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Where To Drink Whiskey & Win Fall

Fall is here in full force, and there’s a choice to make. Do you surrender to the oncoming cold and lock yourself in buildings for the next six months, or do you take advantage of the opportunity to begin celebrating whiskey-drinking season? We choose the latter, and encourage you to join us in this never-ending war against weather.

And if you’re going to drink whiskey, choose wisely by ordering Jameson Caskmates. Jameson Irish Whiskey partnered with a local Irish brewery to finish their whiskey in craft beer barrels. The result was Jameson Caskmates and you can find it at all the bars listed below. Not surprisingly, it also pairs quite well with beer.

Sponsored.This guide is presented by Jameson Caskmates. All restaurants & bars have been selected by The Infatuation. To learn more about Jameson Caskmates, click here.

Glascott's Groggery

2158 N Halsted St

Glascott’s is a classic Lincoln Park neighborhood bar perfect for grabbing a drink any day of the week. It’s also connected to Athenian Room, which means you can order their food while sitting at the Glascott’s bar. And we’d spend every day eating Athenian Room and drinking whiskey at the Glascott’s bar if we could.

Bar Siena

West Loop
832 W. Randolph St.

Bar Siena is kind of trendy spot in the West Loop, but the food is basic Italian including mostly pizza and pasta. That’s something we can always get behind. Go for dinner upstairs and then transition to the downstairs bar for drinks the rest of the night.

The Anthem

1725 W. Division St.

A great Wicker Park bar to hang at in general, but an even better place to watch Chicago sports, particularly hockey. Anthem serves an excellent juicy lucy burger stuffed with cheese, and it’s a guaranteed good time to eat and drink well while you watch Kane, Toews, and Hossa do magical things on the ice.


935 W Webster Ave

Try counting all of the TVs at State - it’s impossible because they have so many. Add in the quality bar food and it’s one of the best Lincoln Park bars to grab drinks and catch a game. You can even watch all of the football, basketball, and hockey games on this fall and winter at the same time. That’s how many TV’s State has.

Lockdown Bar & Grill

1024 N Western Ave

Lockdown also has a lot of TVs, but none of them are showing sports. Instead, you can watch and listen to all of the best metal and hard rock concerts ever recorded at all hours of the day. Add in excellent gourmet burgers and it’s an obvious choice you’re going to need some whiskey here.

Sportsman's Club

948 Western Ave.

Sportsman's Club isn’t that old in actual years, but it has a very old-school neighborhood tavern vibe. It’s the sort of place you can imagine everyone from the block coming to for drinks after work, which is why we like to do the same thing here now. It’s a small place, so posting up at the bar is the best spot, unless it’s nice outside, in which case you should sit outside in the backyard.

Slippery Slope

2357 N Milwaukee Ave

If you’re looking for a dance party in Logan Square then Slippery Slope is the move. And you’re going to need some whiskey to fuel you through your best moves all night long.

The Cubby Bear

1059 W. Addison St.

It’s always a party in Wrigley whether baseball is actually being played or not, come to Cubby Bear to drink and have a good time with your friends. Pop in while there’s live music for guaranteed fun, especially after a Cubs win.

Bar Deville

701 N Damen Ave

With multiple rooms, there are a few different routes you can go at Bar Deville. Hang out in the front, which is a low-key sit at the bar situation. Move to the middle room, where you can try and dominate the pool table. Or head to the party lounge in the back, where you can really get after it. There’s no bad choice.

Beauty Bar

1444 W Chicago Ave

Ever been to a bar where you can get your nails done? Well, Beauty Bar is the place. And it’s not a nail salon that will serve you a drink. This is a bar that will also do your nails. They often host different theme parties throughout the month that are always fun, so grab a drink at the front bar before moving to the dance floor in back.


15 W Illinois St

Fremont is like a Vegas club transplanted in the heart of River North, which makes it fun to relax and have a great time. The retractable roof in this giant two-story space makes it a party whether it’s brunch time in the summer or weekend nights when it’s way colder outside.

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