[Skip to Content]

Chicago Loop Happy Hour Guide


Posted  5 months ago  in  Trending, Eat & Drink, Loop List, Loop Locals

3 MIN READ -- After work, go out for drinks! Happy hour is happening all throughout the Loop, so you can wind down after a long day. Choose from all these unique venues, each with their own style and atmosphere. 

Please Note: All specials can change without noticeAlways call to confirm that happy hour deals are still available before heading over

Elephant & Castle

Elephant & Castle delivers a true downtown English pub experience with North American touches. Their extensive beer list offers a variety of local craft brews along with traditional European imports. Their food menu is composed of classic British dished mixed with American favorites. And their happy hour is not to be missed! Check out their Wabash location and their Adams location Monday-Friday 3-6 p.m. for $5 domestic draughts, $5 house wine, and $5 share plates like crisps and dips, onion rings, mini-sausage rolls, sweet potato fries, and roasted tomato and whipped feta.

elephant and castle

Emerald Loop Bar & Grill

Emerald Loop is an American-Irish bar and grill in the Chicago Loop, serving craft beer and cocktails. They also have outdoor dining, fine hospitality, and lots of sports playing on their TVs. Happy Hour is Monday-Friday 4-6 p.m. Get $4 Miller Lite pints, $6 well drinks, and $8 Aperol spritzers. Everyday deals include $19 domestic buckets, $6 draft beer feature, $4 PBR cans, and $5 Powers Irish whiskey shots.  Learn more here.

Emerald Loop Beer

Land and Lake Kitchen

Land and Lake Kitchen has a warm, wood-accented interior with comfy leather booths. They specialize in Midwestern cuisine with a commitment to good, honest cooking. Happy Hour is served daily from 4-7 p.m. Enjoy fresh cut fries for $3 or get a burger for $6.50. Try original cocktails like Papa Don’t Peach, T.G.I. Sangria, or The Pink Lady for $6.50. They also serve draft beers and wine by the glass. See what’s on the menu here.

Land Lake Kitchen

ROOF on theWit

For extravagant rooftop dining 27 stories above it all, ROOF on theWIT is offering elevated service. Their venue features a stylish design, drifty views of Chicago, private event spaces, entertainment, and a unique dining experience. Wind Down Weekdays occur Monday through Friday 4-7 p.m. Sip on G.H. Mumm, ROOF’s old fashioned of the day, dealer’s choice cocktail, and a rotating glass of red or white wine for $10. Food options include a meat and cheese board for $22 or a whipped ricotta and red pepper spread for $12. See the rest of the menu here.

Photo Credit Roof on theWit


Boleo is a rooftop bar that brings the bold flavors and sultry beats of South America to Chicago. Happy Hour takes place Wednesday through Saturday 4:30-6 p.m. Get half priced yaquitas along with beer of the day for $6, or wine of the day for $8. See the rest of the menu here.

Monet drinks at Boleo


Formento’s serves you the fresh and light flavors of Italy. The earthy brick walls and terracotta tile give the restaurant a rustic Italian look. Happy Hour serves up antipasti and drink deals Monday through Friday 4:30-6:30 p.m. Try the whipped ricotta for $7 or sample nonna's meatballs for $8. All cocktails are $9, all wines are $9, and beers range from $3-7. See the menu here.



Labriola is famous for its artisan bread. Inspired by French, Italian, and German baking methods, Labriola has its own signature twist on baking. Happy Hour is Monday through Friday 3-6 p.m. Labriola offers $5 house wines, draft beer, and well cocktails. Get more information here.

The Godfrey Hotel Chicago

The I|O Godfrey is a sophisticated rooftop lounge with indoor and outdoor space at the Godfrey Hotel Chicago and is currently open with reservations required. Happy Hour is Monday through Friday 2-5 p.m. Get select beverages and food half off. Sip on a Frose All Day or a Ketel One cocktail for $8. For $7, have Alma Mora Malbec, I|O house chardonnay, I|O house rose, and Avissi Prosecco. If you get hungry, try wagyu beef sliders for $9 or indulge in signature black truffle fries for $6. See the rest of the menu here.

Primo Amore Pizza Godfrey


Roanoke showcases luxury finishes, copper accents, and warm lighting with strong lines that transform the original 1913 building. Sit at the counter along the display kitchen, cozy up to the warm, inviting bar, and have a seat near the fireplace for more intimate dining. Happy Hour is Monday through Friday from 3:30-6:30 p.m. Their menu features buffalo cauliflower for $8, mac and cheese bites for $6, or guacamole and tortilla chips for $6. Drinks include tully and brew for $8, purple rain mimosas for $7, red and white canyon wines for $6, and red or white sangrias for $6. Learn more here.