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Best Fun Restaurants in Streeterville

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32 restaurants available nearby

A photo of Upstairs at The Gwen restaurant
4.1
Excellent(282)
Price: Expensive
• American • River North (Chicago)
Booked 31 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
4.7
Exceptional(2349)
Price: Expensive
• Japanese • River North (Chicago)
Booked 37 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
3.6
Very Good(4825)
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
4.5
Awesome(59)
Price: Moderate
• Cocktail Bar • River North (Chicago)
Booked 11 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
4.8
Exceptional(1734)
Price: Expensive
• Italian • River North (Chicago)
Booked 187 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(1902)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 47 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
4.7
Exceptional(1377)
Price: Moderate
• Japanese • River North (Chicago)
Booked 127 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
3.5
Very Good(2763)
Price: Moderate
• American • River North (Chicago)
Booked 33 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 Robert's Pizza and Dough Company restaurant
4.8
Exceptional(2126)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 104 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 Parlay River North restaurant
4.4
Awesome(64)
Price: Moderate
• Sports Bar • River North (Chicago)
Booked 20 times today
A lively ultramodern sports bar located on the first floor of Joy District, Parlay River North, is a haven for Chicago locals and sports fans alike. Surrounded by multiple high definition televisions Parlay River North offers elevated bar fare complemented with thirst quenching beverages.
‘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.

See what locals rave about

From verified diners like you
From verified diners like you
  • Maria
    Chicago / Illinois •3 reviews
    4.0
    Dined 1 day ago
    Overall our server was great…. I was taken by surprise that we were charge 20% service fee and told by the waiter that it doesn’t go to them. It goes to paying every hosts hourly wages and if we did extra tip he would then get that . Like WTH….. don’t be shady like that to the poor waiter. Also don’t tell me toward the end and why do i have to pay everyone’s hourly pay, prices are already high. I felt bad for the waiter because he was great and of course gave him extra . However Wouldn’t go again base on the companies ethics of charging us even more because they have to pay hourly wages not my fault.
    More info
    Sugar Factory - Chicago River NorthPrice: Moderate• American• River North (Chicago)
    3.6
  • Ellen
    Washington, D.C. Area •1 review
    5.0
    Dined 3 days ago
    Accommodations were exceptional, food was excellent and our server went above and beyond!
    More info
    Pizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)
    4.8
  • IanVIP
    Phoenix / Arizona •7 reviews
    4.0
    Dined 5 days ago
    Always a great spot for some cocktails. The atmosphere is very intimate and the dealers choice is a fun and easy way to try some new profiles of drinks. Went with a group of friends and everyone was happy with the experience. Great option for a date or some drinks before going out.
    More info
    The Berkshire RoomPrice: Moderate• Cocktail Bar• River North (Chicago)
    4.5
  • JosephVIP
    Chicago / Illinois •6 reviews
    4.0
    Dined 5 days ago
    Had a coupon from Hugo Boss. At first the waiter was not happy about it and went to check with management. Once it was clear that the coupon was acceptable he was an attentive waiter. The food was great especially the curried peanuts!
    More info
    Upstairs at The GwenPrice: Expensive• American• River North (Chicago)
    4.1
  • OpenTable Diner
    Chicago / Illinois •1 review
    5.0
    Dined on 4 Mar 2025
    Had a 5 star experience at dinner with 10 other gentlemen. They were gracious and put us on the 3rd floor with the in-ground dinning long table. The food was delicious, cooking at our own desired pace and level made it that much more enjoyable. Would highly recommend to anyone going with a big group looking to have a great dinner or celebrate with friends.
    More info
    Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile)Price: Expensive• Japanese• River North (Chicago)
    4.7
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