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The Ultimate List of Non-Touristy Things To Do In Chicago

Chicago is a fantastic place to visit on a solo trip, with friends or with family. I recently went to the Windy City with friends but I was interested in doing more than visiting Cloud Gate, or commonly known as The Bean, the Art Institute of Chicago, Navy Pier, the Willis Tower or Millennium Park. I made it my mission to seek out the top non-touristy things to experience while in Chicago. I stumbled upon some impressive sites and experiences!

Free Chicago Walking Tours

This does sound like a total tourist thing to do but I put it in here because it doesn’t cost you a dime! You can take your family of 12 on a tour of the most popular neighborhoods in Chicago, for two hours, for free! What better way to get to know the city than for free?

Comedy Clubs

The Chemically Imbalanced Theater

A lot of people see Broadway shows while in Chicago which, I don’t blame them. I am quite the Broadway snob. However, switch things up a bit and head on over to a comedy club and set up for a night of laughs! Chicago is chalk-full of comedians grinding for a laugh. For a unique experience check out The Chemically Imbalanced Theater. If you are a fan of improv comedy than this is the perfect theater. They specialize in advanced long-form improv. It is an intimate setting and is sure to provide good laughs and great times. They also have a full-service bar if that suits your fancy…

Second City

Second City has multiple locations around the United States. They have been opened about 60 years and have become one of the greatest comedy empires in the world. Not only does Second provide entertainment but they also provide classes. If you think you are on track to being the next comedian, sign up classes in the Second City Training Center. The comedy shows are hilariously entertaining and the cast even more so. You won’t be disappointed by the friendliness of the staff. Definitely stop in Second City to catch a show.

Neo-Futurists Theater

If you so want to watch a production type of show rather than comedy, there are numerous amounts of small theaters around Chicago. Like I said, you can head to the theater district if you like, but this is a non-touristy article so we will focus on different types! One that was suggested to me was the Neo-Futurists Theater. Smaller theaters provide different types of shows with interesting subjects. According to their website, The Neo-Futurists Theater “aesthetic draws upon Dada, Surrealism, the work of the original Italian Futurists, and an array of other artistic and performance disciplines to create something new and different.” There are a bunch of small, funky theater spaces in Chicago that provide great shows for a fraction of the price.

Necromancer: Near Death Experience

This is a suggestion is for those who are a little more adventurous and curious. Neil Tobin, Necromancer: Near Death Experience is an interactive theater about life and death… but in one of the city’s most historic cemeteries. For this experience, I would say leave the kids at home. I don’t want any kids to be freaked out. However, the show is not scary and hardly morbid. Neil Tobin takes you on a magical journey through the cemetery as he, and the audience, discuss and ponder thoughts about life and death. He intertwines magic into the show and makes a seemingly hard subject, easier to talk about. Neil Tobin is warm, friendly and funny. This experience is one for the books.

The Magic Parlour

I visited Chicago recently and had the opportunity to attend The Magic Parlour. This experience is an intimate, close-up magic experience with third-generation magician and mentalist, Dennis Watkins. Let me tell you… it was fantastic. I don’t think I have ever been captivated so hard (if that even makes sense). Dennis tried to include every audience member and I felt like I was transported to another time. I don’t want to give away any details about the show or the experience, but I will say that it is in the beautiful Palmer House hotel and you are in for a trick. Dennis is passionate about what he does and that is evident in his performance.
The Magic Parlour is not your regular magic show: there is no sawing of boxes, scarves pulled out of hats or juggling of bowling pins. Dennis’s presentation includes many tricks that I still don’t understand the possibility. He takes you on a journey from one trick to the next, telling a story the whole time. From the minute I sat down I was mesmerized by the fluency of his production and accuracy of his wit and charm. If I find myself in Chicago again, I will be attending The Magic Parlour once more. Dress up in your best cocktail attire, have a drink at the bar and prepare to be mesmerized as Dennis takes you on a magical journey (cheesiness fully intended because the show is absolutely amazing).

