Cancel

    Open app

    Search

    Windy City Cigar Lounge

    4.1 (25 reviews)
    ModerateCigar Bars
    Open 11:00 am - 11:00 pm

    Windy City Cigar Lounge Photos

    WINDY CITY CIGAR LOUNGE ATMOSPHERE

    What's the vibe?
    Moderate noise
    Casual
    Outdoor seating
    Good for groups

    Recommended Reviews - Windy City Cigar Lounge

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    Anthony A.

    What a cool Cigar lounge. Local place as most of the people coming in knew each other. Comfortable leather chairs and televisions from most angles. they provides ice and glasses at no charge and a bottle of water is $1.50. The liquor is BYOB which can be dangerous for those that pour too much. The humidor was pretty cleaned out when I was there but I found two good cigars to try. There is a $20 minimum purchase if you bring your own cigars. I have no problem supporting the shops! Renee the manager oversees the operation and makes sure you're comfortable. Clean and comfortable setting with attentive staff, quality people enjoying just like yourself. Just a great place to enjoy a Cigar without having to overpay for anything.

    The floor
    Tierra L.

    Last minute search for something to do turned out a good experience. Limited street parking and even more limited parking lot space available. Went on a Friday night, enjoyed it so much returned Sunday evening which of course was much quieter. 2 cigar per person minimum or $20 cover charge. BYOB. There was a patio although we didn't venture to it. Saturday night DJ was by far the greatest. Ventilation can be improved especially for a cigar bar but overall I enjoyed my time and would return if I lived in Chicago

    Alex C.

    This place is popping! Dropped by impromptu to buy a cigar to go and the dude behind the counter asked me to hang out and chill! Friendly and lively crowd. They didn't have my sweet Betty Cigar but that's ok.

    Fresh sticks and real decent environment. Leather chairs? Three sections, tiled big screens and the FIGHT!   #springBreakDay #mkethpn
    Darion H.

    Been wanting to try the WCCL, today was the day. Perfect timing for me, they just opened and the humidor was waiting on ME!!! Just needed more time, my son and his friends were at the movies and i didn't want to deal with run back home traffic. Thank think i might have found me a refuge for some ME time. Check them out, good vibes and #PSSITA!

    My only critique is I wish they had two same size tables. Bring your own tables so all of your food fits comfortably.
    Sweetesttaboo S.

    Last night I hosted my mother's 60th birthday party here and I couldn't have found a better venue. The location was easy to get to, had parking to accommodate my guests and, I love how large the space is. The owners and the staff went above and beyond my expectations to assist me with setting up and clean up. Their cigar room was excellent with a wide range of assortments for guests. The owner also helped me pick one out for the guest of honor. They play great music here and what I love is that relaxed vibe but then having that little bit of room to get up and two step when your song comes on. Some of the parties or guests can be a little loud but it also adds to the great vibe. Everyone was respectful and actually so sweet when surprising my mom and wishing her a happy birthday. In the end, Windy City Cigar Lounge was perfect for the affair. I look forward to hosting another event here or just stopping by next time I'm home in the Chi! Thank you Maurice and staff!

    Cool relaxing cigar lounge.
    Tracy C.

    Windy City cigar lounge is located on the south side in a black neighbor. It is a very welcoming environment to all people. It costs $15 to enter or a 2 cigar purchase. Great place to see sports events on HD TV, nice comfortable seating. Their filter system is very weak only reason I take one star off, have patio in the back which is nice in good weather. Customer service on point.

    Bar area

    See all

    Photo of Penny W.
    167
    112
    29

    1 month ago

    Came from LA what an amazing place nice cigars owners A+ a must visit in Chi. Girls trip success

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    11 months ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    11 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 9
    Thanks 0
    Love this 8
    Oh no 0

    2 years ago

    Helpful 0
    Thanks 0
    Love this 2
    Oh no 0

    4 years ago

    Business owner information

    Photo of Anthony P.

