Best of 23 happy hours in West Loop
Discover the vibrant bar scene in West Loop during "happy hours." Enjoy specially priced drinks and delicious appetizers at various hotspots, making it an ideal time to unwind and socialize with friends or coworkers. Experience the unique atmosphere and flavors that West Loop has to offer during its popular happy hour events.
- 1. Black Barrel Tavern
- 2. Lone Wolf in West Loop
- 3. The Press Room
- 4. Bar Siena
- 5. SUNNYGUN in West Loop
- 6. Fox Bar
- 7. Green Street Local
- 8. Bandit in West Loop
- 9. Trivoli Tavern
- 10. Jefferson Tap & Grille
- 11. HIDE+SEEK in West Loop
- 12. Eleven | Eleven
- 13. Madison Tavern
- 14. Third Rail Tavern
- 15. Bar Takito
- 16. The CrossRoads Bar & Grill
- 17. New Line Tavern
- 18. The Aviary
- 19. Boqueria Fulton Market
- 20. Bambola
- 21. Slightly Toasted
- 22. Spectrum Bar & Grill
- 23. Prime Bar
1. Black Barrel Tavern
Live music on weekends, cozy atmosphere, and dog-friendly

Black Barrel Tavern is an excellent spot for happy hours, offering reasonable drink prices and a relaxed atmosphere, making it an ideal location to unwind after work. The tavern's happy hour is a popular choice among patrons, featuring delicious cocktails and a friendly staff that contributes to a welcoming environment.
The cocktails at Black Barrel Tavern are a standout, and during happy hour, patrons can enjoy these drinks at a great value. The staff's friendliness and attentiveness further enhance the happy hour experience, making it an ideal time to visit the tavern and enjoy a drink or two in good company.
TOPICS
- Social Gatherings
- American Cuisine
- Mid-Range
- Downtown Spots
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2. Lone Wolf in West Loop
Cozy atmosphere, wall of craft beers, and daily specials

Lone Wolf Tavern, located in Chicago's West Loop, has a happy hour featuring various specials from Monday to Friday. On Monday to Thursday, happy hour runs from 4 PM to 6 PM, while on Friday, it starts earlier and lasts longer, from 11 AM to 4 PM. During these hours, customers can enjoy discounted drinks, including $6 glasses of wine, $6 cocktail of the day, and $8 frozen cocktails, making it an excellent spot for after-work drinks or a relaxing afternoon.
The atmosphere at Lone Wolf Tavern is low-key, providing a comfortable and welcoming environment for patrons to enjoy their happy hour drinks. The specials offered throughout the week, especially the extended hours on Friday, attract customers seeking a place to unwind and enjoy discounted drinks in the West Loop area. Overall, Lone Wolf Tavern is an ideal destination for anyone looking for a relaxed and affordable happy hour experience in Chicago.
TOPICS
- Social Gatherings
- American Cuisine
- Mid-Range
- Downtown Spots
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3. The Press Room
Stylish interior and outdoor patio seating

The Press Room offers a appealing happy hour experience with excellent deals on food and drinks. Oysters are priced at $2 and specialty wines can be enjoyed for just $10. The atmosphere is warm and welcoming, making it an ideal spot for socializing and relaxing.
During our visit, we were impressed by the $8 martinis, which are a must-try alongside the $2 oysters and $10 specialty wines. The Press Room's happy hour offers great value for those looking to enjoy premium cocktails, wines, and oysters. It is highly recommended to take advantage of these deals during your visit to The Press Room.
TOPICS
- Downtown Spots
- Dinner
- Late Night
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4. Bar Siena
Cozy atmosphere, knowledgeable staff, extensive wine list

Bar Siena offers amazing happy hour deals that are not to be missed. The drinks are impressive, with a great taste that is sure to satisfy. The atmosphere is bustling and energetic, making it a fantastic spot to visit after work.
During happy hour, Bar Siena serves up delicious appetizers and offers drink specials that are definitely worth checking out. Whether you're looking to unwind and relax or socialize with friends, this bar is an excellent choice. With its lively vibe and mouthwatering food and drinks, Bar Siena is a must-visit spot for happy hour.
TOPICS
- Italian Cuisine
- Downtown Spots
- Social Gatherings
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5. SUNNYGUN in West Loop
Offers rooftop seating and live music

