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New Yorkers 1st Choice
Local picks in Chicago

Cool spots

A hotel that manages to be cool and culturally relevant without trying so hard that it becomes exhausting to stay there.

Based on 641 Opinions
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Updated April 2026
01
The Neighborhood Hotel Little Italy image 1
The Neighborhood Hotel Little Italy image 2
The Neighborhood Hotel Little Italy image 3
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Suites combine modern design with spacious layouts and quiet, soundproof rooms. Views include city skyline and Italian garden, enhancing a calm atmosphere. Neighborhood buzzes with diverse culture and vibrant food options, creating a lively yet safe environment.

Offers a luxurious and cozy stay with a five-star experience. Accommodates extended visits, including stays with pets, providing a memorable and exceptional hotel environment.

Soft arches and fun pops of color create a standout design. Elevated touches include good coffee, a cool European coffee maker, and nice soaps.

People are saying

"The hotel rooms were spacious, clean, and comfortable."

"The view from the 5th floor terrace is magnificent."

"The kitchen is so well-equipped, it's really cool."

Good to know

1

Parking is limited, but ride-sharing services are affordable and convenient.

2

The hotel is within a 5-minute walk to UIC and RUSH.

3

There are two L stations within walking distance for easy city access.

02
Ray's Bucktown Bed and Breakfast image 1

Eclectic building filled with unique art and quirky decor creates a cozy, bohemian vibe that feels like home. Common areas buzz with interesting people and offer amenities like sauna, steam room, and rooftop lounge. Rooms are comfortable and charming, making the stay personable and inviting.

Located in a charming neighborhood, this inn offers a bed and breakfast experience with a variety of vegan-friendly options unlike typical hotel breakfasts.

Walls and shelves showcase cool vintage and antique paintings alongside unique knick-knacks. A rooftop deck adds a standout spot to explore and enjoy.

People are saying

"The beds here are so comfortable and inviting."

"The hotel breakfast here is made to order and absolutely delicious."

"It's filled with cool art and knick-knacks to explore."

Good to know

1

Breakfast is served from 8 to 11 am daily.

2

The location is a 5-minute walk from the Blue Line train.

3

Street parking is always available near the B&B.

03
Staypineapple, An Iconic Hotel, The Loop Chicago image 1

Historic building blends modern amenities with charming style and comfortable rooms featuring exceptional views. Atmosphere stays fun and welcoming with a calm, chill vibe throughout. Complimentary treats and a friendly bar add to the inviting experience.

Rooms feature very comfortable beds that stand out for quality. Staff members like Marshay provide kind and helpful service. The hotel offers a pet-friendly environment near major shopping and park areas.

Original cage structure in the elevator stands out with a modern lift inside. The building's historic character from 1895 adds a classic vibe that feels really cool.

People are saying

"This hotel's location is great for walking everywhere."

"The beds here are so comfortable and the rooms are clean."

"This hotel is in a really cool historic building."

Good to know

1

Happy hour offers a burger and beer or soda for $10 from 4-6 pm.

2

Every afternoon, enjoy a cookie hour with complimentary beverages.

3

Valet parking is expensive and can be problematic during busy events.

04
Hotel EMC2, Autograph Collection image 1

Hotel combines modern technology with a classic gentleman’s lounge vibe, creating a dark, sultry atmosphere that feels both cozy and sophisticated. Robots deliver room service and amenities, enhancing a unique, artistic experience. Despite central location, the space remains quiet and intimate.

Outstanding staff service creates a welcoming and caring atmosphere. A robot delivers toiletries, adding a unique touch to the stay.

Rooms feature a beautiful glass shower in the middle, adding a unique touch. Robots handle some services, showcasing cool technology. The theme draws from Einstein, creating a weird and different vibe.

People are saying

"The hotel staff made me feel so special and valued."

"The high-tech decorations and electronics make it feel unique."

"The staff here are so friendly and helpful, making check-in a breeze."

