Before heading back to the other side of town, we decided we wanted to have drinks. We opted for this spot because of its proximity to the place we went for lunch, and the fact that we're about to open. We stepped inside to find a cute, seemingly unsuspecting neighborhood bar. Before we walked in, we made a friend that we decided to name Mr. Chicago. He came in and had a round with us. We met a Georgian who'd been in Chicago for 30, but gave us enough conversation about Georgia high school and college football to know that he had a peach flavored soul! The bartender was cool and made us a drink that we dubbed the Westown Connection (Disaronno and grand marnier), which is a spin on a French connection. The bar has been there since the 40s, so there's some history behind it and longevity too! The music was great, as was the bartender (glasses and a killer salt and pepper beard). The cocktails were well mixed and priced right too. If we stay in this area on any of our next visits, I can see us stopping by the Matchbox for a Westown Connection! read more

What's not to love about one of the shadiest, shitty, small bars in chicago that serves up some excellent cocktails?! Love this place. The bartenders are fun, but they don't want to hear your crap. I love them. They play excellent tunes and can whip up just about anything. It's also a given that in the very small space, you will run into some characters...some good and some bad. BUT EVERYTIME, I love it. read more

The Matchbox - Bars Near Me - Chicago, Illinois

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Been coming here for 20 gd years. Lots of changes but I'm hanging with it. And you know what? Im still sticking with it. Our server Kobe was cut from the cloth when it comes to the what I appreciate about the matchbox. Thanks for continuing my hazy memories. read more

Came a few days ago. Decent outdoor seating set up for covid and nice heaters. Social distancing between tables could have been a little better in my opinion. The cocktail menu is good. Got the sidecar and my wife got the gimlet. Both were delicious and they actually give a little extra side small glass of more cocktail with the order. So essentially you're getting almost 1 and 1/2 cocktails for $13, which is great. Bathroom was tiny, just an FYI. read more

The place is tiny hence the name. The outdoor space is lovely. The staff is awesome. Highly recommend.

Visiting the cuz' - around the corner - from SF...she suggested we duck out, leave the napping 2 year old in her care for a gimlet and manhattan at Matchbox. We crossed the bridge and within 2 minutes were perched on barstools in the narrowness....feeling quite at home,familiar cool dive bar atmosphere. The lighting - brilliant - stormy clouds, balmy air. Elbows slipping on the bar-top - purse plopped on floor - I was at home. Quiet humble service....I don't mind. Slow sippin' perfection. Even if for an hour - 'twas divine. read more

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Literally a hole in the wall. This place is tiny and made a little person like myself slightly claustrophobic. I truly wonder how grown men can sit elbow to elbow like sardines and have a good time. The alcohol probably helps... Only one bartender that doesn't seem too chipper. He seemed pretty shocked that we ordered straight shots and the concept of shot glasses also don't exist in his world. He pretty much served us a half a glass of vodka each (equivalent to at least 2 shots). The shot in itself was also warm and did not go down smoothly. We also tried their Dark and Stormy which was AVERAGE and their banana daiquiri which was borderline undrinkable. Wouldn't go back or recommend. read more

The Matchbox - Bars Near Me - Chicago, Illinois

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I almost don't want to write a good review since I want to keep this place my own secret oasis lol but it's truly amazing. Have never been disappointed. read more

This place is about as spacious as a hallway and the service on the patio is questionable, but boy do they have a quality old fashioned. They are not skimpy on the good cherries here either. Despite the cramped quarters, those old fashioneds will bring me back here for sure. Maybe I'll even try the mysterious gin and jam next time. read more

Who designed the layout of this bar. Long bar which goes and goes and when you make it to the end, hope there isn't a person seated there, otherwise you'll have to pay toll by giving them a hump to get past. You get another free hump of their shoulder as you pass to get back. The room narrows as you walk into the back. Makes for funny situations and conversations with passersby as you sit there inebriated, smiling ear to ear due to the superbly created cocktail made by yours truly, Cheech from Cheech and Chong. Except this Cheech doesn't smile, except at ladies and has longer beard whiskers. Cocktails are pricey, but well worth the cost. They are mixed up in front of you and the bartender will leave behind the shaker with some left over you can pour or they will at some point, pour for you. Great place to impress cocktail connoisseurs or liquor up a date. Feels are free. Ginger vodka gimlet & margaritas on the rocks are a must. read more

Cutest smallest bar in chicago! Love it around christmas time with all the lights and decor. It's a good spot for drinks!

