The Top 21 Fun Restaurants in Chicago in 2024
Looking for some amazingly fun restaurants in Chicago? Chicago is a city known for its excellent food, which can be found everywhere from corner diners to Michelin-starred eateries. Some of the best restaurants in Chicago make especially fun outings for all sorts of occasions like birthdays, dates, anniversaries or even just a regular night out.
What makes a restaurant fun? It could be the décor, the experience or the energy of a place. It could be the menu, unique cocktails or live entertainment.
If you’re looking for things to do in Chicago involving both food and fun, we’ve rounded up a few of our favorites that excel in one of the above areas, leading to a uniquely Chicago dining experience that can only be found amid the rich restaurant culture of the city. From luxurious fine dining to neighborhood hot dog stands, there is a fun restaurant in Chicago for everyone!
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Find the Best Restaurants in Chicago
Looking for fun Chicago restaurant options? A perfect way to sample the city’s eats is to join a food tour in Chicago that takes you to a variety of eateries in one go. From new neighborhood highlights among Wicker Park restaurants or River North eateries to classic Chicago fine dining institutions, food tours can help you get a grasp on not only excellent menus but the most fun places to eat in Chicago. You can also find tours devoted to Chicago foods like deep-dish pizza and hot dogs Chicago-style.
Top 21 Fun Restaurants in Chicago
1. Three Dots and a Dash
Named after the Morse code designation of “V” for “victory,” this fun Chicago restaurant and exotic basement bar is just a couple of blocks off the Mag Mile. Three Dots and a Dash offers up a menu full of tropical rum-based concoctions, island-inspired entrées and vintage tiki-style décor.
The Vibe
A semi-secret alley entrance lit by torches gives way to a staircase lined with skulls that feels like a doorway descending into a tropical underworld. The interior is dark, candlelit and usually hopping with both tourists and locals.
What to Order
While their crispy coconut shrimp and their pu pu platter sampler are amazing, the tropical cocktails are really where Three Dots and a Dash excels, arriving in glasses shaped like skulls and mermaids bearing names like Jet Pilot and Strawberry Junglebird. And you should see what you get when you order shots.
Three Dots and a Dash | 545 N. Clark St., Chicago, IL 60654 | $$
2. The Wiener's Circle
A Lincoln Park institution, The Wiener’s Circle is known for fun and feisty service and their amazing Chicago-style hot dogs. Perched on Clark Street, they are a stone’s throw from the Wrigleyville nightlife corridor and open late until 2 a.m., making them a fun restaurant in Chicago every night of the week.
The Vibe
With indoor service and an outdoor window with seating, the vibe at this fun restaurant in Chicago is casual and lively. It’s also a great place to watch the bustle along Clark Street any time of day.
What to Order
A Chicago-style hot dog, of course, but just be sure not to ask for ketchup. They also have a selection of veggie dogs and burgers for non-meat eaters.
The Wiener's Circle | 2622 N. Clark St., Chicago, IL 60614 | $
3. Cindy’s Rooftop
With amazing views overlooking Millennium Park, the skyline and the lake, this popular rooftop restaurant in Chicago is a must-visit. Often making lists of fun Chicago restaurants, Cindy’s sits at the top of the beautiful and historic Chicago Athletic Club Hotel amid the cliff of buildings presiding over Michigan Avenue.
The Vibe
Casual but elevated, the lines downstairs for this popular eatery can sometimes be formidable, especially on weekends, but the beautiful rooftop locale is worth the wait. Reservations are recommended.
What to Order
With a rotating menu of family-style favorites, there is always something new. Try the roasted pork chops and the sweet potato rigatoni. Cindy’s is also known for summertime cocktails and boozy popsicles.
Cindy’s Rooftop | 12 S. Michigan Ave., Chicago, IL 60603 | $$
4. Carnivale
This Fulton Market district eatery’s colorful exterior and interior are hard to miss amid Chicago's more staid gray brick facades. A go-to for celebrations for every occasion, Carnivale is known for exquisite Latin-fusion fare and an extensive cocktail list with something for everyone.
The Vibe
Carnivale’s wild, colorful décor and bustling energy make it a perfect fun restaurant in Chicago for larger groups and free-flowing cocktails for hours set amid great Latin-inspired music. It’s often named as a great place for a birthday dinner in Chicago.
