I love this bar...I my friend and I visited twice and I enjoyed a Last Word each time...a cocktail that is not particularly popular...but it is with me and the drink was served with a smile, well-made, reasonably priced AND they offer a discount if you pay with cash... Great vibe...I am looking forward to my next Last Word! read more

Stumbled upon this bar from a recommendation. On a quiet evening, this was a warm, intimate bar. The music wasn't too loud. The lights were just right. The bartender knew exactly what to recommend based on your drinking preferences. There is a good amount of seating options as well. If I'm in the area, this is somewhere I would stop by at again. The vibes here are top tier! read more

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This is a pretty awesome bar, smallest bar in Chicago! But it gives that friendly atmosphere! Bartender super cool. Still a good alcohol selection with a full bar. It's not cheap dive bar prices but makes sense considering the size. Def a bar to check out at least once! I'll be back for sure read more

Stopped in on a Friday evening and it was busy but not packed. The inside bar truly is the smallest bar in Chicago - very narrow area but once you're through there are a number of other seating areas! We sat in the front screened in porch area and it was super well heated - felt just like being inside somewhere and had nice mini fireplace heaters throughout. Across the group we got a variety of cocktails from a whiskey sour to a gin martini to a woodsman to a daiquiri - all were good and some even came with a little extra! Cute lowkey place, fun red lighting and disco balls throughout, would definitely visit again. read more

The Matchbox - Whiskey Sour - Bars Near Me - Chicago, Illinois

The Matchbox is unique and that is its appeal. As the smallest bar in Chicago, it can be nearly impossible to grab a seat (the indoor bar has only a couple seats) but it's worth it if you do! Service here is spectacular and their cocktail menu is awesome. Prices are steep but you're paying for the quality of the drinks and the atmosphere. This isn't a place you'd come to watch sports (there's only one tiny TV) and it has an upscale feel to it despite being located at the busiest intersection in west town. read more

The Matchbox - Bars Near Me - Chicago, Illinois

Love the vibe at this place and will enjoy it again soon. But not having the food option and having to go around d the block to get the food that IS offered brings this place down for inconvenience. BUT (and it's a big but) everything else about this place is incredible. It's small, cozy, and has great vibes with the lighting, music, closeness and all that goes along with being a mom n pop, hole in the wall in the middle of Chicago! And the food, even though around the corner, was amazing as well. Review of that place coming.... read more

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Underrated small bar! The staff is extremely friendly and prices are very reasonable. A great place to unwind after a long day. read more

Such a festive vibe in December and love the recently opened Good Neighbors bar inside the train car. Fun music and holiday pop up. read more

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The place is a bit small, but has a cute ambiance. Pretty cozy and has an enclosed indoor space, which is nice. The drinks, unfortunately, miss the mark. I got a daquiri and despite the bartender trying it, it was basically just lime juice. Stuck to beer (not a huge selection in draft) after that. They do have a $8 hamms and shot deal, which is nice. Overall, the ambiance is nice, service is ok, but drinks are subpar, especially for the price. read more

Ducked in here on a drizzly Thursday afternoon while waiting to meet a friend. I opted for a simple margarita that was made well, and the excess pour was kept in a cute little glass for me in the side of my main. I loved it! Felt like a neighborhood bar, and the bartenders weren't overly friendly but they mixed a mean drink which is all I ask. Will definitely return on my next trip to the neighborhood, seems like an easy place to while away an afternoon. read more

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Another great experience at Matchbox. Great cocktails and friendly service. Highly recommend for craft cocktails in a beautiful environment! read more

Chill place in River West. The interior inside is small but fun/divy, the large patio out back breaks this vibe with a more sleek and modern design. What's odd is that this larger patio out back is shared with the companion tiki bar (Tiki Tiki), owned by the same owner, that has a waiter coming up and taking orders/bringing drinks - yet for Matchbox you have to walk up to the counter and grab your drinks yourself instead. Made for some awkward misunderstandings when sitting there. I had their featured suggestion, the aguasol paloma, which tasted more like a bland mezcal margarita instead of a refreshing grapefruit-infused summer drink. A bit unfortunate as I heard some great things from the drinks! read more

Everything about this place fills my old dead soul with joy. It's quintessential Chicago. Charming no nonsense and comfortable. Love it love it love it. read more

The Matchbox - Bars Near Me - Chicago, Illinois

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Unfriendly staff, great drinks- okay prices great space. Love the heated patio on a cool Chicago night. Highly recommend the pineapple gimlet! Don't go expecting great service- it's hit or miss if you aren't a "regular" read more