    Anthony P.

    Thanks, glad you enjoyed your visit.

    Helpful 4
    Thanks 0
    Love this 2
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 4
    Oh no 0
    Photo of Darion H.
    219
    27
    77

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    2 years ago

    The friendliness and concern of the staff was important to me with the Right football game on

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Alfred J.
    4
    107
    26

    3 years ago

    Helpful 0
    Thanks 1
    Love this 0
    Oh no 0

    7 years ago

    Helpful 6
    Thanks 0
    Love this 9
    Oh no 0
    Photo of Andre W.
    566
    2123
    1428

    8 years ago

    Helpful 4
    Thanks 0
    Love this 5
    Oh no 0

    8 years ago

    Helpful 3
    Thanks 0
    Love this 3
    Oh no 0
    Photo of Rena D.
    26
    29
    48

    7 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 2
    Photo of Tracy C.
    58
    31
    148

    7 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Business owner information

    Photo of Anthony P.

    Anthony P.

    We are sorry for the error, please stop by again.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0
    Photo of B J.
    0
    113
    6

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Jake W.
    134
    56
    7

    7 years ago

    Great new spot. Even the customers there were extremely nice. I get like I was at cheers bar walking in. This place is a great go to

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    My favorite cigar lounge! Very friendly staff and wonderful humidor selection. Definitely a hit for me.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    Ask the Community - Windy City Cigar Lounge

    Do they sell alcohol or is it BYOB?

    BYOB

    Don’t See Your Question? Ask Away!

    Review Highlights - Windy City Cigar Lounge

    Place is BYOB and have some cool looking seating options in the main area along with a projector.

    Mentioned in 7 reviews

    Read more highlights

    Verify this business for free

    People searched for Cigar Bars 6,429 times last month within 10 miles of this business.

    Verify this business

    The Office

    The Office

    4.3
    (320 reviews)
    5.1 mi
    $$$$

    I really like the office! Cool, cozy, and classic! Service is spectacular of course. Always treated…read morewell. The cocktails are also classic but still modern and very cool. Always a nice spot to go back to.

    The Office is a nice speakeasy! I had wanted to get a floral drink at the restaurant upstairs…read morecalled "the Aviary" but they were actually totally full, whereas the speakeasy wasn't. I sat at the bar downstairs and can confirm the place has a classic speakeasy feel -- the the basement of a place behind a locked door, very dark inside with mood lighting/glass cases and leather chairs/couches around small low tables. It's definitely a great date spot! I took off a star because it's pricey -- I got the "milk punch" on their classic cocktail menu which was $25 and is pretty small, but it's a nice drink and tasted very much like a milk punch drink I got at a speakeasy back home (in Austin, TX). The bartenders were super nice and provided excellent service, no complaints there! The bathrooms were also immaculate. Overall, this is a very nice speakeasy! I've been to many in my day and the ambiance is definitely on par with the best, but I gotta say some other unique ingredients (ideally more floral options!) would really take their menu up a notch! Nevertheless, I would def rec a visit to those visiting Chicago, and would go again even just for vibes :)

    Photos
    Twas a combination of a black manhattan & a vieux carré  Delicious
    Twas a combination of a black manhattan & a vieux carré Delicious
    Basque cheesecake was delicious
    Basque cheesecake was delicious
    Collection

