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Best Fun Restaurants in Old Town

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32 restaurants available nearby

A photo of Utopian Tailgate restaurant
1. Utopian Tailgate
4.2
Awesome(185)
Price: Expensive
• American • Lincoln Park
Booked 18 times today
Utopian Tailgate is a fun spot for grownups, perched high up on Piper's Alley, offering a playground of elevated eats and a never-ending rooftop party. It's all about the fun vibes, with super-sized Jenga, drinking games, disco dance party, and more. Reviewers rave about the 'nice ambiance', 'great vibe', and 'fun games'. The diverse crowd, tasty food, and strong drinks only add to the fun.
A photo of Pizzeria Portofino restaurant
2. Pizzeria Portofino
4.8
Exceptional(1734)
Price: Expensive
• Italian • River North (Chicago)
Booked 160 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
3. Three Dots and a Dash
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. SUSHI-SAN - River North
4.7
Exceptional(1377)
Price: Moderate
• Japanese • River North (Chicago)
Booked 124 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
5. JoJo's ShakeBAR - River North
3.5
Very Good(2763)
Price: Moderate
• American • River North (Chicago)
Booked 36 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
6. Upstairs at The Gwen
4.1
Excellent(282)
Price: Expensive
• American • River North (Chicago)
Booked 36 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
7. Parlay River North
4.4
Awesome(64)
Price: Moderate
• Sports Bar • River North (Chicago)
Booked 19 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.
A photo of Robert's Pizza and Dough Company restaurant
8. Robert's Pizza and Dough Company
4.8
Exceptional(2126)
Price: Expensive
• Pizzeria • Gold Coast / Streeterville
Booked 110 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 Sapori Trattoria restaurant
9. Sapori Trattoria
4.7
Exceptional(4474)
Price: Moderate
• Italian • Lincoln Park
Booked 47 times today
Cozy Italian Restaurant serving fresh pasta & other authentic Italian dishes in Chicago's Lincoln Park & Lakeview Neighborhoods
A photo of La Storia restaurant
10. La Storia
4.7
Exceptional(1062)
Price: Expensive
• Italian • Gold Coast / Streeterville
Booked 14 times today
La Storia is a genuine Italian experience where guests share in the rich culture of the Italian table. Join us in Chicago’s historic gold coast neighborhood and enjoy faithful renditions of beloved regional dishes. Indulge in our specialty handcrafted pastas, made in house, daily in the Sardinian style.Patio seating is first come, first serve. In order to be seated, we ask that you arrive early and with your complete party. We ask guests to assist us by limiting the table times for parties: 2ppl (1hr 30mins), 3-4ppl (1hr 45mins), 5-6ppl (2hrs).

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Discover best fun restaurants in Old Town

Discover the vibrant dining scene in Old Town, Chicago, where the keyword "fun" truly comes to life in its selection of eateries. Whether you're looking for a lively atmosphere for a night out with friends or a cozy spot to enjoy some well-crafted cocktails and dishes, Old Town's dining options are sure to elevate your experience. Each restaurant in this bustling neighborhood boasts unique attributes, from exuberant settings and live music to creative culinary delights that keep the vibe energetic and engaging. Patrons can expect a variety of fun-themed restaurants that cater to all tastes, ensuring that every dining experience is not only delicious but also delightfully entertaining. The area is known for its eclectic mix of dining establishments that seamlessly blend great food and a fun atmosphere, making it a prime destination for those looking to add a little excitement to their mealtime. Enjoy the essence of Old Town where each meal is served with a side of amusement and joy, making it a perfect backdrop for creating memorable moments.

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