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New Yorkers 1st Choice
Local picks

Wine and steakhouse spots in Chicago

A heavy steakhouse meal feels grounded when accompanied by a glass of wine.

Based on 776 Opinions
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Updated June 2026
01
Butcher and the Bear image 1
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Steakhouse offers a dark intimate atmosphere with sophisticated, elegant vibe and beautiful decor. Live singer performances add to the swanky bar area ambiance. High-quality steaks and expertly crafted cocktails define the experience.

Dinner includes a bottle of Pinot noir that they aerate at the table. Cocktails and wine both come out very good.

Offers a wagyu tasting board that stands out among steakhouses. Combines a modern speakeasy atmosphere with quality steaks at reasonable prices.

People are saying

"The steak here is cooked perfectly and full of flavor."

"Our server Caesar gave us great wine pairings and made the experience memorable."

"The Steakhouse staff is so warm and friendly, they really make you feel welcome."

Good to know

1

Expect a 15-20 minute wait for a table on Saturday nights.

2

Happy Hour offers discounted drinks and appetizers; don't miss it.

3

The 'Girl Dinner' special on Sundays includes two martinis and caviar fries for $29.

02
A+ Italian Steakhouse image 1

Old-school Italian steakhouse with classic chandeliers and a spacious dining area creates a cozy, romantic vibe. Valet parking adds convenience while a small bar offers superb cocktails and retro music. Atmosphere stays inviting and comfortable with a touch of elegance throughout.

Offers a large selection of Napa Valley and Italian wines alongside top-notch martinis. The wine list pairs well with great cocktails.

Steaks come with classic steakhouse ambiance and an old school Chicago vibe featuring Sinatra tunes. Prices and parking beat downtown spots, offering a romantic and luxurious dining experience.

People are saying

"The food here is cooked perfectly and packed with flavor."

"The steaks here are cooked perfectly and full of flavor."

"The wine here is perfectly cooked, juicy, and tender."

Good to know

1

Happy hour offers half-price appetizers on Thursday evenings.

2

Reservations are recommended for dinner service, especially on weekends.

3

Expect a wait time of 30-45 minutes during peak dinner hours.

03
Trino Steakhouse image 1
Steak house

Cozy blend of industrial and mid-century modern speakeasy styles with exposed brick, murals, and velvety colors creates a romantic, intimate atmosphere. Soft classic salsa and bachata music sets a warm, inviting vibe. Creative space design and curated cocktail offerings distinguish it from typical steakhouses.

Unique wines from Mexico stand out here. Two bottles, including Flor de Canela, pair perfectly with meals and offer excellent flavor.

Steakhouse offers a perfectly cooked ribeye and a crab tostada that stands out. The space feels intentional and unique, with excellent vegetarian and pescatarian options alongside the steaks.

People are saying

"The food here is delicious, especially the steaks cooked to perfection."

"This is my favorite steakhouse in Chicago."

"The wine pairings here are great and complement the meal."

Good to know

1

Happy hour runs from 4-6pm with discounted appetizers and drinks.

2

Reservations are recommended for busy nights, especially weekends.

3

Trino Steakhouse is closed on Mondays but available for private events.

04
Chicago Chop House image 1

Restored brownstone with early 1900s decor and photos of local celebrities creates a traditional steakhouse atmosphere. Live piano music plays softly, adding to the luxurious and old-fashioned vibe. Comfortable seating and personalized touches enhance a refined dining experience.

A great selection of wine complements the menu well. Staff recommend perfect pairings and offer a complimentary sparkling toast to start.

Steaks here have a classic, old school style with a strong reputation for quality. The menu focuses on delivering a true Chicago steakhouse experience with consistently well-prepared cuts.

People are saying

"I found the steak to be tender and flavorful."

"Alyssa offered a great wine selection and excellent service."

"I thought this was the best steakhouse in the city."

Good to know

1

During the 40th anniversary, all food ordered was 40% off.

2

Valentineโ€™s Day celebrations offer special menu items.

3

Reservations are recommended, especially during holidays.

05
Dฤ“liz Italian Steakhouse image 1

Elegant steakhouse with a darker aesthetic and thoughtfully curated spaces including a stylish main dining room and lounge. Music features a live DJ that enhances the atmosphere without overpowering conversation. Exceptional cocktails and excellent steak define the dining experience.

An extensive and excellent selection of wines suits many palates. Staff recommendations pair well with dishes like steak, enhancing the meal.

Offers a refined dining atmosphere with a balance of elegance, flavor, and attentive hospitality. Serves as a local option for Italian steakhouse fare, replacing a previous spot in the neighborhood.

