Classic American cigar shop with luxurious lounge rooms and both indoor and outdoor seating including a heated patio with big screen TV. Atmosphere stays relaxed and cozy, inviting for chilling out or focused work. Offers a well-organized humidor stocked with fine cigars and a welcoming sense of community.
Rooms offer a gorgeous lounge setting with an aura of relaxation and tranquility. Access requires a minimum purchase of two cigars, and the lounge includes an outdoor patio area.
Outdoor space features a heated patio with plenty of seating and a big screen TV. Both indoor and outdoor areas offer comfortable leather chairs for smoking.
"You'll feel so welcomed when you buy cigars here."
"The outdoor seating has heating elements and a big screen TV."
"I enjoyed the patio with its heating elements and big screen TV."
Good to know
A minimum purchase of 2 cigars is required for lounge access.
The humidor is well-stocked with a variety of high-quality cigars.
They offer a selection of fine cigars and beverages.
Three-story brewpub offers spacious patio, cozy basement lounge, and rooftop bar with a fun, relaxed atmosphere. Outdoor seating includes a heated tent, creating a comfortable space for gatherings. The vibe suits pre- and post-game crowds with a mix of casual and swanky areas.
A cozy downstairs cocktail lounge with a vibe like entering a high-class dungeon offers unique cocktails. The space includes a super patio area and works well for pre and post-game gatherings.
A spacious patio offers a shaded, comfortable spot to enjoy drinks. The outdoor area feels like a hidden oasis with a nice balance of indoor and outdoor spaces.
Good to know
The Devious Lounge is only a two-minute walk to Wrigley Field.
They offer a variety of great beer options and plenty of appetizers.
The brewery is dog-friendly, so feel free to bring your pet.
Retro garage decor and 1950s wallpaper set a unique tone, complemented by a spacious back patio with an open lounge vibe. Energetic music, often with a DJ on weekends, creates a lively atmosphere that can get loud. The place suits larger groups and hosts parties well, offering a functional bingo board as a distinctive feature.
A back open patio lounge offers a nice spot during summer. The lounge serves great drinks and even better bar bites, with a team providing excellent service.
A back open patio lounge offers a chill vibe and a nice spot to relax. The patio feels welcoming and pairs well with fantastic staff service.
Good to know
Karaoke happens every Sunday night at 9 PM, drawing a lively crowd.
Brunch costs around $30 for food and unlimited mimosas.
Bingo night takes place every Monday, adding to the weekly fun.
Spacious cigar lounge with cozy outdoor patio and comfortable seating offers a welcoming, chill atmosphere with a mature crowd and a good mix of women. Music features live DJs playing old-school jams and games on big screens. BYOB policy allows bringing food and drinks, enhancing the relaxed vibe.
Cozy outdoor setting with nice lighting creates a welcoming vibe. The lounge offers a roomy cigar room with good DJ spins and space to relax and unwind. It is BYOB, common for cigar lounges here.
Cozy outdoor setting features nice lighting and an area with TVs. The patio offers a comfortable spot to relax outside.
Good to know
The lounge is BYOB, so bring your own drinks.
You can bring both food and beverages to enjoy.
There is a $20 entrance fee unless you buy a cigar.
Cigar shop with a relaxed, upscale vibe and a friendly, personable crowd. Lounge includes a unique outdoor patio with heaters and fire pit, offering a warm, home-like atmosphere. Space is limited and can be smoky, with multiple TVs creating a lively environment.
A huge selection of cigars fills the lounge, with knowledgeable staff offering great suggestions. The atmosphere feels home like and welcoming, with friendly regulars creating a relaxed vibe.
Outdoor seating features a unique patio with amazing seating and a fire pit that creates a cozy atmosphere.
Good to know
The lounge has a two cigar minimum to sit and enjoy.
The selection of cigars ranges from $7 to over $40.
Parking is limited due to a small lot.
Rooftop bar offers unbeatable city skyline views with both indoor and outdoor lounges. Atmosphere stays peaceful and spacious, with a vibe suited for quiet evenings rather than loud crowds. Cocktails are well-crafted and flavorful, complementing the setting for dates or nightcaps.
A small rooftop lounge sits atop a historic flatiron building now a hotel, offering both outdoor and indoor spaces. No food is served, making it a spot mainly for drinks and waiting.
Small patio space fills quickly, so arriving early or reserving a table helps secure a spot outside. Outdoor seating accommodates guests who want to enjoy food brought from other venues.
Good to know
Reservations are recommended as the space fills quickly, especially on weekends.
The Up Room closes at midnight, but no new guests are allowed after 11pm.
Happy hour is a great time to visit on weeknights for discounted drinks.
