily spend two hours or an entire day. If you have time to spare, you can easily stroll to other attractions, like the Museum of Contemporary Photography or the Museum of Illusions — both within about 10 minutes of the Art Institute.

Chicago also offers museums dedicated to literary arts. Near Millennium Park, the American Writers Museum celebrates authors and songwriters, ranging from Flannery O'Connor to Johnny Cash. For a decidedly darker experience that's not for the faint of heart, check out the Medieval Torture Museum. Often described as one of the most terrifying museums in the U.S., it showcases immersive exhibits featuring over 100 deadly devices that offer a chilling glimpse into medieval history. It also hosts ghost hunts that will make any turbulence on your next flight feel like a walk in the park. If you'd rather end your Chicago layover on a sweet note, take a tasty tour through the Museum of Ice Cream, where sherbet-pink rooms and tasty treats await.

If you have a long layover but feel too anxious to venture into the city for fear of missing your next flight, there are still plenty of ways to kill time without leaving the airport. O'Hare is the larger of Chicago's two airports, so you'll find a bit more to do within its terminals than at Midway. To get a break from the crowds, head to the area between Terminals 2 and 3 on the mezzanine level at O'Hare. The space once housed the Aeroponic Garden, and though the urban oasis has been removed, it remains a relatively tranquil spot to sit and chill. 

Adjacent to the quiet zone in Terminal 3, you'll find a yoga room. Open from 6 a.m. to 10 p.m., the peaceful space features bamboo floors, a wall of mirrors, and plant-lined windows with frosted glass that let natural light filter in. Travel can be stress-inducing, so quiet meditation can help you prepare for your next flight. Although you hopefully won't be running late for your connection, Terminal 3 is also where you can recreate the famous "Home Alone" scene by racing toward your gate like the McCallisters rushing to catch their flight to Paris.

If your layover is at Midway, make time to visit the Battle of Midway exhibit in Concourse A. The airport itself is named after the World War II Battle of Midway, and the display highlights Chicago's role as a Naval training center during the war. Similar to O'Hare, Midway has its own yoga room in Concourse C, in case you'd prefer to give your mind a rest before takeoff.

While there's no shortage of things to do in Chicago — and no way to fit everything into just a few hours — we highlighted some of the city's most iconic sites and activities to help you make the most of your long layover. We also consulted Reddit threads for suggestions from locals and fellow travelers about which places to see (and which to skip) if you're just breezing through the Windy City.

We focused on locations near each major airport to ensure you're not wasting precious layover time in transit. By offering recommendations across dining, shopping, sightseeing, and leisure-focused experiences, we aimed to accommodate a variety of interests and travel styles, so each sightseer can build the Chicago layover itinerary that suits them.

Curious to discover the top attractions in and around other major travel hubs? Get the lowdown on the amazing dining options at America's best airport for a layover here. Or, find more reasons to love Chicago by reading up on why it was named the "world's most beautiful city" in 2025.