What are the best things to do during a layover in Chicago—whether you have 3 or 12 hours. Explore food, sights, and attractions near O’Hare or Midway airports with ease.
Passing through Chicago on a layover? You should not just stay in the airport! You have 3 hours? Or 12 hours? Either way, there is something cool in Chicago to explore. Whether it's deep-dish pizza, a bird's-eye perspective, or walks along the beautiful lakeshores, this city understands how to keep you amused. So, when you find yourself stranded between flights at O'Hare International Airport (ORD) or Midway International Airport (MDW), don't worry; your layover may end up being the highlight of your travel!
Here are short and long layover breakdowns so you have a clear idea of what to do depending on the time you have.
With less than 6 hours in Chicago, you may want to avoid leaving the airport region entirely, but that is not to say you will not have a good time!!
Have no time to see the city? No problem. At the very airports, O'Hare and Midway, one can find a taste of Chicago deep-dish pizza. Look for restaurants such as Giordano or Reilly's Daughter in Midway’s Concourse A. Believe us, Chicago even has great airport pizza.
Both airports offer spas (Terminal 1 and 3 of O'Hare International Airport) where you can squeeze in a quick chair massage as well as have your nails done or even get a mini facial. It was great to cool down after a long flight.
When you are at O'Hare International Airport (ORD), you can explore the artistic side of the airport with its rotating art exhibits and mesmerizing neon tunnel inside Terminal 1. If you are fond of peace, you can visit the yoga room located at Terminal 3.
Seems simple, but it is really entertaining! Buy some coffee and sit down at the large windows and see planes land and take off with the Chi-town skyline as the background. Perfect to get a bit of silence.
With 6 hours or more to spare, you can venture out of the airport and into the real city. Just remember to allow time for getting through security again as well! Public transport in Chicago doesn't make it hard. Chicago is well connected, and the Blue Line to the airport will bring you downtown in approximately 40-45 minutes.
This is something one must do. Go directly to Millennium Park to take a selfie with “The Bean” (formally, it is called Cloud Gate). It is shiny, strange, and becomes Instagram-worthy. Also, the park is lovely to stroll around on sunny days.
Go on a relaxing jaunt down to the river. It is filled with cafes, boats, art, and beautiful architecture. When the weather permits, you can even step onto a brief 60-90 minute architecture boat tour! Such tours are interesting, and they give you the city from a different perspective.
Desire to be on glass 1,353 feet high? Visit Skydeck at Willis Tower (also known as the Sears Tower). The scenery is amazing, and you can even walk out to the so-called edge of the city called The Ledge, which is a glass balcony over the city!
Go to Portillo to get the real deal. The Chicago dog is then crowned with mustard, onions, relish, tomato, pickle, and sport peppers, but not ketchup. It is both dirty and strange, and completely worth it.
Assuming you have a bit more time, an Uber or a train to Navy Pier would be worth it. There is a mini amusement park, food vendors, a large Ferris wheel, and excellent scenery of Lake Michigan. Great for kids or when you simply wish to get the wind and need to experience the state of Chicago.
Chicago is very child-friendly. In Maggie Daley Park (adjacent to Millennium Park), there is a massive playground with climbing walls and slides. At the Navy Pier, there are rides that kids will enjoy. And in the airport? There are children's spaces and family rooms so that small children can expend their energy before the next flight.
If somehow you are at the overnight layover, you can simply book a hotel downtown or somewhere close to the airport and enjoy the Chicago nightlife. Visit the jazz bars, rooftop lounges, and skyline views that can shock you. (Check hours and allow enough time to return.)
Never lose track of time. Install alarms where necessary. And make sure to look up your terminal and gate on the way back to the airport—O'Hare, especially, can present some confusion with many terminals.
A layover in Chicago is not necessarily boring or frustrating. When you do not know what to do and you have a couple of hours or the entire day, there are lots of attractions to see in the neighborhood. That is why I go out, walk, get something nice to eat, and enjoy the atmosphere of this wonderful city.
Soon, you will be jet-setting (the next flight), but until that time comes, why not leave some memories in the Windy City?