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Happy hour and steakhouse in Chicago

Made for those who prefer the high-end service of a steakhouse even when they are just stopping in for a drink.

Based on 678 Opinions
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Updated May 2026
01
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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.

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 ambiance here feels like traveling through time."

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.

02
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.

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 Wagyu steak sandwich during Happy Hour is unbelievable."

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.

03
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.

Offers amazing deals on steak, burgers, and oysters during happy hour. The menu includes a gourmet Big Mac and good oysters that stand out.

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."

"The happy hour steak frites offered the best deal."

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.

04
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.

Happy hour features delicious food with highlights like steak frites. The overall experience is great and enjoyable.

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 service during Happy Hour was amazing, especially from Olivia and Sonia."

"The Steakhouse service was attentive and friendly."

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.

05
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.

Happy hour features $10 margaritas and three tacos for $10, making it easy to enjoy drinks and bites without spending much. Unique appetizers offer enough variety to make a meal out of the deals.

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."

"The happy hour margaritas are amazing and unique."

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.

06
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.

Happy hour features $1 oysters and shrimp cocktail on Wednesdays and Fridays, with half off cocktails and wine. The oyster deal stands out as a rare find since the pandemic.

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."

"Happy Hour oysters are a fantastic deal at just $1."

"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.

07
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.

Happy hour features cocktail specials that work well as a pre-show drink. The atmosphere suits a quick, enjoyable stop before dinner.

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 service during Happy Hour was spectacular."

"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.

08
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.

Happy hour features reasonable specials like shrimp cocktail and drinks. Deals include a burger, fries, and beer or wine combo, plus short rib beignets that stand out.

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."

"The happy hour beignets are to die for."

"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.

09
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.

Great happy hour offers solid drinks and service. Liam at the bar and Dio in the dining room make the experience stand out.

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."

"The steaks at this Steakhouse are cooked perfectly."

"I found Liam at the bar during Happy Hour to be outstanding."

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.

10
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.

An extensive Happy Hour menu launched recently offers a variety of options. Checking the website or calling ahead helps confirm the Happy Hour hours.

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."

"I enjoyed a great Happy Hour experience with amazing deals."

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.

11
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.

Generous happy hour menu pairs foods and drinks that complement each other well. The bar's decor offers a pleasant spot to enjoy happy hour, while food outside the menu is notably pricy.

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."

"You have to try the King Crab during Happy Hour; it's flown in fresh daily."

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.

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Chicago, Illinois

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