Best Fun Restaurants in Jefferson Park

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodMexicanPizzeria

Regions

ChicagoNorthwest Suburbs

Neighborhoods

Bucktown / Wicker ParkGold Coast / StreetervilleLakeview / East LakeviewLincoln ParkLogan SquareOld Town

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Wheelchair access

28 restaurants available nearby

How are Featured results ranked

A photo of Costera Cocina Tulum restaurant

1. Costera Cocina Tulum

4.5

Awesome(1128)

$$$$Price: Moderate

• Mexican • West Loop

Booked 60 times today

Costera Cocina Tulum brings the vibrant flavors of Tulum's coastal and Mayan cuisine to life, blending land-and-sea principles with traditional Mexican dishes. Step into a lively yet serene atmosphere that captures the essence of Tulum's unique intersection of jungle, beach, and bohemian nightlife. Experience our day-to-night philosophy, where "the jungle has two attitudes," and enjoy a dining experience that transports you to this enchanting Mexican getaway.

A photo of Starbucks Reserve® Chicago Roastery restaurant

2. Starbucks Reserve® Chicago Roastery

4.8

Exceptional(59)

$$$$Price: Expensive

• Café • River North (Chicago)

Booked 11 times today

The World's Largest Starbucks.A spectacular destination. Our passion for craft, innovation, and discovery comes to life in an ever-evolving menu of coffee, cocktails and food.An immersive and thoughtfully designed experience, this one-of-a-kind space will bring your event to life in a uniquely memorable way.

A photo of Wonderland at Tree House restaurant

3. Wonderland at Tree House

4.3

Awesome(307)

$$$$Price: Moderate

• Italian • River North (Chicago)

Booked 58 times today

✨ Fall down the rabbit hole into Wonderland—Chicago’s newest pop-up experience where curiosity leads to magic and every corner tells a story! 🌸💫 Think Mad Hatter tea parties, dreamy cocktails, oversized blooms, and photo ops straight out of your wildest imagination.From playful surprises to enchanting decor, Wonderland is the perfect escape for dreamers, romantics, and anyone craving a night unlike any other. Whether you're sipping a "Drink Me" potion or striking a pose with the Queen of Hearts, expect an unforgettable adventure full of charm and cheek.Bring your curiosity, your crew, and your best Wonderland look—it’s time to get wonderfully lost! 🐇

A photo of Upstairs at The Gwen restaurant

4. Upstairs at The Gwen

4.2

Awesome(320)

$$$$Price: Expensive

• American • River North (Chicago)

Booked 49 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!

5. Neon Gardens

4.0

Excellent(111)

$$$$Price: Moderate

• Pizza Bar • Lincoln Park

Booked 51 times today

A crave-worthy haven for Chicagoans to enjoy New York Style pizza, handcrafted cocktails, arcade games, and unique entertainment. To ensure all guests have the best experience possible, we kindly ask that during peak hours, dining is limited to 90 minutes per table. This helps us accommodate everyone while still providing great service. Thank you for your understanding—we appreciate you dining with us!*An 18% auto gratuity will be added to all checks to ensure fair compensation for our staff, especially during busy events. Additional tipping is always appreciated but not required.

A photo of Kit kat Lounge & Supper Club restaurant

6. Kit kat Lounge & Supper Club

4.8

Exceptional(124)

$$$$Price: Moderate

• American • Wrigleyville

Booked 9 times today

The Kit Kat Lounge and Supper Club is a unique dining experience in Chicago with world class table side entertainment by our world famous divas!Nightly drag shows & during our Saturday and Sunday brunches (10:30am/1pm/3:15pm)The menu at Kit Kat Lounge features a variety of globally-inspired dishes with a modern twist. From small plates and shared appetizers to decadent entrees, there is something for every palate. Indulge in creative cocktails, fine wines, and with a choice of over 100 martinis, while enjoying live entertainment from talented performers.The decor is chic and glamorous, with plush seating, dim lighting, and elegant decor. The staff is friendly and attentive, ensuring that every guest feels welcomed and well taken care of. Whether you're looking for a fun night out or a memorable dining experience, Kit Kat Lounge and Supper Club is the perfect destination. Come for the delicious food, stay for the entertainment, and leave with memories that will last a lifetime.

