Best Historic Restaurants in Midway

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

ChicagoNear WestSouth SuburbsSouthwest SuburbsWest Suburbs

Neighborhoods

Bucktown / Wicker ParkBurr RidgeChina TownCiceroDowntown / LoopEvergreen Park

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

Award-winning

MICHELIN

Accessibility

Wheelchair access

68 restaurants available nearby

How are Featured results ranked

1. Toast It IZ

4.4

Awesome(288)

$$$$Price: Expensive

• American • Evergreen Park

Booked 17 times today

Toast It Iz is located near a retail complex in the wealthy Evergreen Park neighborhood. Toast It IZ combines the heart and soul of Southern and Creole-inspired cuisine with a dash of the downtown atmosphere. You may thank the restaurant's breakfast and brunch menu for establishing an enduring dining memory with dishes like gumbo grits and fried catfish, banana pudding waffles, lollipop lamb chops, pancakes it iz!, and mimosa towers.

2. Rockefeller's

4.6

Exceptional(621)

$$$$Price: Expensive

• American • Oak Lawn

Booked 3 times today

Rockefeller’s is a modern take on the traditional steakhouse. Our focus on service and quality is paramount to our guests! With a sleek and stylish aesthetic for all occasions.

A photo of Pizzeria Portofino restaurant

3. Pizzeria Portofino

4.8

Exceptional(2051)

$$$$Price: Expensive

• Italian • River North (Chicago)

Booked 267 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.

4. Cindy's Rooftop

4.4

Awesome(135)

$$$$Price: Expensive

• Contemporary American • Downtown / Loop

Booked 137 times today

Perched atop the 13th floor of the Chicago Athletic Association hotel under a glass atrium, Cindy's welcomes guests with sweeping views of Millennium Park, the ever-changing blues of Lake Michigan, and beyond. Providing a remarkable backdrop for Top Chef contestant Executive Chef Kaleena Bliss and her inspired menu featuring local wild and seasonal produce and fresh seafood. With vibrant service, an all-season terrace, and an extensive beverage menu that intertwines naturally with the dishes, every detail of your experience is thoughtfully crafted to make a lasting memory. For private events: please reach out to cindysevents@caa.bokagrp.com.

5. Alla Vita

4.8

Exceptional(2546)

$$$$Price: Expensive

• Contemporary Italian • West Loop

Booked 205 times today

Serving a casual, family-style menu, Alla Vita is a place to gather and enjoy comfortable Italian cuisine. Alla Vita means “to life” in Italian which recognizes overcoming life's challenges and creating a space for shared meals and memorable experiences. Executive Chef Lee Wolen shares his passion for fresh, delicious Italian food made simply with the best ingredients. From July 23 to July 26, we’ll be hosting a multi-night experience exclusively for Chase Sapphire Reserve® cardmembers. Book now: https://www.opentable.com/r/alla-vita-chi/sapphire-summer-reservedFollow @allavitachicago to stay up-to-date with the latest happenings.

6. Hawksmoor Chicago

4.5

Awesome(646)

$$$$Price: Moderate

• Steakhouse • River North (Chicago)

Booked 43 times today

Welcome to Hawksmoor Chicago, our biggest and boldest steakhouse yet, located in the iconic LaSalle Powerhouse in River North. We've brought everything we've learned from nearly 20 years in the UK, Ireland and the US to create something genuinely special in downtown Chicago - a city that knows and loves great steak. Named the World's Best Steak Restaurant and a James Beard Foundation semi-finalist, Hawksmoor is built on a simple philosophy: buy the best and let it shine. That means incredible beef from family-run farms across the Northeast and Pacific Northwest, cooked over open fire. Our responsibly sourced seafood from the Northeast is treated with the same care. In our 16,500 sq ft space, with barrel-vaulted ceilings and touches from Chicago's Golden Age of Travel, you'll find world-class dining without formality - no stiff uniforms or scripts, just relaxed, knowledgeable teams who love what they do. Join us for Happy Hour (daily 5-6pm), and our award-winning Sunday Roast.