What to Order
Diners recommend the ropa vieja, a mix of shredded beef and vegetables, or an order of their famed fish tacos. Decadent dessert options include a chocolate dome cake, churros and cotton candy.
Carnivale | 702 W. Fulton Market, Chicago, IL 60661 | $$$
5. Gilt Bar
With an old-world speakeasy feel and an Italian-inspired menu of homemade pasta and seafood favorites, Gilt Bar is both a visual and culinary delight, making it a great option for a night out at a fun restaurant in Chicago.
The Vibe
A dark rich interior lined with Chesterfield-style booths makes this restaurant and bar a feast for the eyes. Dark wood paneling, dynamic artwork and a hall filled with photo booth images make every corner something new and interesting to take in.
What to Order
Gilt Bar is famous for homemade pasta, including truffle pasta and ricotta gnocchi, as well as their steamed mussels and roasted bone marrow. Try a cleverly-named signature cocktail from their menu, like the Airmail or the Monte Carlo.
Gilt Bar | 230 W. Kinzie St., Chicago, IL 60654 | $$$
6. Headquarters Beercade River North
If you’re looking for a touch of vintage video games and pinball while you dine, try Headquarters Beercade, just one of many video game-themed bars and fun restaurants in Chicago that are perfect for gamers and novices alike.
The Vibe
Lined with arcade games and filled with nostalgia, Headquarters is usually hopping and casual, with a large selection of beer, cocktails and pub-style favorites to enjoy while playing endless rounds of games like Pac-Man, Frogger and Donkey Kong on vintage machines.
What to Order
Try the Hurricane Fries, which feature everyone’s favorite potato under lime mayonnaise and a soy-ginger sauce sprinkled with nori and sesame seeds. Other favorites include various pizzas and the HQ Burger.
Headquarters Beercade River North | 1610 W. Institute Pl., Chicago, IL 60610 | $$
7. Cafe Ba-Ba-Reeba!
Known for large pitchers of sangria and its extensive tapas selection, this River North favorite is often listed as one of the most fun restaurants in Chicago, making it an equally great stop for a quick dinner or an endless night out with friends.
The Vibe
Cafe Ba-Ba-Reeba! boasts cozy interior dining and covered patio space, making it great for all seasons. Usually bustling with locals from all over the city, it’s particularly hopping during happy hour and weekends.
What to Order
Tapas are where it's at for this eatery, so make sure to try the chorizo-wrapped dates and the spinach and manchego-stuffed mushrooms. Other favorites include the beef tenderloin and the chicken paella.
Café Ba-Ba-Reeba! | 441 N. Clark St., Chicago, IL 60654 | $$
8. Recess
Perhaps the definition of fun, Recess banks on childhood nostalgia, featuring an expansive outdoor patio serving elevated classic fare and a huge selection of signature cocktails.
The Vibe
Decked out in bright, primary colors, the décor at this West Loop restaurant is energetic and playful, offering up a steady schedule of activities like trivia and board game nights. It's perfect for a low-key casual night out at a fun restaurant in Chicago.
What to Order
Diner favorites include the pizza mac and cheese and a selection of tasty burgers. Try the Nutella French toast as a brunch-time option on weekends.
Recess | 838 W. Kinzie St., Chicago, IL 60642 | $$
9. Frontier
If you are a lover of meats of all persuasions, Frontier may be your new favorite dining experience, offering up everything from wagyu beef to alligator. Located in Wicker Park, the restaurant's cozy lodge feel in the middle of a bustling urban center makes it a fun Chicago restaurant experience for diners looking for a tiny woodland escape without leaving the city.
The Vibe
The restaurant's forest lodge feel is augmented by wood planks, taxidermy and multiple fireplaces in a spacious dining room.
What to Order
Try an order of duck tacos or the pulled boar sandwich. As a group, you can also get a unique “whole animal” experience of various traditional meats and game meats like antelope and alligator.
Frontier | 1072 N. Milwaukee Ave., Chicago, IL 60642 | $$
10. Storyville
This tiny corner of New Orleans is tucked into the lively River North neighborhood, where Storyville’s exterior hides the rich dose of French-Quarter-inspired elegance contained in this fun Chicago restaurant.
