10 Unique Things to Do in Chicago

Like A Local Guide • 21 Sep, 2016

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.

2435781042_e547965e1a_bPhoto 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.

2947836237_7106978a2b_bPhoto 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.

27409735012_3102fcfdcc_bPhoto 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.

chicago-architecture-foundation-river-cruise-chica-3Photo 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.

17046366225_e5be29f2e4_kPhoto 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.

1024px-Bridgehouse_Museum_20101009Photo 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.

561612_10151071158784773_1811179806_nPhoto 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.

6823675795_3291ed146f_bPhoto 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!

3167796634_1e003656a7_bPhoto 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!

13321633_10156941705680612_1956090083742940531_nPhoto 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.

temple-cover-finalPhoto credit: National Spiritual Assembly of the Bahá’ís of the United States

DSC_0108Jaclyn 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

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    Great post, I am excited to check out some of these things, the McCormick Bridgehouse Museum is on my list of must-sees! I just moved to a new Freedom home in Gurnee Il, but I work in the city so I don't think it should be much of a problem making it there. Thanks again
    Henry • Mar 30, 2018 • Reply
    Wow, what a great list, You are right I didn't know about many of these places! I will be on the hunt for the bridge museum for sure. I am building my home not too far away so I will be in the city a lot http://www.drhorton.com/Illinois/Chicago/Deerfield ! thanks for the post
    Betsy • Dec 10, 2017 • Reply
    Thanks for the enlightening guide in Chicago sights. I saw some of them when I visited my son at Evanston. I wanted to add the Botanic gardens, like the Bahai Temple it's out of Chicago, but certainly worth the trip. Large, beautiful and variegated, surely a place to pass a few hours. Another place that my son took me to was tge Russian Tea House, right in the middle of the loop - a lovely place to sit on an afternoon of sight-seeing. enjoy!
    Shlomith Kedem • May 30, 2017 • Reply
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