Chicago solo travel guide: Top things to do in Chicago when traveling alone

Iconic architecture. One of the U.S.’s best cities for music, theatre, and art. Barack Obama’s hometown. These are just a few of the reasons to visit Chicago and the city is one of the best places to visit in Illinois. But what if you can’t find friends or family to go with you? Don’t worry — Chicago is a great city to visit by yourself! In this post, you’ll learn everything you need to know to plan a Chicago solo travel adventure. 

The Pros and Cons of Chicago Solo Travel

Before I get into the highlights of Chicago solo travel, it’s worth naming a couple of pros and cons. 

On the plus side, travelling to Chicago solo means you get to do what you want when you want to. Chicago can be an expensive city to visit, so you never have to get into a fight with your travel buddies about whether an activity/meal/drink is really worth the money. And the city has some great hostels — in particular Urban Holiday Lofts, which is in a great location and has ample common space.

But there are a couple of downsides to solo travel in Chicago. First, if you’re not comfortable eating and drinking alone, you’ll miss out on the city’s great bars and restaurants. Second, one of the best activities in Chicago is going to a ballgame at Wrigley Field — which is way more fun with friends.

But perhaps the biggest hesitation for planning some Chicago solo travel is safety. It’s no secret that Chicago’s crime rate is sky-high. The good news is, most things covered in this guide are in the downtown core, where you can safely walk around alone until around 1 am. Neighbourhoods like Pilsen, around Wrigley Field, and Wicker Park are also totally fine. The subway system (called “The El” or “The L” — stands for “elevated”) runs late into the night. Sure, if you’re staying in or venturing to the south side, it can get a little sketchy — but for the most part, safety shouldn’t be one of your top concerns when travelling to Chicago alone.

Chicago Solo Travel Guide: The top things to do in Chicago when travelling alone

So you’ve decided to go for a solo trip to Chicago. That’s great! Now, how can you make the most of this city when travelling by yourself? Below are a few of the best activities to do alone.

Take a river architecture tour

This one is true whether you’re travelling to Chicago alone or with friends — an architecture tour on a boat on the river is one of the best things to do in Chicago. But if you’re alone, it can also be a great way to meet travel buddies.

The tours depart from Navy Pier, cost around $35, and last about 90 minutes. You’ll sit on the open deck of the boat while your guide tells you all about the history of Chicago’s architecture. You learn about how the Great Chicago Fire decimated the city — but also allowed it to rebuild from scratch, using new materials and design styles. The end result was the modern skyscraper, best exemplified by buildings such as the Willis Tower and the Carbide and Carbon Building.

The guides are entertaining, but they don’t talk constantly — so you have plenty of time to chat with your neighbours. You’ll meet fellow travellers from all over the world. A great icebreaker is to ask someone to take a photo of you in front of one of the buildings or to ask what their favourite deep-dish pizza place is.

Do a river cruise at the beginning of your Chicago solo travel itinerary to help yourself get oriented. You’ll pass so many of the downtown landmarks that you’ll be much less likely to get lost later when you’re walking around.

Have drinks at the Signature Room

A classic Chicago experience is seeing the skyline from above, in one of the city’s tallest buildings. The best place to go is the Signature Room, on the 95th floor of the John Hancock Building. The only cost is a pricey beverage (beers start at $8).

If you’re a little uncomfortable going to a bar alone as part of your Chicago solo travel, don’t worry — the atmosphere of the Signature Room is more like a lounge than a rowdy dive bar, and plenty of people go solo. Plus, being alone gives you a huge advantage — you’re much more likely to get a window seat without waiting in line!

The best time to visit the Signature Room is on a Wednesday at 9 pm or Saturday at 10 pm. Get a seat facing the riverfront and you’ll be able to see the amazing fireworks show at Navy Pier. Ladies, don’t miss a visit to the restroom — it has the best view in the entire city!

Time your Chicago solo travel with the Blues Festival

Chicago is perhaps the one American city where blues music is still alive and well. Its legacy as the home of Buddy Guy has carried through to today, and now, the world’s best blues musicians play regular, cheap shows all over the city. The only problem is if you’re travelling to Chicago alone. The shows don’t usually start until 10 pm or later, leaving you to choose between a dodgy walk or a pricey taxi back to your hotel.

