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Best Fun Restaurants in Chicago

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33 restaurants available nearby

A photo of Pizzeria Portofino restaurant
4.8
Exceptional(1487)
Price: Expensive
• Italian • River North (Chicago)
Booked 215 times today
Pizzeria Portofino is a sun-drenched casual restaurant located directly on the Chicago riverfront offering hand-stretched pizzas, coastal wines, an expansive patio and breezy decor that will instantly transport you to the Italian Riviera.
A photo of Three Dots and a Dash restaurant
4.8
Exceptional(1812)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 83 times today
With a secret alleyway entrance, Three Dots and a Dash is a speakeasy-style take on the traditional island bar—ready to transport you to the glamorous bygone eras of Trader Vic, Stephen Crane and Don the Beachcomber. Descend underground to discover a subterranean hideaway featuring a rum-soaked menu of more than two dozen classic, modern and original tropical cocktails and a selection of island fare. We are a 21+ venue.
A photo of SUSHI-SAN - River North restaurant
4.8
Exceptional(1288)
Price: Moderate
• Japanese • River North (Chicago)
Booked 121 times today
Sushi-San serves up the best sushi in Chicago made with the freshest ingredients they can find, all served with a side of old-school hip-hop and ice-cold beer. The bar is kept stocked with rare Japanese whisky, sake, wine and inventive cocktails. Join them for lunch and dinner.
A photo of Robert's Pizza and Dough Company restaurant
4.8
Exceptional(2025)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 99 times today
Robert's Pizza and Dough Company serves it's award winning thin-crust artisanal pizzas with fresh and unique ingredients.
A photo of Upstairs at The Gwen restaurant
4.2
Awesome(244)
Price: Expensive
• American • River North (Chicago)
Booked 27 times today
Experience the premier terrace in River North, located on the 5th floor of The Gwen, a one MICHELIN Key hotel, nestled along the iconic Magnificent Mile! Savor creative cocktails and indulge in delicious small and large plates crafted by Executive Chef Matt Jergens, all while enjoying the warm ambiance of our firepits and the stunning backdrop of towering skyscrapers. Our candlelit indoor lounge and bar offer the perfect setting to unwind, relax, and embrace the good life!Join us on the weekends for Chicago's liveliest, most unique tea service, Tipsy Tea! Featuring scrumptious savory and sweet bites, bottomless beverages, a DJ spinning, and a special themed menu every month, this is one pinkies-down tea service you will never forget!
A photo of JoJo's ShakeBAR - River North restaurant
3.8
Excellent(2642)
Price: Moderate
• American • River North (Chicago)
Booked 155 times today
JoJo’s ShakeBAR is a next-generation restaurant and bar, and River North’s next go-to spot for hangouts, first dates, and family affairs. Its’ modern, yet familiar, diner experience is grounded in nostalgia and focuses on creative desserts and elevated diner favorites.Outdoor Patio Seating is available for reservations and walk-ins. In the case of inclement weather, our team will do our best to accommodate outdoor patio reservations inside, but indoor seating is not guaranteed. Reservations Are Highly Recommended & Walk Ins Are Available Based Upon Availability.
A photo of Parlay River North restaurant
4.4
Awesome(36)
Price: Moderate
• American • River North (Chicago)
Booked 14 times today
Parlay River North, located within the vibrant Joy District at 112 W Hubbard St, offers a high-energy sports bar experience perfect for both casual outings and lively nights out. This modern sports parlor on the first floor serves elevated bar fare alongside a curated selection of drinks in a dynamic and engaging atmosphere. Guests can enjoy American classics while watching the latest sports events on numerous big screens, ensuring they never miss a moment of the action. The stylish and comfortable setting, inspired by contemporary trends, provides a welcoming space for sports enthusiasts and casual visitors alike.Whether you're here for the game, a night out with friends, or a private event, Parlay River North promises a memorable experience with its vibrant ambiance and top-notch service. Come for the sports, stay for the food, drinks, and unbeatable energy.NO OUTSIDE LIQUOR,NO BIG BAGS, 1 BAG PER PERSON, NO RUBBER SOLES…Exceptions can be made on a case by case basis
A photo of Azul restaurant
4.2
Awesome(982)
Price: Expensive
• Seafood • Goose Island
Booked 4 times today
Located along the Chicago river in the burgeoning Goose Island neighborhood, Azul is an upscale mariscos (seafood) restaurant serving an expansive menu of Latin-inspired fare. The concept aims to combine the ethos of an authentic mariscos restaurant with modern hospitality practices and all the touches of a sophisticated, lively spot.Celebrating the rich flavors and fresh ingredients of Latin culinary culture, Azul’s chef-driven menu is brimming with refined representations of classic mariscos cuisine. Created by Executive Chef Michael Hernandez, Azul offers a variety of grilled, baked, fried and raw proteins as well as ceviches, seafood, cocktails and artfully arranged family-style platters.
A photo of Parlor Pizza Bar - River North restaurant
4.7
Exceptional(900)
Price: Moderate
• American • River North (Chicago)
Booked 35 times today
For more information please email info@parlorchicago.com . Entire party must be present to be seated.
A photo of Recess restaurant
4.4
Awesome(1465)
Price: Expensive
• American • West Loop
Booked 5 times today
Located in Chicago’s West Loop, Recess (838 W. Kinzie St.) offers a vibrant, playful, escape to the daily grind. Home of Chicago’s largest patio, Recess encourages guests to adult…like a kid, while serving up delicious American food and drink. The Recess menu taps into the cravings of everyday life, offering casually elevated dishes with playful Chicago swagger, while our beverage program takes a bright, ingredient-driven approach with cocktails both classic and original. In addition to the energetic adult playground vibes and menu offerings, Recess also offers a nostalgic array of indoor and outdoor activities including giant Jenga and Connect 4, all of your favorite board games.Recess is a 21+ establishment.