Bad service, dishonest with pricing, not consistent with making drinks - shady, and the neighborhood deserves better. Skip this place and go elsewhere. read more

My friend and I came here for some after work drinks. The place was empty so we had all the seating options in the world lol. We sat outside in the covered area. This bar is very small and narrow and can see it getting filled quickly on a busy day. I started off with the gimlet which was absolutely delicious. Might become my go to drink (or maybe just when I come here) I then had 2 espresso martini this. They were so delicious and the best I've had so far. Will definitely return and make sure to bring all my friends here. read more

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I've been walking past this place for weeks and have been dying to check it out. My friends and I came on a beautiful Tuesday night, sitting around the Adirondack chairs enjoying a variety of drinks and pizza from across the street. The drinks were solid. Service was adequate. And I wish I could tell you about prices, but my friend stole the check and refused to let anyone else pay. I'll be back! read more

The Matchbox - Bars Near Me - Chicago, Illinois

On a Thursday night, this place gave off a great vibe... I love the patio area with the red lighting all around this place. The way it is laid out is very interesting, but it still felt inviting to me. Our bartender was really friendly, and this was a great way to end our drunken shenanigans after getting too lit at bowling, lol! I hear this place is awesome to come to during Christmas time with all of the decor. Will definitely need to come back for that! read more

The Matchbox - Bars Near Me - Chicago, Illinois

Matchbox is one of my favorite places to go for cocktails in the city. The cocktails from their menu always come full right up to the rim with an extra glass full on the side, and are delicious. Our wait staff are always really great, even allowing us to move our table away from the rain blowing under the rooftop of the patio during my last visit. The location has a super cozy atmosphere, although it should be kept in mind that this may make it difficult to seat large parties. Will continue to come back, and highly recommend! read more

The Matchbox - Cosmopolitan & Lemon Drop - Bars Near Me - Chicago, Illinois

Visited Matchbox for drinks. We were greeted by a dog and a foosball table. Both things we very much enjoyed. Our server was kind and fun. I want to be friends with her. Plus the music being played was pretty good. Overall a chill bar to hangout with. read more

drinks were ok at best. Got hit for a 4% environmental fee and taxed on it. People are sick of this crap. Charge accordingly and pay your people right and let it reflect in the prices instead of being scammed at the end. Wtf is an environmental fee anyways. read more

I specifically recommend the match box during holiday times when it is decked out in decorations. It is festive and cosy but tiny! Part of why I don't come more often is that it's really best if you are with one other person, max of a group of 4. I don't even know if you could find a way to sit with a larger group. The drinks are classic cocktails and delicious. I had a lemon drop Martini recently that was excellent. There is a happy hour menu that features a specific cocktail (recently a highball) at a reduced price. Price is pretty standard for cocktails in this neighborhood. Service was attentive but not overbearing. Enjoyable spot and plan to visit during the holidays for the atmosphere. read more

I have loved this place for years. Impossible to find here without making friends. Best late-night conversations Great margaritas and Manhattans. Friendly staff. I just wish they didn't add on to the space. But most people sit in the main (original) area. read more

Seems like a reoccurring theme. I've also been coming here for decades and this place has just gone down the tubes. Was there this past Saturday night and they had 1 server for the entire outside. She was unpleasant so I went inside and ordered a round and carried my drinks to the table on a tray. Bartender said it was fine, since I was actually helping them out. Then again tried to order from the waitress, no luck. Went to the top to order a drink and that bartender didn't even know how to make a cosmo. She used grapefruit juice instead of cranberry. Bad drinks, bad service poor attitudes. What a stressful night out. I really needed a drink after that. read more

Our group had a great time here. The food was top quality and all of the people were helpful and friendly. We had pork and fish and both were amazing. read more

The Matchbox - Salt crusted salmon - Bars Near Me - Chicago, Illinois

sadly, this great bar that I've been going to for almost 2 decades has lost a step due to a really bad bartender particularly one that is there on Thursday nights, who is lazy, not attentive and very very unresponsive to customers. It is really a shame that this bar is going to suffer from the lack of effort from one particular place I really hope the establishment looks at their Thursday night bartenders and decides whether or not these are probably people to represent their read more

I really enjoyed myself here. Not too many bars can make a rusty nail these days, so thumbs up to that one! I went here with some friends and ordered a rusty nail. The bartender asked the waiter if an 80+ year old man was making the order ha ha ha, and he felt like sharing that with me in front of all of my friends. We laughed and had a good time. I ordered a couple rusty nails and each were equally awesome. My friends enjoyed their drinks as well. It was packed, we had good seats and good conversations. The waiter was full of charisma, which is always appreciated and respected. It's all you can ask for from a bar. read more

