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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.
I've been driving by the Matchbox for a couple years now, and have always wanted to try what appears to be the smallest bar in Chicago. Last weekend I had that chance, and really loved it!
The cocktails are high quality. Handmade Pisco Sours, apricot infused tequila, and many other really interesting items abound here. Also, if cigars are your thing, they seem to have quite a large selection on hand.
The bartender Colleen was great. She definitely walked that fine line between sassy/gruff and friendly that all big-city bartenders should do, in my opinion. Frankly, her tougher approach was charming.
The space itself, and reason I wanted to go there, was pretty fun. Sure, if you're sitting down towards the skinnier part of the bar you have to move when people need to use the bathroom, but if it's on a relatively uncrowded evening, it's a minor hassle. Maybe it's just me used to the crush and density of NYC living for 8 years, but I found it kind of added to the charm too. Great spot for dates!
I probably wouldn't choose an on-peak time (Thurs, Fri, Saturday nights) to visit the Matchbox though -- what gives it its charm seems like it would quickly take it away. Save it for Sunday-Wednesday evenings, and try to show up a little on the early side to guarantee some seats in the wider spot in the bar.
You know I just love this place! The smallest bar in the city.
Pros: Intimate and friendly, one has to be, tight quarters. Great for a date stop in for a drink or two. Extensive beer menu and artsy staff. Also good food to be ordered from the place next store (won't tell).
Cons: It has gotten a bit pricey recently. Staff does have their choice of music, sometimes not always crowd pleasing.
I will always go back! Daytime is the best.
This place is a bit weird. I like that.
Great Cherry Brandy Manhattans. Silver Palm is better for a drink, but the food kinda sucks.
Great for two or three friends to hang out, but wouldn't dare try more. And forgive me for saying, but even exceptionally large people would find this environment to be a bit uncomfortable. That said, excellent beverage selection and neighborhood vibe.
I love this bar. Their margarita is my favorite in Chicago. Ballsy statement, i know. They serve it in a martini glass with a shaker and a powdered sugar rim. I have had a few appetizers here which were all good. The service is great even when they are really busy in the summer and the prices are reasonable. I prefer sitting on the patio because i am not really into small spaces.
This is our favorite place to hit before an event at the United Center. Weekdays around 5:00 PM it's not too crowded but there's a nice mix of people so it feels like a neighborhood bar. I haven't seen a review yet that mentions the Sidecar - (although I haven't read thru all 110) but it is a great mix of brandy, some fancy liqueur and the requisite powdered sugar - both in the drink and on the glass. They also have some great beers on tap to wash it down. The Red Seal from CA is a good hoppy beverage. The music is always good - a selection from the bartenders Ipod - so you take your chances but we have never been disappointed. Park on Ogden - it's less than 10 minutes to the UC - great way to start the evening.
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!
This bar is long and slender and has two bathrooms at the far end. It is, as many people have said, small. Which I enjoy. I like smaller, more chill places. But, get there early if you can, or try to nab a table outside if the weather permits.
I was meeting a friend and I arrived early, as I tend to do because I have a serious hatred for being late. It was 4:41, and there were a few stools available. I sat down, nestled between one man having a martini (one of my favorite drinks) and a man having a mysterious cocktail. My eyes rolled across the full bar and slipped up to the beer selection on the rack high above the bar. It was so great, I just about fell off my chair it was so great. For a tiny bar, their beer selection was staggeringly vast...like an enormous train. They had two of my favorites, Wittekerke and Chimay (white, although red is my favorite.) If I ever come across a bar that has Wittekerke on tap, I think I will simply have to look for an apartment closer to that joint.
The bartender was very sweet and attentive, and she apparently really likes whiskey. After a few beers with my pal, I tried a margarita. Now, I am kind of a snob when it comes to margaritas. I admit it. Mostly because I really just like the way I was I was shown to make them. This was a different bartender than my previous set of drinks too. She was cool, and the drink wasn't bad at all, it was very smooth and elegant. I would've preferred salt on the rim instead of a gentle powdered sugar, but...it wasn't that big of a deal. The cocktails are a wee bit expensive, but...they are cocktails, not beer.
The occupancy is 29, so I can only imagine what this place would have been like once it really picked up. Tight. Snug. Like a sushi roll. I'd definitely go back!
This is hands down the smallest bar that I've been to since moving into town and I'm fairly sure I'll be hard pressed to find smaller. This is not a bad thing to me. I'm from a small town and this smaller then my small town bars.
For sure the best cocktails in town. Go for an old fashion or a margarita. It's not going to be what you expected but in the best possible way. Get selection of all your boozes and a fairly above average beer selection. I'd give their tap a 3 outa 5 but I generally go for the booze not the beers.
The music is always rad, bartenders are always top notch too. I've always got a good laugh from all of my bartenders and 9 times out of 10 I'll land some sort of free one on the bartender and its not like I'm a big spender or a great beauty.
A great choice for start or end of a date location. Just one of those type of places. Being directly (no joke you can see it from the window) across from the Chicago Blue Line stop makes it just too easy to get to not to go, at the very least, every once and again.
The vibe of this something to experience as well. As small as it is it doesn't get claustrophobic. Its more of a homey / intimate setting. Its old as hell too which makes checking the bar and behind always fun. I always notice something new. Try and find the cranes.
Want something mellow, no crowd, go home with a nice layer of booze coating your brain night? The Matchbox is your ticket to happy town.....now boarding. a great choice for start or end of a date location.
If Five Star ever gets hit by a bus I will transfer my best bar in the city title to Matchbox. Ginger Vodka Martini or a Gimlet. Lots of interesting beer too. Say Hi to Chris.
Matchbox is appropriately named. There are 11 bar stools in the entire bar. It's probably no more than 700 sq ft. It is incredibly unique. The cocktails are 2nd to none. Vodka Gimlets, Margaritas, Manhattans are some of my faves. The service is less than admirable. Point blank, the bartenders are a$$holes, but that's because they know that no matter how they treat you, you're going to sit there and wait (sometimes 15 minutes) for a cocktail, because they're just that good.
Neighborhood is a bit dicey, which makes parking easy. Silver linings everywhere.
Great for happy hour if you can beat the crowd and nab a seat. There is an outdoor patio in the summer as well.
I've been multiple times, and I'll be back again. Not bad, not bad...
Chicago has mainstream bars a dime a dozen, but this little gem is worth going out of your way to try.
The bar is small and as you walk back narrows even further so that you can barely open the bathroom door wide enough to fit through. This small atmosphere makes it great for meeting new people and winding down from a tough day. The best part about their drinks is they coat the rim of all their martinis with powdered sugar, a trait I have yet to see copied in all my travels. This makes all the cocktails delightfully sour and sweet - going along with the theme of this tiny neighborhood bar.
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.
The best small bar in the world also makes the best scratch cocktails in the world, particularly their Bloody Marys and Margaritas. Friendly service and great, eclectic crowd. Always worth the wait for a seat at the bar.
If Anthony Bourdain was to compile a "13 Places to Drink Before You Die" list, I think the Matchbox would make the list. It's that honest-to-goodness good. Nope, good isn't a good adjective for this hole-in-the-wall drink emporium. It's like calling El Bulli a nice eating experience. Understatement of the decade! And, Matchbox deserves raves; it excels at what it does.
If you visit, pull up a stool and get ready to shoot the shit with Jackie. She's a hoot and a holler. All sass and class. And, if you're the curious sort (and I am), get ready for a master class on mixology.
Be sure to try the ginger gimlet or - my new favorite - the gin blossom. (yes, that's a play on the 90s band). Jackie concocted this cocktail for a gin competition and makes it with edelweiss liqueur and home brewed ginger ale.
The perfect ending to Yelp Eats #2 at Venus
We went because the reviews were good. We didn't realize that we had been here before, but only to use their bathroom after going to Sonotheque one night - but nevertheless, we were excited to try their mixed drinks because we read that they were "unexpectedly delicious." My friend and I ordered margaritas, and the powdered sugar rim totally won me over. The drink itself was tasty - sweet and tangy but not too overpoweringly so. The garnishes (a lime wedge and a knot of lemon skin) were cute.
However, the bartender was crabby and wasn't very friendly. The space itself is cramped and all of the outdoor seating was full at 930pm on a Saturday night. The crowd was interesting, and then a group of four 40-year old ladies having a "girls night" came in and sat next to us and we knew it was time to leave and go somewhere more .... youthful.
3 stars just for the great margaritas and the cool location.
nice divey little place. straight bar, no mingling room really, its cool. sel cigarettes here i think. good selections. i think ur able to order food from the restaurant right behind it. good vibes, no nonsense bar for when need it
Yay for the Matchbox! How can such a tiny little place be such a huge draw to so many drink lovers? It's easy when the drinks are this good.
It's true this bar is really small. You'd think the designers of it thought they were in Tokyo. Basically the bar and bar stools and about a foot of walking room between the stools and the wall. In the summer months they have an expansive patio set up, but don't expect to find an open table during happy hour.
Back to those drinks. All the martinis and froo-froo cocktails are made with the best ingredients, measured out perfectly, and served straight from the shaker into your chilled glass. It seems like there's always a little extra leftover in the shaker, so they leave it out in front of you and come back and top you off once you've sipped down some of whatever hoochy goodness you ordered. Some recommendations include their margarita (up), a gin and elderflower concoction they invented, their cosmo (divine), or simply their standard but perfect vodka (or gin) martinis and Manhattans.
The bartender Jackie is very friendly and easy to talk to, so don't be shy. I saw someone on here complain about one rude bartender, but so far I've never had a bad experience. I've found that people who get "rude" service have it all in their heads or think service people are happy robots. Talk to the guy like he's a human being, and chances are you'll get treated like one in return.
And yes, this is a "unique" place that won't be for everyone. But its individuality is what makes it charming. It's a hole-in-the-wall that actually gives a shit about serving good drinks. Oh, and it's pretty cheap too compared to nearby River North joints. Martinis are $8, I think.
It might be my new favorite bar in that weird, kinda desolate part of town. Excellent Manhattans, fellow industry folk and an "intimate" space. I loved it. I am absolutely going back, especially after a particularly bad day in the biz - I know there will be sympathetic ears.
a few weekends ago i was walking home from the south loop (i live in logan square) because i had had a very large breakfast burrito, and nothing else to do.
i was taking my time getting home, shopping along the way. a few hours later i was suddenly very thirsty and right across the street from the matchbox.
i called two of my friends and went in, and ordered a water. and a makers mark, neat. at some point my friends arrived and they ordered all of the items that involved the marinated fruit on the bar. each drink was a little better than the one before.
by around 4:30 i was drunk AND not thirsty anymore.
thanks, Matchbox! i love you.
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!
My first thought walking into this place, "Cougar bar"
Not that I'm saying that's a bad thing necessarily...
Good drinks and random crowd/atmosphere.
Get a daiquiri here, one of the few places around that knows how to do it right...
If you have 3 mixed drinks here you will be wasted...
-JA
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.
Totally awesome place. When I go I feel as though I have time traveled into some 1930's movie. The place is pretty old, but nicely kept. Great beer selection, and good mixed drinks. The bartender is nice and plays great music. There are only about 15 seats so it can get a bit claustrophobic. Go here!
Upon walking into Matchbox, my initial reaction was that this is just another undersized, hole in the wall joint. I then grabbed a seat at the bar and quickly took notice of the selection of fine spirits behind the bar. I was impressed with the breadth of brands of liquor. Behind the bar resembled more of a mad scientists cocktail laboratory. The drink menu is very deep and offers a wide array of specialty drinks. I started with a ginger martini. The drink was prepared with great care. The glass was rimmed with powdered sugar, which was a new experience for me. I suggest licking a bit of the sugar prior to sipping the martini, in order to offset some of the sweetness of the actual drink. It also seems to enhance the taste of the ginger.
Only negative here, was the bartender was not the friendliest. For some reason, he just seemed to have a chip on his shoulder.
The smallest bar I have ever been in, hence the name. You can sit one guy at the bar and there is only enough room to walk behind him.
FOOD: You can have anything you want, as long as you bring it.
DRINK: They had an immaculate hard liquor selection. A few taps of which I was not accustomed, but I gave them a try. Very good!
ATMOSHERE: Just a few people hanging out. Bartender was a cool guy. The place seemed to get narrower at the back which actually made me think the bar might end up touching the far wall. I had a good time and I will go back. The bartender played his Ipod with some good tunes.
See you next time.
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.
This is really outside my type of place, but I enjoyed it! Quite frankly, I walked into this place probably looking like a pretentious snot, but made friends with the bartender and folks around me within a few minutes of sitting down.
Yes, it's small, dark and musty (It was super humid out), but the drinks are great (the pineapple gimlet goes down like candy, which means trouble), the people are friendly and it has it's own charm to it.
I took off one star because their bathrooms are kind of scary.
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.
Great space with excellent Manhattans and La Find Du Monde. That's really all I need. Throw in an amicable bartender, a chill evening atmosphere and decent tunes and there really isn't much to complain about. I didn't get to check out the small outdoor patio, but the inside of the place was inviting enough that I don't feel as if I truly missed out. This place sort of remind me of Jam Inn, but by far more easily accessible by train and with a slightly less "we've completely given up on life" atmosphere, which is always good.
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.
I hate the club scene and college frat bars. This is a perfect escape from all those douchebags. Its size is hence the name--as tiny as a matchbox. No tables. Just one line of bar stools that go along the bar leaving no room to stand or crowd. LOVE IT! Cool bartender...very down to earth. Cheap shots. Cool bar that plays nothing but rock n' roll all night :)
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.
When my friend told me to meet her at The Matchbox I wondered if it was a really tiny place because… 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.
I suffer a bit from claustrophobia but it's worth facing my fears for the best cocktails in Chicago. The vodka gimlet was recommended (excellent) but our other drinks were good too - bourbon old fashioned and a bourbon manhattan with brandy soaked cherries. They have a good beer menu too.
One of the most unique bars in Chicago, because of it's size and layout. It's tiny. This is the kind of place that you walk into and if you don't see any open bar stools, you may as well just turn around, because there is no standing room. It's a pretty cool vibe in here. The music and bartender were cool. A decent drink selection. We came in here after going to the Intuit Center for Outsider Art. Since I'm not in this hood very often, I don't know if I'll make it back, but that's probably a good thing for all the locals.
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 Cure on tour earlier this year.
Fun place to start your night right.
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.
Keep up the good work, Matchbox and thanks for being so smart to invent that little margarita.
Neighborhood: River West
Category: American (Traditional)
Neighborhood: River West
Category: Bars
Neighborhood: River West
Category: Performing Arts
Neighborhood: River West
Category: Wine Bars
Neighborhood: Humboldt Park
Category: Lounges
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