Best Fun Restaurants in South Side

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSeafoodMexicanJapanesePizzeria

Regions

ChicagoSouth Suburbs

Neighborhoods

Bucktown / Wicker ParkEvergreen ParkGold Coast / StreetervilleGoose IslandLincoln ParkLower West Side

Top Rated

CharmingGood for groupsGood for special occasionsGreat for brunchGreat for fine winesGreat for happy hour

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

31 restaurants available nearby

1. Pilsen Yards

4.7

Exceptional(1621)

$$$$Price: Moderate

• Latin American • Pilsen

Booked 44 times today

Pilsen Yards is a vibrant and lively restaurant in the heart of Pilsen, offering a unique dining experience with its bar-centric and music-driven atmosphere. The open-air vibe and one of the largest patios in the city create a welcoming and inviting space for guests to enjoy delicious Latin-inspired street food and handcrafted cocktails. Executive Chef Juan Carlos Gutierrez's menu features a variety of creative and flavorful dishes, from tacos and ceviches to hummus and carne asada. The menu is designed to share and encourage guests to try a variety of flavors. The bar program, curated by beverage director Lance Bowman, boasts an extensive selection of mezcal, tequila, whiskey, and other spirits, along with a variety of craft beers and cocktails. Pilsen Yards is the perfect spot for a casual night out with friends, a lively weekend brunch, or a special occasion. The restaurant's spacious interior and expansive patio can accommodate large groups and private events. With its lively atmosphere, delicious food, and extensive bar program, Pilsen Yards is sure to provide a memorable dining experience.

2. 312 Fish Market

5.0

Exceptional(20)

$$$$Price: Expensive

• Japanese • Lower West Side

Booked 4 times today

Hidden inside 88 Marketplace is 312 Fish Market -- a sushi lover's dream. We take great pride in improving upon your favorite nigiri, sashimi, hand rolls, sushi rolls, and party sets in new and creative ways.As we do not compromise on quality, our chef sources the best fish from all over the world including Tuna, Madai, Kanpachi, Uni, Caviar, and more.312 Fish Market is a BYOB establishment.Closed every Wednesday. We are also available for pickup, delivery and catering. Please reach us at 312FishMarket@gmail.com or 872-222-7288.

A photo of Pizzeria Portofino restaurant

3. Pizzeria Portofino

4.8

Exceptional(1734)

$$$$Price: Expensive

• Italian • River North (Chicago)

Booked 224 times today

Pizzeria Portofino is a sun-drenched casual restaurant located directly on the Chicago riverfront offering hand-stretched pizzas, coastal wines, an expansive patio and breezy decor that will instantly transport you to the Italian Riviera.

A photo of Three Dots and a Dash restaurant

4. Three Dots and a Dash

4.8

Exceptional(1901)

$$$$Price: Expensive

• Cocktail Bar • River North (Chicago)

Booked 57 times today

With a secret alleyway entrance, Three Dots and a Dash is a speakeasy-style take on the traditional island bar—ready to transport you to the glamorous bygone eras of Trader Vic, Stephen Crane and Don the Beachcomber. Descend underground to discover a subterranean hideaway featuring a rum-soaked menu of more than two dozen classic, modern and original tropical cocktails and a selection of island fare. We are a 21+ venue.

A photo of SUSHI-SAN - River North restaurant

5. SUSHI-SAN - River North

4.7

Exceptional(1376)

$$$$Price: Moderate

• Japanese • River North (Chicago)

Booked 137 times today

Sushi-San serves up the best sushi in Chicago made with the freshest ingredients they can find, all served with a side of old-school hip-hop and ice-cold beer. The bar is kept stocked with rare Japanese whisky, sake, wine and inventive cocktails. Join them for lunch and dinner.

A photo of JoJo's ShakeBAR - River North restaurant

6. JoJo's ShakeBAR - River North

3.5

Very Good(2763)

$$$$Price: Moderate

• American • River North (Chicago)

Booked 36 times today

JoJo’s ShakeBAR is a next-generation restaurant and bar, and River North’s next go-to spot for hangouts, first dates, and family affairs. Its’ modern, yet familiar, diner experience is grounded in nostalgia and focuses on creative desserts and elevated diner favorites.Outdoor Patio Seating is available for reservations and walk-ins. In the case of inclement weather, our team will do our best to accommodate outdoor patio reservations inside, but indoor seating is not guaranteed. Reservations Are Highly Recommended & Walk Ins Are Available Based Upon Availability.