    See all

    Collection
    NoMI Lounge

    NoMI Lounge

    3.9
    (83 reviews)
    5.6 mi
    $$$

    My husband and I came here for our 26 year anniversary. It was my first time in Chicago. A local…read morefriend of ours recommended NoMi. It was a great recommendation. We were so happy with everything! Our server was wonderful! The entire staff was so friendly and on top of their game! We never waited for anything. They were immediately refilling our waters, offering more bread, removing dirty plates, replacing silverware, and offering the next course. It was perfect! The views!!! I think there's not a table in NoMi that doesn't have an amazing view. The main, large window faces the lake (East). Arriving just at 7, you get the full affect of the city, and lake, and then the sunset and lights of the buildings. It was absolutely magical. I couldn't get enough of it. The inside of the restaurant is beautiful and clean, but honestly it could have been a pit and I wouldn't have noticed. You'll be focused on the views for the entire evening. The food!!! Everything is very fresh. It's all well-prepared. Everything was delicious. There's a good variety of dishes to choose from. Plenty of healthy, low-carb options. We each ordered our own appetizers. I had the crispy Maitake mushrooms and my husband had the mussels. We both loved our food and left nothing on our plates. Excellent choices, that we highly recommend. As our main course we shared the sushi platter. The seafood was fresh and the sushi didn't have too much rice. It was the perfect amount of food with our appetizers. They have an extensive wine and drink menu. For drinks I had a glass of the Sauvignon blanc and my husband had a red blend. For dessert we weren't really hungry enough to eat anything else but my husband wanted a pallet cleanser. They have a few sorbets. My husband settled on the cherry cola sorbet. They brought it out with a little chocolate that said "Happy Anniversary" in French. They did not add it to our bill. Very sweet of them. It was probably one of the best anniversaries we've ever had. The bill was about $230 before tip. We highly recommend coming here for any special occasion.

    My husband and I popped in here to escape the cold and found that NoMI was doing a hot coco…read moreexperience! It was SO awesome! We were able to choose between an alcoholic or non hot coco and load it up so many different toppings. It warmed us up and was decorated so beautiful! My husband then snagged a lobster roll which was so good. We are so excited we found this lounge and will be back!

    Photos
    View from our table
    View from our table
    Crispy Maitake mushrooms
    Crispy Maitake mushrooms
    Sushi Menu

    See all

    Sushi Menu
    The Berkshire Room

    The Berkshire Room

    4.1
    (475 reviews)
    5.3 mi
    $$

    The Berkshire Room is one of my favorite speakeasies in Chicago. While they offer a fantastic…read morecocktail menu and a full bar, I almost always order The Dealer's Choice. You simply choose your preferred spirit, flavor profile, and glassware, then let the mixologist create something just for you. It's one of my favorite cocktail experiences in the city, and they've never steered me wrong. What I especially appreciate is how knowledgeable the bartenders are. They're always happy to offer recommendations if you're unsure what to order, but they're equally excited to create something completely unique if you're feeling adventurous. Watching them craft each drink is part of the experience. I've even hosted a birthday gathering here in their private side room, where we enjoyed charcuterie boards alongside our cocktails. If you're just stopping in for drinks, though, I'd recommend grabbing dinner beforehand, as the food offerings are fairly limited. More often than not though, you'll find me sitting right at the bar. I love watching the bartenders showcase their craft and chatting with them about the incredible selection of spirits they have on hand. It's a great spot for anyone who genuinely appreciates well-made cocktails and the artistry behind them. I'm also a member of their loyalty program, which is well worth joining. It can be used at The Berkshire Room as well as several other excellent restaurants, making it an easy way to earn rewards while exploring some great dining spots around the city. Whether you're a cocktail enthusiast or simply looking for a sophisticated place to unwind, The Berkshire Room consistently delivers. I'll definitely be back for another Dealer's Choice soon! #YelpEliteSquad

    I came here in 2023 and remember constantly remembering how good the cocktails were so decided to…read morestop back in and they were just as good as I remember! I came the night I got engaged so we decided to go on our anniversary as like a cute little celebration after dinner. The service is always amazing and the interior is very chill, great music. They can make anything you ask for but their cocktail list is extensive and has so much to choose from! Highly recommend.

    Photos
    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Host your next event at this speakeasy cocktail and whiskey bar in River North!
    Host your next event at this speakeasy cocktail and whiskey bar in River North!
    Bar

    See all

    Bar

    Windy City Cigar Lounge - cigarbars - Updated August 2026

    Loading...
    Loading...
    Loading...