7. Asador Bastian

4.7

Exceptional(300)

$$$$Price: Very Expensive

• Steakhouse • River North (Chicago)

Booked 15 times today

Asador Bastian is a Chicago chophouse with Basque influences from acclaimed ChefDoug Psaltis. Located in the iconic “Flair House” originally built in 1883, this historictownhouse has been revived and brought back to life with culinary inspiration from thegreat asadors of San Sebastián, Spain to serve the world’s best boutique beef withoutcompromise. The most remarkable dining experience comes from the purest ingredientsdelivered in the supremely thoughtful, welcoming and hospitable manner. This ethoshas directed every aspect of the experience at Asador Bastian, whether you’re joiningus for small bites and libations in our Bar Room or for a more intimate experience in ourDining Room.From July 23 to July 26, we’ll be hosting a multi-night experience exclusively for Chase Sapphire Reserve® cardmembers. Book now: https://www.opentable.com/r/asador-bastian-chi/sapphire-summer-reserved

8. Chemistry

4.5

Awesome(1878)

$$$$Price: Expensive

• American • Hyde Park

Booked 100 times today

Located in Chicago's Hyde Park neighborhood, Chemistry is Chicago's premier Black-owned Steakhouse! Enjoy the most delicious steak while experiencing excellent white-glove service. Chemistry exemplifies black excellence at its finest. When the creator of Chemistry first started dating, he wondered "If there were only a place that was breathtaking upon entry, amazing live bands and DJ's, delicious photographable food, good service, along with a place to get up and dance," he’d show up as much as his pockets could afford. However that place didn’t exist, until now. Chemistry, the perfect mix of a high-end late-night steakhouse, booming brunch spot, and tantalizing nightlife vibes all created to be the perfect place to experience love! *Large Parties over 12 are unable to make an online reservation. Please email your request to reservations@chemistrychicago.com Please note: We are not open for dinner service on Friday nights

9. RPM Seafood

4.6

Exceptional(1979)

$$$$Price: Very Expensive

• Seafood • River North (Chicago)

Booked 220 times today

Introducing RPM Seafood, a dramatic multi-level restaurant overlooking the iconic Chicago River featuring the truest expression of the world’s best fish and seafood.The sister restaurant to RPM Steak and RPM Italian, it marks the third collaboration between partners RJ, Jerrod and Molly Melman of Lettuce Entertain You Enterprises and celebrity couple Giuliana & Bill Rancic.

10. Siena Tavern

4.6

Exceptional(6227)

$$$$Price: Moderate

• Italian • River North (Chicago)

Booked 125 times today

Entirely Rooted In A "From Scratch" Approach, We Present Upscale, Classic Italian Fares, Straight From Top Chef Alum, Fabio Viviani. Siena Tavern'S Extensive Wine List And Our Highly Contemporary Design, Interspersed With Rustic Details, Elevates The Genuine Italian Dining Experience While Simultaneously Maintaining Authenticity. Farm To Fork, Refined And Redefined.

See what locals rave about

From verified diners like you

OT
OpenTable Diner
Minneapolis - St. Paul •5 reviews
5.0
Dined 3 days ago
Amazing views overlooking millennium park. Food was excellent. Highly recommend
More info
Cindy's RooftopPrice: Expensive• Contemporary American• Downtown / Loop
•
4.4
T
Tashana
1 review
5.0
Dined 6 days ago
My experience was great. The food was delicious and it came out in a timely manner. The waiter was courteous and the music was definitely a vibe, even at 10 am.
More info
Toast It IZPrice: Expensive• American• Evergreen Park
•
4.4
T
ThomasVIP
Greater Boston •1 review
5.0
Dined on Jun 16, 2025
I came in for a celebration dinner with my family recently. While I have been to Alla Vita a few times, I was completely stunned at just how special the manager Jo and our waitress Brie made the evening for us. The food is always amazing, the professionalism of the staff was top notch, and both Jo and Brie thought of every detail to make the night special and memorable. I cannot thank them enough for everything! Well done Alla Vita!
More info
Alla VitaPrice: Expensive• Contemporary Italian• West Loop
•
4.8
F
Fabiola
Orlando / Central Florida East •1 review
5.0
Dined on Jun 16, 2025
Unbelievable experience with amazing views Food is amazing i had a great time would totally come back on my next visit to chicago The variety of Spritz are great choice for this summer :)
More info
Pizzeria PortofinoPrice: Expensive• Italian• River North (Chicago)
•
4.8
M
Michelle
Chicago / Illinois •3 reviews
5.0
Dined on Jun 15, 2025
Excellent service and delicious food. We’re so happy we picked this place for Father’s Day dinner.
More info
Rockefeller'sPrice: Expensive• American• Oak Lawn
•
4.6

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