7 Fun & Quirky Restaurants in Chicago You Have to Try

Updated On: November 27, 2023 by   Courtney Augello

Chicago is renowned globally for its food scene. With staples such as Chicago-style hotdogs and deep-dish pizza, the Windy City knows how to create amazing dishes. But what if you want to try some of the more quirky restaurants in Chicago? 

There are many Quirky Restaurants in Chicago

Quirky and unique restaurants are abundant in Chicago if you know where to look. For the best tableside experiences and delicious food, check out our list of quirky restaurants in Chicago that you have to try.

1: SafeHouse Chicago

If you’ve ever wanted to be an international spy, SafeHouse is the perfect quirky restaurant in Chicago to visit. Founded in 1966, it has been a secret staple of Chicago for decades.

The restaurant is located one block from the Magnificent Mile in the River North area and features a bright red door as its entrance. However, finding the restaurant is only the beginning.

Once guests go up to the door, they are greeted by a bouncer named Moneypenny. The bouncer will ask patrons for the password and give them a clearance test before letting them in.

Once you’ve entered the hideout, the restaurant is decorated with authentic spy memorabilia. The menu uses codewords for full immersion and features salads, burgers, bowls, and delicious desserts.

2: 2d Restaurant 

Of all the quirky restaurants in Chicago, this one has the most unique art style. The comic-book-inspired eatery transports guests to 1920s Paris. The walls, floors, and ceilings are painted with black and white panels to replicate a newspaper comic look. 

If you visit Chicago in the summer months, 2d Restaurant also has an outdoor patio that is decorated with the comic book design.

The menu at 2d Restaurant features 2 main items: fried chicken and mochi doughnuts. The chicken is served in sandwiches and on its own, and vegan substitutes are also available. On a sweeter note, the restaurant adds new doughnut flavours each month and even collaborates with brands like the Chicago Bulls and Winnie the Pooh.

3: Ed Debevic’s

This quirky restaurant in Chicago opened in 1984 and has been an iconic part of the city ever since. Ed Debevic’s is fitted with a retro 1950s theme and is known best for its strange take on customer service.

The servers at Ed Debevic’s wear retro uniforms and make snarky comments at the patrons. Each server is their own character, from a jock or nerd to a greaser. They play their role perfectly and will even drop full trays to break into song and dance.

The menu at this restaurant is classic American diner food: burgers, fries, and milkshakes. If you’re looking for a fun experience and enjoy a bit of banter, this is the place for you.

4: The Wiener’s Circle

The Wiener’s Circle is a hot dog stand in the Lincoln Park neighbourhood. This quirky restaurant serves Chicago-style hotdogs and hamburgers and has been feeding the Windy City since 1983.

While the food here is great, that is not what The Wiener’s Circle is known for. What makes this restaurant iconic is the mutual verbal attacks that occur between the staff and patrons. A few steps up from Ed Debevic’s, the staff at The Weiner’s Circle can yell and swear at customers, and the customers are encouraged to give it right back to them.

Another unique part of this restaurant is the sign outside. The staff consistently update the sign to poke fun at current events. One example of this is when the sign mocked the pardoning of former Illinois governor Rod Blagojevich in 2020.

5: Three Dots and a Dash

This quirky restaurant in Chicago opened in 2013. The name Three Dots and a Dash was inspired by the cocktail of the same name and is morse code for the letter V.

The interior of the bar is island themed, and the cocktails all derive heavy inspiration from tiki bars. The interior ceiling of the bar is made to look like a thatched roof, and colourful lights illuminate the space.

Although the food menu is not very extensive, each dish served has an island flare, such as the coconut shrimp or moco loco burger. The real draw of this restaurant is the drinks served there. Three Dots and a Dash has over 150 rums available behind their bar and a great selection of cocktails.

If you want a souvenir from your experience, Three Dots and a Dash also sells collectable cocktail glasses and mugs.

6: EL Ideas

EL Ideas is an upscale restaurant in Chicago but is not flashy, despite being one of the michelin star restaurants in chicago. In fact, the website lists the directions to the restaurant as: “Turn down the dead-end street; EL ideas is the only business whose windows look out onto the street. There is no signage.” It is the most secretive of the quirky restaurants in Chicago. 

Once patrons find the restaurant, they will be welcomed into a unique open-floor dining area and kitchen. This wall-less area allows guests to speak directly with the chef and kitchen staff as their meal is prepared.

EL Ideas serves American classics like barbeque and burgers. They also offer tasting menus and limited-time dining experiences.

7: Carnivale 

For a colourful and quirky restaurant in Chicago, eating at Carnivale is a must. The restaurant opened in 2005 and has brought the excitement of Latin food, exotic drinks, and South American culture to the Windy City.

At Carnivale, dancers in feather crowns entertain between tables of guests, and acrobats can be seen performing from the building’s vaulted ceiling. Dinner options include salads, steaks, seafood, and other Latin-inspired dishes.

Drinks are also a hit at Carnivale, with beer and wine available alongside their signature cocktails, such as the cotton candy martini. For dinner and a show, Carnivale is a great place and one of the best restaurants in Chicago.

Best trendy restaurants in Chicago

Whether you are looking for classic American dishes or to try some exotic flavours, Chicago has restaurants that will tickle everyone’s tastebuds. When you go to one of the quirky restaurants in Chicago, however, you’ll get more than just food. 

Quirky restaurants in Chicago may be tricky to find, but they are worth it. With their bold flavours and brilliant entertainment and performances, eating at one of these quirky restaurants in Chicago will create memories that will last a lifetime.

If you’re planning a trip to the Windy City, check out our list of things you must do in Chicago.