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Best Fun Restaurants in Downtown / Loop

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34 restaurants available nearby

A photo of Pizzeria Portofino restaurant
4.7
Exceptional(1480)
Price: Expensive
• Italian • River North (Chicago)
Booked 57 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(1805)
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 Robert's Pizza and Dough Company restaurant
4.8
Exceptional(2022)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 31 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
4.8
Exceptional(1283)
Price: Moderate
• Japanese • River North (Chicago)
Booked 34 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 Upstairs at The Gwen restaurant
4.2
Awesome(241)
Price: Expensive
• American • River North (Chicago)
Booked 17 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
3.9
Excellent(2623)
Price: Moderate
• American • River North (Chicago)
Booked 69 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(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
A photo of Parlor Pizza Bar - River North restaurant
4.6
Exceptional(897)
Price: Moderate
• American • River North (Chicago)
Booked 20 times today
For more information please email info@parlorchicago.com . Entire party must be present to be seated.
A photo of 10pin Bowling Lounge restaurant
4.6
Exceptional(416)
Price: Expensive
• American • River North (Chicago)
Booked 4 times today
10pin is a Chicago original located in the heart of River North, along the Chicago River. Next to the House of Blues, 10pin offers 20,000 square feet of 24 luxury bowling lanes, ping pong, pool table and table shuffleboard games that cater to all group sizes. When reserving a table on OpenTable you are reserving the lane and table! The rates are $25/hour per person plus shoe rental. For information on booking an event or for groups of 13 or more, please call our event sales team at 312-644-0100. Guests must be 21 beginning at 8pm. Dress code will be enforced, including pants at waist level. 10pin has the right to include any clothing deemed inappropriate. No outside food or drinks. Management has the right to refuse entry to anyone acting in a rude or disrespectful manner.
A photo of Bub City restaurant
4.7
Exceptional(1511)
Price: Expensive
• Barbecue • River North (Chicago)
Booked 7 times today
Bub City is the destination for barbecue, whiskey and live country music and is open for lunch, dinner, weekend brunch and late night dining. The Southern spot offers house-smoked BBQ, more than 125 different whiskeys from well-known and independent distilleries throughout the country and live country music.

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Discover best fun restaurants in Downtown / Loop

Discover the vibrant dining scene in Downtown / Loop, Chicago, where a variety of restaurants offer an exciting and fun atmosphere perfect for any occasion. Whether you're looking for a lively spot with a festive decor or a cozy place with a comfortable ambiance, the area is teeming with options that promise a delightful dining experience. These establishments are celebrated for their exceptional service, high-quality food, and welcoming environments. From fresh seafood to classic Chicago fare and festive Irish pubs, each restaurant brings its own unique flair to the table, ensuring an enjoyable meal out. The dining scene here is versatile, catering to both casual outings and special celebrations, making it a prime destination for food lovers. Indulge in a culinary adventure where the food is as enjoyable as the atmosphere, and experience firsthand why these restaurants are a hit for anyone looking for a fun time in Chicago.

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