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

Matchbox is teeny tiny but very cool! Over the weekend I went on another Milwaukee Avenue adventure. After a heavy dinner at Silver Cloud, my friend and I decided to walk all the way to Richard's. Along the way we stopped at Matchbox. There is barely enough room in Matchbox for the bar, but I really enjoyed this place. I spied the infused vodkas and decided to try the ginger vodka gimlet. Woo boy! That was a good drink! The bartender was really friendly too. I really liked the vibe at Matchbox. It's somewhere between a dive and supper club bar. I wanted to stay at Matchbox longer, but my friend had his heart set on Richard's so we left after a few cocktails. I'll be back to Matchbox for sure! read more

I almost had to whiz into the toilet from the bar...because the bathroom is that small. Came here for post-Slurping Turtle drinks and stomach recovery mode for the Thee Little Piggies sandwich next door at Silver Palm. And technically, I could have ordered it while sitting at the matchbox, I just wanted to be able to sit inside the train car. When we first got to the Matchbox, I'd read and heard about how small the place is. But words can't describe the actual feeling you get upon walking in. This place is seriously tight. Tight like a tiger. When I wanted to hit the head, I had to play musical chairs with the guy that was leaving the bathroom. Seeing how stretched this place could get, with an empty bar, I shudder to think what it'd be like if the place was hopping mad. Knowing my wife, I thought it best to grab an outside table Turned out to be a great choice with the weather being what it was, partly cloudy and 73. Onion rings to share, and a magical Pisco Sour. Magical Pisco Sour how? I'll tell you how! My Pisco Sour magically turned into a Margarita! At first, I thought, man these bitters are really screwing with my pallet here, it's making my brandy taste like tequila. So I drank half the shaker, and then 3/4 of the way through, I let my Margarita expert friend Britt C. taste it. "That's definitely a margarita" Sadness. Not one to ruffle feathers on a first date(with Matchbox), I left it at that and finished my drink. So the good thing was it came with a shaker to continue topping off with. The bad? The wrong drink. Our server was also very non-chalant. It seemed she was genuinely annoyed that we were occupying a table in her section. After receiving the check, we cheerily thanked her, as she rolled her eyes and said with a touch of scorn,"yeah" while rolling her eyes. I'll come back here, but not for Ms. Rolly-Eyes' terrible attitude. I'll come back for the Pisco Sour that I never received. read more

A bar owner that stocks 20 kinds each of high-end tequila, single-malt scotch, and small-batch bourbon and refuses to carry Jaegermeister is my kind of snob! I don't understand why they call it the Matchbox instead of the Matchbook, though, because the way the place tapers towards the south end certainly suggests the latter. read more

When you are entertaining out of town friends, you try and provide them with the best Chicago experience, even if their idea of "going out" involves Bud Light and horseshoes (oh them Nevada folks). After dining at one of my favorites- Ada Street- I looked for a bar to continue the evening, as uncomfortable as it already was. How I would describe Matchbox (besides the aforementioned tiny): In one of the many, MANY OK Cupid quizzes, there's one that asks what a perfect first date would be: a really divey bar, a nice restaurant or a day at the beach (there might be one more choice but I can't remember). Matchbox is an oxymoron- an upscale divey bar. If you judge a book by it's cover, you will be sorely disappointed when you miss out on stellar drinks (try the margarita), a decent bottle beer selection, a pretty extensive choice of liquors, and the caveat of "no red bull, no Jager." (praise Jesus for that one). Yes, it's cozy, but if you're on a date, what better way to see how the night is going to turn out than being squished up against someone (unless, like me, the person you are with is completely uninterested in you). I will mention that I found one of the bartenders to be friendlier than the other, which would bum me out if I came here alone but otherwise wasn't a big deal. Definitely this place is bookmarked for good. read more

Review by B and D: We love this cute little bar! The drinks are delicious and the service is outstanding! All the bartenders are very personable, friendly and attentive. Space is tight... perfect for small to average people. If you are super fat you won't fit. read more

Like the name implies -- this place is as small and tightly packed as, well, a matchbox. It is basically a claustrophobe's nightmare. The restroom was no exception. It was as cramped as an airplane restroom, sans any extras such as - oh, I don't know -- a toilet-paper dispenser! The roll of toilet-paper was 'secured' to the wall via an old nail, off which it promptly slid and rolled away onto the floor in response to my touch. To be fair, however, it made for a funny story and really was consistent with the feel of the place (plus they had soap and warm water, so I can't complain too much). Restroom gripes aside, I did enjoy the Louisville & Nashville Onion Rings. Thick-cut and with a panko breading - they were delicious and quite effective at 'soaking up' the effects of alcohol on an otherwise empty stomach. read more

Krystyna B. has raved about the gimlets at Matchbox for some time now. So, as stop #3 on our mini-barcrawl, we stopped on in. And, yes, she wasn't lying when she said that this place was tiny! AND narrow. But...who cares...such a good time. How can I describe these gimlets? Hmmm. I'd say 'heavenly' for the most part. Ginger-infused vodka, sugar on the rim of the glass and a mere $8. I was intrigued when Krys said that they infuse their own vodka at the bar - ginger, pineapple, lemon?! Amazing. Crowd is friendly, bartenders are fun and it's just an overall great time. I recommend NOT wearing heels (or painful shoes) as you're almost guaranteed to be standing. Unless, of course, you're lucky enugh to score one of the coveted bar stools. One of my new favs! read more

I went to The Matchbox as the last stop on a holiday bar-hop dinner party bonanza with a shitton of service industry people. I was so drunk when I got there that I think I held on to my PBR with both hands and stared at it for a while. Someone handed me a shot of what was probably Maker's Mark and I think I poured it on the floor because there was no way that she was gonna stay down if I took it. I'll have to come back when I'm slightly less shithoused. read more

This is a great bar, but beware.. it is the size of a matchbox. Get your back up off the wall? Well you almost can't but that's okay if you go in the early hours. They have vodka and tequila infused with melons, apricots and pineapples sit in huge bottles, and its booze-soaked cherries. The pineapple gimlet is yummy! It's a great place to hang on a Sunday.... just get there when they open to get a seat. The bathrooms here are quite alarming, but hey it's a dive bar and after a few drinks you won't care....as much. We went a few weeks ago on a Thursday to see Tony, around 6. Perfect time to go, only a few regulars there and I only drank as many drinks as I could without having to resort going to their bathrooms. read more

This bar is quickly becoming one of my favorites in the city. It's prime location on one of the more popular bike routes into downtown definitely helps, and I find myself trying hard to resist its relaxing happy hour, which will inevitably seep all productivity out of my evening. Such a fantastic atmosphere, and great cocktails to boot. It doesn't take much additional effort for a bar to offer a specialty cocktail, and really helps those of us who aren't creative in our own right and will gravitate towards beer instead of a boring gin and tonic. Matchbox easily obliges by offering a pair of infused gimlets. I believe their infused gins change in flavor; a recent trip offered ginger and pineapple. Both were fabulous - the ginger was slightly spicy and the pineapple was subtle and refreshing. I love that the cocktails are edged in powdered sugar and come with a shaker which holds another long pour. At $8.50, you can start your evening off very well. The patio is where I usually hang out, and has a friendly vibe and good people watching. But the bar is equally intriguing, with a squeezed walkway that dares you to invite more than a few friends inside. I haven't tried their food yet, but passing plates looked better than standard pub fare. Of course, there's always the pizza place across the street to ogle at. If only I had a pizza rack on my bike for that wobbly ride home! read more

I don't have much to add that other yelpers haven't but I have to disagree about the smell. Seriously, this place is basically a hallway with a bar in it, but it is surprisingly clean! The smallness is incredibly charming, and the bartenders might not be the chattiest people in the world but they know their stuff. The pineapple gimlet is BETTER than everyone tells you, and you really can't miss it for $8. read more

Can't live without this lovely slice of heaven. Best margaritas (according to CNN, second best in the country). Awesome ambiance. No bullshit. Best bartenders. Best food from sister restaurant, the Palm (try: veggie burger, fried, asparagus and ribs) If you don't agree, please don't come back - I'll happily hog your spot! read more

This place is pretty amazing, but a star off because cramped quarters are not my thing. Is it worth a visit though? As long as you've braced yourself to get VERY cozy with everyone in the bar, yes! We arrived shortly after 5 on a Tuesday and snagged two of the few chairs left (yes, at 5:15 most of the 15ish bar stools were taken!) Drinks are delicious and reasonably priced. My friend drank Ladybirds all night (gin, ginger and yellow chartreuse concoction). I sampled the pisco sour (pretty solid), the gin & jam (sweet but worth a try, it's definitely different - any yes, there's literally jam in it) and the Ladybird. Word to the wise: eat first. After 4 cocktails each, we were pretty gone. We snacked on the salt & vinegar chips available, but regretted that decision the next day.... if you're looking to drink in moderation, you're in the wrong bar ;) read more

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

The drinks and the staff here are unparalleled to just about any place I've been here. Obviously not a place I would go for anything other than a date (sheeeet, no tvs tuned to sports???), but their drinks are ridiculously good, and ridiculously strong. Bartenders are the type of folks that will make you feel at home. Smallest bar I've ever been in. read more

I used to bike past this place every day or two. The Matchbox is small. It is very very small. If you get a seat at the bar keep it. Hold on tight because in five or ten minutes the place will be packed and you will basically hug everyone who walks past. Oh, there is that guy who sits and pretends to read! I get a kick out of that! Man, he can do perhaps 1 page every 10 minutes. Oh, but the atmosphere. This place has it. It has the after workers, the graduate students going on about gentrification (which they cause), and the industry people here having a beer. You may see lots of bartenders and servers from other places. I did. I thought that was funny. Lots of "Haven't you?" or "Don't you?" and that wasn't me. Anyhow, if you can find a seat or a wall to hang against grab a beer or a cocktail and hang for a bit. Classic Chicago joint. read more

We were on an impromptu bar crawl our first night in Chicago. I had scanned yelp to find this bar had great reviews. I loved that it feels like you're drinking in a train. The vibe of this bar was completely different from the other 3 we had just come from. The crowd was a little bit older, less frat-boy like and would be more than happy to leave you alone if you left them alone. We found our bartender very friendly and knowledgeable about suggestions of where else to go for drinks and food. I loved that my Manhattan came with a "friend" (the rest of the shaker). It's like two drinks in one! Then we discovered a very bad thing. Some bars in Chicago have extended last call. And our bartender sent us off to find one of those bars. read more

The best cocktail bar in the city, if you ask me. Tony makes a very good mezcal margarita. A gimlet with Old Raj gin is even better- the powdered sugar on the rim pleases my palette. My first sidecar and sazerac- had them here. The old fashioned is outstanding with tart cherries soaked in sweet brandy. The beer selection encompasses both craft and commercial- one gem is the De Dolle Dulle Teve (Mad Bitch)- a funky Belgium tripel. I enjoy coming in for two drinks during the slower times, in the afternoon, but have also been in for great nights with the female bartenders, forces of nature, playing Fleetwood Mac. read more

The Matchbox - mezcal margarita - Bars Near Me - Chicago, Illinois

I got a little confused looking for this place when I stepped off the El (Chicago-Blue). The El dumps you into an island in the middle of the intersection of Milwaukee, Ogden and.. well, probably two other streets. If you're a little lost, the Matchbox is the black box of a bar on the corner with red lights strung along the eaves. When I got my bearings, crossed the street, and made my way inside, they were out of menus and out of stools, so Danny and I stood by the coat wrack, him sipping on a martini, me wringing my hands over what to order. I leaned over a lady squeezed in at the bar and attracted the bartender with a quick nod. He asked me what kind of liquors I liked. I must have looked unsure (gin? vodka?), so he motioned me away, and came back a couples minutes later with a ginger-infused gimlet. Absurdly good. The gimlet came in the shaker with a sugar-rimmed martini glass, and I got three good pours out of the shaker (or about 2 1/2 martini glasses full of gimlet). The grand total? $7.50. I'm not a Chicago native, so I'm not sure what the average price of drinks is around these parts. But I know in LA or SF, a tasty well-made cocktail, is going to run you about $13--for one martini glass. Calculating out my 2 1/2 glasses, I'd say I saved myself about $25 (not including tip). The bar is tiny and packed (we went at about 6:30 on a Friday), but we were eventually able to secure seats, and standing wasn't bad at all. The music is loud, but good, and the crowd seemed like a mix of old-timers, hipsters, and business professionals. Your standard neighborhood watering hole (or hole in the wall, as it were). Will definitely be back to the Matchbox. read more

So, in my quest to find well-made cocktails within the city of Chicago, I stopped into the Matchbox on Friday night. If you've not been there, it's really small... Some may find it cozy, some may find it awful. I didn't really mind it. I had three cocktails. The first was a Manhattan, which was excellent (and garnished with five real deal maraschino cherries). I followed this by a gin gimlet; well balanced, and the sugared rim is a nice touch. Finally I went with a house-infused ginger vodka gimlet. Also a nice drink - though I'm not really a vodka drinker... If you're looking for a solid cocktail, but aren't up for the effort of VH, this place will definitely fit the bill. read more

Where should I begin. When my friend told me "oh I need to take you a place that serves my favorite drink"...I had high expectations that this would be a nice place. Once we got there....it looked like a hole in a wall southside bar. It was still early to go out so the place was not crowded...but the matchobox is sooo small that it looks like it could get crowded fast. There was an outdoor patio which I was dying to sit at because I felt like an old lady sitting inside this crappy looking bar. Then I looked around and realize that all the people that were there....were 20-30 somethings. So why 4 stars?? Let's talk about their drinks....the pineapple gimlet is AMAZING. They also have other great specialty drinks that they make from scratch. We got our drinks and sat outside and I would have never felt like I was in the tiniest bar ever. Oh and did I mention that the drinks are not northside pricey? Good deal and great drinks....:-) read more

I love it. It is always pretty packed in here, it's too small to be anything but. If you sit close to the bathroom you can't help but meet people because they have to apologize for bumping into you on the way to the "john." Try the lime gimlet, delicious. read more

Before last night, I was here about two years ago on a bad date. It left a scary feeling deep down and I just couldn't venture back for some time. However...I do remember a certain Margarita (which was the only thing that got me through the damn thing) that kept calling my name, " katie......katie.....I have a powdered sugar rim...I'm sweet...I'm tart.....you love me." So I went back. It was all I remembered it to be. And I was totally wrong..this is a great little spot! The bartender left the excess of my Margarita in the shaker to use when I made room in the glass. I also noticed that they had single village mescal. This is a very limited production tequila that is made by making a fire with peat moss and "smoking" the agaves in the fire. The tequila turns out smoky and is great to have about an oz. in your already fabulous powdered sugar rimmed margarita. When i asked about the price to add a little to my drink (the mescals can run anywhere from 6 to 20 dollars per shot...so you've got to ask) The bartender said (shoulder shrug) $2? and they gave me a heavy pour. As my girlfriend and I chatted the place filled up pretty quickly. There are about 20-25 bar seats and the whole place is the bar seats. You only have about three feet behind you until you hit the interior wall...so it's tight. The crowd seemed of the neighborhood and were friendly. My friend wasn't really down with the spot but I liked it. It was like you could be in your own world with your own friend (as in one, b/c that's all that will fit) but the quarters are so close your forced to step outside your shell and talk to the people around you. I like this place too because you can order food. Its the menu from the silver Palm next door and the menu is very inventive. I know a menu is great when I'm torn between multiple options. They have the goat cheese marinara thing, calamari, onion rings but then also really well thought out fish and beef entrees and also inventive sandwiches. I had the chix saltimbucca sandwich with a Cesar salad. The cabata bread was so soft and really matched the textures of the meat. The sage was fresh and the procuttio added the perfect flavor profile to give a rich meat feel on the palate. I really hope I can bring my friend back to this place..I love it. And I'm sure if she's not in someone else will be? read more

I remember driving past this location before it was occupied and thinking, "Man that would make a great place for a bar." Well, if I had capitalised on my ideas more I'd have some money. Any money. Be that as it may, The Matchbox is a great place for a drink. I prefer the inside. Go with someone you don't mind having your arm around and talking face to face. Fun to go when you have a good drink on already. It's a tight squeeze to the bathroom, but bars and concerts are two places you shouldn't feel squeamish about "personal space". Bonus points because you get to make the constant decision of whether to squeeze through people facing them or with your back to them without being offensive. read more

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

Barely wide enough to walk through, the Matchbox feels like a serious drinking bar as soon as you walk in. A well-worn counter and stools line the length of the place, and dimly lit, the place has character. I started off with a Manhattan with Bulleit rye, and it was well-balanced and delicious. They will also leave you the shaker with some remaining drink, which is an added bonus and it's like getting 25% more for the same price. Awesome! I also tried an old fashioned with High West rye, which was one of the best old fashioned I have ever had. It was a little pricier, but worth it. Service is to the point but still friendly. They do not have a kitchen but you can order from the Silver Palm next door and have it at the bar. This is the type of place i would love to make my regular hangout and will definitely come back during my next trip to Chicago! read more

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

This place has a solid but modest bottled beer selection. I would generally recommend steering away from the drafts, only because they sit a long time...that's not what people are here for. The wine selection is all right too, by the way. There's a glass cabinet full of various sorts of cigars of varying size and quality, and I haven't even touched on the two big things about this place yet. The drink-mixing standards at this place are phenomenal. I highly recommend getting a gimlet with one of the high-shelf vodkas, maybe Chopin...it will run you $7, but the lime juice is fresh and the powdered sugar is a lot of fun. If you have the chance (and they will only do this when they have fresh mint in stock) you can get a fantastic mojito. There are certain mixed drinks I've had here that are hands-down the best I've had out in the city. They have so many garnishes. Everything from brandied cherries to pinapple in vodka. You get a huge zest of lemon in your margarita, and pours are generous. Often, you have to crane your head to take a few sips before you can lift your drink off of the bar without spilling. Oh, and did I mention the size? If you direct your eyes up behind the bar, you may note that the Chicago Fire Department has deemed this place for any more than twenty-nine (29) occupants. Just think about how crazy that is. This place is tiny, and so you must go. Don't try to defy that logic. 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 don't get it, or maybe I do. The matchbox is the size of a matchbox. It's a tiny bar that seems like it was built as an afterthought and smells exactly like a college frat house. We came here on a recommendation of a rather lovely gal and was sorely disappointed. The bar is small enough for patrons to sit at and just enough room behind the seat for ppl to walk by and bump you with their sweaty arms. The drinks are alright, they looked imaginative and the tenders make a large portion. They shake up your drinks and give you the shaker to pour out the rest. I wanted to give this place 2 stars, however, the drinks bumped it up. The drinks are cheap, sweet and refreshing. I suppose if the outside area was open my review would be completely different. I just, hate the smell of college frats. read more

It's small. It's a bar. They have a few beers on tap and they are more unique options, which was nice to try. Lots of rye, whiskey and bourbon options for people that like those drinks. They have a TV, but since it's so small in there you really have to strain your neck to get a view of it. All in all, I would stop back in if I were in the area, but I'm not settling up weekly visits any time soon. read more

I think I found my favorite drink. A gimlet with ginger infused vodka. Yeah, I loved it. Less bitter then the ginger drink at Violet hour- I think it was perfect. I mean absolutly wonderful. So what if I have to rub up against everyone at the bar to make it back and forth from the bathroom? This place is small and the bar does not go in to make room for your feet and legs. Whats up with that? Asides from that- the bar has a good vibe, great drinks and is priced right. read more

You will be standing in someone's personal space. Apply a new layer of deoderant before entering- the (obviously) tiny bathroom here is all the way at the back of the bar- so hit up the john at your previous haunt. That said, the customers are friendly and manuever around one another with considerable consideration. The ginger gimlet is excellent- exactly the flavors I like with enough potency. Yeah, it's space prohibitive...that's the fun of it. read more

Unexpectedly magical margaritas. The bar tender knows how to zest his citrus, that's for sure. Well stocked bar, nice lighting, very friendly feel, inexpensive. In other reviews - those who expressed annoyance that this place is too small are kind of missing the point. The gimmik for Matchbox is the size, yes, just like the gimmik for Silver Palm is that it's a train. Why is this so difficult to deal with? Just avoid it on a Fri/Sat and all will be well. Plus -- too hipster? I dunno, I was there on a sunday, and the crowd was by no means hipster, more local and friendly. When we walked in everyone did stare (because we're young and pretty), and because it's small - what else should you do - keep looking away, avoid all eye contact, shoulders hunched over the bar? read more

Went in 8/15. When I walked in I realized just how small this place is. We weren't sure if out door seating was seat yourself. As I stood at the bar while the bartenders were figuring out what kind of shot they wanted to take I interrupted to ask. Yes. Seat yourself and he said first come first serve? We sat ourselves on a sticky, unbalanced table. We waited about 5 minutes before we were greeted. Where I had to ask if the table could be wiped down. The menus were really sticky as well. I went with the mule and my friends went with the gimlets. The drinks were really delicious. I really enjoyed sitting outside. Our server seemed un interested in us, I felt like we had to flag her more than her actually popping in. No small talk nothing. She's a blonde with a pixie. We ordered guacamole, calamari, and bruschett a, All amazing. We asked the server for a salad about 20 minutes after our apps, and she told us they already had last call. (Which we weren't told) She then said she'd ask if the kitchen could throw a salad together, and literally never came back, until they closed the patio. Even when closing the patio I felt like they were really rude. Why would you bring me a full drink ten minutes before you close the patio, then say everyone has to drink up. It was awkward. Food and drinks really good. Service. Pretty bad. This could have been a 5 star. read more

Great martinis, great bartender. Stopped in late on a recent Sunday afternoon, place was full (it's tiny), but my friend and I found seats at the end of the bar. Slightly out of eye sight of the barman, but easy to get his attention. I had a wonderful dirty martini while my friend tried the signature pineapple martini, made with the infused vodkas they keep behind the bar. Also offered a ginger martini, which we might have to return to sample. Just a great little place to catch up with a friend, I wouldn't try to hit it on a weekend, but during off hours, perfect for nice strong, affordable drinks! read more

Excellent little dive bar, come early to get a seat, there are only 17! Powder sugar rims on the cocktails is genius! Get the Sidecar - best in town! read more

The Matchbox - Bars Near Me - Chicago, Illinois

Best. Margaritas. In Chicago. I love a good, ice cold, perfectly frothy margarita. But, you know how they can be kinda sugary and just a little too syrupy? Matchbox has figured out a way to make the non-margarita, margarita. Served in a martini glass and rimmed with powdered sugar, at first glance one will be skeptical, but trust me on this. Whatever they put in these....they're amazing. Amazingly strong too so be careful when you stand up after having more than one. There have been a few too many nights where these puppies have gotten me into trouble. They also have fruit infused vodka, which I've never tried, but looks tempting. And, a full bar, of course. There's also a solid bar-food menu. In winter, the space is super small (it's truly, a matchbox) so be smart about when you go (read: don't try to cram in on a Saturday night). But, if you do, you can always go to the Silver Palm next door (they also serve the margaritas as it's owned by the same people). Come summer, they bust out their huge patio on the front sidewalk facing Ogden, creating an even better, super laid back, I'm wearing flip flops and shorts and heading to the street fest after a couple of these margaritas, atmosphere. Excellent people watching too. And, no need to worry about driving anywhere after you've had too many. The blue line is RIGHT there and cabs are aplenty at that intersection of Milwaukee/Ogden/Chicago. read more