It’s Happy Hour, ladies and gentlemen! We selected five of our favorite spots to enjoy the best time of the day.
Every day, 4:30-5:30 pm
Located in the West Loop in what could very well be the coziest alley in the world, Trivoli Tavern is considered one of the best happy hour spots in town. They offer an extensive $5 food and drink menu. Food wise, we particularly like the Fritto Misto and Pigs in a Blanket. When it comes to the drinks, it is a tough choice between the wines, beers, highballs, and the Teeny Martinis–all just $5 each.
Insider tip: Make sure to get here by (or even before) opening time, as it may get crowded and happy hour cocktails and food are only served in the bar area.
Monday through Friday, 3-5 pm
Located just off the Riverwalk, this chic steakhouse sets the perfect mood for your happy hour. Try a selection of tasty bites like oysters ($3), truffle fries ($6), or beef tartare ($9). Cap off the hour with your choice of cabernet, rosé, or moscato by the glass.
Insider Tip: Match the modern vibe by dressing smart casual.
Wednesday & Friday, 4:30-6:30 pm
We love the $1 oysters and cocktail shrimp at this old school supper club, which is a bit hidden away next to iconic Marina City. On Wednesdays they throw in half price signature cocktails, as well. This is the perfect place to meet up with friends and unwind after a long day.
Insider tip: On Fridays, stay for the live jazz that starts at 7:30 pm
Monday through Thursday, 4-6 pm
This downtown Belgian-style mussels and beer bistro is located at the Kimpton Monaco Hotel and during happy hour features $2 oysters and $6 glasses of wine.
Insider Tip: Come for happy hour, stay for the mussels. They are amazing!
Tuesday through Friday, 5-7 pm
Enjoy the luck of the Irish when you make it to happy hour at this River North staple. $7 will get you fish tacos, a big pretzel, and many other savory snacks to soak up the Irish signature cocktails ($8), premium wines ($6), or the happy hour beer ($6).
Insider Tip: Try the Irish Coffee, considered a signature cocktail here.
Wednesday through Sunday, 5-7 pm
Considered one of the best cocktail bars in the world, this Wicker Park hotspot serves artisanally crafted drinks in true Prohibition style. During happy hour these classic libations come at a discounted price of $13 each: Daiquiri, Gin Gimlet, Tom Collins, Margarita, Sidecar, Manhattan, Negroni and Vieux Carré.
Insider Tip: Do not try them all at once, you can always come back!