I happened to be in the area with a friend and we decided to stop in for a quick drink. The inside was exactly how I remembered it. Tight quarters but that is the charm. We ponied up to the bar and ordered drinks. One of the best vodka sodas i have had in a while. Awesome beer selection.....you will not be disappointed. Great music plays in the background for your audible enjoyment. Bartenders are attentive without being pushy or forceful. Bike parking still on street. Cheers Matchbox. read more

The drinks are excellent!! Strong and delicious! Although they don't serve food, you can get food from pie eyed, which is right around the corner to enjoy with your cocktails. read more

This place has it all: Small: Yup Cheap Drink options: Check Surly Bartender: Fo Sho Gents who appear to be regulars looking at you funny because you wore a cardigan sweater: Indeed that happened. Overall good time: You Bet Your A$$$ read more

I came to Matchbox tonight (3/1) to celebrate a coworkers birthday. As we were arriving and sitting down on their covered front patio, my friend turned and hit her knee on a random bar they have uncovered on the patio, so hard that her knee dislocated. As we were helping her and grabbing a short chair for her to try and sit in, one of the bartenders working tonight (the short one, not the redhead) came out to yell at us for moving the chair. The front patio was entirely empty except for our group, and we grabbed the chair due to the situation unfolding. Once we informed her that someone had been injured, her response was that she didn't want someone to be hurt because it would be bad for the bar. She wasn't concerned that someone was injured, she wasn't concerned about the random bar injuring patrons on their patio, she was concerned about how this may potentially look for the company. Basically, don't go unless Efrain is working because the rest of the employees are 100% garbage. read more

Let's start with first impression... It's extremely small. Max. Capacity is 29 people - so it says on their wall. But don't be turning it down because of that. At first you might think nothing of it, but once you step inside it transforms. Once you start talking to the people there and the bartenders (Jackie & Eric) you will start to see the charm of this place. Definitely a local bar, everyone fits here. Laid back environment with a friendly crowd. We liked it so much we had to go back before our trip was over. Drinks are amazing and strong. By recommendation we tried the Margarita, the Cherry Brandy Manhattan, and the Vodka Gimlet. Could not tell you which one is better, guess it depends on your alcohol preference but they were all good. They also do your regular drinks like vodka tonics - don't worry for overpaying for the tonic, like I said before, drinks are strong, you really are paying for what you went there for, drinks! Oh, and going back to the fact that everyone fits there - we met the drummer of THE LAST VEGAS. They opened for Motley Crue on tour earlier this year. Fun place to start your night right. read more

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This place is very cool. Have not been here in awhile, but had a good occasion to go after dinner for drinks. Had a couple of beers which were good, but they have the best martinis! Especially the chocolate ones. I highly recommend this place if you want one of those after dinner. Great vibe read more

Don't come here. This is my bar. This sardine can sized place gets crowded enough as it is. If you do go there and don't like it just know that you lack good taste and, more importantly, you lack a soul. read more

How have I not written a review of this place until now, I LOVE this place. I've been going here on and off for years. It's got all the booze you need, cheap cans of Schlitz, and the bartender will "start you a napkin". In the summer it spills out onto the street, but the cozy inside part is better. read more

I worked in the River North area for many years and drove past this little bar many times, I was always a little curious and intrigued by the Matchbox and the attached Silver Palm restaurant which is unfortunately closed now. My son was picking me up for a Hawks game and the Matchbox worked out well as a spot for a drink while I waited for him. I came from the Loop which made it quite convenient to exit the Elevated at Chicago Avenue. This bar is dark inside, I mean really dark, I have no problem with that but just want to state that it is really dark inside, actually thought it was closed, nice small bar as the name implies. As usual I ordered an Old Fashioned, later as my eyes focused I noticed that it was one of the drinks featured on a poster behind the bar. All of the drinks highlighted on this poster were $12 and it was an interesting selection of cocktails. I'm always a little thrilled to see the somewhat overlooked Old Fashioned has become a more common drink, and this Old Fashioned was quite good. Now maybe I'm just a little old fashioned, but I do have a little difficulty with justifying spending $12 for a standard cocktail, I know it is kind of the norm these days with all the fancy cocktails out there but just saying that's a lot of money for a drink. It typically keeps me from ordering a second one. As mentioned we were heading to the United Center for the Hawks game and I expected to get hammered with expensive drinks at the stadium but found it a little ironic that my Crown Royal with Ginger Ale was $11.25 per, I had two. The Matchbox is an interesting bar and the Bartender was wonderful, just wish I could enjoy a couple of cocktails for a little less expense. Interesting mix of music as well. (FDV Approved, 3.6 - Function, 4.4; Drinks, 4.0; Value, 2.5) read more

