Windy City Cigars Reviews

Windy City Cigars has an overall rating of 4.5 based on 22 reviews. Customer feedback on Windy City Cigars is mixed: Windy City Cigars reviewers highlight positive aspects like wide selection of cigars, competitive pricing, excellent customer service, fast shipping, which strongly appeal to cigar enthusiasts and casual smokers. However, Windy City Cigars is often criticized for its website navigation issues, occasional stock shortages, limited international shipping options, packaging concerns.

4.5/5.0

22 reviews

5 Stars

8

4 Stars

11

3 Stars

0

2 Stars

0

1 Star

0

All Windy City Cigars Reviews (22)
WilliamMartin_97
April 19, 2026
"They actually had what I was looking for"
I’d been checking a few different cigar sites, it was getting a little annoying because most of them were out of the stuff I wanted. Windy City Cigars actually had it in stock, which already made them feel like a better option to me.

The site was easy to browse, and I liked that I wasn’t wasting time clicking into products just to find out they were sold out. That kind of thing makes a difference when you’re just trying to place an order without a hassle.
My order went through without any issues, and overall I thought it was a solid experience. I’ll probably use them again, especially when my usual picks are hard to find elsewhere
Marian.caffrey
March 31, 2026
"Fresh cigars, shipping was alright"
The cigars showed up fresh and smoked really nice, no complaints there... just wish the box had been packed a little better for shipping
judy_Smith88
March 20, 2026
"Easy checkout, but heads up: no PayPal"
Just a quick heads up for anyone planning to order: the payment process was smooth and there were enough options to get through checkout without any hassle. That said, I was surprised PayPal wasn’t available, so if that’s your preferred way to pay, be aware before you get to the end
martinpotthoff6999
March 02, 2026
"Honestly, the age check was super easy"
I was relieved by how quick it was. It verified me fast with no hassle, which made the whole process feel way less stressful...
thomas1984
February 21, 2026
"Easy enough"
Site was simple to use. Found what I needed fast. Checkout was smooth. Pages loaded fine too
Florence_vogler82
February 17, 2026
"Solid packaging, nothing to complain about"
I ordered from windycitycigars.com and the packaging was good. The box showed up in nice shape, nothing smashed or weird, and everything inside had enough wrapping around it. Not like super fancy packaging or anything, but it worked, which is what matters. It did take me a minute to get it open, lol, but I’d rather that than have stuff crushed. Maybe it could’ve been a little neater inside, just being picky, but overall I’m happy with it. 4 stars from me
ElmerAllen
February 15, 2026
"I had a small issue with my order..."
I had a small issue with my order, so I sent them an email not expecting much. But they got back to me quickly and sorted it out without making it a whole back-and-forth thing. Isn’t that all you really want when something goes wrong? It wasn’t perfect, but the customer service was solid, and I’d use them again
socorro1986
February 07, 2026
"I had a small problem with my..."
I had a small problem with my order and reached out to them. They got back to me and fixed it, though it did take a bit of waiting. Not a huge deal, honestly. AND THEN suddenly everything was handled and I was like, okay, that was actually decent.
hello_jeffery195
January 26, 2026
"Good deals pop up, often"
The coupons worked for me, and I ended up saving a few bucks, so, i’m happy with it
brucepedersen8216
January 24, 2026
"Showed up right when it said it would"
No surprises here. I kept checking the tracking, and it was actually accurate. Said it would arrive that day... and it did. Got it on time, which I really appreciated.
michael-Clark
January 24, 2026
"The return process itself was easy..."
The return process itself was easy, but I’ll admit I got a bit uneasy after paying and then waiting for the refund to show up. It took a few days, so I wasn’t totally sure at first how it would go, but in the end the refund came through and everything was handled fine
doyle_Ballard93
January 08, 2026
"Shipping was a little high"
The cigars were good and I was happy with them overall, but the shipping cost felt a bit much. Something about it just seemed higher than I expected.
Angelique_vasquez98
January 05, 2026
"Fresh cigars, despite my suspicions"
I’ve ordered from windycitycigars.com a few times now, i was half expecting some kind of online cigar racket where the first order is decent and then they start sneaking in dry stock. But nope, every batch I got was fresh, burned evenly, and tasted exactly like it should. Maybe they’ve got their operation tighter than they want us to know. Either way, no complaints from me, the quality has been solid.
joseph.Mcgloin
December 31, 2025
"Good prices, but the shipping needs work"
The prices were fair and I did save a few bucks overall, which I appreciated. That said, the shipping experience wasn’t great and kind of took away from the deal. I’d expect some sort of credit or compensation if delivery is going to be that frustrating.
hello_russell415
December 26, 2025
"Good selection, found most of what I needed"
Windy City Cigars had a solid selection overall. I was looking for a handful of cigar brands and a couple accessories, and I’d say most of what I needed was easy to track down. They had maybe a bit more variety than I was expecting, which was a nice surprise.
I’m going with around 4 stars because a couple things I had in mind seemed to be out of stock. Not a huge deal, though, the selection is still good, and I’ll probably check back again sometime.
HATFIELD
December 24, 2025
"Checkout worked, eventually"
Checkout was easy enough, I guess. Nothing actually went wrong, which is always a nice surprise, but it did take longer than it probably needed to.
PRACH
December 18, 2025
"Everything showed up right"
I ordered from windycitycigars.com and it all came just like I picked it online. Nothing was missing, nothing weird or swapped out. It was straightforward, which is all I was hoping for
mike_Johnke92
December 11, 2025
"Wish the box had arrived in better shape"
I ordered from windycitycigars.com the shipping was quicker than I expected. The tracking updated without any issues too, so that part was nice. I just kind of regret not being a little more careful when it showed up, because the box was beat up and I was worried something inside might be damaged. Thankfully, everything was fine inside.
Heather_sabino79
December 08, 2025
"Pretty sure these are the real deal"
I ordered a couple boxes everything seemed right to me. The bands, wrappers, smell, and seals all matched what I’m used to seeing. Nothing was dried out or looked suspicious. Shipping went smoothly too. I’m guessing they’ve got decent storage or know what they’re doing, because the cigars showed up in good shape. I’d order again, it felt legit to me.

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