As the third-largest city in the United States, it’s easy to find things to do in Chicago. Sure, a visit to the Bean is a must and of course you should try a slice of deep dish. Once you’re done with that, you may be wondering what’s next.
If you have a transit pass (we call them Ventra cards here), you can get to many of the interesting sights that locals love to explore.
Plan to check out these 10 unique spots during your stay!
1. Dive into history at the Pullman National Monument
For those interested in history, the Pullman National Monument is not to be missed. It’s a bit off the beaten path, but certainly worth the trip. The area – the first planned industrial town in America – is unique as it’s still an active residential community, yet you can walk around and see many buildings as they existed in the late 19th century.
Start your journey at the visitors centre to learn more about the Pullman Company and how its founder changed the way people worked and lived, and then take a self-guided walk through the neighbourhood.
Photo credit: Ian Friemuth
2. Spend a rainy day at Garfield Park Conservatory
Rain or shine, the Garfield Park Conservatory is a peaceful and beautiful place to visit. Many locals flock there during the winter months to escape from the bitter cold.
Plants, flowers and trees of all kinds adorn every little space in the different rooms. Make sure to stop in the fern room for a picturesque view of the conservatory.
Photo credit: Erin
3. Get active on The 606
Since its opening in 2015, The 606 has been a popular place to jog, walk and bike.
Running through Logan Square, Humboldt Park, Wicker Park and Bucktown, this elevated trail is easily the most scenic way to see the different north-side neighbourhoods.
If you enjoy cycling, rent a Divvy bike! There are Divvy bike-share stations near several trail access points and throughout the city.
Photo credit: The 606
4. See the city from a different perspective on a river cruise
The Chicago Architecture Foundation River Cruise is the first thing we recommend out-of-town visitors do. It’s one of the best ways to see downtown and learn about the surrounding buildings. There truly is no better way to see The Loop.
Photo credit: Chicago Architecture Foundation
5. Promenade along the lakefront
In Chicago, you can only go so far east until you reach water. That’s because Lake Michigan spans the entire length of the city and beyond!
The Lakefront Trail allows you to enjoy 18 miles of biking and walking near the lake. If relaxing is more your scene, try one of our beaches, Oak Street Beach for example, situated right in the middle of the Gold Coast.
If you’re looking for great views of Chicago, North Avenue Beach or Promontory Point are two great places to relax by the water while admiring the beauty of the Windy City.
Photo credit: The West End
6. Find the well-hidden McCormick Bridgehouse Museum
You’ll easily pass this museum without even realising it’s there. I know I did for years! That is, until I found it inside the Michigan Avenue Bridge.
The McCormick Bridgehouse Museum may be one of Chicago’s best hidden gems, and I’m sure glad I found it.
Take a look at the magnificent Michigan Avenue Bridge from underneath and see what makes the intricate system of bridges along the Chicago River unique.
Photo credit: Jeremy Atherton
7. Go on a treasure hunt at one of the year-round markets
During the summer, farmers markets and festivals can be found in any Chicago neighbourhood on any given weekend. But, as the weather starts to cool down, many of these events pack up for the year.
There are a few exceptions. The Randolph Street Market is year-round and quite the treasure trove, with antiques and vintage items everywhere you look. The Logan Square Farmers Market is also an event you shouldn’t miss, and the locals don’t either! Happening every Sunday, this vast market features local produce and food, and moves indoors when the weather gets cold.
Photo credit: Chicago Antique Market Randolph Street
8. Soak up some art at the Art Institute of Chicago
In the heart of downtown, the world-famous Art Institute of Chicago is certainly worth the stop. Give yourself at least an afternoon to check out notable paintings such as Nighthawks, American Gothic and the Picture of Dorian Gray.
Other unique things to see here include the paperweight gallery and the Thorne Miniature Rooms. When you’re done, head to the peaceful courtyards to sit, relax and take in the city views.
Photo credit: Bill Dickinson
9. Travel back in time at the Green Mill Lounge
Transport yourself back to 1940s Chicago at the Green Mill Lounge. It’s well worth visiting for the nightly entertainment featuring poets and jazz musicians, but it’s the history that really makes this lounge unique.
Many locals in the area know that it was a famous Al Capone haunt – see if you can spot his booth while you’re there!
Photo credit: Rebecca Peplinski
10. Have a good laugh at a comedy show
Finally, no trip to Chicago is complete without a comedy show. After all, so many of the greats have studied here.
The Second City is always a go-to for visitors – you won’t be disappointed. But, if you want to have a truly local experience, check out Improv Olympics (iO) – they have a free improv show every Wednesday night. Or, my personal favourite is Hitch*Cocktails at The Annoyance Theatre, where I guarantee you’ll laugh more than you ever have before!
Photo credit: The Second City
Bonus: Admire the beautiful Bahá’í temple in Wilmette
This one isn’t technically in Chicago so I didn’t want to include it on the “official” list. However, it’s accessible by public transit, so if you have time, it’s certainly worth a visit.
The Bahá’í temple is located In Wilmette, just a few suburbs north of Chicago, and is one of only seven (soon to be eight) in the world.
Its beauty and peacefulness is unmatched. Be sure to visit the welcome centre and speak with the friendly guides who can tell you more about the elaborate architecture.
Jaclyn Crawford is a freelance writer and blogger based in Chicago, Illinois. She loves playing badminton, hosting Airbnb guests, spending time with her dog, Sundae, and going thrift shopping with her husband.
Opening photo credit: Kevin Young