Good to know

1

The hotel offers a brunch for $29.99, including a main course, dessert, and a drink.

2

The hotel is located in the heart of downtown Chicago, close to top attractions.

3

The hotel is dog-friendly, but the attached restaurant with patio isn’t.

05
The Robey image 1

Hotel offers an industrial chic vibe with luxurious, soulful ambiance and phenomenal rooftop views. Multiple bars and a café create a lively, celebratory atmosphere. Location near transit and neighborhood shops adds convenience and local flavor.

Stunning boutique hotel with spectacular lighting from abundant windows. Offers great accommodations in an area with few hotels.

A rooftop bar offers unique views of downtown Chicago. The hotel features a cool Art Deco style. The nearby neighborhood by the Blue Line adds to the vibe.

People are saying

"The hotel staff were so helpful and friendly."

"The rooftop offers what might be the best view in the city."

"The staff here is so friendly and helpful."

Good to know

1

The Cabana Club is open to the public from 4-6 PM for happy hour.

2

Happy hour features discounted drinks and appetizers at The Robey.

3

Story hour at the Clever Coyote takes place every Sunday.

06
ACME Hotel Chicago, Outset Collection by Hilton image 1

Boutique hotel with industrial artistic decor and a strong music theme creates a cool, eclectic vibe. Spacious rooms offer city views and modern amenities, while a lively bar and bakery provide social spots. Loud music and a unique entry system add to its distinctive character.

Rooms offer comfortable, quiet spaces with good showers. Location is central, near a metro station with quick access to major transit points. No resort fee adds to the straightforward stay experience.

People are saying

"This hotel's decor and music give it a fun, cultured vibe."

"The beds are really comfortable and you'll get a great night's rest."

"It's got a cool vibe with hip music playing."

Good to know

1

You need to ring a bell and show your key to enter the hotel at night.

2

The hotel is centrally located near bars, restaurants, and shopping.

3

Parking is available, but consider using Uber or walking to nearby attractions.

07
Hyatt Place Chicago / Wicker Park image 1

Hotel offers a spacious rooftop bar with beautiful city views and heated outdoor igloos. Rooms feel spacious and elegant, though street noise can be noticeable. Fitness center provides a well-equipped gym with free weights and Peloton bikes.

Rooms offer a modern, well-maintained feel with attentive personnel ensuring cleanliness and comfort. Food and drinks come with great service throughout the stay.

Rooftop bar stands out with its cool atmosphere and refreshing vibe. Elevated setting offers a chill spot to relax and enjoy views.

People are saying

"The hotel staff is incredibly welcoming and attentive to your needs."

"The complimentary breakfast here is surprisingly good."

"The lobby area is cool for working during the day."

Good to know

1

Parking costs $50 per night, with valet service only.

2

Breakfast is included with a variety of options.

3

The hotel is a 10-minute walk from the blue line station.

08
Soho House Chicago image 1

Social club combines stylish design with curated cozy rooms and a heated rooftop pool offering breathtaking city views. Atmosphere shifts from cool and relaxed during the day to an amazing late night scene at the bar. Amenities include a huge gym, spa, cinema room, and quality dining options.

Rooms combine Euro-vibes with industrial chic in a warm, tasteful design. Amenities include a Cowshed spa, gym, and access to comedy shows without requiring membership.

Effortlessly cool vibe shapes the atmosphere here. The space feels upscale without trying too hard.

People are saying

"The atmosphere here is effortlessly cool and vibey."

"The Rooftop staff were professional and attentive, making the visit special."

"The hotel rooms here are beautiful, modern, and hip."

Good to know

1

Reservations are recommended for dining, especially during peak hours.

2

Parking is available in a garage one block away from the venue.

3

The hotel does not require a membership for overnight stays.

09
Hyatt Regency Chicago image 1

Hotel offers modern design with spacious rooms featuring river views and comfortable beds. Common areas buzz with activity, creating a lively atmosphere despite occasional crowding. Amenities include a top-notch gym, club level access, and convenient on-site services like car rental and security.

Central location puts you close to the Riverwalk, jazz spots, and museums. Staff delivers exceptional customer service with top-notch attention throughout your stay.

The hotel features a cool bar and bathrooms with unique mirrors. The overall vibe feels super cool and relaxed.

People are saying

"This hotel's downtown location is perfect for walking everywhere."

"I enjoyed the bar each night with excellent service and atmosphere."

"It's so cool how close it is to the river and attractions."

Good to know

1

Restaurants remain open until 1am for late-night dining options.

2

Valet parking costs $80 per night, which is quite high.

3

The hotel does not offer shuttle service to O'Hare Airport; taxi costs around $60.

10
citizenM Chicago Downtown image 1

Hotel offers modern, eclectic design with vibrant colors and creative communal spaces including a bar and terrace with city views. Rooms feature smart home technology and blackout shades, providing a quiet, well-insulated environment. Gym and workstations add to the functional, trendy atmosphere.

Location stands out for being close to everything and easy to get around. Rooms offer comfortable pillows and staff provide personal touches like cards and champagne. The gym ranks among the best hotel gyms experienced.

Lobby offers a really cool vibe with a self-service check-in on iPad that makes the process smooth and engaging.

People are saying

"I loved staying at this hotel; I'll definitely return."

"It's the perfect location for Date Spots, with attractions and shopping within walking distance."

"This place's location is so cool, it's walkable to everything."

Good to know

1

The hotel is located in the heart of Chicago, close to major attractions.

2

Parking costs around $50 a night and is located a block away from the hotel.

3

The gym is one of the best hotel gyms available.

11
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.

Rooms combine historic charm with modern comfort, supported by attentive staff who handle situations with care. The hotel offers a central location and a memorable stay experience.

Design draws from the Doge's palace in Venice, blending past and modern comfort. Rooms feature a cool athletic theme with unique touches like a pommel horse. The lobby offers an engaging space with various games and activities.

People are saying

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

"This hotel's stunning design blends old-world charm with modern comfort."

"The historic design and artistry of this place are really cool."

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.

12
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.

Rooms stay clean and nice with friendly staff providing excellent service. The hotel sits in a great location near theaters and Michigan Avenue, offering strong overall value.

Unique room design stands out with a very cool look. The rooftop terrace offers a cool vibe that adds to the overall atmosphere.

People are saying

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

"The rooftop has stunning city views and is a great place to unwind."

"I found the hotel to be really cool and in a top location."

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.

13
The Blackstone, Autograph Collection image 1

Historic hotel with classic charm and artistic decor creates an elegant and lively atmosphere. Rooms offer spacious layouts and great views, though noise from hallways and street is noticeable. Fitness center shows signs of wear but remains a notable feature.

Historic architecture and art displays create a unique atmosphere. Staff share the hotel's rich history eagerly, adding to the experience.

Lots of cool history fills the building, especially in the historic lobby. Elevators arrive quickly and the rooms feel trendy and clean.

People are saying

"The hotel rooms here are spacious and impeccably clean."

"It's a beautiful historical site with a timeless elegance."

"This place has such a cool, classic vibe with its historic lobby."

Good to know

1

Parking is available at a garage across the street, but no valet service is offered.

2

The hotel charges a nightly resort fee that is not disclosed at check-in.

3

Breakfast and snacks are served Monday through Friday at the hotel restaurant.

14
Hyatt House Chicago - Medical / University District image 1

Hotel occupies a renovated historic hospital with spacious modern rooms featuring kitchens and large bathrooms. Atmosphere is generally quiet and safe, supported by high-tech elevators requiring room key access. On-site amenities include a free gym, restaurant, and museum showcasing the building's history.

A cool remodel of an old hospital gives the hotel unique architecture and large hallways. It sits just 0.3 miles from medical centers and offers a quiet, comfortable suite with ambient lighting.