Chicago Magic Lounge

Secret passageway, cocktails and slight of hand tricks to keep you stunned all evening… that is what you walk into when going to the Chicago Magic Lounge. Inside, in the elegant Blackstone Cabaret, you are intimately seated awaiting the next magician. There are full-service bars and food to accompany you for the evening. The Chicago Magic Lounge has other, smaller and more unique rooms for guests to transport to. The lounge celebrates Chicago’s part in the history of magic and provides a magic-filled night, no matter the room you choose. I have even heard there are secret passageways…

Drinks & Eats

The Aviary

If you are feeling fancy and want a nice cocktail, The Aviary is your go-to destination. It offers a swanky, intimate atmosphere with intricate drinks in creative presentations. When you go to The Aviary you can expect service, production and satisfaction of a 5-star restaurant. Careful thought has been put into the drink’s recipes and the bartenders strive to create a delicious pour in every glass. If you want to experience the small plates and drinks of The Aviary I suggest making a reservation ahead of time because it is a happenin’ place. The unique drinks will have you wanting to come back to try others. You won’t be disappointed by this elegant, cool cocktail lounge.

Kaiser Tiger

Kaiser Tiger is not your average bar and restaurant. The menu has a fantastic variety of food (especially high in meats) and the bar has an even more fantastic variety of beer options. The most interesting part of Kaiser Tiger is the curling rink! While you’re waiting for your brews and food you can take that squad out on the ice. Reserve your curling space ahead of time because the rink is always packed. Kaiser Tiger also has a variety of other games so you and your pals can eat, drink and have fun! You can have a casual fun time in a loungey atmosphere or you can head out back to the patio and beer garden.

Forbidden Root

Forbidden Root is a brewery that specializes in creating iconic botanic beers using all natural ingredients. To go along with their fresh brews, Forbidden Root offers some small plates that are neatly paired with the beer. The mastermind behind Forbidden Root wanted to bring back the once popular use of locally available botanicals like ginger, dandelion, burdock and horehound. You could consider Forbidden Root a brewpub with a twist that has beers infused with earth-grown goodness. Depending on the day, they have awesome daily specials that will make you, and your wallet, happy. The staff is friendly and knowledgeable about all their products. If you are unsure of what beer to try, just ask a bartender! As if this place doesn’t sound awesome enough, they donate 100% of their non-consumable profits to different charities.

Fort Willow

Fort Willow is a lounge that will transport you back to your childhood in the classiest manner possible. The first thing you will notice about Fort Willow is the wooden-slat tree that “grows” out of the floor and canopies over the dining room. If you’ve ever thought about what it would be like to drink and dine in a treehouse, now is your chance to fulfill experience. Grab a cocktail, a “bite” or “big bite” and enjoy your evening in the, dare I say, sexy, intimate atmosphere of Fort Willow. For the adults that are still kids at heart, this environment will make your little-kid self smile. On top of the amazing decor, delicious drinks and food, the staff is uber friendly! If these things don’t get ya, maybe the tree swing will 😉

Godspeed Supper Club

The Godspeed Supper Club was suggested to me by multiple people. I had to see what all the fuss was about and man, I know why it was top of the suggestions! Basically, you sign up for the next Godspeed Supper Club event and when you get the email of details, you show up at the listed location. Godspeed Supper Club will take you out to enjoy a city-spanning night of fun that could include, but not limited to, fine dining, private tours, tableside entertainment and much more. Godspeed Supper Club strives to provide an experience unlike any you have had. You will meet new people, visit exciting new places and learn about local Chicago history. I don’t know about you guys, but I am definitely on the list for event notifications!


Travelle restaurant provides river views for days. The cocktail menu at Travelle is inspired by the 1990’s. With a wall of windows to expose you to the views, Travelle is elegantly designed with a crisp interior. Also, if you are interested, the kitchen is exposed by glass walls so you can watch the chefs in action. Travelle is swanky and will have you feeling like you’re on top of the world, literally (since it is in a hotel). Along with the delightful cocktail menu, you’ll receive a dining menu that will blow you away. Crispy octopus pork belly, ahi poke, hanger steak and lemon pavlova are just a few of the delicious items you will have a chance to try! Great cocktails, food and views… what more could you ask for?

