Tips and Ideas for a Long Layover in Chicago

Tips and Ideas for a Long Layover in Chicago

On our recent trip to Minneapolis, Simon and I did what any good travelers on a budget do: we looked for a cheaper airport to fly into. When you’re heading to the Twin Cities, that frequently means Chicago O’Hare.

After we found a good deal on flights, we decided to book the Megabus from Chicago to Minneapolis, and wound up with several hours to spend in the Windy City on both ends of our journey.

Perhaps you’re catching the train or a bus in Chicago; perhaps you’ve got several hours between flights; perhaps you’re spending a short time there for another reason altogether. Whatever your situation, I hope you find these tips and suggestions useful for your own Chicago layover.

Downtown Chicago from Millennium Park

Getting from O’Hare Airport to downtown Chicago (and/or back again)

Getting from the airport to the city is pretty simple. You want to take the Blue Line train, which leaves from underneath terminal three. (If you arrive at another terminal, just hop on ATS — the Airport Transit System, a free rail service that runs between the airport’s terminals all day.)

As of February 2018, the standard fare from O’Hare is $5 per person. The ride to downtown takes about 45-50 minutes, depending on exactly where you want to go. (Like many cities, Chicago charges a higher fare when you’re coming from the airport; if you’re going the other way — from the city to O’Hare — you’ll pay less.)

See the complete list of Blue Line stops here.

Of course, you can also take a taxi. I have no experience with this personally, but a bit of googling shows cab fare could easily run you $50, more if there’s traffic.

Storing your luggage

If you still have your bags with you and don’t want to lug them around for the duration of your layover, here’s what you can do. Exit the train at Clinton and walk three blocks to Union Station. Follow the signs for baggage claim and you’ll find large lockers you can use to store your luggage.

The lockers are $6 per hour; you pay $6 for one hour upfront, and the rest when you return (you’ll have to pay your balance before you can open the locker again). You can use cash or credit/debit to pay. The machine doesn’t give bills or notes as change, so try to have as close to the exact amount as you can. (There is a change machine located near baggage claim, but I wouldn’t depend on it — those things tend to be out of order more often than not.)

Union Station also has a large amount of seating, free Wi-Fi, a food court, and a newstand/convenience store.

Lake Michigan in Chicago, Illinois

Exploring the city

Now comes the fun part: what to do with just a few short hours in Chicago?

If you’re a first-time visitor, there are a couple of iconic things you can check off your list, especially if you’ve got good weather (or are brave enough to handle Midwestern winter — hats off to you).


Millennium Park

We were lucky to have a bright, sunny, and warm day during our visit — the perfect time to see Millennium Park. That’s where you’ll find the famous Cloud Gate, an outdoor sculpture often referred to as “the Bean,” and Crown Fountain, which you might know better as “the faces that spit water out of their mouths.”

The park is also home to gardens, public art exhibitions, and performance spaces. You could easily while away an afternoon exploring its depths.

Lake Michigan and Navy Pier

Chicago sits on the shores of Lake Michigan — one of North America’s five “Great Lakes.” If you head up to the lake during your visit, you will easily see why this metropolis is nicknamed “the Windy City” (or, I suppose more accurately, you’ll feel why).

Walk north from Millennium Park along the lakeshore and you’ll come to Navy Pier — Chicago’s number-one tourist attraction, probably best known for its iconic Ferris Wheel. The pier also houses shops, restaurants, performance venues, and museums.


Our time in Chicago was brief, and despite my midwestern roots, I’m still a stranger there myself. So I asked a few other travel bloggers if they had other suggestions for a few hours in the city. Read on to see their recommendations.


Chicago Architecture Boat Cruise

Recommended by Jaime at Jaime Says

Chicago Architecture Boat Cruise -- Jaime Says
Photo by Jaime Says

“From March until late October (weather permitting), boats depart every 30 minutes for a 90 minute cruise down the Chicago River and onto Lake Michigan. It is an architecture lover’s dream, and a great way to see the iconic structures of the city. Plus, you can cover a lot of ground in a short time, which makes it perfect for a layover.”

