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Best Fun Restaurants in Downtown / Loop

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33 restaurants available nearby

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A photo of Chateau Carbide restaurant
4.2
Awesome(229)
Price: Expensive
• Cocktail Bar • River North (Chicago)
Booked 91 times today
Bonjour, summer. Meet us on the rooftop for another season atop Chicago’s stunning skyline at Château Carbide, a French-inspired cocktail lounge where hotel guests and locals alike can take in the city’s summer splendor with crisp Möet & Chandon, icy signature cocktails, a spring menu of small bites and favorites, live DJs every weekend, and views…forever. Wednesdays & Thursdays, from 5:00pm to 11:00pm.Fridays & Saturdays, from 5:00pm to 12:00am.Please note the following policies:**Chateau Carbide is a 21+ establishment**Light Bite service is available until 10:00 PM**Outdoor tables are subject to availability, and a reservation does not constitute an outdoor table. We do our best to accommodate all guest seating requests. **Reservations are encouraged but not required, subject to availability.
A photo of Wonderland at Tree House restaurant
4.3
Awesome(299)
Price: Moderate
• Italian • River North (Chicago)
Booked 32 times today
✨ Fall down the rabbit hole into Wonderland—Chicago’s newest pop-up experience where curiosity leads to magic and every corner tells a story! 🌸💫 Think Mad Hatter tea parties, dreamy cocktails, oversized blooms, and photo ops straight out of your wildest imagination.From playful surprises to enchanting decor, Wonderland is the perfect escape for dreamers, romantics, and anyone craving a night unlike any other. Whether you're sipping a "Drink Me" potion or striking a pose with the Queen of Hearts, expect an unforgettable adventure full of charm and cheek.Bring your curiosity, your crew, and your best Wonderland look—it’s time to get wonderfully lost! 🐇
A photo of The Smith - Chicago restaurant
4.7
Exceptional(2856)
Price: Moderate
• American • River North (Chicago)
Booked 102 times today
The Smith is a casual American brasserie with a simple mission — make people happy! We care about every meal and every moment. The menu features bistro classics, seasonal fare, and craft cocktails. Walk in the door and you’re in for a great time. Whether it’s date night, drinks on the town, a big birthday bash, a working lunch, a boozy brunch, or an I-don’t-want-to-cook-tonight night, we’ve got you covered.
A photo of Starbucks Reserve® Chicago Roastery restaurant
4.8
Exceptional(49)
Price: Expensive
• Café • River North (Chicago)
Booked 6 times today
The World's Largest Starbucks.A spectacular destination. Our passion for craft, innovation, and discovery comes to life in an ever-evolving menu of coffee, cocktails and food.An immersive and thoughtfully designed experience, this one-of-a-kind space will bring your event to life in a uniquely memorable way.
A photo of Upstairs at The Gwen restaurant
4.2
Awesome(309)
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 10pin Bowling Lounge restaurant
4.6
Exceptional(427)
Price: Expensive
• American • River North (Chicago)
Booked 13 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 Ghost Donkey - River North restaurant
4.6
Exceptional(58)
Price: Moderate
• Bar / Lounge / Bottle Service • River North (Chicago)
Booked 16 times today
A warm and inviting space with a healthy dose of city grit, Ghost Donkey is rich with vibrant colors and a carefree, fun-loving attitude that evokes notions of Mexican celebration. A true high-low nightlife destination with elevated mezcal and tequila-focused cocktails, classic bites with just enough twist to keep your palette guessing, and an extensive mezcal and tequila list. Ghost Donkey creates an experience-driven, unforgettable moment for every guest that joins the fiesta. Immerse yourself in the heart and soul of Mexican Hospitality while savoring sips of agave-based spirits. Kick back, relax, and enjoy the show, or break out a dance move underneath the sway of the swinging lights.
A photo of Offshore Rooftop restaurant
4.3
Awesome(2802)
Price: Moderate
• Contemporary American • Gold Coast / Streeterville
Booked 97 times today
Offshore is a bright and airy rooftop bar open year-round on the third floor at the East end of Navy Pier. With collapsable floor to ceiling windows you get sweeping views of Lake Michigan and Chicago’s city skyline. Our globally inspired menu features items from coast to coast that include light to substantial fares. Outdoor seating is not guaranteed! It is on a first come first served basis.21 years of age and older after 9pm daily.The last reservation is one hour before closing.
A photo of JoJo's ShakeBAR - River North restaurant
3.9
Excellent(2781)
Price: Moderate
• American • River North (Chicago)
Booked 25 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 Happy Camper Pizza - Old Town restaurant
4.7
Exceptional(637)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 58 times today
Minors must be accompanied by parent or guardian for entry. A valid ID is required for guests age 21+.A chic, outdoorsy pizza haven located in Old Town. Happy Camper boasts a décor that includes Airstream trailers, neon renditions of the Great Lakes, warm wooden accents, and tire swing seating around the bar. A wide variety of colorful pizzas and delicious appetizers await you.F*ckin' Charity Bingo on Sundays at 1:30pm is sat on a first come first serve basis. All reservations will be sat in the non-bingo area.We cannot guarantee inside or outside seating.Neighborhood ordinances require our patio to close by 12am. Your table is weather permitting. If there is inclement weather, Happy Camper reserves the right to cancel your reservation. If you are dining when inclement weather occurs your food will be packed and given your bill. You are more than welcome to head to the bar afterward.

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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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