12 Chicago Happy Hours You Can Actually Make It To After Work

Contrary to popular belief, your workday doesn’t always end at 5-o’-clock on the dot. I know, I know – it’s totally shocking.

But whether you’re livin’ that commute life or simply a busybody at heart, plenty of Chicago bars and restaurants still insist on ending their happy hour specials around 6:30 pm, meaning that, rather than being rewarded for your impeccable work ethic with cheap drinks, you get slammed with the full-price menu instead.

Well, lucky for you, the team at UrbanMatter did some research and found the best happy hour specials in Chicago.

Here are just a few late happy hour specials that workaholics and reverse commuters alike might actually be able to make on time in Chicago.


Rhyme or Reason

Late Happy Hours
Photo Credit: Rhyme or Reason Instagram

1938 West Division 5-8pm, Wednesday through Friday

This Wicker Park restaurant and live music venue in Chicago, Illinois offers a full happy hour from 5-8pm, meaning no matter how late you get off your work day, you might still be able to make it. With $7 cocktails, $7 glasses of wine,  $5 beers and a whole slew of apps and sides to share, you might even start purposefully staying late to take advantage of this happy hour special in Chicago.



Late Happy Hours
Photo Credit: Boleo Instagram

122 West Monroe | 4:30-7pm, Wednesday – Friday 

So sure, rooftop bars may not always represent the pinnacle of cheap drinks in Chicago, but Boleo’s weekday happy hour is totally an exception. The happy hour specials at this Chicago destination include $8 cocktails (as opposed to their usual $12), wines, and other South American snacks. This high-rise bar is one of the best happy hour spots in the city, and they even host live entertainment.


The Barrelhouse Flat

Late Happy Hours
Photo Credit: Barrelhouse Flat Instagram

2624 North Lincoln | 6-8pm, Sunday and Monday

The Barrelhouse Flat may be known as one of the best cocktail lounges and happy hour spots in Lincoln Park, Only offered on Sundays and Mondays, this happy hour spot in Chicago, Illinois is offering $8 mixed drinks, $5 beers, and a $10 cheeseburger that is totally out of this world.


Jojo’s Milk Bar

Jojo's Milk Bar
Photo Credit: Jojo’s Milk Bar Instagram

23 West Hubbard Street

Jojo’s Milk Bar takes late happy hour to a whole notha’ level with their specials from 8 – 10 pm every single day. Enjoy at this fun and refreshing milk bar, $2 malort shots, $4 beers and $6 Tito’s cocktails. Additionally, Jojo’s offers the Chicago Handshake–a shot of Marlort and an Old Style tall boy–for $6 during happy hour times.


The Owl

Late Happy Hours Chicago
Photo Credit: The Owl Instagram

2521 North Milwaukee | 6-8pm 

The Owl in Chicago, Illinois is a late night spot at heart, and that includes their happy hour. With rotating happy hour specials every night of the week, this Logan Square bar’s deals include: 1/2 cocktails and beers from 6-8pm every night, $5 Absolut cocktails on Sundays and $2-$3 select beers on Tuesdays.


Black Bull

Late Happy Hour Chicago
Photo Credit: Black Bull Instagram

1721 West Division | 5-7pm Tuesday – Thursday

Nothing says happy hour quite like tapas, and at Black Bull, they’re keeping the pintxos rollin till 7pm. From 5-7pm, Tuesday through Thursday, the Spanish Happy Hour specials include $5 Sherry and Sangrias.



Late Happy Hours Chicago
Photo Credit: Fremont Instagram

15 West Illinois | 5-8pm Thursday

Visit Fremont in River North of Chicago, Illinois before 8pm on Thursday to enjoy their Sip & Shuck All-You-Can-Eat Oysters and Rosé for $25.



Late Happy Hours
Photo Credit: Henry’s Instagram

18 West Hubbard | 5-8pm, Tuesday through Saturday

This brightly colored bar in River North of Chicago, Illinois is doin $5 wellies and $5 tallboys from 5-8pm on select weeknights. You’re gonna wanna get there ASAP to enjoy the happy hour.


Bridget McNeill’s

Late Happy Hours Chicago
Photo Credit: Bridget McNeill’s Instagram

420 West Belmont | 5-7pm, Tuesdays through Fridays

This Lakeview Irish pub is one of the best happy hour sports in Chicago, Illinois. It offers drafts for $4.20 and $6 glasses of wine every night till 7pm.


Highline Bar + Lounge

Late Happy Hours Chicago
Photo Credit: Highline Instagram

169 West Kinzie | 5-8pm Daily 

Highline in Chicago has happy hour specials each and every day. However, none of the happy hour specials hold a candle to their build you own mule bar on Thursday evenings from 5-8pm. Other daily Chicago happy hour deals include: $7 draft and Jameson combos on Mondays, $5 tallboys on Tuesdays, $20 bottles of wine and FREE PIZZA on Wednesdays, and $30 all you can eat brunch on weekends.


The Izakaya at Momotaro

Late Happy Hours Chicago
Photo Credit: Momotaro Instagram

820 West Lake | 6-8pm, Wednesday, Thursday and Sunday 

Get to the Izakaya at Momotaro in Fulton Market before 8pm on Wednesdays, Thursdays or Sundays for what is, without question, one of the best happy hour deals in the whole damn city. For just $23, you can get a three course meal WITH a beer and a shot. Amazing, honestly.



Late Happy Hours Chicago
Photo Credit: Celeste Instagram

111 West Hubbard | 5-8pm, Tuesday through Friday

Although a sexy River North bar wouldn’t be the first place to look for the best happy hour specials in Chicago, Illinois, Celeste offers an $8 till 8pm happy hour package well worth your hard-earned free-time. Plus, they’re late night food menu is absolutely killer too.


Featured Image Credit: The Barrelhouse Flat Instagram

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