People are saying

"The steak here is seasoned and charred beautifully."

"The Steakhouse's mushroom risotto was rich, balanced, and a showstopper."

"I thought the wine list here was the best in town."

Good to know

1

Reservations are required as the restaurant is often fully booked.

2

Street parking is available, but valet service is also offered.

3

The restaurant has a full menu available at the bar.

06
Sophia Steak Chicago image 1

Upscale steakhouse offers intimate indoor seating and a welcoming outdoor patio with plants and shade. Atmosphere feels warm and inviting with stylish decor including Deco lamps and a flowered canopy. Cocktails and wine pairings complement perfectly cooked steaks in a comfortable setting.

Exceptional wine list offers great options with half off bottles on Mondays. Waitstaff provide thoughtful wine pairings that complement the food well.

Sophia Steak offers a sophisticated, bold-flavored steakhouse experience with an upscale atmosphere perfect for special occasions. The sautรฉed spinach stands out as a notably excellent side dish.

People are saying

"The steak here is melt-in-your-mouth tender and perfectly seasoned."

"The steakhouse's steaks are cooked perfectly with a savory crust."

"The wine pairings here are phenomenal and complement the food."

Good to know

1

Happy hour runs from 4:30 PM to 5:30 PM, including weekends.

2

Reservations are recommended for special occasions like birthdays.

3

Half off bottles of wine are available on Monday nights.

07
Westso Mexican Steakhouse image 1

Modern steakhouse with sleek black decor and comfortable seating creates a friendly yet elegant atmosphere. The vibe balances casual and sophisticated, welcoming guests in casual clothes. Excellent margaritas and steaks complement the stylish setting.

An extensive and well-curated wine list offers options to pair with every dish. Staff provide attentive service and guide with great food and wine pairing, highlighting underrated Mexican wines.

Ribeye steaks show excellent marbling, tenderness, and flavor. The spot offers a true Mexican steakhouse experience.

People are saying

"I thought the food was delicious and amazing."

"The steakhouse's steak was perfectly cooked, juicy, and full of flavor."

"I found the wine here to be excellent."

Good to know

1

Happy hour runs from 4-7pm with $10 margaritas and unique appetizers.

2

Tacos are $10 for three during happy hour.

3

Reservations are recommended for the dueling pianos event on weekends.

08
Charlie Martin's image 1

Cozy space with Hollywood regency decor and mood lighting creates a speakeasy vibe. Bartenders craft exceptional cocktails, including standout Old Fashioneds and martinis. Atmosphere suits jazzy date nights and sophisticated dining with white tablecloths.

Wine pairing enhances the food noticeably. Requests for wines not on the menu get prompt delivery. Both cocktails and wine show careful selection and quality.

Classic steakhouse vibe channels a 1950s supper club feel rather than typical Wisconsin-style spots. Pricing aligns with top Chicago steakhouses and includes a personal touch from the staff.

People are saying

"The seafood, especially the oysters, was super fresh and amazing."

"The service at this steakhouse makes you feel so well taken care of."

"The wine here is delicious and cooked perfectly."

Good to know

1

Reservations are recommended, especially during busy weekend nights.

2

The restaurant closes early at 11 pm, so plan your visit accordingly.

3

They often run out of popular menu items by 8 pm on weekends.

09
The Grillroom Chophouse & Wine Bar image 1

Steakhouse offers a sophisticated, relaxing atmosphere with warm lighting, wood, and leather creating a classic, comfortable space. Music stays at a conversation-friendly volume, supporting a peaceful, romantic vibe. Guests enjoy high-quality steaks and well-crafted cocktails in a setting that balances elegance with approachability.

Offers a nice wine selection with a good choice of options at reasonable prices. The wine pairs well with dishes like lamb chops and scallops.

Steaks come out flavorful and cooked exactly as requested. The atmosphere stays easygoing and not pretentious, making it a straightforward spot for a good steak.

People are saying

"The service at these dinner spots is so attentive and helpful."

"The wine here was perfect and very tasty."

"The steakhouse filet mignon was cooked to perfection."

Good to know

1

Happy hour offers drink specials from 4-6pm on weekdays.

2

Reservations are recommended, especially for weekend dining.

3

A 3% surcharge applies for credit card payments.

10
Hawksmoor Chicago image 1

Steakhouse offers a stylish and warm dining room with quiet sophistication and a relaxed but upmarket atmosphere. Cocktails are expertly crafted, complementing the coal-cooked steaks that define the menu. Private rooms and a dynamic space support both intimate and business gatherings.

An extensive wine list offers a wide range of choices. Sommeliers provide helpful pairing advice and recommend bottles that complement meals well.

Food quality stands out with well-prepared steaks that set a high standard. The ambiance feels like a Downtown London steakhouse, with a building and decor that enhance the dining experience.

People are saying

"The food here was delicious and cooked to perfection."

"The Steakhouse service, especially from Berto, was phenomenal and attentive."

"Our server John gave great wine recommendations."

Good to know

1

Happy hour runs from 5pm-6pm with great deals on steak, burgers, and oysters.

2

Reservations are recommended for the Sunday roast, which is only available on Sundays.

3

The restaurant offers gluten-free options and is knowledgeable about dietary restrictions.

11
North Center Prime image 1

Steakhouse offers a sleek modern design with a cozy, upscale atmosphere that feels both romantic and inviting. The space includes a bar with a nice view, creating a comfortable vibe for dining or drinks. It attracts those seeking quality steaks and a neighborhood spot with a downtown feel.

Good wine list pairs with hot and cold appetizers, soup, and salad. Prices run high, with a bottle and cocktails adding up to nearly $400 for a full meal.

Steaks here match the quality of any downtown spot with high-quality cuts and reasonable prices. The place pairs exceptional food with an inviting atmosphere and top-tier service.

People are saying

"I thought the steak was tender and juicy."

"The steaks here are fantastic and perfectly cooked."

"The steaks and sides here are fantastic."

Good to know

1

Parking costs $5 for two hours on Saturday nights.

2

Reservations are recommended, especially on weekends.

3

Expect to pay around $400 for a meal for two with drinks.

12
Boeufhaus image 1
Steak house

Steakhouse combines intimate, cozy vibe with a loud, lively atmosphere reminiscent of a low profile pub. Steaks are displayed in a front cooler, adding an old school, unique touch. The place fits many guests in a small, well-designed space with an open bar area.

A spectacular wine selection offers funky, contemporary, and high-quality options. Staff provide great wine pairings and the owner shares insights about the wine philosophy and list.

Steaks here have a rich flavor and perfect tenderness. The place stands out as a top choice for steak lovers.

People are saying

"The steak frites here is phenomenal."

"I loved their spectacular and funky wine selection."

"The Steakhouse's dry-aged beef is cooked perfectly."

Good to know

1

Happy hour runs from 4-6pm with discounted drinks and appetizers.

2

Reservations are recommended due to limited seating and high demand.

3

The happy hour includes a burger, fries, and a drink for a great price.

13
Adalina Prime image 1
Steak house

Steakhouse offers a stunning build-out with indoor and outdoor seating and a warm, modern feel. Atmosphere feels elegant and refined, with exceptional service and playful touches like a salt library for customizing steaks. Bar features include top-notch martini service and a variety of strong, well-crafted cocktails.

Knowledgeable servers and a skilled sommelier guide wine choices. The wine pairings complement the food well and the list offers solid options.

Offers a unique and incredible menu that changes the classic steakhouse experience. Features curated foods with new ideas that set a new bar for steakhouses in the city.

People are saying

"The food here was delicious and flawlessly executed."

"Our server Trey recommended a great wine pairing."

"The steaks at this Steakhouse are cooked perfectly."

Good to know

1

Happy hour runs from 4-7pm on weekdays with half-price appetizers.

2

Reservations are recommended due to high nighttime traffic.

3

Trivia night happens every Tuesday at 8pm with a $5 entry fee.

14
The Alston image 1
Steak house

Dining room offers spacious elegance with a unique interior design and tableside presentations like duck press. Atmosphere blends pre-Covid hospitality with a lively, upscale crowd. Bar serves impressive cocktails alongside expert wine pairings.

A sommelier guides wine choices with insightful recommendations like the Keenan Capstone Spring Mountain Cabernet Sauvignon. The wine cellar offers a chance to explore outstanding bottles paired well with meals.

Bold French twists on classic steakhouse fare create a distinctive dining experience. Great service and an astounding dining room add to the appeal in a crowded steakhouse scene.

People are saying

"The steak here is outstanding, and the service makes you feel well taken care of."

"The steakhouse here serves expertly aged and impeccably cooked steaks."

"I loved their huge and thoughtfully curated wine list."

Good to know

1

Reservations are recommended to secure a table, especially during peak hours.

2

A 3% service charge is added to all credit card transactions.

3

Happy hour features a curated menu of food and drinks.

