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Best Fun Restaurants in Streeterville

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34 restaurants available nearby

A photo of Upstairs at The Gwen restaurant
1. Upstairs at The Gwen
4.2
Awesome(243)
Price: Expensive
• American • River North (Chicago)
Booked 13 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 Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile) restaurant
2. Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile)
4.7
Exceptional(2327)
Price: Expensive
• Japanese • River North (Chicago)
Booked 81 times today
Founded in Tokyo in 1996, Gyu-Kaku has become the world’s #1 Japanese BBQ brand! Thanks to our devoted fans we have reached over 700 locations worldwide. Each day, hundreds of thousands of people gather around the table-top smokeless grill, a centerpiece of our dining concept, enjoying selections of premium meats, just off the grill, and other freshly prepared foods from our kitchens, inspiring laughter, conversation, and a magical dining experience.Our authentic yakiniku (grilled barbeque) dining experience crowns you the chef. Share a variety of delicious appetizers and premium cooked meats over a flaming grill, paired with Japanese sake, frosty cold beers, or other alcoholic and non-alcoholic options of your choice. We're the perfect spot to enjoy time with friends and family, organize an office party, or to spend quality time with your significant other!Before you go, don't forget to taste our best-seller Harami Skirt Steak or Prime Kalbi Short Rib among other must-try dishes!
A photo of Sugar Factory - Chicago River North restaurant
3. Sugar Factory - Chicago River North
4.0
Excellent(4779)
Price: Moderate
• American • River North (Chicago)
Booked 52 times today
Sugar Factory - Chicago River North is a fun place with a unique atmosphere. Customers praise it as a great family place and a must-visit location in Chicago. It offers a wide variety of food, from pancakes to steaks, and is particularly famous for its sweet treats, like Couture Pops and King Kong Sundae. The reviews suggest that it's a lively and kid-friendly place with great service, making it a perfect spot for a family celebration or a fun date night.
A photo of The Berkshire Room restaurant
4. The Berkshire Room
4.6
Exceptional(47)
Price: Moderate
• Cocktail Bar • River North (Chicago)
Booked 7 times today
The Berkshire Room is an upscale lounge specializing in craft cocktails all created by a talented team. The atmosphere is retro classy and definitely worth a visit before or after dinner for cocktails with friends. There is ample seating either in the private side rooms, the booths in the lounge area or at the bar. The clientele that frequent the Berkshire Room rave about the dealers' choice, which allows guests to choose the spirit, flavor profile and glassware. The bartender then customizes a unique and customized cocktail. Besides the tasty cocktails and the relaxing ambiance, the Berkshire also offers bar snacks and small dishes. The Berkshire room is located within River North's swanky ACME hotel.
A photo of Pizzeria Portofino restaurant
5. Pizzeria Portofino
4.7
Exceptional(1480)
Price: Expensive
• Italian • River North (Chicago)
Booked 85 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
6. Three Dots and a Dash
4.8
Exceptional(1806)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 63 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 Robert's Pizza and Dough Company restaurant
7. Robert's Pizza and Dough Company
4.8
Exceptional(2025)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 96 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 SUSHI-SAN - River North restaurant
8. SUSHI-SAN - River North
4.8
Exceptional(1283)
Price: Moderate
• Japanese • River North (Chicago)
Booked 102 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 JoJo's ShakeBAR - River North restaurant
9. JoJo's ShakeBAR - River North
3.8
Excellent(2627)
Price: Moderate
• American • River North (Chicago)
Booked 221 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
10. Parlay River North
4.4
Awesome(35)
Price: Moderate
• American • River North (Chicago)
Booked 6 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
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

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