Neighborhood pub with eclectic decor and a laid-back vibe offers live Americana music and a well-maintained pool table. Outdoor patio provides a relaxed space often visited by a friendly cat. Atmosphere stays friendly and welcoming, attracting open-minded locals who enjoy good humor and art.
Cozy, laid-back vibe with great art and fun entertainment. An outside lounge area exists but feels out of place in the neighborhood.
A beautiful patio offers a relaxed outdoor lounge area. A friendly cat often roams the back patio, adding a unique touch to the space.
Good to know
Trivia night happens every Tuesday at 8pm with a $5 entry fee.
Live music events often start in the afternoon on weekends.
Food delivery is allowed, but limited food options are available on-site.
Modern restaurant offers a luxurious city vibe with top-notch interior design and a gorgeous outdoor terrace featuring a private bar and downtown views. Atmosphere feels warm and inviting, blending trendy energy with a clean, bright space. Popular spot draws lively crowds, especially on weekend evenings.
Upstairs offers a lounge with indoor/outdoor space and a great view of downtown. Dinner service is available there, making it a solid spot for private parties and celebrations.
Upstairs lounge offers a combined indoor/outdoor space with heaters in the outdoor area. This setup lets people enjoy drinks outside comfortably after eating.
Good to know
The upstairs space is ideal for private events and celebrations.
Brunch is served on Sundays from 11am to 2:30pm.
Happy hour features outstanding oysters and drinks on Sundays.
Speak-easy bar with dim lighting and comfortable lounge seating creates an intimate, cozy atmosphere ideal for quiet conversation. Upstairs event space offers a mingle-friendly setup with leather couches and high-top tables. Outdoor patio is dog friendly and opens to the sidewalk, blending indoor and street vibes.
Dim lighting and velvet lounge chairs create a cozy, low key atmosphere. Comfortable seating and beautiful decor make it easy to talk and suitable for dates.
A small patio offers a cozy outdoor spot with dog friendly access. The space pairs well with cocktails like a Manhattan and features gorgeous decor.
Good to know
Happy hour runs from 4-7pm on weekdays with discounted drinks.
Live music performances occur on Wednesdays and Thursdays.
The venue offers a spacious event space suitable for 40-50 guests.
Rooftop lounge offers incredible 18th-floor views with a chic, modern design featuring plush seating and ambient lighting. Atmosphere stays vibrant and inviting, balancing lively music and conversation without overwhelming noise. Guests enjoy thoughtful cocktails and a mix of small plates in a stylish, energetic setting.
Cozy rooftop lounge with a mid-century modern design featuring leather couches, emerald green accents, and brass hardware. Atmosphere shifts from sun-soaked to chic lounge as the evening progresses.
Outdoor seating includes a patio with heaters and comfortable couches that create a calm, ambient vibe. Both indoor and outdoor spaces offer lively atmospheres suitable for dining.
Good to know
Reservations are recommended for the best seating experience.
Pandan offers Southeast Asian inspired small plates and unique cocktails.
The outside seating area can fill up quickly.
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.
The rooftop lounge offers a spectacular city view with the Chicago skyline visible from the bar. It serves excellent food and provides a great spot for grabbing drinks or food.
Rooftop patio features heated igloos and outdoor heaters. The space offers an amazing view and stays comfortable even in cold weather.
Good to know
Parking costs $50 per night, with valet service only.
Breakfast is included with a variety of options.
The hotel is a 10-minute walk from the blue line station.
Massive walk-in humidor offers one of the largest and most impressive cigar selections in the area. Spacious lounge includes multiple rooms with leather seats, TVs everywhere, and a members-only area, creating varied spaces for both socializing and quiet relaxation. Outdoor patio under roof adds a welcoming outdoor option to the experience.
Spacious lounge offers several rooms to enjoy cigars with friends. It features an excellent selection, great atmosphere, and supports good conversation and laughter.
A covered patio offers outdoor seating that feels like an added bonus. The space is wonderful for enjoying fresh air while staying sheltered.
Good to know
The selection of cigars is one of the largest in the Chicagoland area.
Customers can bring their own beverages while enjoying cigars.
The lounge hosts great cigar events and dinners regularly.
Lounge offers a cozy outdoor heated patio tent with televisions and a live band alongside a DJ playing great music. Atmosphere stays chill and friendly, attracting a mature, seasoned crowd who enjoy laid-back vibes and dancing. Space suits private parties and after-work drinks with a safe, trouble-free environment.
A mature and relaxing lounge with a great sound system and an outdoor patio with a TV. Offers excellent food and entertainment and hosts activities like Bingo in a lively atmosphere.