The Matchbox - Old Fashioned! (keepsmilingphoto.com) - Bars Near Me - Chicago, Illinois

Love this bar. I have always had great bartenders who give good recommendations and are very friendly. The last time I went, I ordered an Old Fashioned - one of the best I've had. They had jars of home made cherries that they muddled in my glass - amazing. The bartender recommended a great beer for my friend and another great cocktail for me - a twist on the Negroni. The place is TINY and does not have a lot of seats so try to go at off times or else you will be uncomfortable. 88/365 read more

The Matchbox - Old fashioned - Bars Near Me - Chicago, Illinois

One of, if not the best little bars in Chicago. Top shelf ingredients and great bartenders. Be ready to be social, as the the further you get inside the smaller it gets. read more

Was with a group of friend and we weren't there for more then 30 - 40 minutes. A friend of ours was a dumb ass and didn't tip but the bartender then had a shit fit saying we were taking up space forever and that we didn't tip. Excuse me but the rest of tipped and if one person didn't tip then suck it up. Shit bar read more

Best cocktail bar in Chicago! The reviews claiming that it's cramped are ridiculous--what did you expect at a place called The Matchbox?! My husband and I are in our 40s, but you'll see all ages here--just adds to the charm. This is pretty much our standing date night spot. Sometimes we go for dinner first, sometimes not; but Matchbox is pretty much a given. Their margaritas are TDF although I swap out their sugar rim for salt, and my husband favors a Manhattan or Jameson and ginger ale. Neither of us have ever had a bad drink. We've been coming for a few years, but the current Friday/Saturday night team of Trinidad and Johanna is top notch!! See you Friday, Matchbox!! read more

The Matchbox - Bars Near Me - Chicago, Illinois

This place fucking sucks- it was my 26th birthday and there were 6 of us. I had one friend who forgot an id, clearly 26, and told them that she wasn't going to drink. They wouldn't let us in even though no one was there??? And it would've been obvious if my friend had ordered a drink. They lost out on so much business and the workers were assholes, especially the main door guy, and treated us horribly. Don't come here, go literally anywhere else. read more

Service was subpar I've been coming here for many years and have always recommended that people from out of town come here but that will never happen again- wha happened to the amazing service - experienced bartenders who actually know how to make great drinks not the sugar filled cocktails I was serviced - $15 for a cup of sugar served by a rude sever who seemed to need a lesson in customer service- and the receipt has the name of a guy named Kevin not a female who served us read more

It tries so hard to be cool, kitchy, and hip(ster), in one of the cool Chicagoan neighborhoods (it's kinda cool). But, when have a place that is indeed the size of a matchbox, it's impossible to go during any hours respectable to grab a drink. Fortunately, I was drinking when it was not indeed respectable, so rather enjoyed myself, but it was still almost impossible to find a seat. It's one of those places you have to try at least once, because of its trendy appeal, but it'd be hard to go regularly if every time you might not actually get to stay. read more

Great service. Amazingly warm patio. I am in a sleeveless shirt and it is 5 degrees outside. Definitely worth the stop. read more

The Matchbox - Bars Near Me - Chicago, Illinois

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Amazing neighborhood, literal hole in the wall Chicago bar. It's the size of a matchbox - with seating for about ~15 people max. Along with the unusual sized place, what makes this place unique is there cocktail menu. No frills, no BS, just the old school classics simply put on a chalkboard wall. The Silver Palm next door allows you to order food from their menu and they'll bring it over to you at the bar. I only drank, but would be interested to know how the food is also. Overall, great casual spot for classic drinks. My boyfriend and I live near this spot and I can't wait to go back and try more from their menu. read more

Small bar with lots of edge. Quaint and low key. Lots of character. Tight space, one size doesn't fit all.

