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Best Restaurants for People Watching in Old Town

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45 restaurants available nearby

A photo of Happy Camper Pizza - Old Town restaurant
1. Happy Camper Pizza - Old Town
4.8
Exceptional(597)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 20 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 Gibsons Bar & Steakhouse - Chicago restaurant
2. Gibsons Bar & Steakhouse - Chicago
4.7
Exceptional(8834)
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 123 times today
Gibsons Bar & Steakhouse has been a Chicago icon since partners Hugo Ralli and Steve Lombardo opened its doors in May 1989. The classic American steakhouse serves Gibsons Prime Angus Beef and Gibsons Grassfed Australian Beef. Gibsons also features fresh fish, classic cocktails, an extensive wine list and exceptional service. Celebrities, Chicago visitors and loyal neighborhood residents enjoy three distinct locations: Chicago, Rosemont and Oak Brook. Beautiful private dining and events spaces available.
A photo of RL Restaurant restaurant
3. RL Restaurant
4.9
Exceptional(7213)
Price: Expensive
• American • Gold Coast / Streeterville
Booked 108 times today
If you do not find availability online, please call the restaurant directly at 312-475-1100.Located adjacent to the Ralph Lauren Chicago flagship store on Michigan Avenue, RL Restaurant features the vision and décor of Ralph Lauren in a modern club atmosphere. RL Restaurant offers classic American cuisine inspired by Ralph Lauren’s personal favorites. Seasonal dishes range from a chopped vegetable salad to a lobster roll sandwich, grilled fish of the day and steaks. On the cocktail list, guests can choose from classic drinks and a diverse selection of wines and other fine spirits.
A photo of Legal Sea Foods - Chicago restaurant
4. Legal Sea Foods - Chicago
4.0
Excellent(210)
Price: Expensive
• Seafood • River North (Chicago)
Booked 24 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. Serving New England specialties such as Boston's best Clam Chowder and Half Pound Lobster Rolls, as well as new signature dishes and local favorites. 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 Cabra - Chicago restaurant
5. Cabra - Chicago
4.7
Exceptional(3033)
Price: Expensive
• Peruvian • West Loop
Booked 34 times today
Perched atop the Hoxton Hotel in the heart of Chicago’s Fulton Market, Cabra Chicago is a lively rooftop escape, inspired by the bold and vibrant flavors of Peruvian cuisine. Led by James Beard Award and Top Chef winner Stephanie Izard, alongside longtime partners Rob Katz and Kevin Boehm of Boka Restaurant Group, Cabra serves up crave-worthy dishes in a colorful and energetic setting. The restaurant’s airy, plant-filled ambiance, paired with its open kitchen and sweeping city views, creates a dynamic dining experience. Guests can savor a variety of shareable plates, from ceviches to savory meats, all bursting with the rich, fresh flavors of Peru.
A photo of Rosebud Steakhouse - Chicago restaurant
6. Rosebud Steakhouse - Chicago
4.8
Exceptional(3482)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 37 times today
*Rosebud Steakhouse is a special occasion restaurant, with an UPSCALE BUSINESS CASUAL Dress Code Policy. For clarification please review the policy at https://rosebudsteak.com/dress-code/ and we thank you for your courtesy. Welcome to a rare steakhouse, well done! Rosebud Steakhouse knows a thing or two about the fine art of cooking. Located on Walton Street, a stone's throw from Michigan Avenue, this relaxing hideout is the perfect place to enjoy an unforgettable meal paired with a glass of wine from our impressive wine list. The extensive menu features prime steaks by Meats by Linz, fresh seafood and Italian specialties. The beloved hamburger, voted number one in the city of Chicago by the Chicago Tribune, graces our dinner menu. Rosebud Steakhouse invites you to enjoy an unforgettable fine dining experience in a romantic setting. Rosebud Steakhouse is a Creative Hospitality Concepts restaurant. Visit our second location, coming soon to, Munster, Indiana.
A photo of Tavern on Rush restaurant
7. Tavern on Rush
4.4
Awesome(3502)
Price: Expensive
• Steak • Gold Coast / Streeterville
Booked 83 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
8. Jake Melnick's Corner Tap
4.4
Awesome(308)
Price: Moderate
• American • Gold Coast / Streeterville
Booked 22 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 il Porcellino restaurant
9. il Porcellino
4.7
Exceptional(4173)
Price: Moderate
• Italian • River North (Chicago)
Booked 112 times today
Il Porcellino, located in the heart of River North in downtown Chicago, is a neighborhood restaurant offering classic Italian-American comfort food in a casual setting. Our seasonal menu focuses on housemate pastas, vegetable antipasti and daily specials, all crafted with ingredients sourced from quality artisans, purveyors, and local farmers. The fun and approachable wine program encourages sharing with selections primarily from Italy. As a way to offset rising costs associated with the restaurant (food, beverage, labor, benefits, supplies), we have added a 3% surcharge to all checks. We do this in lieu of increased menu prices. You may request to have this taken off your check, should you choose.
A photo of Mercadito - River North restaurant
10. Mercadito - River North
4.6
Exceptional(6256)
Price: Expensive
• Mexican • River North (Chicago)
Booked 61 times today
We are the city’s top Mexican restaurant for authentic modern cuisine, specialty tequila and mezcal cocktails, located in the heart of River North. Our culinary team features popular Mexican dishes, including our signature tacos, as well as fresh salsa and guacamole, ceviche, esquites and more.Mercadito's lounge is nestled in the lower level of Mercadito. It offers a speakeasy-style experience with a chic and exclusive ambiance. The space features banquet-style booths and dim lighting that enhances the elegant wood furniture, creating an inviting and intimate atmosphere. Once inside, guests can enjoy the full Mercadito menu, with the same delectable cuisine and beverages that our restaurant is known for.

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