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    The Matchbox

    4.1 (327 reviews)
    ModerateBars, American
    Open 3:00 pm - 2:00 am (Next day)

    The Matchbox Photos

    THE MATCHBOX ATMOSPHERE

    What's the vibe?
    Divey
    Moderate noise
    Outdoor seating

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    Recommended Reviews - The Matchbox

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    Reviews With Photos

    Whiskey Sour
    Sarah V.

    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.

    Lisa S.

    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.

    The lighting inside the patio! Great vibe!
    John A.

    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....

    Joan N.

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

    Margarita
    Rue N.

    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.

    Allie P.

    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.

    Gimlet
    Marlene S.

    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.

    Marissa M.

    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!

    Andrew P.

    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!

    Cosmopolitan & Lemon Drop

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    5 years ago

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

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    3 years ago

    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!

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    Page 1 of 9

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    Gus' Sip & Dip - The Original Wagyu Beef Dip

    Gus' Sip & Dip

    (154 reviews)

    $$

    Near North Side

    This is by far the cheapest regular drink price I've seen in a while and the setting is very…read moreintimate. The lighting is good, it's just right, not too bright, and perfect for dating or just for a casual hangout with friends. At busy hours usually there is often a line so do be aware of that. I also tried their ceviche; this is also very flavorful, very good. We couldn't finish the chips and drinks. I tried almost all of their gin drinks; they are definitely my go-to so highly recommend

    Came here after seeing they made the 2026 North America's 50 Best Bars list and realizing I've…read morenever been! It was about a 45 minute wait for a seat at the bar, so we just walked around until they texted us. They do not take reservations and it's first come first serve, which I actually appreciate nowadays in a world where reservations have become the norm and it can be impossible sometimes to even try certain restaurants/bars. Upon entering, I loved the vintage vibe. They serve French-inspired food and have a long cocktail menu filled with their versions of classics. Their prices are cheap for Chicago ($12 for each cocktail), especially for a bar located downtown. The service was great and we were in and out pretty fast. I tried the Clover Club and it was strong but good. I also tried the Milk Punch and it was so delicious!! I would definitely come back just for that drink. We also got the frites fromage as a snack before eating dinner somewhere else. The fries were perfectly crispy and fresh. The bowl of cheese on the side was also a great amount to really cover each fry in it. The cheese sauce was so delicious that you could eat spoonfuls of it, which might be why they put a spoon on the plate (I'm definitely guilty of eating a spoonful of cheese when we ran out of the fries).

    Ila's Restaurant & Bar

    Ila's Restaurant & Bar

    (57 reviews)

    Near North Side

    We weren't planning on stopping in here but it looked cute from the outside! We went after happy…read morehour on a Friday and sat at the bar. Our bartender Miguel was awesome! Super friendly and nice, we chat with him for a while. Our drinks were delicious! We also had some shots, shoutout Miguel, that tasted like a margarita. Very cute inside, would come back!

    Very cute interior, great service, lively atmosphere, definitely hit the mark on elevated casual…read more We were able to get dinner reservations on the day of. For parking you definitely should use Spothero or ParkWhiz, as it's in a very busy/lively part of River North. We loved meeting the owner who was chatting with and checking on guests in the dining room. The menu was really creative and sounded amazing, totally up my alley, so was super excited to try Ila's out for the first time. Unfortunately, and it pains me to say this, but the food itself was a miss for me, and the prices felt steep for the portions. We ordered the empanada duo, grilled scallops, birria lamb pierogis, and sweet corn agnolotti, then the Japanese cheesecake and drip coffee. The positives were that everything tasted fresh, and the flavors of the dishes were good ~ especially the empanadas, scallops, and agnolotti. The main issue was the texture of some of the foods. Other than the empanada (which had a great texture and flavor), the agnolotti and pierogi dough were not right ~ thick, rubbery, and dry, which was exacerbated by not having enough consommé for the pierogis. And the coffee - it honestly tasted like Folgers (though I'll give them the benefit of the doubt) - which took me aback as it was a $7 drip coffee. I'm not discounting Ila's and I truly wish them success. But I think there's some work to be done in terms of execution.

    O'Callaghan's - Waffle chili cheese fries

    O'Callaghan's

    (314 reviews)

    $$

    Near North Side

    Sat at the bar because it was Friday night and the tables were all taken. I liked the variety of…read moremusic, the ambience, the atmosphere....and the burger and fries! That burger----was SOOOO GOOD (Char Burger) and the waffle fries were kind of crispy- good! They had an NBA game playing on the tvs. Service from both bartenders was great- Our main server had great attention to detail. (realized they forgot the mustard without me saying anything) All in all- great! (Skip the fish and chips- get the char burger!)

    I came in with three friends and we grabbed a high-top table. We ordered a few rounds and…read moreeverything was going fine. Toward the end of the night, two of my friends left, and the remaining two of us paid our bill and were finishing our drinks while waiting for our Uber. At that point, the bartender came over and told us she needed our table for a large group. The table wasn't reserved, and we were clearly just finishing up. We told her we were about to leave anyway, but the way it was handled felt really abrupt and rude. What made it worse was that she immediately brought a group over to take our table, and even they were apologizing to us because they seemed uncomfortable with how it was handled. I've worked in bars and restaurants myself, so I completely understand needing to manage space, but there's a way to do it respectfully, and this wasn't it. Unfortunately, this experience left a bad impression, and despite having been here multiple times before, I won't be returning.

    The Matchbox - bars - Updated May 2026

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