Best Romantic Restaurants in Midway

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

ChicagoNear WestSouthwest SuburbsWest Suburbs

Neighborhoods

BerwynBronzevilleBucktown / Wicker ParkCiceroDowntown / LoopHinsdale

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

63 restaurants available nearby

How are Featured results ranked

1. Cindy's Rooftop

4.4

Awesome(179)

$$$$Price: Expensive

• Contemporary American • Downtown / Loop

Booked 120 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. 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.

2. RPM Seafood

4.6

Exceptional(2105)

$$$$Price: Very Expensive

• Seafood • River North (Chicago)

Booked 189 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.

3. Alla Vita

4.8

Exceptional(2595)

$$$$Price: Expensive

• Contemporary Italian • West Loop

Booked 131 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.

4. Asador Bastian

4.7

Exceptional(314)

$$$$Price: Very Expensive

• Steakhouse • River North (Chicago)

Booked 18 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

5. RPM Steak

4.8

Exceptional(6485)

$$$$Price: Very Expensive

• Steak • River North (Chicago)

Booked 69 times today

Located in Chicago’s River North neighborhood, RPM Steak is an updated take on the classic steakhouse and features a contemporary, chef-driven menu, an award-winning wine list and a well-curated craft cocktail program. The sister restaurant to RPM Italian, RPM Steak marks the second collaboration between Lettuce Entertain You Enterprises and Bill and Giuliana Rancic.

6. Lýra

4.6

Exceptional(2226)

$$$$Price: Moderate

• Greek • West Loop

Booked 93 times today

Lyra, with its earthy, indoor-meets-outdoor space and an 8,000-square-foot imprint, is a perfect spot for a romantic evening. Reviews rave about the 'amazing food and service', the 'fantastic food, service and atmosphere', and the 'beautiful restaurant' ambiance. One reviewer even celebrated a boyfriend's birthday here, highlighting the 'beautiful restaurant' and 'fun cocktail menu'. The restaurant's fresh, holistic fare, combined with its unique Greek concept, make it a popular choice for a date night.

7. Hawksmoor Chicago

4.6

Exceptional(688)

$$$$Price: Moderate

• Steakhouse • River North (Chicago)

Booked 51 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.

8. Obelix

4.8

Exceptional(222)

$$$$Price: Very Expensive

• French • River North (Chicago)

Booked 50 times today

From the Poilevey's La Sardine and Le Bouchon, Obélix offers an elevated dining experience that celebrates the flavors of contemporary French cuisine with a subtle twist. Located in River North, the ambiance of Obélix, designed with elegance and charm, provides the perfect backdrop for an unforgettable meal. From the moment you step inside, you're transported into a world of culinary excellence, where artfully crafted dishes are complemented by exceptional French focused wine featuring both classic and nouveau selections. Signature dishes like the Beef Wellington, foie gras terrine, and an indulgent rotating soufflé offer a glimpse into the restaurant's commitment to quality and flavor. Ideal for intimate dinners, celebrations, or simply an evening of indulgence, Obélix is where tradition meets innovation in every bite. With exceptional service, an inviting atmosphere, and a menu that speaks to both the heart and the palate, Obélix is a neighborhood gem in Chicago's culinary scene.

9. Siena Tavern

4.6

Exceptional(6263)

$$$$Price: Moderate

• Italian • River North (Chicago)

Booked 91 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.

10. Fioretta

4.7

Exceptional(1098)

$$$$Price: Very Expensive

• Steak • West Loop

Booked 74 times today

Fioretta is reminiscent of a new-age Copacabana, celebrating old-world Italian cuisine with an opulent twist, a steady flow of impressive cocktails and wine, world-class live entertainment, and a glamorous vibe cast over the entire experience.Seamlessly blending steakhouse fare with elevated versions of old-world Italian cuisine with help from Italian-American Chef, Joe Rizza. The menu pays homage to the Italian immigrants who graciously first introduced Americans to southern Italian classics. Fioretta’s custom-built solid-fuel hearth and open kitchen allows Rizza and his culinary team to impart superb flavor, char and texture to each dish. The menu strives to strike the perfect balance between nostalgia and innovation.

‘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

J
JamesVIP
Pittsburgh / Western PA •8 reviews
5.0
Dined 1 day ago
Great experience. Service and food were excellent.
More info
RPM SteakPrice: Very Expensive• Steak• River North (Chicago)
•
4.8
R
Ranj
Hawaii •3 reviews
5.0
Dined 2 days ago
Great place to grab a drink and get some beautiful views
More info
Cindy's RooftopPrice: Expensive• Contemporary American• Downtown / Loop
•
4.4
E
Elvis
Chicago / Illinois •1 review
5.0
Dined 4 days ago
Food was amazing and staff were very friendly, attentive, and made the occasion very personable.
More info
RPM SeafoodPrice: Very Expensive• Seafood• River North (Chicago)
•
4.6
OT
OpenTable Diner
Chicago / Illinois •1 review
5.0
Dined 5 days ago
We had an absolutely amazing experience at Asador Bastian. The food was incredibly good—every dish was packed with flavor and beautifully prepared. I loved the unique touch of being shown the steak selection and the fresh seafood of the day before ordering; it made the experience feel so special. The presentation of the steak, and seafood was stunning, and everything tasted as amazing as it looked. We even got a quick tour of the kitchen and saw the steak cooler, which was such a cool behind-the-scenes moment. The service was exceptional—professional, attentive, and warm. We enjoy fine dining, but this was by far one of the most beautiful and memorable dining experiences we’ve ever had. Highly recommend!
More info
Asador BastianPrice: Very Expensive• Steakhouse• River North (Chicago)
•
4.7
H
Hunter
Chicago / Illinois •1 review
5.0
Dined 7 days ago
Great experience, bread and vodka pasta were amazing
More info
Alla VitaPrice: Expensive• Contemporary Italian• West Loop
•
4.8

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