A cozy and inviting patio offers a safe outdoor spot with a TV. It serves as a great place to watch games, especially with perfect weather.
Good to know
Parking can be a challenge if there is a large party.
All street parking is available, but avoid the bus lane.
The lounge is for mature adults only.
English pub-style space combines wood paneling, snugs, and velvet lounges for a mix of casual and sophisticated vibes. Warm lighting and personable staff create a comfortable atmosphere where conversation flows easily. Multiple TVs show major European soccer leagues, making it a popular spot for sports fans.
Upstairs offers an old school English lounge vibe with comfy couches and a knowledgeable bar staff. The space feels cozy and intimate, perfect for date nights or small gatherings.
Lots of outdoor seating lets you enjoy the sun comfortably. The patio offers a nice spot for a beer or to relax outside.
Good to know
Happy hour offers half-price appetizers from 4-7pm on weekdays.
Trivia night occurs every Sunday at 7pm with a competitive atmosphere.
The burlesque shows are held on Saturday nights with a lively crowd.
Cafe offers a clean, minimalist interior with modern decor and outdoor seating. Atmosphere stays calm and cozy with jazz music playing softly. Sandwiches feature artisanal breads and fresh ingredients, creating a relaxed spot for conversation and brunch.
A welcoming atmosphere sets the tone with fresh food and careful service. The lounge offers pan seared salmon and cocktails like the White Russian for a relaxed night out.
Outdoor seating includes two small blue cafe tables that offer a clean and minimalist vibe. The space feels peaceful and works well even in light rain.
Good to know
Happy hour is on Thursdays with discounted drinks and appetizers.
Live music evenings are scheduled regularly at the cafe.
Tips are cash only, so bring cash for gratuities.
Rooftop bar offers panoramic lake and skyline views with a vibrant nightlife featuring loud music and DJs. Interior spaces feel cozy and quaint but show signs of wear and outdated decor. Amenities include a rooftop pool, sushi restaurant, and convenient coffee shop, creating a neighborhood boutique vibe.
Spectacular views of downtown, the lake, and Old Town define the rooftop lounge. Access to this beautiful space adds to the appeal, with delicious drinks and food served.
Street parking sits right outside with a meter that runs until 10pm. Rainy nights offer a view of cars passing by through the window.
Good to know
The rooftop bar may be closed for private events, check in advance.
Expect limited access to the rooftop bar during busy times.
Complimentary happy hour drinks are available on the rooftop.
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.
Rooftop lounges offer fantastic views and a gorgeous atmosphere. Multiple areas like the cocktail lounge and pool bar provide unique experiences within the same venue.
A gorgeously restored old building hosts a rooftop bar with outdoor seating featuring nice tables and some of the best views outside downtown.
Good to know
The Cabana Club is open to the public from 4-6 PM for happy hour.
Happy hour features discounted drinks and appetizers at The Robey.
Story hour at the Clever Coyote takes place every Sunday.
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.
Lounge spaces feature modern decor and a great bar that create a relaxing and inviting vibe. Cleanliness stands out across the lounges, rooms, and even the lounge toilets.
Rooftop and patio areas offer a very relaxing atmosphere. The outside patio works well for unwinding after a long day of walking.
Good to know
The hotel is located in the heart of Chicago, close to major attractions.
Parking costs around $50 a night and is located a block away from the hotel.
The gym is one of the best hotel gyms available.
Large, well-decorated space features a library-themed course and a rooftop area with notable views. Atmosphere combines jazz music with a fun, social vibe suited for couples and groups. Miniature golf includes a digital scoring system enhancing the experience.
Cozy, eclectic, and upscale vibes create a stylish lounge atmosphere. Rooftop bar and lounge areas feature beautifully designed furniture for a cool bar feel.
Space flows between the outdoor sliding doors leading to the rooftop and the indoor golf course. The patio offers great views of West Loop. It fits groups of 13 with both indoor and outdoor seating.
Good to know
Reservations are recommended, especially for larger groups or events.
The bar is wheelchair accessible, but the golf courses are not.
Expect upscale pricing for food and drinks at the venue.
Upscale cigar shop with private rooms and well-ventilated lounges offers a wide selection of premium cigars. Seating varies from cramped public areas to spacious, comfortable VIP lounges. Atmosphere balances cozy social spaces with clean, organized environments for relaxation and gatherings.
Upscale and world class lounge with great ventilation and plenty of televisions for sports. Staff are knowledgeable and friendly, creating a cozy, welcoming atmosphere perfect for cigar lovers.
Outdoor seating includes a patio with a nice atmosphere and several lounges inside. Servers greet guests outside and offer drinks, though humidity can make sitting outdoors less comfortable.
Good to know
They do not sell alcohol and you cannot bring in your own alcohol.
There was plenty of parking available.
The front lounge is for non-members, and you can use it by purchasing a cigar.
Mansion-style cigar lounge offers a vintage decor and classic sophistication with comfortable seating and excellent ventilation. Atmosphere stays relaxed and masculine, attracting cigar smokers from various places. Large walk-in humidor features a world-class cigar selection, including unique blends.
The lounge offers a fabulous cigar selection and a classic, elegant atmosphere. It stands out as a premiere cigar lounge with a beautiful and fancy interior.
A nearly empty patio offers outside seating but it is reserved for members. A $100 fee applies to non-members who want to sit outside and smoke, with signage explaining this policy.
Good to know
A $100 fee is required for outdoor seating and smoking cigars.
Only members can access the outdoor smoking area.
Non-members have limited seating options available indoors.
Tiki-themed lounge with irreplicable decor and a vast cocktail menu featuring classic drinks served in themed mugs. Atmosphere stays cozy and relaxed even when busy, with a quirky back patio offering outdoor seating and fans. Food options are minimal, focusing mainly on chips and salsas.
Cozy, dimly lit setting with seating for various party sizes creates an incredible atmosphere. Huge menu offers a wide range of tiki cocktails and mocktails, focusing solely on drinks without food service.
A beautiful outdoor seating area features a back patio with a fun, quirky ambiance and a tropical vibe. An indoor outdoor patio with couches creates a more intimate setting for groups.
Good to know
Hala Kahiki Lounge offers only drinks and does not serve food.
Hula dance shows occur on select weekend nights.
Expect to pay around $20 for a mixed drink.
Huge patio with fire pits and live music creates a lively outdoor space. Seasonal holiday-themed pop-ups and decorations add immersive, festive vibes. Loud music fills the air, making it energetic and social.
Enormous patio creates a cool cocktail lounge vibe. Seating options include bar, table, and lounge areas with consistent service issues.
An enormous dog-friendly patio creates a relaxed vibe with art-filled walls and a cool cocktail lounge feel. The outdoor space works well for afternoon drinks and casual hangs.
Good to know
Happy hour offers $5 drafts on Fridays from 4-7pm.
Live music occurs every Sunday, featuring DJ Gloria on 'Soulful Sunday.'
The venue hosts special pop-up events for Halloween and Christmas.
Piano bar offers live piano music with a phenomenal, engaging pianist in a small, crowded space that encourages standing and dancing. An outdoor cigar lounge provides additional seating with couches and ashtrays. The atmosphere is lively and packed, creating an intense but vibrant vibe.
Speak-easy style cigar lounge offers a cozy, calm atmosphere with a well-stocked selection. Staff provide attentive service, and management often mingles in the lounge, adding to the welcoming vibe.
A hidden outdoor cigar lounge sits behind a secret pathway, creating an exclusive vibe. The outside deck offers the only seating and blends well with live music and drinks inside.
Good to know
Expect large crowds on weekends, especially after 10 PM.
Reservations are recommended for special events or large groups.
Happy hour offers discounted drinks from 4 PM to 7 PM on weekdays.
Modern hotel with spacious lobby and indoor and outdoor pools offers a comfortable stay despite occasional noise from parties and hallways. Shuttle service connects to nearby shopping, and breakfast features notable breakfast potatoes instead of hash browns.
Large lounge offers plenty of nooks and crannies for work or relaxation. The exclusive M Club lounge provides a relaxing atmosphere, but staff show clear bias against Asians and female guests.
Outdoor space features a clean outdoor pool with excellent water temperature and a pretty wooded area view. An outdoor tent serves for breakfast and events like baby showers, offering a nice setting.
Good to know
Parking costs $7 per night, which may not be disclosed during booking.
Wi-Fi was out of service for two days during some guests' stays.
The hotel offers a shuttle service to the mall for guests.
Hotel offers a rooftop pool with city views and a grand, elegant lobby. Atmosphere tends to be loud and busy, with frequent noise from construction, sirens, and lively groups. Rooms feel comfortable but somewhat outdated.
Staff at the lounge deliver excellent service with standout team members like Jose A. The lounge offers a gourmet experience that goes beyond typical hotel bars, paired with a rooftop pool and lounge area for a relaxed vibe.
Outdoor space features a pool with city views and a terrace. Games like Cornhole, Jenga, and pool table add fun to the hangout area.
Good to know
Parking costs $62 per day, regardless of discounts.
Breakfast is not included with the room rate, despite some bookings indicating otherwise.
The rooftop pool is closed until mid-July, which is not disclosed on the booking site.