Large hallways highlight the cool remodel of the old Cook County Hospital. A Peloton bike can be requested for private exercise, and a pool table sits at the bar on the second floor.

People are saying

"The staff here makes breakfast so enjoyable and welcoming."

"The hotel staff was so nice and welcoming."

"It's cool how they remodeled the old hospital into this hotel."

Good to know

1

Valet parking costs $5 plus tip for patients.

2

Expect to pay $30 for open car parking per night.

3

Breakfast is served from 7 to 10 am on weekends.

15
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.

Freshly renovated rooms create a modern vibe. Staff show exceptional communication and ownership in handling issues. Location is perfectly central for easy access.

Cool sculptures and cool rooms set a unique tone inside. The restaurant offers a cool ambiance with great food, while the rooftop bar features a bartender who crafts memorable drinks and a barback who shares cool stories and impressive skills.

People are saying

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

"The rooftop bar has a lively atmosphere and great skyline views."

"The staff here are so nice and helpful, it's really cool."

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.

16
Hyatt Place Chicago – Medical / University District image 1

Repurposed hospital building showcases beautiful architecture and spacious, modern rooms with minimal furniture and plugs. Atmosphere varies from quiet and comfortable to noisy with echoing hallway sounds. Amenities include a large, well-equipped gym, a lounge with a pool table, and a kitchen for self-preparation.

Rooms stay clean and modern with a complimentary breakfast included. The hotel offers designated parking and a gym with unique equipment like an assault sprinting treadmill and a Peloton bike.

The building stands out for its old hospital vibe, which feels unique and interesting. Its location offers convenient access to both the pink and blue lines of the L train.

People are saying

"This hotel is beautiful and pristine, with gorgeous rooms."

"I thought the breakfast was fantastic."

"It's cool staying in this old hospital building."

Good to know

1

Parking costs $30 daily, and it's not complimentary.

2

The hotel is within walking distance to the United Center.

3

Breakfast is included with your stay.

17
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.

Boutique hotel offers a beautiful setting with a great location near the Amtrak station. Features include a free water refill station on the ground floor.

An old building restored into a cool hotel with rooms featuring a roaring 20's vibe. The decor and atmosphere keep the place feeling nice and stylish.

People are saying

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

"The bartenders here are amazing and so welcoming."

"The rooms have a cool, unique vibe and architectural theme."

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.

18
Hampton Inn Chicago Downtown/N Loop/Michigan Ave image 1

Historic building showcases art deco style and original lobby with high ceilings and wonderful views. Rooms feel spacious and cozy but street noise and HVAC sounds create a loud atmosphere at night. Lobby bar adds a fun social spot amid a busy downtown setting.

Location stands out with walking distance to major attractions like Millennium Park, the Magnificent Mile, and the theater district. The hotel features a spectacular art deco style and staff are consistently friendly and helpful.

The lobby features a cool historical design that stands out. The building overall has a very cool design that feels unique.

People are saying

"The breakfast location is great, right in the city center."

"The beds here are so comfortable."

"This hotel's location is unbeatable, right in the city center."

Good to know

1

The hotel is conveniently located downtown, within walking distance of major attractions.

2

Breakfast is served until 10am daily.

3

Only one of the three elevators was operational during the weekend.

19
The Emily Hotel image 1

Lobby offers a welcoming atmosphere with a hip vibe and space for socializing. Rooms are spacious and chic but can be affected by loud music from the bar and rooftop nightlife. Rooftop features include a cinema experience and great views, enhancing the energetic ambiance.

Outstanding service elevates the stay, with front desk staff providing helpful, last-minute assistance. The hotel offers easy access with nearby parking and valet, plus a location close to restaurants.

A rooftop cinema creates a peaceful vibe where birds casually snack on popcorn dropped on the outdoor carpet.

People are saying

"The hotel staff here is unbelievably awesome and friendly."

"The rooms are modern, clean, and really comfortable."

"The rooftop cinema experience was pretty cool."

