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the Loop's best

Relaxing cocktail spots

You want a cocktail in a space where you can actually hear yourself think.

Based on 628 Opinions
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Updated April 2026
01
Bar Pendry Chicago image 1
Bar Pendry Chicago image 2
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Small bar with cozy fireplace and plush seating creates a warm, relaxed vibe. Music stays at a comfortable level, supporting a laid-back atmosphere with a hint of 80s living room style. Space suits small groups and afterwork drinks, offering period-inspired cocktails and a quiet place to unwind.

Period-inspired cocktails stand out with interesting flavors. Many drinks, like the Crimson and Carbide, taste perfect and suit afterwork vibes well.

A younger vibe fills the space with a DJ playing music at a comfortable volume. The lounge and bar offer a spot to relax by the fire and enjoy a drink.

People are saying

"The food here is amazing; the staff is so friendly and attentive."

"The bar staff was so attentive and friendly."

"It's a great spot to relax by the fire with a drink."

Good to know

1

Bar Pendry Chicago can get packed during happy hour.

2

The bar's small size makes it not suitable for larger groups.

3

Expect a busy atmosphere in the evenings.

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.

Cozy and comfortable atmosphere creates a very relaxed environment. It offers a great spot to unwind and enjoy jazz music.

People are saying

"I enjoyed the great live jazz performances here."

"I enjoyed the excellent cocktails and draft beers."

"I found the atmosphere here to be very relaxed and comfortable."

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
The L Station image 1
Restaurant

Small, beautifully decorated restaurant offers a cozy yet elegant atmosphere with an intimate feel. Live DJ spins strictly R&B music, creating an upbeat and fun vibe that keeps energy lively. Known for spectacular lamb chops, perfect margarita flights, and a warm, welcoming ambiance.

Cocktails feature beautiful presentation and excellent service. Bartenders like Tee and Jada craft top-notch drinks with care and hospitality.

Warm and inviting atmosphere creates a cozy and classy setting. Music and scenery add a relaxed yet energetic vibe that suits solo treats, dates, or casual meals.

People are saying

"The food here is fresh and delicious."

"Tee's handcrafted cocktails are unbelievably delicious."

"The food and drinks here are so fresh and flavorful."

Good to know

1

Reservations are required for parties of 10 or more.

2

Expect a two-hour wait without a reservation.

3

The kitchen closes at 7pm, so arrive early.

04
The Game Room image 1

Bar combines vintage decor with modern games like pool, shuffleboard, and skeeball. Atmosphere varies from relaxed upscale to loud and sketchy depending on the crowd. Large space offers ample seating and diverse activities throughout.

Specialty cocktails crafted with care stand out here. Classic drinks come well made, making it a solid spot for a cocktail.

A relaxed, upscale setting creates a pleasant atmosphere for unwinding. The space offers a vibrant environment where people enjoy drinks, friendly competition, and connecting with others.

People are saying

"It's a fun place with a lively vibe and great games."

"The cocktails here have a cool, historic vibe."

"This Relaxing Spot has a vibe that's both relaxed and vibrant."

Good to know

1

Reservations are recommended for large groups to ensure space availability.

2

The venue has a minimum food and beverage requirement for private events.

3

Expect a surcharge if you exceed the agreed-upon food and beverage minimum.

05
Reserv image 1
Restaurant

Rooftop bar offers breathtaking views and a cozy lounge creates an intimate setting. Music plays loudly with a live DJ during brunch, setting a lively atmosphere that suits both unwinding and starting a night out.

A signature cocktail is crafted when choices stall. The mixologist explains the cocktail list clearly. The spot feels safe and comfortable to unwind with drinks and music.

Rooftop bar offers a great spot to unwind with cocktails and great music. The atmosphere stays relaxed but lively, making it easy to feel safe and comfortable while hanging out.

People are saying

"It's packed for live sports, especially the Bears games."

"You can unwind over a cocktail in this cozy, intimate lounge."

"It's a great spot with a cool atmosphere and awesome vibe."

Good to know

1

Trivia night happens regularly, providing a fun atmosphere for guests.

2

Street parking is available, along with nearby garages for convenience.

3

The steak skillet costs $14, offering great value for a meal.

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.

1st-floor lobby, coffee shop, and game room offer quiet spots to unwind or work. The space features beautiful holiday decorations and serves amazing drinks to help escape the cold.

People are saying

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

"This historic building is a charming Relaxing Spot 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
Pendry Chicago image 1

Historic building with Art Deco design offers spacious rooms featuring city views and luxurious amenities. Lobby and rooftop lounge provide a resort-like atmosphere with music and entertainment. Downtown location brings loud street noise at all hours, affecting room quietness.

Rooftop cocktail bar offers a special setting with a standout menu. The lobby bar serves delicious cocktails, while downstairs provides a swanky vibe ideal for drinks or work.

A wonderful lobby offers a great spot to relax. Suites provide ample space for kids to run and adults to unwind. The cozy bar area serves as a chill place to wait or relax before checking out.

People are saying

"The hotel staff were so friendly and helpful."

"The rooms here are super quiet, making it a truly relaxing spot."

"Dolapo's hospitality made our cocktails truly memorable."

Good to know

1

The Cadillac experience is available only on select days and hours.

2

Escalade service operates on Fridays and Saturdays for rides within a two-mile radius.

3

Happy hour is offered daily at the restaurant.

08
LH Rooftop image 1
Restaurant

Rooftop bar offers unparalleled city views including river and Gothic architecture. Atmosphere is lively with loud music, making conversation difficult. Outdoor space features igloos and fire pits, with indoor area hosting a live DJ to maintain energy.

Creative cocktails come with fast service and stunning river views from the terrace. Drinks are consistently incredible and enjoyable with a beer or cocktail option.

Balcony views showcase city lights that create a romantic and relaxing atmosphere. The vibe stays friendly and laid-back, perfect for unwinding with solid food.

People are saying

"The rooftop city views are stunning and beautiful."

"The cocktails here offer amazing views of the river and city."

"The views from this relaxing spot are absolutely stunning."

Good to know

1

Reservations are required to secure a table at LH Rooftop due to limited space.

2

Expect long wait times during peak hours, especially on weekends.

3

Bring your ID as it is required for entry; no photos accepted.

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