When asking yourself about something to do near me in Chicago with a group of friends or family, consider
Up Down Cigar

Why Up Down Cigar is a fun option when searching for things to do near me with friends and family
Up Down Cigar, located in Chicago's historic Old Town neighborhood, is a renowned destination for cigar lovers and enthusiasts. Opened originally in 1963 by Diana Silvius as part of an experimental art gallery, it evolved into a celebrated tobacco shop and became a neighborhood institution known worldwide. The store's unique ambiance reflects its artistic roots, featuring architecture and sculpture that complement an extensive selection of premium cigars, pipes, humidors, and accessories. Up Down Cigar offers a finely curated collection of rare and high-end tobacco products, making it an ideal meeting place for friends who appreciate quality and tradition. Besides its impressive inventory, the welcoming atmosphere attracts both locals and visitors who enjoy a relaxed, knowledgeable environment to explore tobacco culture. Its history of nearly six decades also adds a rich cultural layer, connecting patrons with the legacy of a pioneering woman in the tobacco industry. Additionally, customers can order online or by phone, with reliable shipping services ensuring access to their collection beyond Chicago. This blend of heritage, quality offerings, and community spirit makes Up Down Cigar a truly special place to gather and enjoy fine tobacco.
Here's what people think of Up Down Cigar
As of recent, Up Down Cigar holds a 4.8-star rating based on 260 reviews.
Reviews for Up Down Cigar overwhelmingly reflect a positive experience with the business, earning a high rating of 4.8 out of 5 from 260 reviews. Customers appreciate the store's welcoming and authentic atmosphere, which is steeped in its unique history and artistic origins. Positive reviews often highlight the knowledgeable and friendly staff, who assist both novices and seasoned aficionados with expert recommendations and service. Many praise the broad and rare selection of cigars, pipes, and tobacco accessories that satisfy even the most discerning tastes, emphasizing the store's dedication to quality and variety. Furthermore, reviewers commend the elegant and distinctive store design that enhances the overall visit.
On the other hand, some negative reviews mention occasional issues with online ordering and shipping delays, especially considering that orders made on Fridays ship out the following Monday. A few customers have noted the limitation regarding payment methods, such as the store's policy of not accepting MasterCard for mail or internet orders, which can cause inconvenience. Despite these minor criticisms, the overall sentiment remains strongly favorable.
In summary, Up Down Cigar is widely regarded as a must-visit shop for cigar enthusiasts due to its rich historical legacy, exceptional product selection, and excellent customer service. The positive experiences far outweigh any negatives, solidifying its reputation as a premier destination in Chicago’s tobacco scene.
Highlights from reviewers (Most Relevant)
R Lee
Enjoyed the staff and customers at Up Down. Good selection, but they closed at 9p. Right in the middle of the NBA playoff game. Disappointing.
Dennis
Great atmosphere! Great selection of cigars the staff is friendly and very knowledgeable. Other clientele are approachable and friendly. Overall great experience.
Bruce Cooper
Very nice lounge, nice smoking area out back. Good prices. If I lived in the area, I would be here a lot more, but now I got a nice place to go to.
Maria Madden
I am a novice when it comes to anything cigar. I was extremely satisfied with the help I received. I explained to the gentlemen that greeted me that I was a novice and I need a 80th birthday gift for a casual smoker. Not only did he explained some different brands and flavors but he helped me some accessories as well. They even gift wrap for free! While he was in the back gift wrapping my purchase his co-worker let me know they had used cigar boxes for only $3! I was lucky to find this place.
Ryan Thomas
Hands down, best cigar shop I've been to. Went there 2 days in a row. The 3 different people who I came in contact with were friendly, and incredibly knowledgeable. It's a unique building, with fantastic architecture and a craft amount of rare cigars. If you are in Chicago, go to Old Town and check them out. You guys are killer! Keep kickin' ass!!