SUNNYGUN offers a Happy Hour promotion from Monday to Friday, between 3:00pm and 6:00pm. During this promotion, customers can enjoy a selection of discounted food and drink options. The Happy Hour menu includes $8 Frosé, $8 Beer & A Bao, and $8 Midori Sour.
The Happy Hour promotion at SUNNYGUN takes place every Tuesday to Friday, from 3:00pm to 5:00pm. The discounted drinks available include $8 Frosé, $8 Beer & A Bao, and $8 Midori Sour. This promotion provides an excellent opportunity for customers to enjoy a variety of refreshing drinks at a lower price.
TOPICS
- Chinese Cuisine
- Downtown Spots
- Social Gatherings
6. Fox Bar
Unique and intimate atmosphere with a speakeasy vibe

Fox Bar is a great spot for happy hours with a unique selection of cocktails and a cozy atmosphere that makes it perfect for unwinding after work. The ambiance is especially enjoyable during the winter months, making it an ideal destination to escape the cold.
The cocktails are a standout feature of Fox Bar, with a carefully curated menu that is sure to impress even the most discerning drinkers. The cozy atmosphere, coupled with the top-notch drinks, makes it a must-visit spot for anyone looking for a great happy hour experience. Whether you're looking to unwind after work or catch up with friends, Fox Bar is the perfect destination.
TOPICS
- American Cuisine
- Downtown Spots
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7. Green Street Local
Sustainable, eco-friendly, and community-focused

Green Street Local offers a variety of daily specials and happy hour deals for customers to enjoy. On Mondays, the establishment features a "Happy Hours" promotion from 4:00 PM to 7:00 PM. During the rest of the week, there are additional specials available every day, including weekends, providing something new and exciting to look forward to each day.
The "Friday Hoppy Hour" is a particular highlight, taking place between 4:00 PM and 7:00 PM. Throughout the week, Green Street Local also offers other daily deals, making it an excellent spot for anyone looking for a great value meal or drink. The constantly changing specials ensure that there is always something new and exciting to try.
TOPICS
- American Cuisine
- Italian Cuisine
- Downtown Spots
- Lunch
- Dinner
8. Bandit in West Loop
Cozy atmosphere with outdoor seating and friendly service

Bandit offers excellent happy hour deals that are easy on the budget. On Mondays through Thursdays, from 4:00 pm to 6:00 pm, and on Fridays, from 12:00 pm to 3:00 pm, customers can enjoy discounted eats and drinks. The happy hour specials include $6 Rose, $7 Spritz, $6 Tito's Cocktails, and $4 Dad Beer of the Day. Additionally, bar bites are available at half-off, making it an ideal place to relax and unwind after work.
The $6 cocktails and discounted bar bites are a great value. During the happy hour, customers can enjoy a variety of delicious drinks and food at a fraction of the regular price. Whether you're looking to try something new or stick to your favorites, the happy hour deals at Bandit are not to be missed. With a relaxing atmosphere and affordable prices, it's the perfect spot to catch up with friends or colleagues after work.
TOPICS
- Social Gatherings
- Asian Cuisine
- Happy Hours
- Downtown Spots
9. Trivoli Tavern
Family-owned and operated for over 40 years, serving authentic Greek and American cuisine

Trivoli Tavern offers a happy hour from Monday to Friday, between 4:00pm and 5:00pm, featuring deals on drinks and oysters. A visitor recommends arriving early for happy hour as it can get very crowded right after 4:00pm. During their visit, they enjoyed four drinks and ordered rolls and crab rangoons to celebrate an early anniversary.
The happy hour at Trivoli Tavern includes discounts on drinks and oysters, making it an ideal spot for weekday relaxation. The reviewer suggests that arriving early is crucial as the tavern fills up quickly. They ordered rolls and crab rangoons, along with two drinks each, to mark a low-key anniversary celebration. This early bird approach allowed them to enjoy the happy hour offerings without the crowds.
TOPICS
- Social Gatherings
- Mexican Cuisine
- Happy Hours
10. Jefferson Tap & Grille
This establishment is known for its friendly staff, lively atmosphere, and numerous TVs for sports viewing.