Good to know

1

Selva rooftop bar offers happy hour bites and cocktails until 1:00 am.

2

Brunch is served at 10 am on Saturdays and Sundays.

3

Afternoon delight promotion includes coffee and pastry discounts from 1-3 pm.

20
Millennium Hotel Knickerbocker Chicago image 1

Classy hotel with old school luxury and vintage charm offers a quiet, spacious atmosphere. Rooms blend modern bathrooms with some outdated features, while a small martini bar provides a casual spot for drinks. Location near a major avenue adds convenience to the experience.

Historic charm blends with luxurious accommodations and outstanding service in this hotel. Its prime location adds to a memorable and exceptional stay.

Historic architecture and a rich past give this hotel a cool vibe. Events held here add to its unique charm downtown.

People are saying

"This hotel is in a great location."

"The rooms were quiet and comfortable, letting me rest well."

"This place has a really cool history, like an antique hotel."

Good to know

1

Happy hour is available on Fridays and Saturdays.

2

Breakfast starts at 6:30 a.m. daily.

3

Valet parking costs $78 per day, with no hotel parking available.

21
The Hoxton, Chicago image 1

Boutique hotel blends vibey lobby with rooftop views and a speakeasy bar. Noise from nearby elevated train and thin walls affects quiet moments. Spaces include live music venues and a small rooftop pool with age restrictions.

High-energy vibe with three bars and two on-site restaurants featuring live music creates a lively atmosphere. Location near the metro station offers easy access, and the hotel accommodates guests flexibly in emergencies.

Speakeasy style creates a cool vibe throughout the lobby, dining, and bar areas. The atmosphere suits hanging out and unwinding after work.

People are saying

"The basement bar was elegant and the lobby bar had a great vibe."

"The train noise at this hotel is quite noticeable."

"The vibe here is really cool and inviting."

Good to know

1

The pool is open to the public after 4 PM on Sundays.

2

The pool closes at 2 PM on Saturdays, so plan accordingly.

3

Expect a lively nightlife scene in the lobby on weekends.

22
Aloft Chicago Mag Mile image 1

Hotel features stylish decor and modern rooms with breathtaking city views from glass walls. Lobby buzzes with lively bar and social spaces, while upper floors offer a full-sized gym and indoor pool. Noise from nearby hospital sirens and thin walls affects overall quietness.

Located near the loop, the hotel offers great location with most destinations reachable within 15 minutes on foot. Rooms have good soundproofing, making it a solid choice for a place to sleep amid many city activities.

Industrial style shapes the modern lobby and bar area. Views from the 19th floor showcase buildings and rooftops that add to the cool vibe.

People are saying

"The hotel staff were all so friendly and helpful."

"The city view from my room was amazing."

"The lobby has a cool, modern vibe with neon lights."

Good to know

1

Public parking garage across the street charges less than $50 for 24 hours.

2

The hotel has a happy hour with music on weekends.

3

A DJ plays at the downstairs bar from 5 to 7 PM on weekends.

23
The Chicago Hotel Collection River North image 1

Rooms feature triple bunk beds and a sports-themed decor with hallways painted like a pool and a scoreboard in the kitchen. The atmosphere mixes a hostel-style vibe with a lively common area where young couples gather to chat and play games. Noise from nearby trains and other guests is noticeable, creating a lively but sometimes loud environment.

Offers a unique budget stay with simple, affordable rooms. Located within a short walk to restaurants and shops, it has its own character and does not feel like a typical chain hotel.

Rooms feature a bunk bed setup that stands out. The place has a hostel type feel with comfortable beds.

People are saying

"This hotel is simple, affordable, and has its own character."

"The staff here are so friendly and always willing to help."

"The interior design is really cool and unique."

Good to know

1

The hotel has limited parking; expect to pay $24 for 24 hours at a nearby lot.

2

A daily resort fee is charged, which may not be disclosed during booking.

3

Expect an additional $40 amenity fee on top of the room rate.

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