Last updated: 07:06 PM ET, Wed October 26 2016

Chicago vs. Cleveland: Who Has Better Bars?

Destination & Tourism Gabe Zaldivar October 26, 2016

Chicago vs. Cleveland: Who Has Better Bars?

PHOTO: AliveOne in Chicago sparkles with beer and live music. (Photo courtesy Instagram/aliveOne Chicago)

Chicago and Cleveland meet in what may be a historic World Series, but all this really means is both cities are about to endure one nasty hangover once the dust settles.

One town will pop champagne to celebrate and the other will head to the bottom of the bottle to drown their sorrows.

Fortunately, both these cities boast a world-class drinking scene. Much like a championship series, there can be only one victor. Let’s slice up some of the particulars and see what city has the better bar scene with a few suggestions in each category. Note: We pored over Yelp, Thrillist and other publications for the following locations.


Cleveland – Porco Lounge & Tiki Room; Velvet Tango Room;

Chicago – GreenRiver; Lost Lake; The Whistler

Game 1: Chicago

Both cities feature so many historic bars that tout wonderfully diverse drinks. Every last category, including this one were decided by the smallest of margins, but when you take into account the various, meticulously crafted cocktails you can get in so many diverse settings the edge here goes to Chi Town.

Dive Bar:

Cleveland – Harbor Inn; Mitzi Jerman’s Café; Ugly Broad

Chicago – T&A Two; Friar Tuck; Lodge Tavern

Game 2: Cleveland

There is something about slinking into the door of a nearly hidden bar that leaves just about every ounce of pretention at the sidewalk. And that is exactly where you leave your stress and worries.

Cleveland gets that sentiment, welcoming every visitor to its watering holes and making them family.  

Live Music:

Cleveland – The Brothers Lounge; Happy Dog; Edison’s Pub

Chicago – aliveOne; Andy’s Jazz Club; Blue Chicago; Buddy Guy’s Legends

Game 3: Chicago

Sorry, Cleveland.

There is perhaps no other place outside Austin, Nashville and New Orleans that offers such an eclectic and resplendent opportunity to hear live music.

There is something so romantic about slipping into a blues bar, ordering a few beers and swaying to the rhythm of the night.

Wrigley Field vs. Progressive Field:  

Cleveland – You can find myriad beers around the park, but The Corner offers 40 brews on tap for Indiands fans to enjoy.  

Chicago – Wrigley Field is beat when it comes to overall price and selection within its confines, but it has one amazing attribute going for it that gives it the narrow win.

Game 4: Chicago

As the Chicago Tribune once noted, there is a veritable plethora of bar choices right around the park.

While Progressive is nestled near awesome attractions like Quicken Loans and various hotels and restaurants, Wrigley is embedded into the neighborhood in a special way that makes every game seem like a block party.

Visitors will note the smell of dogs grilling and bar hopping taking place pre, during and post-game.

The party simply doesn’t stop in Wrigley-ville.

READ MORE: 7 Things To Do in Chicago While Waiting for a World Series Game to Start


Cleveland – Brick and Barrel; Buckeye Brewing; Fat Head’s Brewery

Chicago – Goose Island; Lagunitas Douglas Park; Revolution Brewing Tap Room

Game 5: Cleveland

This area is simply chockablock filled with wonderful craft brews that will sate the most discerning IPA or stout-craving palate out there.   

Wine Bar:

Cleveland – Corks Wine Bar; Rocky River Wine Bar; Humble Wine Bar

Chicago – Webster’s Wine Bar; Rootstock; Volo; 404 Wine Bar

Game 6: Chicago

Another close game, but a cursory glance revealed such an amazing array of locations in Chicago that offer many variations of experiences.

This is a city that has numerous bars that will cater to the wine snob that is used to pouring out extravagant sums for vino to those who want some reasonably priced food to go along with their reasonably priced wine. And the amount of wine offered is insane – but that good kind of insane we enjoy.

Extra Innings:

Hopefully, the real World Series is as close and as exciting as this breakdown has been. Obviously, much of this is subjective, so we welcome your thoughts and suggestions.

However, here are a few more watering holes to consider before we go.


Jazz Showcase:

The J. Parker:



Platform Brewery: