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Cigar spots with outdoor seating

You prefer to enjoy your cigar in the open air where the smoke can clear and the environment stays comfortable.

Based on 739 Opinions
+736
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Updated May 2026
01
Cigar Oasis Oak Park image 1
Cigar Oasis Oak Park image 2
Cigar Oasis Oak Park image 3
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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.

Luxurious interior creates a perfect spot to chill and enjoy high-quality cigars. The shop offers a good selection of fine cigars and a welcoming atmosphere with fantastic coffee and select beverages.

Patio offers plenty of seating with heating elements and a big screen TV. Outdoor area blends with lounge and includes indoor and outdoor smoke seating with comfortable leather chairs.

People are saying

"You'll feel so welcomed when you buy cigars here."

"The outdoor seating has heating elements and a big screen TV."

"You'll feel so welcomed when you smoke cigars here."

Good to know

1

A minimum purchase of 2 cigars is required for lounge access.

2

The humidor is well-stocked with a variety of high-quality cigars.

3

They offer a selection of fine cigars and beverages.

02
Ph.D Pub Chicago image 1

Spacious outdoor patio with heated covered smoking area invites cigar enjoyment until late. Calm, chill vibe blends a diverse crowd in a well-put-together sports bar setting. Offers full bar, darts, and plugs at tables, with a relaxed pace and reasonable prices.

A spacious outdoor patio lets you smoke cigars until 2 AM while ordering drinks all night. The pub stocks a small humidor with high-priced boutique cigars but offers a cigar-friendly vibe without costly memberships.

A heated outdoor patio offers a spacious, covered smoking area where drinks and cigars are allowed until 2 AM. Tables have lots of plugs, and attentive staff serve guests in the quaint outside space.

People are saying

"The outdoor seating lets you smoke cigars until 2 AM."

"I enjoyed the great food and beer here."

"You can smoke cigars on the spacious outdoor patio until 2 AM."

Good to know

1

No food is available at the pub.

2

You can bring your own food to the pub.

3

Street parking can be challenging.

03
New Havana Joe's Cigar Store & Lounge image 1

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, exceptional selection of cigars fills the store, all fairly priced. Staff offer knowledgeable suggestions, making it a solid spot to enjoy a quality cigar.

Outdoor seating features a unique patio with a fire pit that adds warmth and ambiance. The space offers a classy touch and a beautiful setting when open.

People are saying

"The Day Lounge staff always made me feel welcome and cared for."

"The staff here is so friendly and helpful when you smoke cigars."

"The staff here is so friendly and helpful."

Good to know

1

The lounge has a two cigar minimum to sit and enjoy.

2

The selection of cigars ranges from $7 to over $40.

3

Parking is limited due to a small lot.

04
Humidor Of Lisle image 1

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.

An excellent selection of cigars and accessories fills the lounge. Knowledgeable staff like Sam, Tim, and Joe help pick cigars, especially for rookies. Complimentary soft drinks and water come with cigar purchases.

A covered patio offers outdoor seating with shelter. The outside seating area adds extra space to relax.

People are saying

"I found the cigar selection here to be massive and impressive."

"I found the cigar selection to be massive and excellent."

"The selection of cigars here is one of the largest in Chicagoland."

Good to know

1

The selection of cigars is one of the largest in the Chicagoland area.

2

Customers can bring their own beverages while enjoying cigars.

3

The lounge hosts great cigar events and dinners regularly.

05
Windy City Cigar Lounge image 1

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.

A welcoming and clean environment offers a great spot to smoke cigars with helpful staff who guide newcomers on how to enjoy the experience properly. The lounge features good DJ spins and a relaxed vibe for conversation and unwinding.

Cozy outdoor setting features nice lighting and an area with TVs. The patio offers a comfortable spot to relax outside.

People are saying

"It's a welcoming spot to smoke cigars and vibe with good people."

"The nightlife here feels like home, everyone's so welcoming."

"The outdoor seating is so welcoming, they'll even teach you how to smoke a cigar."

Good to know

1

The lounge is BYOB, so bring your own drinks.

2

You can bring both food and beverages to enjoy.

3

There is a $20 entrance fee unless you buy a cigar.

06
Byron Cigar Lounge image 1

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.

A wide selection of premium cigars fills the lounge, paired with a top-notch ventilation system that keeps the air fresh. Staff offer knowledgeable recommendations and create a cozy, clean space perfect for relaxing alone or with others.

Outdoor patio offers a nice spot to sit with drinks after selecting cigars. Servers greet guests outside, creating a welcoming vibe despite some humidity that might push people indoors.

People are saying

"I found a ridiculous assortment of the best cigars to buy."

"They have a great selection of cigars and accessories."

"The outdoor seating here is a blessing at dark."

Good to know

1

They do not sell alcohol and you cannot bring in your own alcohol.

2

There was plenty of parking available.

3

The front lounge is for non-members, and you can use it by purchasing a cigar.

07
Redhead Piano Bar image 1

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.

A hidden outdoor cigar lounge offers a private spot for smoking with a separate smoking area and an on-site humidor selling a great cigar selection. The space pairs well with drinks and live piano music for a relaxed vibe.

A hidden outdoor deck serves as a cigar-friendly lounge accessed through a secret pathway. This space offers exclusive vibes alongside live music and drinks.

People are saying

"This piano bar is the perfect spot to end your night."

"It's a great spot to smoke cigars and enjoy the live piano music."

"The outdoor seating offers a hidden, cigar-friendly space with great live music."

Good to know

1

Expect large crowds on weekends, especially after 10 PM.

2

Reservations are recommended for special events or large groups.

3

Happy hour offers discounted drinks from 4 PM to 7 PM on weekdays.

08
Biggs Mansion Chicago image 1

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.

A spectacular selection of cigars includes unique options like Atabey. The lounge offers a fancy, classic vibe and reasonable prices for a great cigar experience.

Outside seating includes a nearly empty patio reserved for members. A $100 fee applies for non-members to sit outside and smoke cigars, but this is not clearly explained upfront.

People are saying

"I loved the great cigar selection here."

"I enjoyed the great cigar selection here."

"I didn't realize the outdoor seating was members only."

Good to know

1

A $100 fee is required for outdoor seating and smoking cigars.

2

Only members can access the outdoor smoking area.

3

Non-members have limited seating options available indoors.

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