The frigid Chicago winter leaves all of us questioning our choice to settle in the Arctic of the Midwest. That is until the first signs of spring appear and we find ourselves attempting to sunbathe in 60-degree weather (or is that just me?). What better way to celebrate the coming of a new season and, naturally, perfect day drinking weather than with a list of my favorite spots to hit up after work.
So you like fresh air?
Boleo | The Loop
Boleo is located in the center of the Loop and has a retractable glass ceiling which makes this the perfect spot to grab an after-work cocktail throughout the year. Boleo’s pisco sours and disco punch paired with mouthwatering anticucho specials make it one of my favorite spots on this list.
Happy hour deals Wednesday-Friday from 4:30-7pm.
Cabra (Hoxton Hotel Rooftop) | West Loop
Cabra is one of Chicago’s newest additions, and I already have high hopes for this rising star. If the expertly curated Latin playlist doesn’t win your heart, Cabra boasts an entire menu of dangerously smooth pisco sours which are sure to make you swoon.
Waydown (Ace Hotel Rooftop) | West Loop
What can I say? I have a thing for rooftops and glorious views of my favorite city. In addition to a great location, Waydown also has fantastic bartenders who can always whip up the perfect drink to match your cravings.
Varying weekday deals.
Beatnik on the River | The Loop
Inside or out Beatnik on the River is a charming place to unwind at the end of a hectic day. My favorite happy hour snack here is baba ghanoush with French fries. It may sound like an odd combination, but don't knock it till you've tried it.
Cindy’s | The Loop
Basic? Yes, I know. However, the basic b*tches have this one figured out. Great view, good booze, and you have your pick of food and drinking venues to stumble upon once you’ve taken your Instagram of the bean. If you need me I’ll be in the Game Room eating loaded tots editing my selfie. (Kidding. No one takes selfies anymore.)
Devereaux (Somerset Hotel Rooftop) | Gold Coast
A little party never killed nobody and the Somerset Hotel truly embraces this ideology with their progressive happy hour. The party starts at Somerset restaurant from 4-5:30pm and moves to their rooftop, the Deveraux from 5:30-7pm Mondays through Fridays.
Happy hour deals Monday-Friday 4-7pm.
Mad Social | West Loop
Indoors or out Mad Social has you covered with awesome food and a lively (but not obnoxious) atmosphere that provides the perfect spot to end the day.
Varying weekday deals.
Queen Mary | Wicker Park
There are few things I appreciate more than a good pub and having grown up on a lake I adore the nautical vibe of this charming place. If the “Navy Strength Old Fashioned” doesn’t have you hopping in an Uber how about Tuesday Movie Nights? Watch your favorite classics paired with themed cocktail specials.
Oyster Happy Hour Sunday-Monday from 5-7pm.
If it’s raining or you simply prefer a dark corner to the sun.
Franklin Room | River North
Sun or no sun, I would happily spend my evening here. The best happy hours have great food and lots of whiskey - and trust me, Franklin Room has no shortage of either.
Everyday deals! Happy hour starts at 5 pm Monday-Saturday.
Good Measure | River North
Good Measure is a new bar in River North with deliciously creative spins on classic cocktails and great food. This place has a great divey vibe with killer aesthetics.
Happy hour deals Monday-Friday from 4-6pm.
Pink Taco | River North
There is truly nothing better to quench the warm weather margarita cravings than a burnt orange margarita and Taco Tuesday deals from Pink Taco.
Happy hour deals Monday-Friday from 4-7pm.
The Press Room | West Loop
Deals of the night including half off cheese and charcuterie boards and half off whiskey pours. What else could a girl ask for?
Varying weekday deals.
Violet Hour | Wicker Park
So you had a rough day? No better way to cure that than with “Absinthe Happy Hour.” Please try to drink responsibly...
Happy hour deals Monday-Thursday 6-8pm.
Chicago summers are embraced by all the city residents, including some of it’s most spectacular institutions.
MCA | Streeterville
Tuesdays on the MCA terrace are filled with jazz music and great food. Entrance is free for all.
Marisol, MCA’s in-house eatery, also boasts happy hour specials Tuesday-Friday from 4-6pm.
Shedd Aquarium | South Loop
Jazzin’ at the Shedd has become a well-known and much-loved tradition. After all, who doesn't love to drink like a fish with the fish? Admission is $19.95 for Chicago residents, $24.95 for non-residents, and free for members. We recommend buying your tickets in advance.
*This list is subject to updates.