Best Restaurants for People Watching in South Side

43 restaurants available nearby

1. Atwood

4.2

Price: Expensive

• American • Downtown / Loop

Booked 22 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.

2. Sociale - Chicago

4.4

Awesome(617)

Price: Moderate

• American • South Loop

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.

3. RL Restaurant

4.9

Exceptional(7317)

Price: Expensive

• American • Gold Coast / Streeterville

Booked 145 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

4. Gibsons Bar & Steakhouse - Chicago

4.8

Exceptional(8977)

Price: Expensive

• Steakhouse • Gold Coast / Streeterville

Booked 157 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.

5. Cabra - Chicago

4.7

Exceptional(3054)

Price: Expensive

• Peruvian • West Loop

Booked 87 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 Quartino - Chicago restaurant

6. Quartino - Chicago

4.5

Awesome(11020)

Price: Moderate

• Italian • River North (Chicago)

Booked 182 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

7. RPM Italian - Chicago

4.6

Exceptional(12274)

Price: Expensive

• Italian • River North (Chicago)

Booked 140 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 Legal Sea Foods - Chicago restaurant

8. Legal Sea Foods - Chicago

4.0

Excellent(258)

Price: Expensive

• Seafood • River North (Chicago)

Booked 38 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 Happy Camper Pizza - Old Town restaurant

9. Happy Camper Pizza - Old Town

4.8

Exceptional(606)

Price: Moderate

• Pizzeria • River North (Chicago)

Booked 42 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 Rosebud Steakhouse - Chicago restaurant

10. Rosebud Steakhouse - Chicago

4.7

Exceptional(3521)

Price: Expensive

• Steak • Gold Coast / Streeterville

Booked 19 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.

See what locals rave about

From verified diners like you

J
Jena
Chicago / Illinois •2 reviews
4.0
Dined today
We had a great first visit to Cabra! The food was delicious and well-balanced. We missed out on an item that we ordered, and service was slightly slow at the start, but the server was so personable and kind so we didn't mind. They sent us an incredible salad to compensate for the lag in service and we felt we'd had the perfect amount of food. Thank you Cole for your hospitality!
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Cabra - ChicagoPrice: Expensive• Peruvian• West Loop
•
4.7
D
Darren
Fort Lauderdale •1 review
5.0
Dined 1 day ago
Amazing! Martini with blue cheese stuffed olives. Ambiance in the bar felt like stepping back in time. The ribeye and fries, I will repeat tomorrow!
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Gibsons Bar & Steakhouse - ChicagoPrice: Expensive• Steakhouse• Gold Coast / Streeterville
•
4.8
D
Daniel
Chicago / Illinois •2 reviews
5.0
Dined 1 day ago
Delicious lunch and the best atmosphere and service! Jaafar made us feel like his personal guests the moment we sat down and everyone was so helpful and kind.
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RL RestaurantPrice: Expensive• American• Gold Coast / Streeterville
•
4.9
A
Amy
Chicago / Illinois •2 reviews
5.0
Dined on Dec 22, 2024
Delicious food, great service and yummy drinks! It’s in a beautiful old building and had a bustling and lively atmosphere. Service was helpful and friendly. We stayed the Staypineapple Hotel so we ate a couple times at the Atwood and every meal was delicious I had the grilled cheese and the savory waffle which exceeded my expectations. The Brussels sprouts and cauliflower were seasoned and grilled perfectly.
More info
AtwoodPrice: Expensive• American• Downtown / Loop
•
4.2
L
Leslie
Chicago / Illinois •2 reviews
5.0
Dined on Dec 21, 2024
We had a great time. Food was delicious and wine list is full of surprises.
More info
Sociale - ChicagoPrice: Moderate• American• South Loop
•
4.4

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Best Restaurants for People Watching in South Side

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43 restaurants available nearby

1. Atwood

2. Sociale - Chicago

3. RL Restaurant

4. Gibsons Bar & Steakhouse - Chicago

5. Cabra - Chicago

6. Quartino - Chicago

7. RPM Italian - Chicago

8. Legal Sea Foods - Chicago

9. Happy Camper Pizza - Old Town

10. Rosebud Steakhouse - Chicago

See what locals rave about

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