7. Geja's Cafe

4.9

Exceptional(5713)

$$$$Price: Expensive

• Fondue • Lincoln Park

Booked 22 times today

For over 60 years, fondue dining at Geja’s Café has been a favorite indulgence for Chicagoans as well as out-of-towners. It’s a perfect way to kindle romance, celebrate a special occasion or simply join family and friends for a fun and unforgettable dining experience.To start we offer a Swiss Gruyere cheese fondue, served with fresh breads, fruits and vegetables for dipping. Our crisp house salad, dressed with tangy Dijon vinaigrette, offers a counterpoint to the rich, warm cheese fondue appetizer.Next, you’ll cook your choices of Australian lobster tail, Gulf shrimp, beef tenderloin, fresh sea scallops or boneless chicken breast in a pot of sizzling soybean oil or broth. The main course is served with fresh vegetables and eight gourmet dipping sauces.Our famous chocolate fondue is flamed table-side, and presented with marshmallows for roasting and other delectable dippers.A 4 % operational fee is added to all checks to work in concert with Chicago's One Fair Wage Ordinance.

8. STK – Chicago

4.2

Awesome(6723)

$$$$Price: Expensive

• Steakhouse • River North (Chicago)

Booked 97 times today

STK – Chicago is a lively and fun place to dine, with its trendy decor and high-energy atmosphere. As one reviewer puts it, it offers an 'elegant environment' with 'great music, even better food and drink options.' The live DJ, frequent sparklers, and attentive service add to the vibrant ambiance. The food is consistently praised for its quality and taste. It's an excellent choice for a memorable fine dining experience.

A photo of Paradise Park | Pizza + Patio restaurant

9. Paradise Park | Pizza + Patio

4.8

Exceptional(1369)

$$$$Price: Moderate

• Pizzeria • Bucktown / Wicker Park

Booked 38 times today

Trendy bar and pizzeria in Chicago’s Wicker Park neighborhood, Paradise Park brings you the fun and the flavor! From the team that brought you Homeslice in Lincoln Park and Happy Camper in Old Town/Wrigley, we invite you to indulge in our creative cocktails and extensive beer selection, paired with specialty pizzas and mouth-watering appetizers. All can be enjoyed on our kitschy trailer park themed patio open year-round! Come for the food. Stay for the vibes.Minors must be accompanied by parent or guardian.We only accept Credit Card. No Cash.

A photo of Sugar Factory - Rosemont restaurant

10. Sugar Factory - Rosemont

4.1

Excellent(5633)

$$$$Price: Expensive

• American • Rosemont

Booked 36 times today

Sugar Factory - Rosemont is a delightful spot, loved by both adults and kids alike. Reviewers rave about its 'fun atmosphere' and 'fanciful candy theme decor'. The menu offers a mix of savory and sweet American dishes, with creative milkshakes and desserts like the famous King Kong Sundae. The place is also known for its signature smoking candy goblets and specialty martinis. It's a great place for a unique dining experience with 'fantastic service from start to finish'.

‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you

A
AmandaVIP
Denver / Colorado •4 reviews
5.0
Dined 1 day ago
Mini trompo and the cavatelli pasta was amazing! Excellent service, and great atmosphere! We will return for sure.
More info
Costera Cocina TulumPrice: Moderate• Mexican• West Loop
•
4.5
R
RichardVIP
Chicago / Illinois •183 reviews
5.0
Dined 4 days ago
Upstairs at the Gwen is a bargain during happy hour, 4-530. Two flatbreads, hummus, bread service, cocktails, and wine are all priced at $12. The food is delicious. We wanted to eat outside but there were not enough umbrellas for shade which was the only down side. Service is attentive but not overbearing. Inside or out it is a perfect way to end the day. With these bargain prices it should be packed wall to wall but while partially full there were plenty of seats. I recommend this place especially at happy hour.
More info
Upstairs at The GwenPrice: Expensive• American• River North (Chicago)
•
4.2
G
Grace
Cincinnati / Dayton •1 review
5.0
Dined 4 days ago
Private tour for just the two of us with a very knowledgeable barista and roaster. They were friendly and wanted to answer any questions we had. We were able to taste two freshly roasted varieties of coffee paired with two chocolate truffles. An exquisite experience!
More info
Starbucks Reserve® Chicago RoasteryPrice: Expensive• Café• River North (Chicago)
•
4.8
P
Patrick
Chicago / Illinois •2 reviews
4.0
Dined 7 days ago
Fun time with great nostalgia. Good service. Everyone is super helpful. Food is pretty good
More info
Neon GardensPrice: Moderate• Pizza Bar• Lincoln Park
•
4
S
Shamaya
Chicago / Illinois •1 review
5.0
Dined on Jun 28, 2025
Nice server good food beautiful setting for pictures
More info
Wonderland at Tree HousePrice: Moderate• Italian• River North (Chicago)
•
4.3

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