The Infatuation's guide to the 22 Best Happy Hours in Chicago highlights spots for discounted food and drinks. The list includes a variety of options, such as bars, restaurants, and cafes, that offer special deals during specific hours of the day. Visitors can enjoy a range of cuisines, from classic American to Asian, and take advantage of deals on drinks such as cocktails, wine, and beer.
Foursquare's list of the 15 Best Places with a Happy Hour in Chicago offers a selection of restaurants and bars with affordable food and drink options. One of the recommended spots is Gyu-Kaku Japanese BBQ, which offers a happy hour special with 50% off hibachi meats and veggies. These lists can help visitors and locals alike discover new places to enjoy discounted meals and drinks in the city.
TOPICS
- American Cuisine
- Mid-Range
- Downtown Spots
- Dinner
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11. HIDE+SEEK in West Loop
Intimate speakeasy vibe with hidden entrance

The happy hour at this location is a popular event, attracting many visitors who want to relax and enjoy a well-made cocktail after work. It takes place every day from 4:00 pm to 6:00 pm, making it easy for people to plan their visits around this time. The bar is known for its creative cocktails, which are a hit with the happy hour crowd.
During happy hour, patrons can take advantage of discounted drink prices while enjoying the bar's inviting atmosphere. The ambiance is perfect for unwinding and socializing, making it a hot spot for happy hour enthusiasts. Overall, the combination of affordable prices, delicious cocktails, and a cozy environment make this happy hour a standout option for those looking to unwind and enjoy a night out.
TOPICS
- American Cuisine
- Downtown Spots
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12. Eleven | Eleven
Eleven boasts a cozy and intimate atmosphere with a chic and modern interior design.

The Paloma Mia is a notable drink at this establishment, featuring a unique twist of cinnamon syrup that sets it apart from traditional Palomas. The drink selection is varied and features strong options for patrons to enjoy.
The food at this establishment receives mixed reviews, with some reviewers praising the pasta and Thai chicken dishes. However, other reviewers find the prices to be too high, indicating that the food may be overpriced for some. Overall, the food is generally well-received and offers tasty options for patrons.
TOPICS
- Social Gatherings
- Fusion Cuisine
- Mid-Range
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13. Madison Tavern
Extensive beer and cocktail menu, indoor and outdoor seating, and located in the heart of Chicago's West Loop

Madison Tavern is a popular spot for happy hour, offering an impressive selection of local and craft brews in a relaxed atmosphere. It's an ideal location to unwind with colleagues after work. During happy hour, the drink specials are highly appealing, and the food is even more impressive.
The bacon-wrapped jalapeño shrimp is a standout dish, highly recommended for those looking for a tasty treat. Overall, Madison Tavern provides a great happy hour experience with excellent food and drink options.
TOPICS
- American Cuisine
- Mid-Range
- Downtown Spots
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14. Third Rail Tavern
Featuring a vintage train car decor and a lively atmosphere

Third Rail Tavern is a great location for happy hour with excellent deals on drinks. The $5 craft drafts and $8 cocktails are bargains that are hard to beat. The atmosphere is energetic and perfect for winding down after work, making it an ideal spot to relax and socialize with friends or colleagues.
The staff at Third Rail Tavern is known for being friendly and attentive, which adds to the overall positive experience. The happy hour drink specials are one of the best aspects of this establishment, making it a popular spot in the West Loop. Whether you're looking for a place to stop by for a quick drink after work or a place to spend the evening, Third Rail Tavern is a great choice.
TOPICS
- Social Gatherings
- Happy Hours
- Late Night
15. Bar Takito
Modern Mexican cuisine with a rooftop bar

The first paragraph describes a pleasant experience at a restaurant on a warm day, taking advantage of their $2.95 Taco Tuesday Special. The person ordered a variety of tacos, with the fish, shrimp, and vegetarian options being their favorites. They also enjoyed a cucumber margarita, which they found to be refreshing.
The second paragraph shares the individual's positive impression of the restaurant during their first visit. They appreciated the music and the delicious food, as well as the perfectly prepared margaritas. The managers and staff were friendly and enjoyable to interact with, making it an ideal location for a date night or girls' night out.
TOPICS
- Social Gatherings
- Mexican Cuisine
- Happy Hours
16. The CrossRoads Bar & Grill
Cozy atmosphere with a vintage vibe and outdoor seating

The happy hour experience is highly enjoyable due to the lively atmosphere and friendly staff. The environment during this time is energetic and welcoming, making it a great place to relax and unwind with friends or coworkers.
TOPICS
- American Cuisine
- Vegan Options
- Mid-Range
- Downtown Spots
17. New Line Tavern
Cozy atmosphere with a vintage charm

