8 Things to Do Alone in Chicago
Chicago is one of the best big cities in the US to visit on your own. It’s friendly, it’s easy to get around on the L, and so much of what makes it great is about walking, looking and eating, all of which you can do perfectly well by yourself.
In this guide
- 1. Take an architecture river cruise
- 2. Spend a morning at the Art Institute
- 3. Walk or bike the Lakefront Trail
- 4. See the Chicago Cultural Center
- 5. Hear live jazz at the Green Mill
- 6. Escape to the Garfield Park Conservatory
- 7. Eat at the counter
- 8. Go up the Skydeck
- Is Chicago safe for solo travelers?
- Where to stay alone
- A solo day in Chicago
- Common questions
Here are eight things to do alone in Chicago, with a few tips for feeling comfortable as a solo traveler.
1. Take an architecture river cruise
If you only do one paid activity in Chicago, make it this. The Chicago Architecture Center’s river cruise runs about 75 to 90 minutes and floats past more than 40 buildings, with a guide explaining each one.
Solo travelers do well here because you just need one seat, and single tickets are often available even when couples can’t find two together. Sit near the front on the upper deck. The season runs from spring to late fall, so check dates if you’re going in winter.
2. Spend a morning at the Art Institute
The Art Institute of Chicago is one of the best art museums in the world, and going alone means you can move at your own pace. Stand in front of Nighthawks for as long as you like. Nobody’s waiting for you.
Arrive right at opening to beat the crowds. Don’t miss American Gothic, A Sunday on La Grande Jatte and the miniature Thorne Rooms in the basement, which are weirdly hypnotic. Give yourself at least three hours.
3. Walk or bike the Lakefront Trail
The Lakefront Trail runs about 18 miles along Lake Michigan, with beaches, parks and skyline views the whole way. It’s busy with runners and cyclists, which makes it feel safe and lively.
Rent a Divvy bike and ride north from Navy Pier to North Avenue Beach, or just walk a section of it. On a sunny day, it’s the happiest place in the city. Bring headphones and a playlist, or just listen to the waves.
4. See the Chicago Cultural Center
The Chicago Cultural Center, right across from Millennium Park, is free and has one of the largest Tiffany glass domes in the world. Most visitors walk right past it.
Head up to Preston Bradley Hall on the third floor and look up. The dome glows, especially on a bright day. The building also hosts free exhibits and lunchtime concerts. Afterward, walk across to Millennium Park to see the Bean.
▶ Watch This Before You Go
5. Hear live jazz at the Green Mill
The Green Mill in Uptown has been open since 1907, and it’s one of the best places to hear jazz in the country. It’s dark, small and full of history. Al Capone supposedly had a favorite booth.
Going alone is completely normal here. Grab a seat at the bar, order a drink and listen. The cover is usually low, and on Sunday nights there’s the famous Uptown Poetry Slam. Bring cash, and take the Red Line to Lawrence.
6. Escape to the Garfield Park Conservatory
The Garfield Park Conservatory on the West Side is one of the largest greenhouses in the country, filled with palms, ferns and a fern room that feels prehistoric. Entry is free, with a suggested donation.
It’s peaceful, warm and perfect for a slow solo afternoon, especially in cold weather. Take the Green Line to the Conservatory stop, which drops you right outside. Reserve a free time slot online first.
7. Eat at the counter
Chicago food is perfect for solo travelers, because so much of it is eaten at a counter. Grab a Chicago-style hot dog, with mustard, relish, onions, tomato, a pickle and celery salt. Never ketchup.
Deep-dish pizza is trickier alone, since it takes 45 minutes and feeds three. Many places, like Lou Malnati’s, sell individual sizes, so ask. Or try an Italian beef sandwich, dipped, with hot giardiniera.
8. Go up the Skydeck
The Skydeck at Willis Tower has glass boxes that stick out over the city, 103 floors up. It’s touristy, sure. But it’s also a genuinely thrilling view, and someone in line will always offer to take your photo.
Book a time near sunset to see the city by day and by night. If you prefer to skip the glass box, 360 Chicago at the old Hancock building has views over the lake.
Is Chicago safe for solo travelers?
The main tourist areas, like the Loop, River North, Lincoln Park and the lakefront, are busy and generally safe. Use the same common sense you would in any big city. Keep your phone out of sight on crowded L platforms, stick to busy streets at night and take a rideshare if you’re out very late.
Where to stay alone
For a first solo trip, stay in the Loop or River North. You’ll be close to the L, the river and plenty of places to eat. Lincoln Park and Wicker Park are great if you’d rather feel like a local. Hostels like HI Chicago are a good budget option with a social vibe.
A solo day in Chicago
Here’s a plan that works well on your own. Start at the Art Institute right when it opens and spend the morning there. Walk across to Millennium Park and the Cultural Center, then grab a hot dog or an Italian beef for lunch.
Take the architecture cruise in the early afternoon, when the light on the buildings is good. Rent a Divvy bike afterward and ride the Lakefront Trail north for an hour. In the evening, take the Red Line up to Uptown for dinner and a set at the Green Mill.
Doing it alone actually helps here. You can linger, change your mind and say yes to whatever looks interesting, and nobody has to agree with you. That’s the best part of solo travel, and Chicago is a great city for it.
Common questions
How many days do I need in Chicago?
Three days covers the highlights without rushing.
Is it weird to eat alone in Chicago?
Not at all. Sit at the bar or counter and you’ll fit right in.
What’s the best time of year to visit?
Late spring through early fall. Winter is cold but cheap and less crowded.
Do I need a car?
No. The L, buses and Divvy bikes cover everything here.
Is the river cruise worth it?
Yes. It’s the one activity almost everyone calls the highlight of their trip.
