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 an exceptionally long layover between flights; perhaps you’re spending a short time there for another reason altogether. Whatever your situation, I hope you find the tips and suggestions here useful!

Downtown Chicago from Millennium Park

Getting to downtown Chicago from O’Hare Airport (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 September 2016, the 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 from the airport; if you’re going 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 that 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.

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.”

Cloud Gate (the Bean) in Millennium Park, Chicago

The Bean in Chicago, Illinois

Kids playing in the water of Crown Fountain in Millennium Park, Chicago

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

Pritzker Pavilion in Millennium Park, Chicago

Outdoor art exhibit in Chicago, Illinois

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 lakeshore during your visit, you will easily see why this metropolis is nicknamed “the Windy City” (or, I suppose more accurately, you’ll feel why).

On this particular day — when the temperature was easily 30C/86F and we’d been walking for a couple of hours — the breeze felt nothing short of heavenly.

Lake Michigan in Chicago, Illinois

A short walk along the water will bring you 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.

Navy Pier, Chicago's number-one tourist attraction

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

“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 lovers dream, and great way to see the iconic structures of the city. You can cover an incredible amount of ground in a short time so it is perfect for a layover.”

Chicago Architecture Boat Cruise -- Jaime (Jaime Says)

Art Institute of Chicago and 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.”

Art Institute Chicago -- Carol (Wayfaring Views)

“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. Their exhibits are moving on a very human scale, and it’s humbling to see this side of soldiers and war.”

Pritzker Museum in Chicago -- Carol (Wayfaring Views)

Gino’s East Pizza

Recommended by Katie at 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!”

Gino's East Pizza in Chicago -- Katie (Creative Travel Guide)

Thanks to the above bloggers for their recommendations (photos and words provided by each one as noted). Feel free to share your own suggestions for Chicago in the comments!

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