15
Tortoise Supper Club image 1
American restaurant

Elegant supper club blends live jazz music with a cozy, lively atmosphere featuring dark wood and colorful jazz-inspired wallpaper. Dining spaces include a private room with a bar, creating intimate vibes amid a bustling crowd. The setting combines elements of a jazz club and restaurant for a unique experience.

Friday happy hour features half off wine and $1 big oysters and shrimp. Staff offers great wine recommendations that enhance the experience.

Carries on the spirit of classic steakhouses while adding a unique Chicago twist. Faces strong competition from many 5-star steakhouses in the city.

People are saying

"The food at these dinner spots was spectacular and delicious."

"The wine knowledge here is wonderful and the servers are attentive."

"The Steakhouse service was incredible."

Good to know

1

Reservations are required for private events and should be made well in advance.

2

Happy hour runs from 4-6pm on weekdays with discounted drinks and appetizers.

3

Valet parking costs $16 for three hours, making it convenient for guests.

16
Tango Sur image 1
Argentinian restaurant

Cozy interior with candle-lit tables and rustic charm creates a warm, romantic atmosphere. Live guitarist plays Argentine music, encouraging engaging sing-alongs. BYOB policy lets diners bring preferred wines, complementing authentic Argentine steaks and dishes.

A wall of wine stands out and guests can bring their own bottles to be opened and served. Staff quickly provide wine glasses and serve wine efficiently, complementing dishes like filet with red wine sauce.

Offers Argentinian-style steaks known for quality and flavor. Serves meat that stands out in the city's steakhouse scene.

People are saying

"The steaks here are cooked to perfection."

"The empanadas at this Steakhouse were moist, flavorful, and straight up incredible."

"The food here is so flavorful, I can't stop thinking about it."

Good to know

1

You can bring your own wine to Tango Sur.

2

Reservations are recommended on weekends due to high demand.

3

Expect wait times of up to two hours during peak dinner times.

17
STK Steakhouse image 1
Steak house

Modern steakhouse blends trendy club vibe with live DJ sets and bold neon decor. Atmosphere feels lively and energetic, with music often loud enough to dominate conversations. Cocktails stand out as fresh and flavorful highlights amid the setting.

Staff offer knowledgeable wine recommendations tailored to dishes like lamb. The wine list is great and wines are served in crystal glasses for a refined experience.

Steaks come out perfectly cooked, even well-done ones taste great. Service stands out with attentive staff making the experience smooth and enjoyable.

People are saying

"The food here is delicious and high quality."

"The Steakhouse service was attentive and friendly."

"The wine recommendations here are excellent."

Good to know

1

Happy hour offers great deals on food and drinks from 4-7pm on weekdays.

2

Expect a one-hour wait for a table during peak dining hours.

3

Cocktails are priced at $9 during happy hour.

18
Mastro's Steakhouse image 1
Fine dining restaurant

Elegant dining space features dim, cozy lighting and live music performances that create a romantic, upscale atmosphere. The lounge offers an upbeat vibe with talented singers and pianists providing background entertainment. Seating is close together, enhancing a lively, intimate feel.

Wine pours come in large servings. Staff show deep wine knowledge and suggest perfect pairings for steaks. The wine selection impresses and complements the drinks well.

High-end steakhouse offers exceptional cuisine with a focus on quality and flavor. Staff provide wonderfully kind and professional service, creating a welcoming atmosphere for celebrations and special occasions.

People are saying

"The steak here is amazing, with attentive and friendly staff."

"The Steakhouse staff made me feel like family."

"The manager Agim is a true wine expert who guided us."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted appetizers.

2

Reservations are recommended for dinner, especially on weekends.

3

Valet parking is available and recommended for convenience.

19
BLVD Steakhouse image 1
Steak house

Steakhouse offers an upscale look with an incredible interior and a beautiful atrium that contrasts with a moody dining room. The atmosphere feels romantic and chic, supported by exceptional music and a fantastic drinks bar. Outdoor seating provides an excellent patio experience during warmer months, though it sits near noisy subway tracks.

A curated selection of wines pairs well with the steaks. A wine station near the entrance lets guests start with a drink right away. Staff offer personalized wine suggestions that can lead to buying a bottle to go.

Steakhouse offers excellent steak and food with a beautiful setting and amazing service. The ambience feels special, making it a great spot for celebrations.

People are saying

"The food and drinks at these dinner spots were delicious."

"The food at this Steakhouse is always great."

"The wine here is stunning, dark, and dreamy."

Good to know

1

Reservations are recommended, especially for busy nights and special events.

2

A 20% gratuity is automatically added to all bills, including for large parties.

3

Happy hour offers significant discounts on drinks and appetizers during weekdays.

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