10 Chicago Hidden Gems & Secret Places Most Tourists Miss

“She is always a novelty; for she is never the Chicago you saw when you passed through the last time” ~ Mark Twain.

Ever wondered what the secret is to having the most enjoyable trip possible? Welcome to my “Be Invisible” series – your ultimate guide for how to avoid looking like a tourist on your next adventure and guaranteed to boost your entire travel experience.

Bursting with helpful tips and tricks, I’ve asked locals from particular cities around the world to share their insider knowledge on the best ways travellers can become “invisible” when visiting their city and enjoy it like a local. If you’re ready to challenge travel stereotypes, overcome language barriers and embrace what I like to call invisible tourism, you’ve come to the right place!

This post contains affiliate links, at no extra cost to you. I may earn a small commission if you click through and make a purchase.

You could say that Chicago is a touristy city. After all, over 50 million people visited the city in 2017! Chicago is the largest city in America’s Midwest, and it’s the third-largest city in America. 

Chicago draws big tourist crowds because it has a reputation for incredible museums, world-class dining, limitless shopping, and all kinds of entertainment. Tourists certainly take advantage of these exciting opportunities. Unfortunately, they tend to flock to the same places…

If you’re looking to get off-the-beaten-path in Chicago, this is your ultimate guide. You’ll find a discussion on the most popular activities for tourists in Chicago, and how you can best avoid them. Plus, you’ll get the inside scoop on Chicago hidden gems that will ultimately give you a much richer experience.

10 Chicago hidden gems & non-touristy things to do

In general, if you are seeking to avoid crowds, it’s best to plan your activities during the workweek. No matter what activity you decide to do (hidden gem or not), it will be more popular on the weekends. 

Also, you may consider visiting Chicago in spring or fall (autumn). During the summer, the city becomes much more touristy and congested. During winter, temperatures get quite chilly and the city tends to hibernate. 

Chicago is a a stylish city where people dress to impress. Check out this Chicago outfit guide for what to wear so you don’t look like a tourist. 

Find the best view of the Chicago Skyline

One of the top things to do in Chicago is to catch an unforgettable view of the phenomenal skyline. Chicago is world-famous for unique architecture, and there are over 1,300 high rises in the city! It’s no wonder that tourists flock to observation decks like 360 Chicago at the John Hancock tower or Skydeck at Willis Tower (formerly known as the Sears Tower). 

TIP: Skip the John Hancock tower! Skip Willis Tower! Locals know that there are incredible views of the skyline that you can get for free.

One of the best free Chicago skyline views can be found at Navy Pier. It’s an unconventional location that many tourists miss. However, if you take the elevator to the top floor of the Navy Pier parking garage, you’ll be rewarded with a panoramic city view behind the iconic Centennial Wheel. Another secret skyline lookout spot is located in Chicago’s Lincoln Park neighbourhood.

This one is also in a parking garage. Named for the Children’s Memorial Hospital previously across the street, the ‘Children’s Memorial Parking Garage’ or ‘Lincoln Garage’ boasts fabulous skyline views from its top floor. It’s right across the street from Philz Coffee. 

Bike ride along the lakeshore

One of the most touristy experiences you can have in Chicago is the Segway tour of Millennium Park. Nothing says ‘tourist’ quite like a Segway. Locals prefer to walk or bike.

Bikes are very easy to get a hold of in the city of Chicago. There are Divvy rentals all over, and if you download the Divvy app you can easily find the one nearest to you. Since 2020, Divvy has also come out with a fun fleet of electric bikes. So, you can peddle when you want to or relax and enjoy the cruise if you prefer.

With a Divvy e-bike, you can choose to hit up the 606-trail, or bike along the Lakeshore trail (over 18 miles of traffic-free paved path). 

Experience the Chicago River like a local

Most tourists know to visit the Chicago Riverwalk. It’s a lively public space lined with restaurants and sculptures. You can access the Chicago Riverwalk from the DuSable Bridge or the William P Fahey Bridge. It’s below street level.

The Chicago Riverwalk is an iconic city experience, and most tourists visit here. However, less realise that there’s another cool way to enjoy the Chicago River!

Locals know that the best way to soak in the Chicago Riverwalk views is from the comfort of a kayak. Yes, you can kayak along the Chicago River! This is one of the most unique experiences to enjoy in Chicago. 

Waterriders is one of the best kayaking companies that take visitors on tours along the Chicago River. You can rent kayaks and choose-your-own-adventure. Or, you can join a tour group that offers a bit of history. Learn about Chicago’s history, architecture, or ghosts while you paddle along the river. 

Look for art in unexpected places

The Art Institute of Chicago is notoriously touristy. It’s one of the most famous museums in Chicago. Over a million people visit the Art Institute of Chicago yearly, and with good reason… It’s one of America’s oldest and biggest art institutions.

That’s all well and good, but what if you’re looking for art off the beaten path? Consider visiting the Wabash Arts Corridor. The Wabash Arts Corridor is an open-air museum in Chicago’s Loop neighbourhood that features a diverse collection of larger-than-life murals and public artworks. 

TIP: The Wabash Arts Corridor is a hidden gem in Chicago, and one of the best free art experiences Chicago has to offer. 

