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New Yorkers 1st Choice
Top picks in the Loop

Unique cocktail spots

A drink that defies the standard menu makes the night feel like an event. It is about the curiosity of trying something that was crafted with intention.

Based on 641 Opinions
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Updated April 2026
01
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Mexican restaurant

Space features vibrant Mexican-inspired decor with colorful lights and intricate metalwork. Atmosphere feels fun and lively, enhanced by live mariachi music and reggaeton beats. Unique self-serve tequila and mezcal stations invite guests to sample drinks at their own pace.

Cocktails come in a diverse range with strong flavors and careful preparation. The Carajillo stands out for espresso martini fans, and bartenders serve drinks with a friendly smile.

Creative dishes and a pour yourself mezcal and tequila station stand out here. The space features colorful sculptural metal scaffolding and unique lighting, all paired with reggaeton music for a distinct vibe.

People are saying

"The food here is delicious and fresh."

"Sebastian made really good cocktails and a welcoming atmosphere."

"The food and drinks here are unique and delicious."

Good to know

1

Happy hour runs from 4-7pm with great deals on drinks and appetizers.

2

Friday night features live Mariachi performances starting at 8pm.

3

The venue plans to host live DJ performances in the future.

02
Ayayay - Mexican Eatery image 1
Mexican restaurant

Urban, modern space with Tulum-inspired decor and stunning interior architecture creates an authentic Mexican canteen vibe. Great music energizes the atmosphere, while seating ranges from stools at larger tables to intimate spots for two. The setting feels like a slice of Mexico City with a lively, welcoming energy.

Delicious cocktails stand out with a mix of flavors that complement the food well. Drinks come at a reasonable price, adding to the overall enjoyable experience.

The menu offers unique flavor combinations in tacos, including a nutty tostones dish that grows sweeter as you chew. The atmosphere and interior also stand out with a distinctive vibe.

People are saying

"I found the food here to be delicious and well-seasoned."

"The food here has a unique, pleasantly nutty flavor."

"I tried the best margarita I have ever had."

Good to know

1

Happy hour runs daily from 2 to 6 pm.

2

$3 Taco Tuesdays offer great value for visitors.

3

Wednesday features a special margarita deal.

03
Drunk Shakespeare Chicago image 1
Performing arts theater

Small, intimate theater with benches opposite each other and bookshelves on all walls creates a cozy, engaging space. Performers deliver high-energy, hilarious Shakespearean plays while interacting closely with the audience. Drinks and food arrive at seats via QR code ordering, enhancing the relaxed, lively atmosphere.

Signature cocktail features homemade lemonade, makers, and blackberry liqueur. Drinks come with a welcome shot and pair well with snacks like caviar.

The show delivers a unique blend of humor and audience participation that keeps things wild and engaging. It offers a fun, loud, and innovative experience unlike typical performances.

People are saying

"It's hilariously fun and unpredictable."

"It's a unique experience; I laughed the whole time."

"The cocktails were delicious, especially the welcome shot."

Good to know

1

Must be 21 to enter; ID checked for all ages at the door.

2

The show is rated R and not suitable for the faint of modesty.

3

Expect a fun and unique experience with a comedic twist on Shakespeare.

04
Seville Chicago image 1
Restaurant

Rooftop restaurant offers stunning city views and a relaxed atmosphere with friendly staff. The space features beautiful ambiance suitable for quiet meals or lively happy hours. Cocktails and small plates complement the setting, creating a charming dining experience.

Cocktails feature bourbon blackberry and blackberry whiskey sangria styles like Running with the Bulls. Gin and vodka drinks come out impeccably crafted and refreshing with reasonable prices.

Dishes feature unique and flavorful tastes that stand out. The Moroccan wings have a unique spice and fall off the bone, while the sea bass offers a distinct flavor that exceeds expectations.

People are saying

"You'll love the inventive cocktails, many are sweet."

"The food here is delicious, super juicy and flavorful."

"The food here has unique, flavorful tastes."

Good to know

1

Happy hour runs from 3:30 to 5:30pm on weekdays.

2

Happy hour offers great deals on food and drinks.

3

The restaurant is located on the 16th floor of the Hilton hotel.

05
Chicago Athletic Association - The Unbound Collection by Hyatt image 1

Venetian-Gothic architecture shapes a stylish hotel with ornate woodwork and intricate carvings. Lively atmosphere fills public game rooms and a rooftop bar with great views of the lake and park. Athletic-themed amenities include basketball, bocce, and yoga, blending historic charm with active recreation.

Extensive bar offerings include custom cocktails crafted with the in-house restaurant. Both rooftop and indoor bars serve delicious cocktails alongside attentive service.

Rooms show detailed character with a style that stands out from modern hotels. The space features amazing architecture and a unique atmosphere that feels more inviting than sterile.

People are saying

"It's a striking historical site with authentic charm and artistic details."

"The rooftop bar has an awesome view of Millennium Park."

"The cocktails here have an awesome view of the park."

Good to know

1

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

2

Expect wedding crowds on weekends due to the hotel's wedding venue status.

3

Reservations are required weeks in advance for dinner at Cindy's Rooftop.

06
Bistro Monadnock image 1
French restaurant

Historic building hosts a French bistro with European charm and elegant design. Live jazz music creates a relaxing atmosphere complemented by a skilled bar offering standout cocktails. The space feels cozy and stylish, attracting those seeking a refined dining experience.

Cocktails stand out for their delicious flavors and creative mixes. The melon sour and a dealerโ€™s choice cocktail/mocktail crafted by Eric the bartender highlight the menu's variety and quality.