See what locals rave about

From verified diners like you
From verified diners like you
  • Jackievip
    Chicago / Illinois •13 reviews
    5.0
    Dined 1 day ago
    Had a wonderful time at this unique location! Will be back!
    More info
    Three Dots and a DashPrice: Expensive• Cocktail Bar• River North (Chicago)
    4.8
  • Courtney
    Chicago / Illinois •3 reviews
    5.0
    Dined 1 day ago
    I have been eagerly trying to secure a reservation at Pizza Portofino for quite some time, and I was absolutely thrilled when I finally had the opportunity to dine there. From the moment I walked in, the restaurant's coastal ambiance immediately set the tone for a truly exceptional experience. The drinks were superb, and the food was nothing short of extraordinary. I highly recommend the whipped ricotta and fig bruschetta, the crispy parmesan fries, the meatballs, the black truffle and three cheese pizza, and the sausage and fennel pizza – though honestly, I believe you can't go wrong with any dish on the menu. While the food and drinks were phenomenal, what truly set this experience apart was the exceptional service. From the bartenders, who were so welcoming as we enjoyed a few cocktails while waiting for our table, to our attentive server, every member of the team exceeded expectations. However, it was the manager, Heather, who truly stood out. Her warmth and hospitality made us feel incredibly special, and she went above and beyond to ensure our experience was memorable.
    More info
    Pizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)
    4.8
  • danielle
    Grand Rapids / Western Michigan •1 review
    5.0
    Dined 4 days ago
    I was here a few years ago and remembered how fantastic it was, so I suggested it for a group lunch for some people coming out of town!
    More info
    SUSHI-SAN - River NorthPrice: Moderate• Japanese• River North (Chicago)
    4.8
  • Marilyn
    San Diego •5 reviews
    5.0
    Dined 5 days ago
    We had a terrific Thanksgiving at the Gwen. Our grandchildren were treated royally and we all enjoyed the food and service.
    More info
    Upstairs at The GwenPrice: Expensive• American• River North (Chicago)
    4.2
  • Scottvip
    Chicago / Illinois •12 reviews
    5.0
    Dined on Nov 26, 2024
    The Detroit Pizzas on Tuesday nights are a delicious addition to the menu!
    More info
    Robert's Pizza and Dough CompanyPrice: Expensive• Pizzeria• Gold Coast / Streeterville
    4.8
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