During our visit, we had the pleasure of experiencing happy hour at New Line Tavern. We were immediately impressed by the wide variety of cocktails and appetizers available. The atmosphere was relaxed and welcoming, making it the perfect place to unwind after a long day.
The staff at New Line Tavern were particularly noteworthy. They were friendly, attentive, and went above and beyond to ensure that we had a great experience. The happy hour deals on drinks were also impressive, making it an excellent value for anyone looking to enjoy a night out without breaking the bank. Overall, we would highly recommend visiting New Line Tavern during happy hour for a fun and enjoyable evening.
TOPICS
- Social Gatherings
- Happy Hours
- Dinner
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18. The Aviary
Stylish decor, knowledgeable staff, cozy ambiance

The Aviary, a cocktail bar renowned for its creative drinks, offered a memorable happy hour experience. Although on the pricier side, the cost is justified by the innovative and high-quality concoctions.
During my visit to The Aviary, I was impressed by the unique cocktails and the overall atmosphere. Happy hour at this establishment is highly recommended for anyone seeking a special and exciting drink selection.
TOPICS
- American Cuisine
- High-End
- Downtown Spots
- Dinner
19. Boqueria Fulton Market
Authentic Barcelona-style market experience in Chicago

Multiple locations offer happy hour specials featuring small plates, Spanish wine, and craft cocktails. One establishment provides these deals Monday-Friday from 3pm-6pm and Saturday-Sunday from 4pm-6pm, encouraging a lively atmosphere for customers to enjoy. Another establishment, perfect for unwinding after work, offers happy hour Monday-Friday from 2:30 pm-5:30 pm, serving tapas and drinks in a relaxing setting.
Both venues provide a great opportunity to enjoy reduced prices on food and drinks during specific hours. The first location, with its vibrant atmosphere, caters to customers looking for a place to socialize and enjoy Spanish-inspired offerings in the late afternoon or early evening. Meanwhile, the second establishment offers an earlier and more extended happy hour period, perfect for those seeking a relaxing spot to wind down after work with delicious tapas and beverages.
TOPICS
- Fusion Cuisine
- Social Gatherings
- Mid-Range
- Downtown Spots
20. Bambola
Cozy atmosphere with a lively bar scene

Happy Hour is available at our establishment Tuesday through Saturday from 4pm to 7pm. During this time, guests can enjoy our house cocktails and wines by the glass at a discounted price of $10, both at the bar and in the dining room.
Our events team is skilled and passionate about planning various types of gatherings, ranging from intimate happy hours to significant milestones and corporate events. They are ready and equipped to assist in organizing and executing a perfect occasion, whether it is a small gathering or a complete buyout of the establishment.
TOPICS
- Italian Cuisine
- High-End
- Downtown Spots
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21. Slightly Toasted
Local ingredients, Comfort food, Slightly upscale diner

Slightly Toasted provides a happy hour menu with various daily specials, including $1 off draft beers and $7 glasses of wine. These deals are a popular choice among customers. In addition, the bar offers $6 Old Fashioneds, which are considered a great value.
The atmosphere at Slightly Toasted is perfect for unwinding after work, making it an ideal spot to take advantage of their happy hour deals. Whether you prefer draft beers, wine, or Old Fashioneds, there are options available at affordable prices. The happy hour menu is sure to satisfy anyone looking for a great deal on drinks.
TOPICS
- Social Gatherings
- American Cuisine
- Downtown Spots
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22. Spectrum Bar & Grill
Cozy atmosphere with a vintage sports bar theme

Spectrum Bar & Grill is a great spot for happy hours, known for its lively atmosphere and reasonable drink prices. It's a popular choice for after-work gatherings. The staff at Spectrum Bar & Grill is friendly, and they offer delicious food, especially their flavorful lamb chops.
In summary, Spectrum Bar & Grill is a top pick for happy hour, boasting a vibrant atmosphere and affordably priced drinks. Its friendly staff and tasty food, particularly the mouthwatering lamb chops, further enhance the experience, making it an ideal place to unwind after work.
TOPICS
- American Cuisine
- Downtown Spots
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23. Prime Bar

TOPICS
- Happy Hours
- Downtown Spots
- Social Gatherings
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