Unique appetizers like Smoked Walleye stand out on the menu. The wine list features distinctive selections curated with a sharp eye for originality.

People are saying

"The escargot here is outstanding and alone worth the visit."

"I found the cocktails to be exceptional and well prepared."

"This French restaurant offers a unique, modern twist on classic recipes."

Good to know

1

Reservations are recommended, especially on weekends, to avoid being turned away.

2

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

3

Expect a $10 charge for each cheese on the charcuterie board.

07
Sports Illustrated Resorts Chicago image 1

Hotel offers great views and modern, comfortable rooms with thoughtful amenities like in-room kettles and a well-equipped gym. Rooftop bar and club create a loud atmosphere with bass noise permeating halls late into the night. Design is upscale and clean, but overall vibe is not warm or welcoming.

Drinks include classic cocktails and unique house creations. The bartender shows outstanding knowledge and balances speed and quality while making intricate cocktails and chatting.

Rooms feature unique design with beautiful spaciousness and practical touches like many outlets and good lighting for makeup. Drinks include classic cocktails and creative house specials.

People are saying

"The hotel staff went above and beyond to make me feel welcome."

"The cocktails here are perfectly balanced and packed with flavor."

"The bartender's attention to detail and charisma make for a unique experience."

Good to know

1

Rooftop parties occur on weekends, featuring house music and a vibrant atmosphere.

2

Happy Hour offers complimentary drinks for guests from 4-5pm daily.

3

Reservations for special events like birthday celebrations are recommended for personalized services.

08
Francois Frankie Le Carousel Bar image 1

Rotating carousel bar moves slowly, completing a full turn about once per hour, creating a unique focal point. Upscale ambiance combines with comfortable seating and a perfect noise level for conversation. Jazz duo adds to the atmosphere, making it lively yet approachable.

Cocktails here are very well made and creative, with standout drinks like the old fashioned and French 75. The bar's vibe matches the drinks, looking just like a carnival carousel.

Rotating slowly while drinking creates a carousel bar experience. The space divides into three sections: the bar, nearby tables, and a separate dining area, all with unique decor.

People are saying

"The Amish chicken at this Bar is tender, juicy, and perfectly seasoned."

"The cocktails are creative and the bar looks just like a carnival carousel."

"They brought every vision to life and then some."

Good to know

1

On Tuesdays, enjoy a $10 cocktail and oyster night with live jazz music.

2

Happy hour features discounted drinks and appetizers from 4-7pm on weekdays.

3

Expect to spend around $60 per person for a meal with drinks and tip.

09
Monk's Pub image 1

Classic pub with dark wood and exposed brick creates a cozy, old-world atmosphere filled with Belgian beer memorabilia and vintage decor. The space feels packed and lively, offering a laid-back vibe ideal for socializing. Music leans toward garage rock, punk, and blues, enhancing the authentic pub experience.

Manhattan cocktails here beat those in NYC. The Rum Punch canned cocktail stands out and packs a punch. Beer and cocktail selections are excellent and the overall cocktails are good.

Authentic unique vibe fills the space with super unique decor. The flatbread stands out with crispy toasted pita topped with hummus, feta, pickled onions, and tomatoes.

People are saying

"The beer selection here is extensive and solid."

"You have to try the cocktails; the Manhattan is better than anything I've had in NYC."

"I loved the unique decor and atmosphere."

Good to know

1

Happy hour gets crowded, so arrive early to secure a spot.

2

Reservations are not accepted after 6pm, so plan accordingly.

3

Parking is available under the elevated tracks on Lake Street.

10
The LaSalle Chicago, Autograph Collection image 1

Hotel combines old-fashioned charm with a modern twist in a sheek, elegant setting. Rooms are quiet, cozy, and spacious with attention to detail throughout. Public spaces include a quieter bar with jazz and offer great city views.

Quiet bar on the 21st floor features a jazz band and better cocktails. The lounge and restaurant serve creative cocktails throughout the day alongside food options.

Distinctive features include an upside down layout and a sheek atmosphere. The hotel blends classy and quaint elements with an expansive feel.

People are saying

"The hotel staff here is so friendly and helpful."

"It's a unique, beautiful, and classy hotel."

"You'll find creative cocktails served throughout the day."

Good to know

1

The Grand Ballroom on the 22nd floor hosts weddings and events.

2

Jazz nights occur every Friday and Saturday at the in-house restaurant.

3

Check-in is located on the 21st floor, right outside the elevators.

11
Canopy by Hilton Chicago Central Loop image 1

Quiet, spacious rooms with luxurious decor and modern amenities create a cozy, home-like atmosphere. Heavy carpeting and thoughtful design keep noise low despite nearby urban sounds. Facilities include a well-equipped fitness center, free water refill stations, and a rooftop restaurant open for dinner.

A Running with the Bulls cocktail offers a sangria-style drink that fits the Spanish theme. Friendly staff serve drinks in a lobby with a nice ambience for both coffee and cocktails.

Rooms feature unique decor with a modern American art deco style. The hotel offers a boutique experience with a standout lobby and restaurant/bar area.

People are saying

"This hotel's decor is beautifully designed and visually appealing."

"The decor here is so unique and charming, with a real retro vibe."

"The cocktail bar staff were super knowledgeable and friendly."

Good to know

1

Parking at the hotel costs $75 a day, which can be high on weekends.

2

The hotel is located just 2 blocks from Union Station, making it accessible.

3

Wi-Fi issues may occur, as some guests reported authentication problems.

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