The Vibe
Casual but glamorous, this fun restaurant in Chicago provides a low-lit and antique-filled nod to the South, lined with red booths, chandeliers and touches of neon and dynamic art.
What to Order
New Orleans favorites abound, including beignets, seafood gumbo and catfish nuggets. Try their bananas Foster for a sweet way to end the meal.
Storyville | 712 N. Clark St., Chicago, IL 60654 | $$
11. Red Lion Pub
In business for nearly 40 years along Lincoln Avenue, Red Lion Pub has inhabited its larger and stylishly remodeled footprint for the past decade, offering the unique feel of an old English pub.
The Vibe
This pub is cozy all year round but is an especially fun Chicago restaurant in winter, when the huge fireplace offers endless opportunities for lingering over a few ales. It also features Tudor-style trim, bookshelves and British memorabilia on the wall.
What to Order
Red Lion is famous for its fish and chips, of course, as well as a menu of English favorites like shepherd's pie and bangers and mash.
Red Lion Pub | 2446 N. Lincoln Ave., Chicago, IL 60614 | $$
12. Revolution Brewing
A great stop for beer lovers, Revolution Brewing is an on-site brewery with a formidable menu of both craft beers and food set amid a raucously fun Chicago restaurant atmosphere. They also offer regular tastings and tours.
The Vibe
Revolution Brewing is a casual, laid-back brewery. Their large open floor plan features windows displaying the brewing process and ample seating for dining and drinking for larger groups.
What to Order
Try the Hombre burger and the sweet potato cakes with a bowl of cheddar ale soup.
Revolution Brewing | 2323 N. Milwaukee Ave., Chicago, IL 60647 | $$
13. Venteux Brasserie Cafe & Oyster Bar
If your idea of amusement is bottomless mimosas or bloody marys, this fun restaurant in Chicago is a must-see. Located in the Pendry Hotel in the historic Carbide & Carbon Building, Venteux Brasserie is a Michigan Avenue favorite.
The Vibe
A little fancy and upscale, this light-filled space feels like a classic French bistro with celadon seating, towering floral murals and classic European elegance.
What to Order
Weekend brunches include bottomless mimosas, bloody marys and rosé, rounding out a menu of French bistro fare with a contemporary twist. Great choices include the croque monsieur, foie gras, steak frites and, of course, oysters.
Venteux Brasserie Cafe & Oyster Bar | Pendry Hotel Chicago, 224 N. Michigan Ave., Chicago, IL 60601 | $$$
14. Odyssey Chicago Brunch Cruise
With a focus on the Chicago River and its beautiful array of history and architecture, these luxurious Odyssey brunch cruises are offered each weekend and feature two-hour tours with a three-course brunch prepared by award-winning chefs, making this a fun alternative to traditional brunch restaurants in Chicago.
The Vibe
Learn about the city’s rich architectural history while floating and dining. With cocktail attire required, the experience has a formal and upscale feel perfect for special occasions.
What to Order
The brunch cruise includes bottomless mimosas with a menu that varies weekly, including breakfast favorites like pastries, eggs and French toast, as well as seafood, steak and a children’s section of kid-friendly foods.
Navy Pier | 600 E. Grand Ave. Navy Pier, Chicago, IL 60611 | $$$
15. BLVD Steakhouse
Inspired by old 1920s Hollywood glamor, BLVD Steakhouse offers a great backdrop for special occasions and fine dining with art deco design flair.
The Vibe
Definitely high-end and formal, the glittering interior takes you back decades into Hollywood glamor of old with rich velvet seats, chandeliers and jewel-colored interiors. The décor makes it a fun Chicago restaurant for old movie lovers.
What to Order
Options include American classics and delicacies like octopus, Alaskan King crab and grilled lamb chops with generous portions. Desserts include decadent strawberry cheesecake and crème brûlée.
BLVD Steakhouse | 817 W. Lake St., Chicago, IL 60607 | $$$$
16. The Signature Room
For one of the most stunning high-rise views of the city, the Signature Room can’t be beaten as a fun place to eat in Chicago. Located in the building formerly known as the John Hancock Center, this 95th-floor restaurant and lounge offers expansive views of the city and lake in all directions.
