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Best Restaurants for People Watching in Old Town

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37 restaurants available nearby

A photo of Tre Dita restaurant
4.8
Exceptional(947)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 101 times today
Led by Chef Evan Funke, Tre Dita, Italian for "three fingers", pays homage to the precise measurement of bistecca Fiorentina. If booking in the dining room at Tre Dita, you will enjoy a menu of antipasti, handmade pastas, signature entrees and steaks. If booking in the Bar Tre Dita, you will enjoy a smaller menu of stuzzi, antipasti, handmade pastas and entrees. The full cocktail, wine list and dessert menu is available in both locations.Please note that Tre Dita only accepts reservations 7 days in advance.
A photo of Happy Camper Pizza - Old Town restaurant
4.8
Exceptional(614)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 23 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 Quartino - Chicago restaurant
4.6
Exceptional(11080)
Price: Moderate
• Italian • River North (Chicago)
Booked 110 times today
Quartino Ristorante is a lively, authentic Italian restaurant and wine bar in Chicago's River North neighborhood. Our menu features Italy's regional specialties including artisanal salumi, Neapolitan thin-crust pizza, house-made pasta, and seasonal dishes. Menu items, served in moderate portions and meant to be shared, are perfect for adventurous diners ready for a unique experience.
A photo of RPM Italian - Chicago restaurant
4.6
Exceptional(12346)
Price: Expensive
• Italian • River North (Chicago)
Booked 92 times today
Located in Chicago’s River North neighborhood, RPM Italian is modern in approach and Italian in spirit, featuring a contemporary menu with dishes meant to be shared. The sister restaurant to RPM Steak and RPM Seafood, RPM Italian marks the first collaboration between partners RJ, Jerrod and Molly Melman of Lettuce Entertain You Enterprises and celebrity couple Giuliana & Bill Rancic.
A photo of Tavern on Rush restaurant
4.5
Awesome(3669)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 42 times today
Tavern On Rush is the premier dining destination for steaks & seafood in Chicago. The upscale, contemporary steakhouse features multi-level seating, private dining, a bustling bar, and Chicago's favorite outdoor patio.
A photo of Jake Melnick's Corner Tap restaurant
4.5
Awesome(324)
Price: Moderate
• American • Gold Coast / Streeterville
Booked 17 times today
Come for the wings, stay for the party! Jake Melnick's Corner Tap has been a neighborhood favorite since opening its doors in 2002. The menu features mouth-watering BBQ dishes, classic American pub-fare and world-famous chicken wings – named the “Top Chicken Wings in the U.S.” by the Today Show. Relax and sip on local craft beers while you catch the game or enjoy a casual night out. The cozy indoor dining room and picturesque patio make it the perfect choice any time of year.
A photo of LAUREL restaurant
4.4
Awesome(35)
Price: Expensive
• American • River North (Chicago)
Booked 3 times today
LAUREL, nestled in Chicago's iconic Talbott Hotel, blends New American creativity with Mediterranean flavors, sourcing local and seasonal ingredients. Experience Mediterranean warmth paired with cosmopolitan flair in our full-service yet casual setting, offering a culinary journey for any occasion. Our design pays homage to the Mediterranean's diverse landscapes and artistic influences, creating a modern ambiance. Welcome to LAUREL, where craftsmanship meets creativity, and every meal celebrates flavor, community, and the art of living well.
A photo of Legal Sea Foods - Chicago restaurant
4.0
Excellent(300)
Price: Expensive
• Seafood • River North (Chicago)
Booked 17 times today
Legal Sea Foods Chicago is now open along the vibrant Riverwalk in the bustling River North neighborhood at the famous Marina Towers. Legal's first Midwest location features two floors of upscale casual New England vibes with sweeping riverfront views and an outdoor space. The brand-new restaurant features a large main dining room, bar area, private event space, and outdoor terraces. Enjoy New England favorites, including Boston's best clam chowder, oysters and raw bar, lobster, grilled and fried seafood, as well as steaks, pasta and more! Legal Sea Foods combines New England's coastal fishing traditions with modern culinary flair. A taste of New England in the Mid-West.
A photo of avec West Loop restaurant
4.8
Exceptional(899)
Price: Moderate
• Mediterranean • West Loop
Booked 65 times today
avec, a wine-focused restaurant in Chicago, features Midwestern takes on Mediterranean classics. Inspired by the sun-drenched wine regions of the Mediterranean, avec West Loop has been a Chicago favorite for over 20 years. Originally conceived as a wine bar, avec is the second concept from celebrated one-off hospitality, with communal and bar seating—it is a high-energy, intimate, and interactive experience.For parties of 6 or more, please call us at 312-377-2002.
A photo of Bar La Rue restaurant
4.5
Awesome(262)
Price: Expensive
• French American • West Loop
Booked 46 times today
Bar La Rue celebrates French-American cuisine with an inventive cocktail program in the heart of Fulton Market. The stylish space boasts a beautiful all-season, street-side, walk-in-friendly pergola bar and dining area, perfect for a cozy patio experience. The menu incorporates French plays on approachable American comfort foods, offering an inviting setting for lunch, brunch, or dinner. Whether you're enjoying cocktails at the bar, celebrating birthdays, or planning a romantic date, Bar La Rue provides a Mediterranean-inspired atmosphere perfect for any occasion.

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