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Best Fun Restaurants in Chicago

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33 restaurants available nearby

A photo of Pizzeria Portofino restaurant
4.7
Exceptional(1509)
Price: Expensive
• Italian • River North (Chicago)
Booked 178 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(1815)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 58 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(1295)
Price: Moderate
• Japanese • River North (Chicago)
Booked 118 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(2044)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 67 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 JoJo's ShakeBAR - River North restaurant
3.6
Very Good(2665)
Price: Moderate
• American • River North (Chicago)
Booked 150 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 Upstairs at The Gwen restaurant
4.1
Excellent(247)
Price: Expensive
• American • River North (Chicago)
Booked 14 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 Parlay River North restaurant
4.5
Awesome(40)
Price: Moderate
• American • River North (Chicago)
Booked 19 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 Parlor Pizza Bar - River North restaurant
4.7
Exceptional(900)
Price: Moderate
• American • River North (Chicago)
Booked 37 times today
For more information please email info@parlorchicago.com . Entire party must be present to be seated.
A photo of Azul restaurant
4.2
Awesome(983)
Price: Expensive
• Seafood • Goose Island
Booked 10 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 Fulton Market Kitchen restaurant
3.7
Very Good(701)
Price: Expensive
• Contemporary American • West Loop
Booked 4 times today
Inspired by the 1980s NYC art scene and the Wynwood Walls in Miami, Fulton Market Kitchen offers guests the rare opportunity to enjoy dining, drinking, and the work of incredible artists in a single, truly unique setting. Executive FMK presents a refined, contemporary American cuisine with a global influence. We offer seasonal presentations with ingredients sourced from regional farms, local markets, and our neighbors from Fulton Market Street. FMK's Bar Team, delivers one of the West Loop’s most innovative cocktail programs, executed with fresh ingredients and small batch spirits pulled from a carefully curated collection. Together they have developed an impressive spirit list that boasts over 650 bottles with a special focus on hand-selected barrels, limited allocations, and rare vintages.

See what locals rave about

From verified diners like you
From verified diners like you
  • April
    Utah •2 reviews
    4.0
    Dined 1 day ago
    Came to enjoy the holiday and Christmas themed items and ambiance. Overall, it was a fun atmosphere that’s great for friends, family, or a date environment to enjoy. Do not recommend the food, but do recommend going for any of the shakes or hot chocolates!
    More info
    JoJo's ShakeBAR - River NorthPrice: Moderate• American• River North (Chicago)
    3.6
  • Michellevip
    Denver / Colorado •10 reviews
    5.0
    Dined 1 day ago
    A lively restaurant on the Ogden slip featuring delicious pizza along with a selection of very good italian options. Very busy but the wait staff is friendly, knowledgable and attentive. Well worth a visit...but I suggest you make a reservation given this is a very popular restaurant!
    More info
    Robert's Pizza and Dough CompanyPrice: Expensive• Pizzeria• Gold Coast / Streeterville
    4.8
  • Teresa
    Chicago / Illinois •1 review
    5.0
    Dined 2 days ago
    The food is delicious!!! The service was amazing!!! We really enjoyed our time in the restaurant. It’s a great location, friendly staff and worth the visit!!! Teresa
    More info
    Pizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)
    4.7
  • Roy
    Chicago / Illinois •1 review
    5.0
    Dined 5 days ago
    Shout out to Bamboo Room bartender and rum expert Taylor for another fantastic experience! My wife and I are regular guests at Bamboo Room, which never disappoints. But on this particular trip, I ordered two rounds of the Bamboo Daiquiri - this was my first time with that drink. The guest is offered to choose a blend of three rums with just a touch of lime and sugar. Taylor asked me if I had a preference, but I asked him to please put one together for me and I'd like to learn from it. The results were spectacular. He made two different daiquiri's with three rums - both were delicious and were two different drinks based on the rums he chose. The he offered to give me a sip of each rum and walked me through the characteristics. What a great experience, and we look forward to having drinks with Taylor again!
    More info
    Three Dots and a DashPrice: Expensive• Cocktail Bar• River North (Chicago)
    4.8
  • Marlena Roseboro
    Raleigh / Durham / Chapel Hill •6 reviews
    5.0
    Dined 5 days ago
    Sushi-San was an incredible experience! Watching the sushi being made fresh right in front of me was such a treat—absolutely top-notch. The drinks, food, and music created an energetic vibe that made me want to dance while savoring every bite. Everything exceeded expectations, and nothing fell short. I can’t wait to visit again the next time I’m in Chicago!
    More info
    SUSHI-SAN - River NorthPrice: Moderate• Japanese• River North (Chicago)
    4.8
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