Always one of my staple last calls. Especially in that tight sexy environment. Isabella on a Tuesday made the best Gimlets ever. Powdered sugar and a sidecar.. amazing. Thank you read more

I know it's old news, but their margaritas are delish. Very different with the bit of powdered sugar, but I love it. Yes it's super small here. I'd say the best time to come here is late night, when hopefully it's not too crowded. I haven't been back in forever, need to make a visit! read more

In the early days of the pandemic last year when bars were shutdown and we were all chilling at home got in discussion with some folks on Twitter telling me when places reopened I had to come here to check out the margarita with the sugared rim. They're the only place I know that does it this way. Last night I finally went. Did not leave disappointed. They put the powdered sugar on the rim of the glass in addition into the shaker during the shake. There were some really charming people next to me which is why I ended up staying a little longer. Had a miller high life, shot of fernet, shots of Malort and Seipps Pale pilsner. If you're not from Chicago you have to try Malort at least once. It's cozy in the bar area they have a covered patio for additional seating. I liked the bartender and the server. The bartender is so talented she wasn't measuring the spirits in a jigger for the margarita. I love that you also get a tiny carafe of extra margarita so when you finish with the glass you still have a Lil bit leftover. read more

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Really cool concept - good vibes and decorations inside and out. But their cocktails tasted quite disappointing. You could taste the alcohol but all other flavors watered down. The other irritation was the lack of transparency in pricing. Menus didn't show prices and the prices are higher than you would think for a small casual place. They also charged a 4% "Environment Fee" without mentioning it or having it written anywhere. Based on other reviews this place seemed like a real winner but I'm not a fan and won't be coming back or recommending to anyone. read more

Wowy Wow WOW! What a time to strike the proverbial Box. I came, people saw, and the experience kicked butt(s)... For the faint of heart I recommend the backside of the menu. For the rest of you I suggest a Monday afternoon of sorts with an intellectual convo for the ages with Matt, all while raising your glass filled with Brooke's tasty acumen, and finally finish it off with Katherine's Ginger Gimlet. Strap your boots up cuz you'll be remiss if you forget what the best drinks in town feel like upon your pallet. I mean... They're literally something to get behind! read more

This place is a favorite of a friend of mine. It's a very fun spot with great cocktails and great service.

Love the vibe, service was good, however it gets a little bit chilly in the train car in the winter so don't forget your jackets!

Wow best cocktails bar in Chicago. We really enjoyed our experience. The bartender was really cool and helpful. The drinks are delicious and the service is outstanding. Overall decent prices, excellent service and awesome drinks . Best in town and definitely will be back soon read more

The Matchbox - Bars Near Me - Chicago, Illinois

Pretty decent scene. The music selection was good. The staff was cool. We stopped in for one drink before dinner. She had a glass of wine. Cheap wine that even at West Loop Michelin awarded restaurants is $13-$14. I had a Paloma. The chili salt was all over the glass not just the rim. The bill was $36, $5 of that was tip. That's just pushing it too far. Some of these places have taken inflation and covid and ran with it. The pendulum need to swing back. read more

The fact that my last review for this place got removed by a complaint from the owner means that it was seen exactly where it was intended to be. So I restate- this place is awesome and genial, the lighting and the music are very cozy and inviting, the drinks are just fine and the staff was-- to a person--wonderful to be around and chat with. The only detraction, and it was a major impedance to this customer's experience, is the pall cast by the presence of management that doesn't mind openly abusing authority and staff in front of customers with demeaning language, belittlement, and condescension. read more

We love The Matchbox! Best cocktails you'll ever have! Our favorites were the ginger gimlet and the old fashion. Such a great story behind the bar, truly is a Chicago staple. 10/10 recommend! read more

The Matchbox - Ginger gimlet - Bars Near Me - Chicago, Illinois

Would give this place a 0 if I could. We live down the street so we ALWAYS visit Matchbox. We show up on a Tuesday night with 6 girls for a friends birthday at midnight. One of the girls doesn't drink, so she came just to celebrate the birthday at midnight and leave, so didn't bring an ID. We were all denied entry to the OUTSIDE even though our friend said she had no intentions of drinking, just wanted to spend time with us. That isn't our problem- our problem is how rude the staff was to us about the matter. Literally brutal. Will never be returning read more

Such a rude environment, and very poorly staffed. It will take you hours to even get water. Came here for a birthday party and they would not let the seven of us be seated, and made us stand awkwardly in the front like zoo animals. I used to come here often, but not anymore!!! Why would they not want business?? Could use the money to hire more staff to Get the water read more