Discover the less-hyped sculptures unique to Chicago

Every tourist photo in Chicago includes the iconic ‘Bean.’ Formally known as Cloud Gate, the giant bean-shaped reflective sculpture in Millennium Park draws tourists from all over. It weighs nearly 100 tons and beautifully reflects the city skyline.  

Cloud Gate is pretty awesome, but it’s not the only massive sculpture you can find in Chicago’s downtown. Get off the beaten path and snap a photo of the impressive untitled Picasso sculpture. Sometimes also referred to as ‘the Picasso,’ this 50ft tall 160-ton behemoth would tower over ‘the Bean’ if it could.

The Picasso is located in Daley Plaza. It was gifted by the famous artist Pablo Picasso to the city of Chicago. 

Visit an off-the-beaten-path rooftop bar

Every Chicago itinerary includes Cindy’s Rooftop Bar. It is a popular spot that promises an upscale brunch experience along with fabulous views of Millennium Park. For nightlife, tourists crowd the Signature Room on the 95th floor of the John Hancock tower. This place boasts views of Navy Pier and has a reputation for being frequented by celebrities. 

So, where do the locals go? Chicago has an assortment of really cool rooftop bars. You’ll have plenty to choose from besides the two most popular touristy rooftop bars. The J Parker in Lincoln Park has stunning views of Lincoln Park as well as the skyline.

IO Godfrey’s offers panoramas of skyscrapers in all directions from its central River North location. Another low-key spot is the Apogee Lounge which is open year-round and has a summertime patio. 

You may also consider the Waydown in Fulton Market or Devereaux near Gold Coast. You won’t be disappointed with any of these non-touristy establishments and hidden places in Chicago. 

Eat pizza that’s not deep dish

Yes, yes! Chicago is famous for deep-dish pizza. The best places to eat deep dish are Lou Malnati’s or Gino’s East, and this is where all the tourists go. Although, deep dish isn’t the style of pizza served in Chicago. 

There are other types of pizza you can try if you’re looking for a more unique experience. Bonci Pizza offers traditional Roman-style pies as well as suppli (Roman-inspired rice balls stuffed with cheese). Bonci has two locations, one in Rome and another in Chicago. It’s an authentically Italian experience that beats deep-dish any day!

Another awesome and untraditional pizza option is Dimo’s Pizza in Wicker Park and Lakeview. Dimo’s has awesome pizza, but it’s also a community staple with an eclectic artsy ambiance and a mission to serve the local community. Most of all, Dimo’s is known for unique flavour combinations and innovative pizza toppings.

Popular menu items include the macaroni and cheese pizza, bbq chicken pizza, or chicken and waffles pizza. Vegan options are also available. 

Have a fresh brew of coffee

The most sought-after cup of coffee in Chicago is served at the Starbucks Reserve Roastery. This is also one of the biggest tourist traps in the city! Ever since it opened, it’s been an ultra-busy, super-congested spot. While the food and drink is quite good, navigating the crowds is extra annoying. 

One of the most relaxing place to enjoy a cup of coffee in Chicago is the Windy Kitty – Chicago’s premier cat café. Sip some cold brew and snuggle up next to a cuddly Chicago kitten. 

Hidden places in Chicago to shop for oddities

Most tourists know that the Magnificent Mile on Michigan Avenue is the best place to shop. This is where the luxurious 900 North building and Water Tower Place mall is located. There’s also a 3-story Banana Republic, Disney Store, UNIQLO, and much more!

TIP: Michigan Avenue is a really pretty street lined with art and charming landscaping. Although, there are much less touristy places to go shopping in Chicago. 

If you love thrifting, the Salvation Army on Clybourn Avenue is notoriously awesome. It’s located in Lincoln Park, so you’ll be able to find posh items – some with tags still on. This store also has a very extensive book section. Other great places for thrifting include Brown Elephant, Crossroads Trading Co, or P.O.S.H. Chicago.

Other interesting shops in Chicago include Woolly Mammoth Antiques and Oddities, Precious Possessions, or the Secret Agent Supply Company. 

Visit an unconventional museum

Chicago is world-famous for its museums, but tourists visit the same few. You’ve likely heard of the Field Museum or Museum, the Museum of Science and Industry, or the Adler Planetarium. Although, you’ve probably never heard of the Museum of Surgical Science, the Driehaus Museum, or the Museum of Contemporary Art in Chicago.

These off-the-beaten-path museums are virtually untouched by tourists, and they’re worth your time!

 

Ready to ‘be invisible’ in Chicago?

Now you’ve uncovered these Chicago hidden gems, perhaps you’re ready to make the trip! Why not compare hotel prices here? 

If you’d like to learn learn my strategies for how to not look like a tourist ANYWHERE, take a look at my  book – it was a #1 Amazon New Release!

Do you have any Chicago travel tips or other Chicago hidden gems to add to this list? Let me know in the comments below.

I hope you enjoyed this instalment of my Be Invisible series! If you found this helpful, please share it or follow me on Facebook, Pinterest, Instagram and TikTok for more!

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Kitten image credit: Pixabay
All remaining photography copyright to Valentina’s Destinations and used with permission. This guide to Chicago hidden gems contains some affiliate links, at no extra cost to you. I may earn a small commission if you decide to make a purchase and if you do, thanks for your support! This helps with the costs of running my blog so I can keep my content free for you. As always, I only recommend a product or service that I genuinely love and use myself!

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