29 Best Fun Restaurants in Midway

29 restaurants available nearby

How are Featured results ranked

A photo of Punch Bowl Social - Chicago restaurant

1. Punch Bowl Social - Chicago

4.5

Awesome(177)

$$$$

• Unspecified • River North (Chicago)

Booked 34 times today

Perfect, amazing staff and food. I will definitely be here again!

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2. Alla Vita

4.8

Exceptional(3234)

$$$$

• Contemporary Italian • West Loop

Booked 121 times today

Service, staff and food was wonderful. Celebrating a birthday and although it was not mine as mine is on the 20th the team at the host stand acted on this info and included an extra dessert for me. Everyone was friendly and we enjoyed everything we ordered. Thank you!

3. Piccolo Sogno

4.8

Exceptional(7515)

$$$$

• Italian • River West

Booked 74 times today

Fresh delicious food with incredible service. Everything is good and this time we tried the sea bass and it was the best we've ever had at any restaurant.

4. Momento Cantina

4.6

Exceptional(236)

$$$$

• Mexican • Downtown / Loop

Booked 46 times today

Great experience. Our server Sergio was wonderful- gave good recommendations and paced our meal perfectly. Get the mango margarita! Will return next time we're in Chicago.

5. Bub City

4.7

Exceptional(1584)

$$$$

• Barbecue • River North (Chicago)

Booked 40 times today

Best BBQ and atmosphere in Chicago. Get the brisket. It’s sooo good!

A photo of Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile) restaurant

6. Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile)

4.5

Awesome(2302)

$$$$

• Japanese • River North (Chicago)

Booked 63 times today

Great food and service! One of our favorite places

7. The Ives

4.4

Awesome(72)

$$$$

• American • Downtown / Loop

Booked 39 times today

My experience at The Ives was exceptional from beginning to end. The atmosphere was warm, inviting, and sophisticated, with a genuine sense of hospitality throughout the evening. The service was outstanding, with a knowledgeable, attentive, and personable team that made the entire experience feel effortless. The food was equally impressive. We enjoyed the crab dip, prime rib, Ives potato, and Baked Alaska, all beautifully prepared and delicious. What stood out most was the team's professionalism, attention to detail, and visible management presence. It's refreshing to dine somewhere that clearly takes pride in both its culinary execution and guest experience. The Ives delivers a memorable dining experience, and I look forward to returning. Highly recommended!

A photo of White Castle - Chicago - S. Western Ave. restaurant

8. White Castle - Chicago - S. Western Ave.

5.0

Exceptional(1)

$$$$

• American • Albany Park

We had a great time for the Valentine's Day meal! The tables were set up nicely, the food was hot and fresh, the lobby was clean and my husband and I had a good time.

9. Hiro Izakaya

4.8

Exceptional(165)

$$$$

• Japanese Speciality • West Town

Booked 28 times today

Food was amazing! Loved the Al pastor hand rolls, great service

A photo of Parlay River North restaurant

10. Parlay River North

3.7

Very Good(163)

$$$$

• Sports Bar • River North (Chicago)

Booked 17 times today

Emily WAS AMAZING!!!! GREAT CUSTOMER SERVICE AND AMAZING ENERGY!! Will definitely be coming back here for brunch time to try that out. If you come here ask for Emily as your server

Best Fun Restaurants in Midway

Price

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Award-winning

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29 restaurants available nearby

1. Punch Bowl Social - Chicago

2. Alla Vita

3. Piccolo Sogno

4. Momento Cantina

5. Bub City

6. Gyu-Kaku Japanese BBQ - Chicago, IL | Streeterville (Magnificent Mile)

7. The Ives

8. White Castle - Chicago - S. Western Ave.

9. Hiro Izakaya

10. Parlay River North

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