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Best Restaurants for People Watching in South Side

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36 restaurants available nearby

A photo of avec West Loop restaurant
1. avec West Loop
4.8
Exceptional(921)
Price: Moderate
• Mediterranean • West Loop
Booked 92 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 Atwood restaurant
2. Atwood
4.2
Awesome(4562)
Price: Expensive
• American • Downtown / Loop
Booked 18 times today
Atwood proudly offers alluring libations and a wildly guest-pleasing menu filled with your favorite all-day American cuisine courtesy of Executive Chef, David Fingerman. Whether for happy hour cocktails, a theater dinner, or the date of a lifetime, Atwood is Chicago’s premier spot to mix, mingle and delight in the joys of food and drink.Atwood’s soaring dining room is strikingly modern with white marble surfaces, glossy subway-tiled walls, and massive windows ideal for watching the State Street shoppers stroll by.
A photo of Sociale - Chicago restaurant
3. Sociale - Chicago
4.5
Awesome(625)
Price: Moderate
• American • South Loop
Booked 1 time today
Sociale reflects fun, friendly, fresh, neighborhood inspired dining. Literally translated from the Italian word for "social", this concept delivers diverse and elevated comfort foods, accented by a community-focused casual setting. Accompanying these bold flavors are our handcrafted beverages and wine offerings from around the world.
A photo of Tre Dita restaurant
4. Tre Dita
4.7
Exceptional(1032)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 133 times today
Led by Chef Evan Funke, Tre Dita, Italian for "three fingers", pays homage to the precise measurement of bistecca Fiorentina. Whether you're booking in the dining room at Tre Dita or Bar Tre Dita, you will enjoy the full menu of antipasti, handmade pastas, signature entrees and steaks. The full cocktail, wine list and dessert menu is also available in both locations.Please note that Tre Dita only accepts reservations 7 days in advance.
A photo of RL Restaurant restaurant
5. RL Restaurant
4.8
Exceptional(7424)
Price: Expensive
• American • Gold Coast / Streeterville
Booked 106 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 Gibsons Bar & Steakhouse - Chicago restaurant
6. Gibsons Bar & Steakhouse - Chicago
4.8
Exceptional(9099)
Price: Expensive
• Steakhouse • Gold Coast / Streeterville
Booked 137 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 Quartino - Chicago restaurant
7. Quartino - Chicago
4.6
Exceptional(11112)
Price: Moderate
• Italian • River North (Chicago)
Booked 141 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 Happy Camper Pizza - Old Town restaurant
8. Happy Camper Pizza - Old Town
4.8
Exceptional(617)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 68 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 Legal Sea Foods - Chicago restaurant
9. Legal Sea Foods - Chicago
4.0
Excellent(311)
Price: Expensive
• Seafood • River North (Chicago)
Booked 41 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 Bar La Rue restaurant
10. Bar La Rue
4.5
Awesome(274)
Price: Expensive
• French American • West Loop
Booked 54 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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