Pretentious. This used to be a great bar back in the day. Now the music is garbage for the most part, egg whites are in every drink for some reason, which would be fine if they were done fresh daily (which I know they are not) as opposed to a day or two or three before... Definitely come here for a $15 cocktail plus tax and tip with possible bits of congealed raw egg whites in your teeth! And some of these bartenders.... Take yourselves less seriously, yikes !!! They care way more about themselves and their friends than your average customer, it's ridiculous. This bar is not for everyone. I deeply regret the dollars myself or groups I've been there with have given away in tabs and tips to this ungrateful place. Depressing to think about, but lesson learned! read more

If you're a fan of stiff classic cocktails like a Manhattan, you're going to get along just fine with The Matchbox. Right in River West, this is another bar in Chicago I've been to countless times, yet somehow never gotten around to reviewing it. Tsk tsk. There's not much for breathing room inside, as it's a tiny sliver of a place. Who knows what the square footage is, but one thing's for sure; you only have about three feet between the wall and the bar. If you don't mind tight spaces, you'll be fine. Claustrophobic bar goers may want to take some anti anxiety medication before agreeing to meet anyone for drinks on a Friday or Saturday night... Always a fun soundtrack, friendly bartenders, and never once have I been disappointed with a cocktail. If you haven't been, I suggest you change that ASAP. read more

If you want to be treated like a loser, this is your place. If you want to feel like you're in high school when it comes to pissing off the staff (for a reason you're totally unsure of) and getting the silent treatment - this is the place for you. If you've never written a Yelp review and want to be so compelled by a shitty experience - this is a place for you! If you wanna have bad time, The Matchbox is here for you! Great, ambiguous hours, stubborn staff and watered down drinks ... I mean what else could you ask for! Have a bad time today and visit ! read more

I really love this place and let me tell ya why. A story, if you don't mind. My boss farts. No really, she farts; in my cubicle sometimes, even. They smell. I can hear them. If you're reading this and you want a bright, autonomous, creative, writerly type to work for you let me know, because my boss is not only crazy, but she farts. As you can imagine, this can sometimes be very distressing to me. Sometimes it is so distressing that I have to stop my commute home half way through and drink martinis alone in probably the smallest bar in Chicago. This happened last Friday after a long week down wind. I stopped for just 1 dirty martini, and you can imagine what happened. The gorgeous bartenders at The Matchbox washed me clean of strife and pain, that's what!! I got a dirty martini that was perfectly mixed and chilled and had no problem sucking it down while standing pushed against the wall watching the window outside while it rained. If I'd been smoking it would have been a fucking art movie it was so perfect. Then I got a seat and made nice with some folks next to me and had the Pineapple Gimlet recommended. I ordered it on a whim because their drinks are SO fucking cheap it's a crime not to have at least 2. The nice man with the shaker and the vodka made a HUGE pour and set a pretty, frothy, icy pineapple drink, with a powdered sugar rim down in front of me. "$8" he said, as he set ::THE SHAKER:: on a coaster next to my glass. I looked at him suspiciously, "Is that for me?" "Yeah", he nodded. My eyes widened. I proclaimed it "like a milkshake" (the extras on the side I meant), won the lottery, was voted best looking in the bar unanimously, and then the sun came out after 3 days of rain, a double rainbow formed, and leprechauns danced around me tossing gold doubloons my way. Of course I gave the doubloons to the elderly and less fortunate, having already won the lottery mere seconds before. That all really happened to me last Friday at 6:30 PM in The Matchbox. Oh yeah, and then my boss called and told me she'd never fart in my cubicle again because it's a disgusting and disrespectful thing to do to a gem of a person such as myself. All this, on top of getting 3 perfect, delicious martinis, for the price of 2. read more

After the Jamaican Me Yelpy event, I wasn't quite ready to call it a night so I met a good friend here for a nightcap. I hadn't been to Matchbox since I lived in the 'hood many moons ago, but I had always remembered that I liked it, so I was anxious to see if it was still a cool place. Indeed it was. I arrived first (as usual; I am terminally punctual) and claimed the last two seats at the bar and ordered a glass of red wine. It probably would have been a better idea to order a martini, but I was craving a robust red and wanted a Cabernet. The bartender was only able to scrounge up a Shiraz, but anyone that knows me is well aware that I do not discriminate when it comes to red - I happily drink it all. My friend arrived and ordered a Scrimshaw pilsner. I am not a beer drinker and had never heard of it before so kudos to MB for stocking a hidden gem. We were engrossed in conversation when I heard the opening riff of "Come Together". Yep, MB was playing "Abbey Road" - the perfect soundtrack. We stayed a while and chatted with the bartender, who was very sweet, and commended her on her musical selection. Matchbox is as good as any place in the area. I'm not sure I'd be brave enough to come on a weekend night as the crowds would probably render me completely claustrophobic, but I'll definitely be back on a weeknight. read more

Some places get 5 stars for being odd, unique, particular, interesting and bizarre. Matchbox is all of these and then some. If you are claustrophobic, have a really large need for personal space, hate being close to strangers or cant stand smelling what someone had for lunch - don't go here. If you like the company of others - right in your face - and good martinis, margaritas, draft beer and cocktails then go here. The bar has to be the smallest in the whole city. Smaller than Foley's on Irving and also Brendan's on Broadway. It starts off at the entrance at its largest and just tapers to a smaller and smaller and smaller bar as the stools spread back to the end of the place. If you are in need of a bathroom break you will most likely end up rubbing your junk on someones back or front - depending on what side they choose to face you with. Its one of the many places that makes Chicago awesome, so if you have never been there try it at least once. Go there - you will remember it forever. read more

If we could, both Rob Thomas and I would give this place 20 stars. Since we can't 5 will have to cover it. Not necessarily applicable in this winter weather, but the patio is pretty dope with way more seating on the sidewalk then inside the bar itself. Until a warmer climate comes you''ll have to fight for one of the maybe 30 spots inside, but if you're lucky enough to get one you'll enjoy awesome drinks cheaper than almost any craft cocktail bar in town. Perfect to post up at alone and enjoy some convo with the bartenders or bring a date to showcase your coolness. Matchbox makes for an awesome spot to start off a night of almost any occasion if you're not rolling with a deep crowd. read more

My friend and I walked in here by accident last night and couldn't get much further than he door. It was packed to the max and in order to go to the bathroom you have to exit the building and enter through another door farther down the building... then when you get in there, prepare to get VERY friendly with any bar patron sitting between you and the water closets. Calling it "The Matchbox" is no joke. I think this bar is defo 4 star worthy if you get there early enough to get a good seat... but sadly, we did not and were asked by one friendly patron if we were Avon ladies... uhm, what? I had just come from a Yelp Elite event and had a cobra painted on my face... no, we are not Avon ladies. Oh, and I think I was propositioned by an elderly couple for a threesome... you folks seemed nice but no thanks. I'm pretty young but I'm also old enough to know better. 3 stars is where Matchbox sits for now... I take offense to being profiled as an Avon lady. read more

The Matchbox is probably as big as/ just as dive-y looking the apartment I once had on Bowery in Manhattan. Unlike that terrible living situation, The Matchbox is well-stocked with house infused liquors (pineapple vodka, anyone?) and bartenders who know how to make a mean cocktail. The bartenders are extremely down-to-earth and friendly; this isn't the type of cocktail bar where you are scoffed at if you've never heard of celery bitters. Your friendly Matchbox bartenders will gladly offer suggestions, describe flavor profiles, and check in on you periodically to make sure you're having a good time. The bartenders are also particularly nice to the regulars. It's like a dive bar joined forces with a fancy cocktail bar to provide you with the best of both drinking experiences. Even if you're like me and despise sweet drinks, try the pineapple vodka gimlet. It is somewhere between "Patio Pounder" (you know, one of those really easy to throw back cocktails) and something a bit more tangy and complex. The pineapple vodka, infused in-house, is a real treat. Because The Matchbox boasts a very interesting tequila and mezcal list, I've also had many iterations of a well-balanced margarita. At about $8 a drink (technically for two drinks, as the bartenders are pretty generous when they are mixing and will top you off with the remnants of the drink shaker), this is probably the best value-to-fun ratio to be had along all of Milwaukee. read more

As good a way to end an afternoon in West Town as any. I hadn't been to Matchbox in a decade, and it smelled as if they had not cleaned up much since then. But it's still a fun, even if grunge, place to hang out for a little while and have a fairly priced beer. read more