Art Institute of Chicago + Prizker Military Museum

Recommended by Carol at Wayfaring Views

“I once had a transcendent moment at the Art Institute. I was standing in front of the Van Gogh self portrait listening to Don McClain’s “Starry Starry Night”, a song about Van Gogh’s struggles with sanity. It was a free Thursday night and the room was packed but it was as if I didn’t see anyone but Van Gogh. The Art Institute will do that to you. It’s my favorite art museum; any visitor to Chicago should step through its doors and let magic happen.

After the Art Institute, head across the street to the Prizker. Its mission is to acquire and maintain an accessible collection focused on the Citizen Soldier. It includes a book collection on military history, letters, military propaganda posters, notebooks and photography.

But the museum isn’t just for military buffs. The exhibits are moving on a very human scale, and it’s humbling to see this side of soldiers and war.”

Chicago Riverwalk

Recommended by Patti at The Savvy Globetrotter

Chicago Riverwalk -- The Savvy Globetrotter
Photo by The Savvy Globetrotter

“One of the best things to do in Chicago when you’re short on time is to head to the Riverwalk. The Riverwalk is a mile-long pedestrian waterfront on the banks of the Chicago River, and it’s a great way to see downtown Chicago and its amazing architecture. It’s also one of the best spots in the city for people watching; you’ll see both locals and tourists out walking, jogging, eating lunch, or just relaxing. And of course, there are plenty of restaurants, shops, and places to sit along the way.

The Riverwalk is a great alternative in the winter, when the river is frozen and boat tours cannot operate.”

Nutella Café

Recommended by Priya at Glorious Sunrise

“Nutella Café at North Michigan Avenue is a dream destination for foodie lovers who delight in the world-famous chocolate-hazelnut spread. This new hot spot sees long queues, especially on the weekends, but it’s well worth the wait. If you have the time to spare during your stay, you should definitely make a stop here. The French toast is especially delicious!”

Gino’s East Pizza

Recommended by Katie at Creative Travel Guide

Gino's East Pizza in Chicago -- Creative Travel Guide
Photo by Creative Travel Guide

“There’s a debate about whether Gino’s East started Chicago’s deep dish pizza, or another restaurant called Pizzeria Uno. Either way, the pizza is amazing — and you can write on the walls, chairs, and tables too!”

Kingston Mines + Buddy Guy’s Legends

Recommended by Bernadette at A Packed Life

“Whatever your taste in music, if you find yourself with an evening to spare in the Home of the Blues, you’ll have a great time at Kingston Mines. Recipient of many awards, this Lincoln Park club has two stages, seven sets a night, and quality acts on its program. We visited on a snowy, windy Monday in February, and the place was buzzing, with strangers dancing with new friends and enjoying some quality BBQ noms. Get yourself down to Blues Alley and get ready to dance.

For daytime visitors, check out Buddy Guy’s Legends for free acoustic sets at lunchtime. Grab a Catfish Po-Boy and soak up a bit of the Deep South in the Midwest.”


Thanks to the above bloggers for their recommendations. Feel free to share your own suggestions for Chicago in the comments!

• • •

All photos not attributed otherwise are my own.

Traveling from O'Hare airport to the city, how to store your luggage, and what to see and do during a long layover in #Chicago, Illinois. | #Midwest #UnitedStates #USA

Traveling from O'Hare airport to the city, how to store your luggage, and what to see and do during a long layover in #Chicago, Illinois. | #Midwest #UnitedStates #USA

Traveling from O'Hare airport to the city, how to store your luggage, and what to see and do during a long layover in #Chicago, Illinois. | #Midwest #UnitedStates #USA | Photo by Mason Hopfensperger

Traveling from O'Hare airport to the city, how to store your luggage, and what to see and do during a long layover in #Chicago, Illinois. | #Midwest #UnitedStates #USA | Photo by Sawyer Bengtson

Like this post? Check out: