Greg RaMar via The Matchbox/Faceook


If you don’t know the person next to you at this tiny 460-square foot corner bar, you will by the end of the night. As one of the smallest bars in Chicago (yes, smaller than Smallbar), this local institution has stood at the corner of North Ogden and Milwaukee for over 75 years -- having been privy to plenty more than just idle small talk over the decades. Head to “The Box” for a low-key beer or classic cocktail like a gimlet or Manhattan with strangers. Leave as friends. It’s the Matchbox way.

Mini Hut/Facebook

Mini Hut

This Southwest Side hole-in-the-wall offers little more than a tiny entrance and three yellow booths, yet offers large rewards in the form of some of the best fried chicken in the city, thanks in large part to its ridiculously addictive “butter crust.” You can order your chicken by the boat (breast and thigh or leg and thigh) and, if you’re too lazy to get off your bar stool, they also deliver to bars in the area.

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Bunny Bakery and Workshop/Facebook

Bunny, the Micro Bakery

What the heck is a micro bakery, you ask? It’s a miniature Lakeview confection slinger where little more than a counter and a couple of bench seats set the scene for your deep dive into a rotating selection of some of the city’s finest donuts, plus adventurous small plates like handmade toast and jam topped with a tiny dollop of owl-shaped foie gras.

Calumet Fisheries/Facebook

Calumet Fisheries

There is no seating. There are no bathrooms. You order your food and you eat it in your car parked out front. The reason this far South Side shack is so cramped for space? Because it’s one of the few places left that smokes their fish on-site thanks to its natural wood smokehouse located out back. They’ve been doing it like this since 1948 and have made fans out of all who have made the pilgrimage, including Anthony Bourdain.

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Permanent Records Chicago/Facebook
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The Drifter

With nine barstools and a total capacity of 37, The Drifter is not only one of the smallest speakeasies in Chicago, it’s also one of the most authentic. The tiny space tucked away beneath the historic Green Door Tavern was an actual speakeasy during Prohibition. These days the space has been revived with drinks on tarot cards and all manner of oddball antics, from burlesque to bands and jugglers and contortionists.

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The Hideout

One peek inside its friendly, unassuming environs and it’s easy to see why it’s called “Chicago’s Most Loved Small Venue” -- it’s actually been described as looking like the real-life version of the house from Up. Check out up-and-coming indie acts and the occasional oddball comedy show. Stick around for the late-night dance party and good-time vibes that envelop the place at all hours of the night.


Celeste's rooftop

Few first-date spots in Chicago are more of a guarantee of a second date than the impossibly cute (it really is the only way to describe it) rooftop at Celeste, a luxurious space of Victorian-style seating and ivy-covered walls tailor-made for sharing punch bowls with that special someone (or the person you just swiped right on) while digging into appropriately small plates like grilled octopus, pork and beef meatballs, or the always romantic meat and cheese board. Space is extremely limited, so plan ahead if you know what’s good for you, and for that all-important third date.

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1. The Matchbox 770 N Milwaukee Ave, Chicago, IL 60622

As the self-proclaimed "most intimate bar in Chicago" at only 460sqft, The Matchbox is not for those who require substantial personal space. It is, however, for folks who enjoy high-quality cocktails like fresh lime juice gimlets and Manhattans garnished with tasty french cherries, paired with emphatic conversation with friends and strangers at very close range. Having stood at the corner of Ogden and Milwaukee for over 75 years, the divey hallway-eqsue space is a Chicago staple, with red tin ceilings, a dark-wooded bar, and ever-present rows of christmas light dangling above shelves crammed with liquor. The place serves a handful of bar snacks -- panko-crusted mozzarella, bacon-wrapped-scallops, wings -- and in the warmer months, there is side walk seating available (with far more space and far less character than the joint's interior).

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2. Mini Hut 6659 W Archer Ave, Chicago, IL 60638

Hidden on a one-way side street past Midway in a location that would make a pool hall feel classy, this is the Southwest side’s antidote to everything trendy about fried chicken: just perfect bird, extendedly marinated and slow-fried for 20 minutes, with a famously rich, buttery breading. The frill-less décor -- a tiny weather-beaten canopy outside, stark walls and low ceilings inside -- proves to be the ultimate Chicago restaurant bluff.

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3. Bunny The Micro Bakery 2928 N Broadway St, Chicago, IL 60657

Michelin starred chef Iliana Regan's bakery pulls out all the stops and is quickly becoming one of the most creative bakeries in Chicago. The bakery might be small, but the flavors it's making are huge. From and leek and seeded rye toasts and donuts to pierogi and house-made cereal with nut milk, we know where we're headed for breakfast tomorrow (and every day after that).

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4. Calumet Fisheries 3259 E 95th St, Chicago, IL 60617

It's no wonder Calumet Fisheries, on the far south side of Chicago, was featured on Anthony Bourdain's No Reservations. Open since the 1940s, the family-owned seafood shack is one of the only smokehouses left in Chicago that smokes fish naturally over a wood fire. It offers an endless variety of smoked fish -- from salmon, sturgeon, and white fish to trout, catfish, and shrimp. Not to mention, its fried stuff is pretty good too.

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5. The Drifter Chicago 678 N. Orleans, Chicago, IL 60654

The Drifter is an intimate basement-level former speakeasy/cocktail bar with eccentric nightly entertainment and a tarot card-inspired cocktail menu. Located below the Green Door Tavern (which was an actual speakeasy during Prohibition), its burlesque shows goes down quick and dirty with no announcement and no advance warning on a small stage that makes it feel like the show is just for you. Members of the Chicago Starlets shake their stuff in between musicians and variety acts amidst charming, vintage décor.

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6. The Hideout 1354 W Wabansia Ave, Chicago, IL 60642

What looks like a modest two-story house in a neighborhood full of warehouses and chain stores is actually one of Chicago's top indie performance venues. The building was originally built in the 1890s, and it's been in continuous operation as a bar (under various names) since a year after Prohibition. Now, the Hideout mostly operates as a quasi-community center that hosts everything from live music and bingo to dance parties and writing clubs.

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7. Celeste 111 W Hubbard St, Chicago, IL 60654

Every floor at this River North cocktail bar has a different vibe. On the first floor, The Bar is loud and bustling with good music. The upstairs Deco Room is more glamorous and sultry, aka perfect for a date. Finally, the garden rooftop is like a cozy urban oasis with ivy-covered walls and Victorian-style seating (tables are available first come, first served). Expect craft cocktails, beers, and fine wine on all levels, plus upscale bar bites.