11 Chicago Bars You Absolutely Must Visit

If you are spending any time on the Chicago food scene, you know that it is also a serious drinking town.  One joke goes that “Chicago is a drinking town with a sports problem.”  There are over 100 craft breweries, legendary neighborhood dive bars and classy cocktail and whiskey lounges.  After imbibing my way through this beautiful yet gritty town over the last twelve years, I’ve rounded up 11 Chicago Bars You Absolutely Must Visit.  In the interest of drinking responsibly, I recommend that you ride the rails (and buses) to these thirst-quenching locations.  Grab your Ventra card and let’s go!


Longman & Eagle


Chicago bars Longman & Eagle Logan Square

Wonderful Old Fashioned and cheese plate


What:  A contemporary bar/inn in Logan Square featuring

a stellar whiskey list, award-winning food, and 6 cool guestrooms on Chicago’s north-west side.

Where: 2657 N. Kedzie Ave. (across the street from the Logan Square ‘L’ stop on the Blue Line))



Lost Lake


Chicago bars Lost Lake

Lost Lake is a tropical Tiki bar helmed by Paul McGee, a Chicago bartending star. Photo credit: Lost Lake


What:  A festive, tropical Tiki bar featuring cocktails by award-winning Beverage Director, Paul McGee (Chicago Athletic Association Hotel‘s Milk Room, Cherry Circle Room, and the Game Room) located on the border of Logan Square and Avondale

Where: 3154 W. Diversey Avenue  (1 1/2 blocks north of the Logan Square ‘L’ stop on the Blue Line).




Chicago bars Delilah's

Whiskey heaven in Chicago’s Lakeview neighborhood. Photo credit: Delilah’s


What:  An institution in Chicago’s Lakeview neighborhood since 1993.  The good folks here serve over 800 whiskeys and other spirits from around the globe.  DJs spin punk rock, ska, and other music.  Local artwork rotates and they are available for purchase.  An eclectic array of rock music and horror films are screened here.

Where:  2771 N. Lincoln Ave. (3 blocks west of the Diversey ‘L’ stop on the Brown and Purple Lines)





Chicago bars Hopleaf's back bar

I love the ski lodge feel at this Belgian-style bar!


What:  A popular Andersonville bar focused on Belgian fare and brews.  It boasts one of the best patios in Chicago with the loveliest green apple tree.  It’s the perfect spot for a bucket of mussels and a pint!  Don’t even think about bringing your kids because Hopleaf has a strict 21+ policy.  It’s a bar first!

Where: 5148 N. Clark St. (A 10-minute walk west from the Berwyn ‘L;’ stop on the Red Line or take the #22 Clark bus straight there). 


The Violet Hour


Chicago bars The Violet Hour

The Violet Hour is a James Beard Award-winning bar in Wicker Park, Chicago. Photo credit: The Violet Hour


What:  A beautiful James Beard Award-winning cocktail bar in Chicago’s Wicker Park neighborhood which is divided into three distinct sections with varying ambiance.  The outside facade of The Violet Hour features rotating murals which are the focal point of the entrance.

Where:  1520 N. Damen Ave (One block south of the Damen ‘L’ stop on the Blue Line)



Chicago bars Feeding Off The rails



River Roast







What:  A sprawling bar/restaurant/catering hall situated on the Chicago River with a jaw-dropping view of the skyline.  This stunning spot has potent drinks and equally delicious food.  It’s the brainchild of local star Chef Tony Mantuano (Spiaggia, Terzo Piano) and Chef John Hogan.  The Bloody Mary is a must-do!

Where:  315 N. LaSalle Dr.  (One block east of the Merchandise Mart ‘L’ stop on the Brown and Purple Lines; One and a half blocks north of the Clark/Lake ‘L’ stop on the Blue, Green, Pink, Brown, Orange and Purple Lines.


Check out my Ultimate Guide to the Best Restaurants of 2017

Cindy’s Rooftop


Chicago bars Cindy's Rooftop in Chicago

Cindy’s Rooftop is one of the hottest dining destinations in Chicago.


Chicago bars Cindy's at Chicago Athletic Association

View of Millennium Park from Cindy’s Rooftop Terrace


What:  One of the best Chicago bars and restaurants with a bird’s eye view of Millennium Park and Lake Michigan.  It’s located inside the recently restored Chicago Athletic Association Hotel on Michigan Avenue.  The cocktails here are very creative and there is a mocktail/apothecary menu which I highly recommend.  The glass dome and outdoor balcony are stunning and there are heat lamps and a fire pit where you can enjoy your drinks and the stunning views of the park.

Where:  12 S. Michigan Avenue (One block east and one block south of the Washington/Wabash ‘L’ stop on the Green, Pink, Purple, Brown and Orange Lines).


Milk Room


Chicago bars Milk Room at Chicago Athletic Association Hotel

Milk Room at Chicago Athletic Association Hotel


What:  An exclusive, 8-seat bar inside the gorgeous, Italian gothic Chicago Athletic Association Hotel.  Reservations and tickets are required.  This is not an inexpensive place, folks!.  It sounds a bit pretentious but I don’t think there is another bar like this anywhere else in Chicago.  You arrive at your designated reservation time and the bartender delights you with a historical liquor lesson in the form of pricey, hand-crafted cocktails.  There are spirits here that are seriously old and which cannot be found anywhere else.  This is one of the Chicago bars that is for serious drinkers.  Milk Room is also run by award-winning Paul McGee of Lost Lake (described earlier above)

Where:  12 S. Michigan Avenue (One block east and one block south of the Washington/Wabash ‘L’ stop on the Green, Pink, Purple, Brown and Orange Lines).



Moody Tongue Brewery & Tasting Room


Chicago bars Pilsen brewpubs Moody Tongue menu

Moody Tongue’s tasting room is sexy!


What:  This huge brewery/tasting room in the Pilsen neighborhood doesn’t look like much more than a warehouse from the outside but it features incredibly unique beer blends.  There is no full bar here, folks!  Grab some friends and try some of the memorable seasonal brews like the Blueberry Pilsner or my favorite staple, the Chocolate Caramel Churro Porter.  The food menu is limited to a legendary 13-layer cake (meant for sharing), oysters and charcuterie.  Tours of the brewery are available.  There are cozy chairs, a bookcase, and fireplace which reminds of something out of Bruce Wayne’s house!

Where:  2136 S. Peoria St.  (Four blocks north of the Halsted ‘L’ stop on the Orange line or take the #8 Halsted bus to 21st Street and walk one block west).


Maria’s Packaged Goods & Community Bar


Chicago bars Maria's Packaged Goods & Community Bar

Photo credit: Maria’s Packaged Goods & Community Bar


What:  A neighborhood liquor store/dive bar in the Bridgeport neighborhood that you do not want to miss!  It has recently expanded next door to include Kimski which features more of the Polish-Korean food featured inside Maria’s Packaged Goods bar.  The cocktails and beer selection are on point.

Where:  960 W. 31st St. (Take the #8 Halsted bus to 31st and walk 3 blocks west – connect for bus at Halsted ‘L’ stop on the Orange Line))


The Duck Inn


Chicago bars The Duck Inn cocktails



What:  My favorite place to hang out on the south side of Chicago.  Chef/Owner Kevin Hickey opened The Duck Inn a few years ago as a love letter to the Bridgeport neighborhood where he grew up.  Brandon Phillips is the award-winning bartender here who is crafting some tasty and potent cocktails.  The building is from the pre-Prohibition era and it has been updated with a retro design.  The backyard patio is one of the best spots to be in the summer months.

Where:  2701 S. Eleanor St.  (7 blocks west and 3 blocks north of the Halsted ‘L’ stop at the corner of Eleanor and Loomis.  The #62 Archer Ave bus stops just 3 blocks south of the restaurant at the corner of Archer and Loomis.)


Thirsty yet?


Ditch the car and ride the rails to experience these eleven must-visit Chicago bars.  Do you have a favorite bar or brewery in the Windy City?  I would love to hear all about it!  Leave a comment and I’ll get back to you.

In keeping with the spirit of Feeding Off The Rails, I encourage you to leave your car at home and take the CTA trains and buses to these Chicago bars.  Save on gas.  Avoid traffic, road rage and parking. Reduce pollution. Don’t drink and drive!