How to reach Up Down Cigar
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Website: None

Why Up Down Cigar may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out
Why rally at Up Down Cigar with your friends? This cigar lounge in the heart of Chicago’s Old Town offers an unbeatable blend of ambiance, quality, and camaraderie that makes it the destination for gathering with friends or family. With its eclectic yet classy atmosphere, Up Down Cigar creates a cozy, inviting space that feels both historic and modern. It’s not just about smoking a cigar; it’s about sharing an experience filled with conversation, laughter, and the satisfaction that comes from enjoying premium cigars in a space made for connection. The staff treat every visitor like family, with expert knowledge and warmth that instantly puts everyone at ease. Whether you’re a cigar aficionado or trying one for the first time, they ensure you’re comfortable and informed. Plus, its unique layout—offering both indoor and a covered outdoor patio with heaters—means you can enjoy your time year-round regardless of Chicago’s unpredictable weather. For those seeking a memorable meetup spot that combines good vibes, high-quality cigars, and a welcoming atmosphere, Up Down Cigar stands out as the perfect rallying point.
What kinds of activities can you enjoy at Up Down Cigar?
Up Down Cigar offers multiple activities that make it ideal for a group meetup. Primarily, you can explore their well-curated humidor, which houses a meaningful selection of premium cigars thoughtfully maintained for freshness and quality. While the humidor may not be the largest in Chicago, it features a range that caters to every taste, including exclusive blends found only at this shop. Here, you and your friends can embark on a shared journey of discovery, trying different cigars and swapping opinions. It’s a hands-on experience for cigar lovers and novices alike. After selecting your cigars, you can head to their lounge area designed for enjoyment and conversation. Though the lounge isn’t sprawling in size, its intimate setting enhances the social vibe, encouraging close-knit interactions and discussions. The furniture and layout preserve a unique charm that can’t be replicated elsewhere, honoring the space’s history while offering comfort. Furthermore, the covered outdoor patio with heaters is a fantastic addition, allowing for a relaxed setting in fresh air when the weather permits. This variety of spaces lets groups of friends or family choose their ideal atmosphere to unwind together.
Why is Up Down Cigar perfect for a group meetup?
Up Down Cigar stands out as a perfect group meetup destination because it balances a premium cigar experience with a vibrant social environment. The friendly, knowledgeable staff facilitate an atmosphere where questions and conversations about cigars flow naturally, which makes it easy for everyone to participate, regardless of experience. This welcoming approach breeds a sense of community that is rare in many other venues. The lounge’s blend of old-school charm and modern touches creates a comfortable ambiance where groups feel at home, making conversations flow and laughter easy. Additionally, the shop’s size encourages intimacy without feeling cramped — it’s just right for groups who want to enjoy quality time together without the distractions of a larger, more chaotic space. Beyond cigars, the staff’s dedication to customer service and creating an unforgettable experience ensures your group will feel valued and cared for. Finally, the outdoor patio, with its covered and heated area, is a unique feature that allows groups to enjoy fresh air and a relaxed vibe even when the temperature drops. Together, these elements make Up Down Cigar not just a cigar lounge but a hub for memorable meetups with friends and family.
What kind of ambiance can you expect at Up Down Cigar?
When you step into Up Down Cigar, you enter a place that is steeped in history yet refreshingly modern—a rare combination that adds a unique layer to your meetup experience. The lounge showcases a beautifully maintained space that never feels tired or worn despite its old-school inspiration. Every detail, from the lighting to the furniture, reflects a deliberate effort to preserve its authenticity while maximizing comfort. This results in an ambiance that feels both nostalgic and vibrant, encouraging patrons to savor their cigars slowly and engage deeply with their company. The scent of fine tobacco mingles with the warmth of the room, creating an inviting sensory backdrop. Even though the physical space is on the smaller side, it never feels crowded because of the thoughtful layout and good management. Whether you’re sharing stories with longtime friends or making new connections, the ambiance here supports genuine interaction and relaxation unlike many other cigar lounges.
How knowledgeable and friendly is the staff at Up Down Cigar?
