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Top picks in the Loop

Cocktail nightlife

Made for those who view the late-night hours as the only time worth being out and require a cocktail to anchor the experience.

Based on 567 Opinions
+564
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Updated May 2026
01
Bar Sotto image 1
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Hidden underground bar with soft red glow and jazzy atmosphere creates an intimate, cozy vibe. Space feels mysterious and character-rich, attracting an upbeat crowd for fun nights out or romantic dates. Creative cocktails and unique design details add to its distinct charm.

Cocktails here show a creative spin with options like a fruity fernet and an espresso martini with Parmesan. Signature drinks include the creamy, salty Reggiano and the gin-based Purple Monster, all crafted with a speakeasy vibe and a jazzy atmosphere.

A basement lounge offers dark disco vibes with a romantic, rustic atmosphere. The space feels like a speakeasy with touches of European nightlife and serves craft cocktails, Italian beer, and wine.

People are saying

"The bar staff here feels like family and makes you feel right at home."

"You have to try the espresso martini with Parmesan; it's intriguing."

"The craft cocktails and shareable bites here are excellent."

Good to know

1

Happy hour offers discounted drinks and bites after work.

2

The bar features a rotating menu of small shareable plates and pasta.

3

Reservations are recommended for busy evenings, especially weekends.

02
Jazz Showcase image 1
Jazz club

Intimate jazz club with historic dรฉcor and excellent acoustics creates a cozy, relaxed atmosphere. Live performances feature talented musicians playing in a setting that honors jazz legends. Dim lighting and comfortable seating offer a balanced sound experience ideal for soaking in pure jazz.

Jazz and great cocktails come together here. The cocktail menu offers excellent choices, though it lacks a signature house cocktail.

Classic jazz club vibe with top flight musicians performing in an intimate venue. Offers a quintessential Chicago jazz experience with a strong, traditional program.

People are saying

"I enjoyed the great live jazz performances here."

"I enjoyed the excellent cocktails and draft beers."

"The jazz club's atmosphere is intimate and historic."

Good to know

1

Admission is $20 per person for entry.

2

Jazz Showcase does not serve food but allows patrons to bring their own.

3

It is advisable to buy tickets in advance as shows often sell out.

03
Copper Club image 1
Restaurant

Stylish escape inside an office building lobby offers a cozy setting with wide chairs and a large bar. Atmosphere shifts from peaceful and calm to lively and loud as the evening progresses. Known for affordable meals and a strong whiskey selection, it attracts those seeking good food and drinks after work.

Cocktails feature strong cucumber flavors in large glasses and aged spins on classics. Options include a well balanced gin-based drink, an espresso martini, and a cocktail similar to an old fashioned.

Stylish escape inside an office building lobby offers a peaceful atmosphere and phenomenal appetizers. Staff delivers kind and attentive service alongside delicious cocktails.

People are saying

"The food here is tasty and delicious."

"I enjoyed delicious cocktails here; they were well balanced."

"The nightlife here is amazing, the bartenders are so friendly."

Good to know

1

Reservations are essential for happy hour due to high demand.

2

Happy hour specials include discounted drinks and slider options.

3

Copper Club is only open on weekdays.

04
Adamus Lounge image 1
American restaurant

Circular bar anchors a stylish, comfortable lounge with eclectic furniture and spacious seating that supports quiet conversation. Atmosphere stays chill but classy with a slow, relaxed pace. Cocktail offerings stand out with well-crafted drinks amid a cozy, clean setting.

Cocktails come with a fancy lounge setting and plenty of seating. Drinks are solid but a bit pricy, matching other downtown hotel lounges.

A chill but classy vibe defines the lounge, with a fancy look and plenty of seating. Cocktails come at a pricy rate, and happy hour runs until 7, offering a decent option for a relaxed evening.

People are saying

"The Night Lounge's drinks are on point, especially the Old Fashioned."

"The drinks here are on point, and the truffle fries are next level."

"Manuel whipped up some fantastic cocktails and made the visit."

Good to know

1

Happy hour runs until 7pm with special drink prices.

2

The lounge is located just inside the hotel to the left.

3

They do not accept cash; only credit cards are accepted for payment.

05
Era Social Club image 1
Night club

Urban club with cool lighting and lively atmosphere hosts DJs playing hip hop hits geared toward millennials. Crowd is diverse and inclusive, creating a fun vibe where people come to celebrate and enjoy music all night. Rooftop area adds an extra dimension to the overall experience.

Creative mixes define the cocktail menu. Expect exceptional flavors and good variety throughout.

Offers an upscale club experience with great music and a DJ. The vibe is LGBTQIA-community friendly and welcoming, with respectful staff and strong security. Bottle service and cocktails add to the lively atmosphere.

People are saying

"The bottle service girls here provide excellent, attentive care."

"The nightlife service here is amazing, with friendly and fast staff."

"The cocktails here have an awesome vibe."

Good to know

1

Entry is $100, but free tickets are available before 11pm.

2

Social Saturdays are a popular event at the club.

3

Parking can be risky; consider using Uber instead.

06
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.

A restored 19th-century athletic club offers a speakeasy room, rooftop lounge with views of the Bean, and a game room. Bars and lounges create a vibe like stepping into a time machine.

People are saying

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

"The Drawing Room is a cozy nook for drinks with old-world charm."

"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.

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.

Rooftop club offers amazing drinks, music, and skyline views at night. The bar club atmosphere creates strong vibes with a unique cityscape backdrop.

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 rooftop nightlife offers amazing skyline views and vibes."

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
theWit Chicago, a Hilton Hotel image 1

Hotel offers lively rooftop bar with great city views and vibrant atmosphere. Rooms and common areas feature funky artwork and a comfy, eclectic design. Nighttime brings street noise and energetic crowds, especially near the club and light rail.

Sushi and vodka cocktail stands out at the rooftop bar. The drink list features cocktails, draft beers, bottles, and cans with solid local options. Cocktails are also available on the first floor.

A nightclub on the rooftop offers a beautiful setting to party after concerts. The location provides walkable access to theaters, riverwalk, and other nightlife spots in the heart of the Loop.

People are saying

"The hotel's five-star service made my day better."

"The rooftop bar's nightlife is lively and usually busy."

"The rooftop bar cocktails were awesome and the best I've ever had."

Good to know

1

The rooftop bar hosts a brunch buffet on weekends.

2

Private events frequently close the rooftop bar, limiting access.

3

Valet service is recommended as there is no parking available.

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