I’m taking a walk down memory lane today and sharing my Chicago travel guide. It includes all the top things to do in Chicago, plus places to eat and where to stay.

As it turns out, you guys like North American content. My posts on both Canada and the US have been doing very well lately. So I thought I’d fill in the content gaps and bring you some guides to other American cities I really, really like. My big solo trip around North America was a few years ago now, but I still remember walking down Michigan Avenue and eating the best pizza of my life like it was yesterday. Without further ado, here’s my Chicago travel guide.

Things to do in Chicago

1. Do a free walking tour

This North America trip ignited my love for free walking tours. I did them everywhere: Boston, Charleston and of course, Chicago. Free Tours by Foot offers several different free walking tours of Chicago. I did the Loop & Millennium Park Tour and learned so much about Chicago’s history. The city’s architecture is also equal parts historic and beautiful.

2. Stroll down the Magnificent Mile

You can’t visit Chicago without seeing the Magnificent Mile. It’s an upscale section of Michigan Avenue that stretches from the Chicago River to Oak Street. I just window shopped, as it’s home to luxury department stores and all the designer boutiques. But you will also find a Hershey’s store here, where I might have treated myself to a mini cupcake. The next few Chicago attractions are located near/on the Magnificent Mile – how convenient ;)

3. Visit Navy Pier

One of the best things to do in Chicago is to visit Navy Pier. A lot is going on over there. It’s home to an IMAX Theatre, the Chicago Children’s Museum, the Centennial Wheel, daily cruises, restaurants and so much more. Personally, I loved the photos you can capture of the city skyline from Navy Pier. You can purchase express tickets to the Centennial Wheel here and a 40-minute sightseeing cruise around Lake Michigan from Navy Pier here.

4. Take all the photos at Millennium Park

Millennium Park is where you will find Cloud Gate a.k.a The Bean a.k.a perhaps the most Instagrammable location in Chicago? Wikipedia tells me it’s the number one tourist attraction in the Midwest – there you go! 25 million people visit Millennium Park annually and you should most definitely be one of them.

Besides capturing cool photos at The Bean, other things to do in the park include catching a show at the Jay Pritzker Pavilion and visiting Crown Fountain, which is a public art/video sculpture. While in the area, don’t miss Buckingham Fountain and its hourly water shows either.

Here are the other cities I recommend visiting solo in the US

5. Head to the skies

Two of the top attractions in Chicago are the Willis Tower and the John Hancock building. Willis Tower is the second tallest building in the Western Hemisphere. Down below are corporate offices, while up in the sky is Skydeck and The Ledge. The latter is a glass floor viewing platform on the 103rd floor. Purchase tickets for the Skydeck here. Meanwhile, there’s the 360 Chicago Observation Deck in the John Hancock building. Not to be outdone, it has TILT!, which is exactly what it sounds like. You “tilt” out over the Magnificent Mile from 1000 feet in the air. No biggie. Here’s a link to 360 Chicago tickets, so you can skip the lines.

6. Visit the Art Institute of Chicago

Trying to figure out what to do in Chicago on a rainy day? Head inside and check out the Art Institute of Chicago, which is home to one of the world’s largest French impressionist art collections. Tickets aren’t cheap, so I’d suggest this activity is only for those that love art. Another option is the Museum of Contemporary Art.

7. See a show at Second City

Second City is the most popular comedy club in Chicago. Its alumni just casually include comedians like Dan Aykroyd, Bill Murray, Tina Fey, Amy Poehler and many more. Seeing a show at Second City is a guaranteed fun night out in Chicago.

8. Go cruisin’

I had the weirdest weather in Chicago. It was hot and humid on my first day, and then cloudy and cold the next. If you visit Chicago on a pleasant sunny day though, I’d recommend doing a river cruise. An architecture cruise sounds even better to me! While we’re on the top of the river and sunny days, the Chicago Riverwalk is a pedestrian waterfront area lined with restaurants. Add it to your summer list of things to do in Chicago.

9. Take the kids to Lincoln Park Zoo

One of the best places for families to visit in Chicago is Lincoln Park Zoo. It’s open 365 days a year and it’s free. Some of the animals you can spot here include an African lion, camels, giraffe, polar bears and many, many more.

Speaking of free things, here’s my USA budget travel guide

10. Go for a walk

There are a couple of popular walking trails in Chicago. The 606 is similar to the High Line in New York City. It’s an abandoned elevated rail line that opened in 2015. Like its counterpart, there’s art to spot along the route, which is just over four kilometres long. Otherwise, the Lakefront Trail is a path that stretches for nearly 30 kilometres alongside Lake Michigan.

11. Visit Garfield Park Conservatory

Visiting Garfield Park Conservatory is another great thing to do on a rainy or cold day in Chicago. It’s home to eight indoor display gardens and features a tropical temperature year-round. There’s also 10 acres of outdoor gardens, plus a children’s play area. The best part is, it’s free!

12. Check out the Field Museums

The Field Museum is one of the world’s largest natural history museums. Inside, check out the Ancient Egypt exhibition, say hi to Maximo the Titanosaur, take the kids to the Science Hub and see the Birds of America.

13. Get a photo at Chicago Theatre

The Chicago Theatre sign is an unofficial city emblem, but it does look very good in photos. Although you could just take photos outside, the theatre does host concerts, musicals and theatre performances year-round too. Visit the website to find out what’s on during your visit.

Where to eat in Chicago

Although I didn’t do a heck of a lot of eating in Chicago, I knew I had to try deep dish pizza. I did some research and discovered Giordano’s, which has been serving deep dish since 1974. They have a lunch special, which is perfect for fellow solo travellers exploring Chicago. You get a small deep dish pizza, plus a side and drink. DO IT. Another pizza place I’d heard mentioned numerous times was Pequod’s.

Some other recommendations: Manny’s Deli is popular, as is Al’s Italian Beef, which apparently serves the best sandwich in Chicago. I’ve seen several local bloggers mention Cindy’s Rooftop too, which has awesome views and delicious food – the perfect combo, right? Another place with a good reputation and an Instagrammable interior is Summer House Santa Monica. Finally, for those looking for a sweet treat, I’ve got you covered.

Where to stay in Chicago

Budget

I stayed in a female dorm at Chicago Getaway Hostel, which is a fantastic hostel located in Lincoln Park. Yes, it isn’t located downtown, but I liked being in the suburbs. It was very easy to get both a bus into the city and directly to the Greyhound bus terminal as well.

Another budget accommodation option in Chicago is the HI Chicago, which is located in the city and has a very good Hostelworld rating. I’ve stayed in Hostelling International properties around the world and they are always high-quality.

Mid-range

I feel like your best bet for mid-range accommodation in Chicago is Airbnb (click this link for money off your first Airbnb stay). You could follow my lead and stay in Lincoln Park – this studio is under $150 per night.

Luxury

If you have the cash to splash, check into the Waldorf Astoria. It is so fancy – even the entrance is grand! But can we also talk about the Godfrey Hotel? From the outside, it looks ultra-modern.

I hope this travel guide helps you plan your own trip to Chicago. There’s plenty of things to do and eat, that’s for sure!

Follow along: Facebook | Twitter | Bloglovin’ | Instagram | Pinterest

In case you missed it…

♥ My entire North America itinerary (with corresponding blog posts), my USA budget travel guide and hostelling tips for fellow solo travellers.