A photo of Upstairs at The Gwen restaurant

7. Upstairs at The Gwen

4.1

Excellent(282)

$$$$Price: Expensive

• American • River North (Chicago)

Booked 29 times today

Experience the premier terrace in River North, located on the 5th floor of The Gwen, a one MICHELIN Key hotel, nestled along the iconic Magnificent Mile! Savor creative cocktails and indulge in delicious small and large plates crafted by Executive Chef Matt Jergens, all while enjoying the warm ambiance of our firepits and the stunning backdrop of towering skyscrapers. Our candlelit indoor lounge and bar offer the perfect setting to unwind, relax, and embrace the good life!Join us on the weekends for Chicago's liveliest, most unique tea service, Tipsy Tea! Featuring scrumptious savory and sweet bites, bottomless beverages, a DJ spinning, and a special themed menu every month, this is one pinkies-down tea service you will never forget!

A photo of Parlay River North restaurant

8. Parlay River North

4.4

Awesome(64)

$$$$Price: Moderate

• Sports Bar • River North (Chicago)

Booked 21 times today

A lively ultramodern sports bar located on the first floor of Joy District, Parlay River North, is a haven for Chicago locals and sports fans alike. Surrounded by multiple high definition televisions Parlay River North offers elevated bar fare complemented with thirst quenching beverages.

A photo of Robert's Pizza and Dough Company restaurant

9. Robert's Pizza and Dough Company

4.8

Exceptional(2126)

$$$$Price: Expensive

• Pizzeria • Gold Coast / Streeterville

Booked 114 times today

Robert's Pizza and Dough Company serves it's award winning thin-crust artisanal pizzas with fresh and unique ingredients.

A photo of 10pin Bowling Lounge restaurant

10. 10pin Bowling Lounge

4.6

Exceptional(423)

$$$$Price: Expensive

• American • River North (Chicago)

Booked 20 times today

10pin is a Chicago original located in the heart of River North, along the Chicago River. Next to the House of Blues, 10pin offers 20,000 square feet of 24 luxury bowling lanes, ping pong, pool table and table shuffleboard games that cater to all group sizes. When reserving a table on OpenTable you are reserving the lane and table! The rates are $25/hour per person plus shoe rental. For information on booking an event or for groups of 13 or more, please call our event sales team at 312-644-0100. Guests must be 21 beginning at 8pm. Dress code will be enforced, including pants at waist level. 10pin has the right to include any clothing deemed inappropriate. No outside food or drinks. Management has the right to refuse entry to anyone acting in a rude or disrespectful manner.

See what locals rave about

From verified diners like you

S
ShannonVIP
Chicago / Illinois •7 reviews
5.0
Dined 1 day ago
I brought a corporate group for happy hour. Bobby and the team were so helpful and accommodating. The food was delicious and everyone had a great time. Would love to come back again!
More info
SUSHI-SAN - River NorthPrice: Moderate• Japanese• River North (Chicago)
•
4.7
P
PrimaVIP
Chicago / Illinois •5 reviews
5.0
Dined 1 day ago
I've had dinner and lunch here with family and friends multiple times and every time the service, quality of the food and ingredients, and ambience are consistently excellent. The staff is always pleasant and my group and I are always able to be seated right away. Beautiful setting anytime of the year, and it helps that it's sooo close to our office in River North.
More info
Pizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)
•
4.8
J
joanne
Chicago / Illinois •3 reviews
5.0
Dined 5 days ago
First time here, exceptional service and exceptional food!
More info
Pilsen YardsPrice: Moderate• Latin American• Pilsen
•
4.7
C
Cruz
Los Angeles •2 reviews
5.0
Dined 5 days ago
Incredible. Everything was fresh and taested amazing. 11/10 experience. I will be back 100%
More info
312 Fish MarketPrice: Expensive• Japanese• Lower West Side
•
5
S
Samantha
Chicago / Illinois •4 reviews
5.0
Dined 7 days ago
So fun, drinks were great, good bar snacks, and great service.
More info
Three Dots and a DashPrice: Expensive• Cocktail Bar• River North (Chicago)
•
4.8

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