The Vibe
While the look and glittery vistas scream “formality,” you will have all levels of casual and formal in this popular spot, where jackets and ties are optional. It’s known for being a great place for special celebrations and a fun Chicago restaurant for getting engaged amid stunning views.
What to Order
The menu is traditional American fare, featuring a raw seafood bar, steaks, chicken dishes and appetizers. Try the lobster bisque and the miso honey-glazed salmon. There is also a cocktail lounge open later one floor above the restaurant.
The Signature Room | 875 N. Michigan Ave., Chicago, IL 60611 | $$$
17. Paradise Park
From the creators of the popular Home Slice and Happy Camper eateries, this RV tropical paradise-inspired restaurant serves up amazing pizza and cocktails in a festive environment. This is one fun restaurant in Chicago that oozes mid-century nostalgia.
The Vibe
Casual and largely outdoors, the Paradise Park patio is a bustling spot filled with tropical charm, RV park touches and neon accents, making it a fun Chicago restaurant and perfect destination for summer evenings.
What to Order
Paradise Park is known for its pizza, so try one of their signature pies like the Special K Pizza with Italian sausage, sun-dried tomatoes and ricotta or the Party Boi Pizza with pepperoni and pepperoncini.
Paradise Park | 1913 W. North Ave., Chicago, IL 60622 | $$
18. Kaiser Tiger
Billing itself as Chicago’s best beer garden. Kaiser Tiger is one of the most fun Chicago restaurants unique for its ample outdoor summertime activities, including bocce ball and bean bag tournaments. They also have an extensive beer selection and a unique bacon and sausage-filled menu.
The Vibe
Kaiser Tiger is perfect for summertime fun in the city when the bocce and bag competitions pack the beer garden with riotous fun.
What to Order
Regulars swear by the bacon-wrapped dates and the Bacon Grenades, which are beef and pork-wrapped meatballs. The Spicy Gaucho sandwich features Argentinian chorizo sausage topped with fresh guacamole and tequila sour cream.
Kaiser Tiger | 1415 W. Randolph St., Chicago, IL 60607 | $$
19. La Luna
This Pilsen favorite fun Chicago restaurant is a perfect spot for groups and larger celebrations, serving a host of new twists on Mexican favorites and generous pitchers of margaritas.
The Vibe
A colorful and lively hot spot, La Luna boasts colorful décor pulsing with Latin and jazz music every evening.
What to Order
They are famous for both their tacos and margaritas, so try washing down a carne asada or fish taco with a pitcher of their Luna margaritas.
La Luna | 1726 S. Racine Ave., Chicago, IL 60608 | $$$
20. Buddy Guy’s Legends
Blues and music fans love this historic bar and fun restaurant in Chicago that has hosted decades of performances in the South Loop. Buddy Guy’s South Loop location is two stories filled with artifacts and ephemera dedicated to the history of Chicago’s importance to the musical genre.
The Vibe
Casual and bustling, this low-lit spot features nightly performances by both newer acts and blues legends, including the famous Buddy Guy himself, who occasionally makes appearances.
What to Order
The menu is extensive and Cajun-inspired with favorites like po’boys, gumbo and a great selection of signature burgers.
Buddy Guy’s Legends | 700 S. Wabash Ave., Chicago, IL 60605 | $$
21. Machine Engineered Dining and Drink
This fun Chicago restaurant and bar combined with a flower shop offers unique combinations of cuisine and cocktails to suit all tastes, including creative Sips & Stems flower arranging nights.
The Vibe
Casual but upscale, Machine Engineered Dining and Drink has industrial and creative energy with a focus on offering a signature dining experience. They also offer a dog-friendly patio space with gourmet dog treats on the menu.
What to Order
Try the crispy chicken tacos or the unique duck gnocchi followed up with their almond cream blueberry pie. If you come for brunch (which you should at some point), the French toast is fantastic, as is the glazed pork and potato hash, made with Korean glaze and caramelized kimchi.
Machine Engineered Dining and Drink | 1846 W. Division St., Chicago, IL 60622 | $$
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Whether you are looking for a casual restaurant, an exciting night out in Chicago with friends or a formal dining occasion, there’s a wealth of fun restaurants in Chicago that are both entertaining and varied in cuisines, flavors, styles and vibes. Which spot is perfect for you?
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