Chicago is a late night kind of town. Some bars are open until 4am … though I wish you luck if you try to make it until then. Expect both incredible cocktail bars, talented bartenders, and some of the diviest bars just about anywhere. It’s a town of great food and drink, so prepare your stomach and your liver.
DRINK//EAT//DO//STAY
DRINK
LOST LAKE | This campy tiki lounge in hip Logan Square has some of the most ornately garnished drinks I’ve ever seen. (One of my drinks had a banana dolphin on it … amazing.) The staff is friendly and fun, and this is definitely a great late night spot.
3154 West Diversey Avenue (Logan Square)
(773) 293-6048
lostlaketiki.com
$$
VOL. 39 | This hotel bar is anything but. Haute cocktails made exquisitely, a marble bar top, and sleek black and brass decor–what more could you want?
39 South La Salle Street #200, inside The Kimpton Gray Hotel (The Loop)
(312) 634-7966
vol39.com
$$$
BOLEO | This rooftop lounge features live music, craft cocktail, and a menu with street food with a decidedly Latin flavor. Make sure to say “hi” to Dallas transplant Phillip Smith while you’re there!
122 West Monroe Street, inside, inside The Kimpton Gray Hotel (The Loop)
(312) 750-9007
boleochicago.com
$$$
SCOFFLAW | Great food, great drinks, their own expression of Old Tom Gin, and warm cookies served at midnight make this slightly haute neighborhood spot cozy.
3201 West Armitage Avenue (Logan Square)
(773) 252-9700
scofflawchicago.com
$$
THREE DOTS AND A DASH | Another fantastic tiki spot … the decor is fantastic and the staff is friendly. The food is a great way to extend your fun here (because you’ll need some sustenance between tiki cocktails).
435 N Clark Street (Downtown) – enter through the alley behind the building
(312) 610-4220
threedotschicago.com
$$
SPORTSMAN’S CLUB | This spot is where you’ll find the local bartenders relaxing on their nights off. If the weather’s nice, pop onto the back patio.
948 North Western Avenue (Logan Square)
(872) 206-8054
drinkingandgathering.com
$
THE AVIARY | This high brow craft cocktail spot has some of the most imaginative drinks you’ll find paired with some really incredible presentations. Make sure to make a reservation well in advance for a tasting in the kitchen, a food and drink pairing, or a table in the dining room … and DO NOT be late.
955 West Fulton Market
(312) 226-0868
theaviary.tocktix.com
$$$$
GO TAVERN AND LIQUORS | There are a handful of hybrid bars/liquor stores left in Chicago … weird for Texans, right? Stop in and pick up some Malört (a somewhat foul tasting spirit made almost exclusively in Illinois) and grab a drink.
3219 West Armitage Avenue (Logan Square)
(773) 227-4052
gotavern.com
$
THE WALK IN | Another bar brilliantly connected to the a liquor store, but this one boasts that they’re “friendly as fuck”. Expect a lounge feel offering well made and thoughtful craft cocktails along with some more basic options like the old fashioned, which they’ll even let you get it “Milwaukee style”, brandy instead of whiskey.
2727 N Milwaukee Avenue (Logan Square)
(773) 697-8726
$$
THE SIGNATURE ROOM at the 95TH | Grab a quick (and effing expensive) drink here just for the view (which is insane). I wouldn’t judge you if you had a soda and bitters. 😉 Make sure to get a seat where you’re not in direct sunlight. (Because, that high, you’re closer to the sun. duh.)
875 N Michigan Avenue (The Loop)
(312)787-9596
signatureroom.com
The Terrace at Trump International Hotel & Tower® | “Chicago’s premier rooftop offers unrivaled views, refreshing libations and delectable bites. The urban paradise located on the 16th floor seats 250 guests and offers unobstructed, picturesque views of Lake Michigan, the city’s iconic architecture, the Chicago River, and its famed bridges.”
401 N Wabash Ave (The Loop)
(312) 588-8000
trumphotels.com/chicago
$$$
LONGMAN AND EAGLE | L&E is a neighborhood bar fueled by (plenty of) whiskey–like, 300 of them. Check out their daily feature that you can get for $3 a shot. Look for seasonal craft cocktails, draft beers, small batch wines, and more. Don’t want to have to make your way back home after? L&E has six rooms for rent starting at just $95! (Just make sure that you’re prepared to be sleeping above a bar.)
2657 North Kedzie Avenue (Logan Square)
(773) 276-7110
longmanandeagle.com
$
EAT
AU CHEVAL | If you’re going to eat a burger in Chicago, it should be here. It’s their specialty, and they do it real GD well. They’re open until 1am on weekends, which is ideal for those boozy munchies. (Don’t forget to order the pickles for the table.)
800 W Randolph Street
(312)9294580
auchevalchicago.com
$$
THE PURPLE PIG | Holy cow pig. This charcuterie-and-wine-heavy bar is a must-visit. Ask for their daily features, and make sure to give yourself plenty of time to devour the Purple Pig Platter, because it’s real damn big.
500 N Michigan Ave (The Loop)
(312) 464-1744
thepurplepigchicago.com
$$
PEQUOD’S PIZZA | This pizza is f**king amazing. Their deep dish is a legend thanks to the crusts which gives the perfect crisp to their pie. Open until 2am on weekends!
2207 N Clybourn Ave (Lincoln Park)
(773)327-1512
pequodspizza.com
$
GIRL & THE GOAT | Visit this lovely spot for small plates of delicious comfort food by Stephanie Izard. If you can’t get a reservation, hop across the street and visit their sister restaurant, The Little Goat.
809 W Randolph Street
(312)492-6262
girlandthegoat.com
$$$
STEADFAST | This sleek and luxe American eatery offers creative, haute food items and also features an incredible selection of rare spirits. The plates are small, so go for multiple courses.
120 West Monroe Street, inside, inside The Kimpton Gray Hotel (The Loop)
(312) 801-8899
steadfastchicago.com
$$
GLAZED AND INFUSED | Check out this cheeky donut shop for daily features like their hibiscus tea old fashioned. Go for minis so you can try more. (Obvi.)
multiple locations
goglazed.com
RJ GRUNTS | If you like a salad bar, this neighborhood restaurant and bar offer a huge one. Grab a quick bite and a beer before taking a walk in Lincoln Park right across the street and visiting the zoo.
2056 N Lincoln Park W (Lincoln Park)
(773)929-5363
rjgruntschicago.com
$
DO
ARCHITECTURE TOUR
SECOND CITY
ZOO | Their zoo isn’t too big to tackle in an hour. And they have beer. And it’s free entry!
STAY
The Kimpton Gray
This hotel is one of my favorite hotels that I’ve ever set foot in. After an extensive remodel of an office building, the hotel is clad with marble and brass and feels perfectly luxe. With Vol 39, a high-end craft and classic cocktail bar, Steadfast restaurant, and Boleo, an Argentinian-inspired rooftop bar, you could spend your entire trip in the hotel and have been treated to some of the best options Chicago has to offer. (And Kimpton hotels as a whole have the best scent that I wish I could bottle and use as air freshener.)
122 West Monroe Street (The Loop)
(312) 750-9012
Renaissance Hotel Downtown