Three Dots and a Dash

Want to pretend you are on a tropical island while drinking a tiki drink? You can at Three Dots and a Dash! This bar is hidden underground below River North. In this secret “destination staycation” you can dive into a drink made with the freshest of fruits and the booziest of liquors. Getting into the tiki bar is the fun part… down an alley, some stairs and tiki-torch lit hallway… eventually you will find paradise 😉 Some of the prices may be a bit expensive but you get what you pay for. Some drinks come in fancy cups, treasure chests, etc. I’m not going to give away too much! There is a reason it is hidden underneath the city.Three Dots and a Dash is no tacky tiki bar. The staff is tastefully dressed and will help whisk you away to your island in the sun. Tiki bars are all the rage, what better one to start with than Three Dots and a Dash?

Tasting Escapes

What better thing to do on a Saturday morning than enjoy some relaxing yoga and wine? Nothing! After enjoying a vinyasa yoga class,  turn your matt into your seat and transition into the wine tasting portion of the session. You are guided through tasting six different artisan wines that are paired with small bites. Pop-up yoga and wine is a great way to meet the locals and enjoy some drinks in different corners of the city. The yoga instructor, Chelsea Renee, guides the class through breathing exercises, meditation and has a rockin’ yoga playlist to accompany the class. Check out the website for class locations and times!

The Blackstone Hotel

The Blackstone Hotel is an amazing hotel inspired by the 1960’s. Beautifully crafted interior and exterior are enough to make any visitor happy. Once nightfall strikes, the Blackstone Hotel lobby transforms into a popular place for hotel guests and anyone interested to stop by, grab a drink and hang out. On Wednesdays and Fridays, you can swing back in time with their live jazz performances. If you are a guest of the hotel, you can also receive a 50% off admission to the premiere Buddy Guy’s Legends blues club! As if that wasn’t cool enough, The Blackstone also has a partnership with Iwan Ries & Co. which offers guests exclusive access to The Iwan Ries Lounge, downtown Chicago’s only smoking lounge. The Blackstone Hotel is a great experience because it isn’t your typical bar or club and you get to hang out in a stunning hotel while you have fun.

Chicago Detours

Chicago Detours tours are a great way to get an inside look at the Windy City. They offer tours of interior architecture, historic bars, jazz and blues and Chicago neighborhoods. Many places the tours stop are places that Chicago locals don’t even know about! The tour guides are friendly, knowledgeable and are chalk-full of information about the places you visit. They engage the whole group and are eager to teach the group about the city. If you are wanting to learn more about different, intriguing places around the city, Chicago Detours is the way to go.

Wrigley Field

Obviously while in town you can catch a game or two at Wrigley Field but since we are talking non-touristy things to do in Chicago we aren’t talking about games. What a lot of people don’t know about Wrigley Field is that you can take tours around the stadium. You and your family can get a tour around the stadium and field that has over 100 years of history, cool right? Check the calendar and weather because they conduct tours rain or shine! Pop on over to their website to pick your tour date!


Like most cities, Chicago has a zillion museums. The Art Institute and The Field Museum of Natural History are a couple of the popular ones. Like most cities, Chicago has a lot of smaller, but just as awesome, museums. Check out the Museum of Broadcast Communications, International Museum of Surgical Science, Busy Beaver Button Co. & Pin-Backed Button Museum, the Driehause Museum, Museum of Contemporary Photography or the Illinois Holocasut museum. Some of them may be a bit more quirky than others but they are all interesting and fun for the whole family or solo trips!

As you can see, Chicago has a lot to offer. Intertwine the uber-popular stuff with things I mentioned here and you are bound to have a full agenda. Most of these activities and locations are great no matter the weather! Have fun in the city and enjoy 🙂

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