Embrace the joyous moments of leisure in the heart of Chicago as we unveil the city’s Best Happy Hour spots, where time slows, and every sip becomes a celebration. From trendy rooftop bars offering panoramic views to cozy neighborhood joints with unbeatable deals, this exploration guides you through the art of unwinding in style. Chicago’s vibrant spirit comes alive during these golden hours, where craft cocktails and delectable bites create the perfect ambiance for socializing and relaxation. Join us on a journey through the city’s diverse and lively Happy Hour scene, where each venue adds its unique flair to the evening, promising a delightful escape from the hustle. Get ready to raise your glass and discover the art of savoring the happiest moments in Chicago’s bustling atmosphere.
Happy hour is a festive occasion that pairs well with karaoke. Brando’s Speakeasy, located between Willis Tower and the Art Institute of Chicago, offers one of the best happy hour experiences. Brando’s is a vintage tavern with a dimly lit cocktail lounge and a separate karaoke room. The space has a romantic feel to it, from the dazzling crystal chandeliers over the bar to the intimate lounge seating. Drinks are the main focus at Brando’s, however, they offer customizable small and large pizzas. They also have a daily happy hour from 5-7 pm. Select canned seltzers and classic cocktails are on sale for $5 each. I recommend the Paloma or the Moscow Mule.
Nothing says happy hour quite like authentic Spanish tapas. At Cafe Ba-Ba-Reeba guests can enjoy a wide range of tapas, pintxos, and paella. They also have an extensive sangria, beer, and cocktails menu in addition to a selection of authentic Spanish wine. This beloved Chicago restaurant has indoor and outdoor seating. Both spaces are thoughtfully designed and atmospheric. Happy hour at Cafe Ba-Ba-Reeba lasts from 4-6 pm in the bar area. They serve bite-size tapas popular in Northern Spain, such as deviled eggs with crispy Jamon serrano. Other tapas dishes include chilled gazpacho soup, garlic potato salad, or spicy potatoes with tomato aioli. The featured drinks at Cafe Ba-Ba-Reeba’s happy hour include a selection of beer for less than $5 and pitchers of classic red sangria for $22.
If you’re in the mood for a romantic, dimly lit bar with happy hour specials, you will love Gilt Bar. The atmosphere here alone makes it one of the best happy hours in Chicago. Crystal lamps, dark floral wallpaper, and private leather booths fill the space. It feels intimate no matter where you sit or how busy the bar is. The bar is on the south end of the River North neighborhood, only a couple of blocks away from the river. Gilt Bar’s happy hour takes place every day from the time the bar opens until 5:30 pm. Gilt Bar also offers Wine Wednesday specials, with 50% off all bottles throughout the day.
Sparrow is a recently renovated lobby bar in the historic Gold Coast neighborhood. The building has been around since 1927 and is currently home to several apartments. The art deco bar is frequented by the building’s residents but is open and welcoming to all. Sparrow offers an extensive list of spirits, liqueurs, beer, and wine. They also have a list of incredible craft cocktails. My favorites are the La Floridita, a rum-based drink, and the Mandarin Punch made with citrus, mint, clove, and soda water. They offer guests happy hour specials Monday through Friday from 4-7 pm. Wines by the glass are $10 during happy hour, and draft beers are $5.
Arbella hosts happy hour from 5-7 pm Monday through Saturday. They have one of the best happy hour menus in Chicago, with several cocktails, wine, beer, and small plates to choose from. Arbella is a fun and youthful establishment that serves several casual American-style foods and unique craft cocktails. During my visit to Arbella, I tried the potato tacos and the Chicago Fire Extinguisher, a cocktail with scotch and smoked bitters.
The Walk-In is the best happy hour in Chicago if you like fun, good service, and great drinks. The restaurant sits in the northern part of Logan Square near The Logan Theatre. They are a cocktail bar and liquor store. At The Walk-In, guests can expect to enjoy the best cocktails in the city. Daily happy hour specials include discounted cocktail creations such as the Go-Go Gimlet, Lucky’s Explanation, or the Rosey Cheeks. My favorite cocktail at The Walk-In was the Green Light, a refreshing mixture of rum, lime, and mint. The Walk-In also does shot specials, including bourbon, tequila, and select cocktails for $6.
In the heart of Chicago’s West Loop sits The Press Room. The Press Room is a stunning, sophisticated restaurant known for good vibes, great service, and the best wine in town. The menu consists of fresh seafood, pasta, grilled veggies, and customizable charcuterie boards. Everything pairs well with The Press Room’s exceptional wine bar. Happy hour takes place on Tuesdays and Thursday from 4-6 pm. Guests enjoy a dozen freshly shucked oysters for $1 and several traditional cocktails. I recommend the penicillin or the Old Fashioned.
Broken Shaker is a hotel bar inside Freehand Chicago in the River North neighborhood. The bar serves award-winning cocktails made with garden infusions, housemade syrups, and unique elixirs. The food menu is reminiscent of street food from around the world. There are so many cocktails to choose from. I recommend the Malibu’s Most Wanted, Noah’s Old Fashioned, and the James Bond Type Beat. They also have an extensive wine and beer list. I sampled a glass of superb Spanish wine called Orlegi De Luberri that any wine lover will appreciate. Happy Hour at Broken Shaker runs Monday through Thursday from 4-6 pm.
The best happy hour bar in Chicago’s rooftop bar scene is Cindy’s Rooftop. The bar is on top of the Chicago Athletic Association Hotel. Every seat in the bar offers gorgeous panoramic views of the city, including Millenium Park and Lake Michigan. The bar serves seasonal, family-style comfort food and fresh seafood. It is open year-round and has a comfortable ambiance enjoyable for all. The plates are bright and colorful, which compliment the glass walls and ceilings, exposed brick walls, and outdoor fire pits. Whether you enjoy your cocktails inside or out on the balcony, you can enjoy one of the best happy hours in Chicago. Happy hour specials are seasonal and run Monday through Wednesday between 4-6pm.
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We compiled all the findings in one location and sorted them by the frequency of mentions to ensure you receive top-notch recommendations. We strive to present you with a curated list of establishments that truly stand out, allowing you to enjoy the best dining experiences possible.
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