Best Happy Hours Around the Willis Tower


When it’s freezing outside in Chicago, what can warm you up? After work Happy Hours of course! Work Better’s Chicago location is in the regal Willis Tower, and here are some spots just a short walk away that are worth checking out:

*Note HH=Happy Hour

1. South Branch Tavern & Grille

100 S Wacker Dr, Chicago

Distance from Work Better: 5 minute walk (0.1 miles)

About: South Branch Tavern & Grille is a bold and contemporary restaurant that offers a modern American menu that ranges from salads with all the trimmings, to original burger concoctions, to dinner entrées, and a chef's catch of the week.

Tips: Go around 4pm because it fills up fast, and it can get crowded on some days. Get a table outside if it’s a nice day.  It’s the “place to be” for business people in the Spring and Summer. Buffalo Chicken Rolls come highly recommended by regular patrons and are the perfect complement to their great beer selection.


2. Brando’s Speakeasy

(HH Mon-Thur 5pm-7pm)

343 S Dearborn St, Chicago

Distance from Work Better: 10 minute walk (0.5 miles)

About: A vintage Chicago tavern with on-demand karaoke. Need we say more? Oh and $3 Happy Hour appetizers.

Tips: This place is great for groups with a $2 PBR Friday Happy Hour Special, affordable drinks, rave-worthy pizza, and a casual atmosphere. While this place is touted as a great location to pregame, be aware that it is a popular bachelorette party destination and there is no coat check.


3. McCormick & Schmick's Seafood Restaurant (HH 3pm-6pm)

1 E Wacker Dr, Chicago

Distance from Work Better: 6 min drive (1.0 mile)

About: Ranked #1 Happy Hour in America by USA Today. Upscale feel and the menus reflect seafood from the Pacific Rim, Atlantic Ocean, and Gulf of Mexico. They also source products from local ranches, farms, and wineries to showcase regionally inspired dishes.

Tips: Elle from Foursquare stated “$3.00 burgers with fries!!! & I mean real 1/2 lb burgers. Try the cajun burger with pepper jack... oh and martini specials for $6.95”  $6 glasses of wine, great skyline patio view, and people can’t get enough of their lobster bisque.

4. Ceres Cafe (Official Beer HH 2pm-4pm, but many cocktails are under $9 on the normal menu)

141 W Jackson Blvd, Chicago

Distance from Work Better: 6 min walk (.3 miles)

About: Located in the North lobby of the Historic Chicago Board of Trade Building, this restaurant has been in the same family for 5 generations. Ceres Cafe serves American traditional food with a great outdoor area.

Tips: Reviewers all say the drinks here nice and strong during happy hour. In fact Rajvir J from FourSquare described them as the “Stiffest drinks in the city.” Great for groups, free popcorn, place to find lots of traders and fund managers. Doesn’t take reservations and the Buffalo chicken wraps get great reviews. This cafe does not accept reservations but they do offer free popcorn and is a popular choice for traders and fund managers. Be sure to try the Buffalo chicken wraps!

5.Sweetwater Tavern and Grille

225 N Michigan Ave, Chicago

Distance from Work Better: 9 min drive (1.3 miles)

About: Sweetwater Tavern & Grille is a vibrant bar and restaurant that offers full views of the city from its indoor seating and outdoor patio. A modern American food menu is complemented by a great craft beer list, seasonal cocktails, and an upbeat atmosphere.

Tips: Fills up fast, so sit on the patio if it’s not too cold. With several TVs available, this is a great place to watch the game while you try one of their burgers.  Reviewers describe their pretzels and sweet potatoes as happy hour favorites.  



  • Ebonee’s Picks: See what one of our Willis Tower Community Associates thinks are worth the visit.


1. Franklin Tap

325 S Franklin St, Chicago

Distance from Work Better: 4 min walk (0.2 miles)

About: Franklin Tap is located a block away from the building and is a perfect happy hour spot for any beer lover. The restaurant features daily specials, 80 beer choices, and 12 rotating taps.

“Franklin Tap offers a wide selection of local craft beers and has the best hand-made burgers you'll find in the Loop.” -Ebonee’


2. Cactus Bar & Grill 

404 S Wells St Chicago

Distance from Work Better: 6 min walk (0.3 miles)

About: Cactus Bar & Grill offers outdoor seating that is the perfect after work spot during the summer months. The restaurant offers a variety of local craft beers and a free shuttle service to Bears games.

“Cactus Bar & Grill is an upbeat, lively bar known for its amazing hand-shaken margaritas.” -Ebonee’

3. Jackson Tavern

216 W Jackson Blvd, Chicago

About: Jackson Tavern is located just a half block from the Franklin entrance of Willis Tower. It is the closest place to enjoy 25 different beers on tap, delicious street tacos, and an extensive mixed drink menu.

“Jackson Tavern is the perfect place to cozy up and enjoy a stiff drink and great smoked wings.” - Ebonee’

Who are we? We think we know a thing or two about cocktails, but more importantly, we offer luxury private offices in the Willis Tower (along with meeting rooms, conference rooms, and day offices for rent). We are more than just office space. We have free coffee, tea, and snacks available for members as well as helpful and friendly Community Associates to help you work better. Our technology is fast and secure, and guess what? We host monthly Happy Hours for members if you just can’t get enough of them after sampling the local ones. Come by and see the space. We can’t wait to meet you! Lori is the head honcho in Chicago, and you can contact her at

Would you like to know about our
special offers and promotions?


More Success Stories


A Truly Moveable Feast: A Breath of French Air for a Small Business Owner


Think an office sublet is the right choice? Think again