If you still want to see great blues artists without the hassle of late-night clubs, consider visiting Chicago in June during its annual Blues Festival. For three days, Millennium Park hosts dozens of home-grown and national artists. Blues is the focus, but you’ll also hear R&B and rock. And best of all, it’s totally free!

Order your pizza at the bar

Deep-dish pizza is the one food you simply must try during your Chicago solo travel. It’s delicious, filling, and totally unique. Pizza rivalries run deep in this city, and everyone has their favourite place, but you can’t go wrong with Gino’s East.

The only downside to deep-dish pizza is it takes a really long time to prepare. Like, upwards of an hour. So if you don’t want to sit at a table by yourself for that long, consider eating at the bar instead.

Chicagoans are extremely friendly, and if you sit at the bar alone, you’re sure to make a couple of new connections — whether it’s with the bartender, other solo diners, or a group who’s sitting at the bar so they can watch the Cubs game. Sports are always a popular topic of conversation.

At Gino’s East, you can also pass the time waiting for your pizza by writing and drawing on the walls! You could spend hours reading all the messages previous guests have left.

Visit some of the amazing museums

Chicago has a world-class museum scene, and no visit here would be complete without checking out at least a couple of them. Plus, museums are a great solo travel activity — no need for travel buddies as you contemplate amazing artwork.

The top museum in the city is the Art Institute of Chicago. This is one of the best museums in the entire United States — it rivals the Met in New York — and you could spend days here and barely scratch the surface. Plan on at least an entire morning. Tickets cost $25.

Alternatively, head to the neighbourhood of Pilsen to check out the Mexican Art Museum — the largest collection of Latin American artwork in the United States. It includes everything from painting and sculpture to folk art and weird modern multimedia works. Most of the artists featured are from Chicago’s Mexican community. And best of all, the museum is totally free! (Get a caffeine fix beforehand at the neighbourhood classic Cafe Jumping Bean.)

If you want something more low-key, the Chicago Cultural Center displays rotating exhibitions from local artists. It’s free to enter and the building itself is gorgeous.

Ride the L

Chicago has one of the best public transportation systems in the country. You can get anywhere in the city within about half an hour — all for $2.50.

Better yet, the trains simply ooze the early-20th-century-America atmosphere. They cut between and even through skyscrapers on rickety old bridges. They travel along the river, providing amazing city views. There really is no better way to see the city.

The L generally runs from 4 am to 1 am and is safe at all hours of the day and night. Maps are available in every station, but it’s pretty easy to figure out (far easier than New  York’s subway). You can also use the L to get to and from the airport for just $5.

See the public art in the Theater District and Millennium Park

The final must-do during your Chicago solo travel adventure takes a walk through the Theater District. This area of downtown, known as The Loop, contains incredible public artworks from artists like Picasso.

Perhaps the most famous work of public art in Chicago is known as “The Bean” (actual name: Cloud Gate) — the giant metal … thing … in the middle of Millennium Park. If you’re travelling solo, one of the best things to do in Chicago is to take a selfie of your own reflection in the sculpture! (This is easiest from underneath.)

Other favourites are Picasso’s “Untitled” (the one that looks like a giant dog) and the “Monument to Standing Beast.” But there are dozens of smaller sculptures in the area, so it’s worth spending an hour or two aimlessly wandering.

Overall, Chicago is one of the easiest cities in the United States to travel solo. Public transportation means you can easily and safely get wherever you want to go. River cruises, friendly locals, and great bars all offer the chance to make new friends. And the art — both public and in the museums — is enough to keep you occupied for days.

So don’t hesitate to visit one of America’s most iconic cities, even if you can’t find a travel buddy!

HAVE YOU TRAVELED TO CHICAGO? DID YOU TAKE THE TRIP SOLO? WHAT DID YOU LIKE MOST ABOUT CHICAGO SOLO TRAVEL? TELL ME IN THE COMMENTS BELOW!

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Carrie is a guest writer for The Wandering Core. She has been solo traveling the world for the last seven years. On her blog, you’ll find stories and tips to get you way off the beaten path — from Ethiopia to Laos to Nicaragua and beyond — on your own, and on the cheap. She writes at Trains, Planes and Tuk Tuks. You can also follow her on Facebook and Instagram.

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