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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
4.8
Exceptional(897)
Price: Moderate
• Mediterranean • West Loop
Booked 85 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
4.2
Awesome(4563)
Price: Expensive
• American • Downtown / Loop
Booked 13 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
4.4
Awesome(623)
Price: Moderate
• American • South Loop
Booked 5 times 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
4.8
Exceptional(942)
Price: Very Expensive
• Italian • River North (Chicago)
Booked 103 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 RPM Italian - Chicago restaurant
4.6
Exceptional(12346)
Price: Expensive
• Italian • River North (Chicago)
Booked 99 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 Quartino - Chicago restaurant
4.6
Exceptional(11080)
Price: Moderate
• Italian • River North (Chicago)
Booked 117 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 Legal Sea Foods - Chicago restaurant
4.0
Excellent(297)
Price: Expensive
• Seafood • River North (Chicago)
Booked 33 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 Happy Camper Pizza - Old Town restaurant
4.8
Exceptional(614)
Price: Moderate
• Pizzeria • River North (Chicago)
Booked 31 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 Bar La Rue restaurant
4.5
Awesome(260)
Price: Expensive
• French American • West Loop
Booked 49 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.
A photo of Jake Melnick's Corner Tap restaurant
4.5
Awesome(324)
Price: Moderate
• American • Gold Coast / Streeterville
Booked 13 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.

See what locals rave about

From verified diners like you
From verified diners like you
  • Kimmy
    Chicago / Illinois •1 review
    5.0
    Dined 2 days ago
    Our waiter was wondering. He was very kind and accommodating. Food was good and large portions. We asked to sit in a different spot and host was very accommodating too.
    More info
    AtwoodPrice: Expensive• American• Downtown / Loop
    4.2
  • Eric
    Detroit / Eastern Michigan •3 reviews
    4.0
    Dined 2 days ago
    Food is excellent. I was hoping for a bit more from the front of house. Valentine’s Day is a busy night and there I am happy to receive service from the bartender. I also could have navigated the menu better on my own end, but above and beyond service might have helped deliver an elite dining experience.
    More info
    avec West LoopPrice: Moderate• Mediterranean• West Loop
    4.8
  • LauriVIP
    Chicago / Illinois •21 reviews
    5.0
    Dined 3 days ago
    The food was great and the service outstanding. Also a great value. Cocktails, appetizers, main courses and dessert for two under $200 - a rare find in Chicago!. A cold night in chicago so the restaurant was not crowded. But still an overall good experience. Will definitely return
    More info
    Sociale - ChicagoPrice: Moderate• American• South Loop
    4.4
  • SunshineVIP
    Chicago / Illinois •13 reviews
    5.0
    Dined 4 days ago
    Beautiful atmosphere and decor with incredible views. House music played in the background, the bar is gorgeous and the people are here to see and be seen. Thankfully, the food and service stands up to the see and be seen portion of this experience. Service was amazing, our server was warm, friendly, happy to make suggestions, and funny. We really enjoyed her. The food was delicious - panzanella salad "like summer in a bowl" followed by the wild boar ragu (divinely rich and silky) and then a filete di manzo with parmesan roasted fennel and smashed potatoes. The steak is smoky, with a nice crust on the outside but rare, sweet and tender on the inside. At first, we had FOMO over the pasta, thinking we should have ordered two pastas. Once we had tiramisu for dessert (which was impossibly creamy and rich), we were glad we didn't order a 2nd pasta because we were so full. We ate very well and laughed about it as we rolled out of the St Regis to the car. We had the Blanco Bianco Amargo, a tequila/mezcal drink, and it was divinely crafted with a lovely finish. Everything here is well thought out and carefully executed. I asked our server to surprise me with a glass of red wine suitable for the pasta and steak. She gave me a Barbera, which worked well with the intense richness of the boar and beef. This is a romantic atmosphere, with lots of space and service is such that it allows privacy and the staff understand that. Highly recommend the experience for a date night!
    More info
    Tre DitaPrice: Very Expensive• Italian• River North (Chicago)
    4.8
  • SusanVIP
    San Francisco Bay Area •2 reviews
    5.0
    Dined 4 days ago
    The service and food were outstanding. We were celebrating a family birthday and the team reached out ahead of time to find out specifics and make the evening even more special!
    More info
    RPM Italian - ChicagoPrice: Expensive• Italian• River North (Chicago)
    4.6
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