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Best Fun Restaurants in Old Town

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45 restaurants available nearby

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A photo of Utopian Tailgate restaurant
1. Utopian Tailgate
4.1
Excellent(200)
Price: Expensive
• American • Lincoln Park
Booked 28 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 SUSHI-SAN - River North restaurant
2. SUSHI-SAN - River North
4.8
Exceptional(1433)
Price: Moderate
• Japanese • River North (Chicago)
Booked 133 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 Happy Camper Pizza - Old Town restaurant
3. Happy Camper Pizza - Old Town
4.7
Exceptional(642)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 52 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.
A photo of Parlay River North restaurant
4. Parlay River North
4.0
Excellent(97)
Price: Moderate
• Sports Bar • River North (Chicago)
Booked 20 times today
Located in the heart of River North, Parlay at Joy District is a lively, ultramodern sports bar perfect for catching the game, weekend brunch, or after-work happy hour. With high-definition TVs throughout, elevated bar fare, and thirst-quenching cocktails, it's a go-to for Chicago locals and sports fans alike. The vibrant atmosphere and versatile private event space make Parlay River North ideal for game days, group gatherings, and special celebrations.
A photo of Frontier restaurant
5. Frontier
4.7
Exceptional(601)
Price: Expensive
• American • West Town
Booked 31 times today
Frontier's Executive Chef Brian Jupiter has created mouthwatering dishes celebrating American contemporary cuisine, blending game and other seasonal ingredients into classic and approachable fare.The seasonal dinner menu includes small plates, vegetables, sandwiches and entrees designed to share. Frontier’s menu also features 8-10 varieties of oysters to order a la carte with dinner, or to enjoy with a bottle of beer at the bar. Over the weekend, patrons may indulge in brunch offerings including a wide selection of Frontier signature dishes alongside traditional brunch items. Complimenting Frontier's savory menu items are unique wines by the glass & bottle, specialty craft cocktails including creative punches and frozen cocktails along with an array of draft, canned and bottled beer.Frontier is closed Monday & Tuesday but will open for private events along with Sunday evenings & weekday afternoons. Email jen@pioneertaverngroup.com to inquire today!
A photo of Olio e Più - Chicago restaurant
6. Olio e Più - Chicago
4.5
Awesome(1244)
Price: Expensive
• Italian • River North (Chicago)
Booked 93 times today
OLIO E PIÙ brings Italian tradition and true sense of Mediterranean liveliness to the vibrant neighborhood in Chicago.As an authentic trattoria, its cuisine is based on classic Italian dishes. As you dine at OLIO E PIÙ, you’ll be transported not just by the flavors of Italy but also by the authentic atmosphere that surrounds you. It’s a place where time slows down, and conversations flow freely, just as they do in a true Italian household. Here, the spirit of 1970s Italian elegance lives on, and every meal is a celebration of life, love, and the joy of shared moments, especially with the open kitchen concept.OLIO E PIÙ is more than just a restaurant; it’s a portal to a different time and place, where the essence of Italy’s rich culinary and cultural heritage is captured in every detail.*Please note that kitchen hours may differ.
A photo of Wonderland at Tree House restaurant
7. Wonderland at Tree House
4.3
Awesome(307)
Price: Moderate
• Italian • River North (Chicago)
Booked 48 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 Hubbard Inn - River North restaurant
8. Hubbard Inn - River North
4.3
Awesome(230)
Price: Expensive
• American • River North (Chicago)
Booked 9 times today
Located among an ever growing number of River North restaurants in Chicago, Hubbard Inn creates a unique dining experience with delicious options for brunch, dinner, late night dining and everything in between.Whether you're looking for an intimate dinner for two, a table for a large group, or a late night restaurant, Hubbard Inn is the perfect option for out-of-town guests and locals on the hunt for dinner and drinks or a quick bite to eat!
A photo of La Storia restaurant
9. La Storia
4.5
Awesome(1095)
Price: Expensive
• Italian • Gold Coast / Streeterville
Booked 10 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).
A photo of Sapori Trattoria restaurant
10. Sapori Trattoria
4.7
Exceptional(4502)
Price: Moderate
• Italian • Lincoln Park
Booked 51 times today
Cozy Italian Restaurant serving fresh pasta & other authentic Italian dishes in Chicago's Lincoln Park & Lakeview Neighborhoods

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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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