One of the hallmarks of Up Down Cigar’s popularity and top rating (4.8 out of 260 reviews) is the exceptional customer service provided by its staff. Visitors consistently praise the employees for their deep knowledge of cigars, including blends, flavors, and proper smoking techniques. This expertise is shared generously and with genuine enthusiasm, helping patrons feel confident in their choices and more connected to the cigar culture. The staff do much more than sell cigars; they foster connection by recognizing regulars and welcoming newcomers alike as part of the “family.” They are approachable and patient, always ready to answer questions, make recommendations, or simply chat about the history and nuances of premium cigars. This level of personalized service transforms the visit from a simple purchase into an educational, enjoyable experience that keeps groups engaged and coming back. Their friendly approach reassures those new to cigar smoking, ensuring a non-intimidating environment where all feel included and valued.
Why choose Up Down Cigar over other cigar lounges?
Choosing Up Down Cigar means opting for quality, atmosphere, and relationships over sheer size or flashiness. While some cigar lounges may have larger humidors or more extensive seating, few can match the balance of intimacy, history, and comprehensive service that Up Down provides. Its curated selection focuses on quality over quantity, ensuring every cigar available is premium and well cared for, a vital factor for connoisseurs and casual smokers alike. The lounge maintains a distinct personality, carefully preserving the legacy of its original founder while innovating to meet modern tastes and comfort needs. The covered outdoor area with heating extends the usability of the space year-round, catering to diverse preferences and weather conditions. Unlike clubs that require memberships, Up Down retains an accessible, welcoming vibe that appeals to walk-ins and groups without friction. For a meetup spot where the focus is on authentic enjoyment, connection, and superb product knowledge, Up Down Cigar presents a compelling, distinctive choice that stands apart in Chicago’s bustling cigar scene.
What should visitors expect when planning a meetup at Up Down Cigar?
When planning a group meetup at Up Down Cigar, visitors should anticipate an experience focused on quality, connection, and comfort. Because the lounge is cozy and intimate rather than massive, planning for a moderate-sized group works best to ensure everyone has space to enjoy their cigars comfortably. The friendly staff can facilitate introductions to different cigar selections and help newcomers ease into the cigar experience. Visitors should also consider making reservations or arriving early during busy times to secure seating, especially for larger groups. The lounge’s ambiance and layout encourage lingering, so it’s ideal for groups who want to spend several hours chatting, relaxing, and savoring cigars. Those interested in the outdoor patio can enjoy a different environment with fresh air, perfect for warmer days or evenings with the heaters on colder nights. Lastly, guests can expect a sense of community and warmth that elevates the meetup from a simple gathering to a memorable occasion infused with shared enjoyment and relaxation.
How accessible and convenient is Up Down Cigar's location?
Situated at 1550 N Wells St in Chicago, Up Down Cigar enjoys a prime, easily accessible location in the vibrant Old Town neighborhood. This central spot positions it within convenient reach of many local attractions, restaurants, and nightlife options, making it an excellent start or end point for any day or evening out with friends. Public transportation and parking options nearby add to the venue’s accessibility, accommodating visitors who prefer to come by train, bus, or car. The location’s walkability also enhances its appeal — groups can easily combine a visit to Up Down Cigar with nearby dining or entertainment plans without hassle. Its setting in a well-known, lively neighborhood assures a safe and welcoming environment at virtually any hour. This convenience helps ensure that meetups can be punctual and stress-free, allowing every guest to focus fully on enjoying the company and atmosphere without logistical distractions.
What special features make Up Down Cigar unique?
Among the many features that make Up Down Cigar exceptional are its dedication to personalized service, a carefully curated humidor, and the preservation of a distinct ambiance that honors its roots. Unlike larger commercial lounges where customers can feel like just another number, here you’re treated like family, with knowledgeable staff who take pride in their work and connection to patrons. The shop’s selective cigar inventory includes blends exclusive to Up Down, appealing to aficionados seeking something rare and unique. The blend of historic charm with modern touches ensures that visitors feel a special sense of occasion every time they visit. Additionally, the covered outdoor patio with heaters is a rarity among cigar lounges in Chicago, providing a comfortable space year-round and adding versatility for different seasons and group preferences. This combination of history, intimacy, exclusivity, and practical amenities culminates in a truly one-of-a-kind place to meet, relax, and enjoy premium cigars with the people who matter most.