Oh, Chicago. Home of the Bears, Cubs, Bulls, Blackhawks, White Sox, and more. The Windy City has it all. Unique restaurants, local shops, and dedicated sports fans. Happy hours are the perfect way to explore the city without breaking the bank. Plus, they're a great excuse to treat yourself while also supporting local businesses. With dine-in seating opening back up in Chicago, it's exciting for everyone!

Lucky for you, Checkle did the work so you don't have to. Our team has searched high and low to find some of Chicago's favorite and most beloved happy hour spots. Why wait in traffic for an hour when you could be soaking up all these good happy hours? This list is just getting started. Here we go!

Monday: Happy Hour @ McCormick & Schmick's

When a restaurant has a rep for being named the #1 Happy Hour Spot in America by USA Today, you know we had to check it out. Let us say, this Chicago Happy Hour did not disappoint. McCormick & Schmick's Seafood and Steak offers guests Happy Hour specials every weekday from 3:30-6:30 p.m. You'll score bites starting at $4, $5 well spirits, $6.50 glasses of wine, and $7.50 gold margaritas! It's the perfect go-to after work spot to let off some steam after a long day.

Score bites starting at $4, $5 well spirits, $6.50 glasses of wine, and $7.50 gold margaritas every weekday from 3:30-6:30 p.m. at McCormick & Schmick's Steak and Seafood.
#1 Happy Hour in America — USA Today

Tuesday: Happy Hour @ Cafe Ba-Ba-Reeba

Get an authentic taste of Spain with tapas, pintxos, and sangria right in Chicago! Cafe Ba-Ba-Reeba offers Happy Hour specials every weekday from 4-5:30 p.m. Bites starting at $1.50, $3 Estrella Damm Bottles, and $20 sangria pitchers. This is the perfect one stop shop for Chicago Happy Hour food & drinks. Stop by and share a pitcher with co-workers, a first date, family, or friends!

Check out Cafe Ba-Ba-Reeba for Happy Hour featuring bites starting at $1.50, $3 Estrella Damm Bottles, and $20 sangria pitchers every weekday from 4-5:30 p.m
Grab an authentic taste of Spain right in Chicago!

Wednesday: Whiskey Wednesday @ Fat Cat

Whiskey might not solve all of your problems, but it's worth a shot! Celebrate hump day at Chicago's favorite Whiskey Wednesday spot— Fat Cat! Every Wednesday from 4-7 p.m. get your whiskey fix for only $7! Choose from classic Manhattans, the signature Fat Cat Old Fashioned, Hot Bourbon Cider, Kentucky Mule, or Bourbon Over Broadway. I mean, who doesn't need a little mid-week pick-me-up?

Celebrate Whiskey Wednesday at Fat Cat with $7 Manhattans, Fat Cat's Old Fashioned, Hot Bourbon Ciders, Kentucky Mules, and Bourbon Over Broadways from 4-7 p.m.
Did we mention Fat Cat's has a fireplace patio?

Thursday: Happy Hour @ Osteria Via Stato

Join the Osteria Via Stato crew for the happiest hour in Chicago! That's right. Sunday through Friday from 5-6 p.m. you can score 1/2 OFF Roman-style thin crust pizzas and glasses of wine! We're talking Classic Cheese, Margherita, Mushroom, House-Made Fennel Sausage, and Charred Pepperoni pizza! Pair it with a fancy glass of Pinot Grigio, Chardonnay, or maybe even a nice Rosé. This Chicago Happy Hour will leave you craving more!

Sunday through Friday score 1/2 off Roman-style thin crust pizza and glasses of wine from 5-6 p.m. at Osteria Via Stato.
We know you want a pizza this.

Friday: Happy Hour @ Elephant & Castle

Hip, hip, hooray— it's Friday! It's been a hectic work-week and you just want to kick back, relax, and soak up the weekend. Lucky for you, Elephant & Castle has a weekday Happy Hour to help you unwind. Monday through Friday, you can score $4 domestic draughts and $4 glasses of house wine from 3-6 p.m. Perfect for grabbing drinks with co-workers or date night with your significant other!

Head to Elephant & Castle for $4 domestic draughts and $4 glasses of house wine Monday through Friday from 3-6 p.m.
Wine down the workweek with $4 glasses of wine!

Saturday: Bottomless Mimosas @ Bistronomic

Okay, you had us at bottomless. Check out one of Chicago's favorite brunch spots for Bottomless Mimosas! Every weekend you can score 1.5 hour Bottomless Mimosas for only $19.95 with the purchase of a brunch entree. Bistromonic is open for brunch from 10 a.m.-2:30 p.m. So, pick your 1.5 hours for Bottomless Mimosas and drink up, buttercup!

Check out Bistronomic for Chicago's favorite brunch featuring 1.5 hour Bottomless Mimosas for $19.95 with the purchase of an entree.
If it's not bottomless, it's not brunch!

Sunday: Bottomless Brunch @ Zia's Lago Vista

Bottomless brunch is the only thing that gets us through the workweek. This Chicago Brunch spot is serving up all your favorites BOTTOMLESS! That's right, we're talking mimosas AND bloody marys. On weekends from 10 a.m.-3 p.m., you can score unlimited bottomless mimosas and bloody marys for only $15! It'll be the best $15 you ever spent. You can thank us later.

Head to Zia's Lago Vista for $15 bottomless mimosas and bloody marys from 10 a.m.-3 p.m. every weekend.
Mimosas + Bloody Marys = Happy Sunday.

There you have it Chi-Town! Looks like you've got some new spots to add to your list. The Windy City is home to hundreds of unique and local restaurants just waiting to be explored. Happy Hours are the perfect excuse to enjoy delicious food & drinks, while also supporting your local and small businesses. Have a favorite spot in town? Let us know! We'd love to check it out. Catch ya next time, Chicago!

— Ashley

Food Lover & Pun Enthusiast