WHY YOU SHOULD TRUST HIM: If there’s anyone you should trust to recommend the best happy hour in Chicago, it’s Will. There’s truly no moment on any given day that Will won’t justify as an appropriate time to have a drink, and for over ten years, he’s been systematically seeking the best watering holes in the fine city of Chicago. It’s no easy task, as there’s an endless list of bars in the Windy City, with new spots opening almost daily. So while this isn’t a complete list, you can trust that this list has been vetted by one of the best drinkers in the city.
1. Your recommended budget happy hour location?
For those looking to drink on the cheap (and the early), The Ogden is your spot. From 1-4pm, this great restaurant and bar, which is walking distance from the United Center, has half-priced drinks with no limits and no exceptions. If you need to pregame a Bulls or Blackhawks event, and you have spent all of your money on game tickets, this is the best happy hour in Chicago!
2. The best neighborhood for a Bachelor Party Bar Crawl?
Traveling to the Windy City for a Bachelor party? Its likely someone will suggest Wrigleyville, the six square blocks surrounding Wrigley Field which have over 40 bars. And you should go through Wrigley…and then keep going in your Uber (or better yet, your chartered Trolley, a Chicagoland classic) on a microbrew crawl! Chicago has become a center for great craft beer, and a day or more can be made touring the many local options. I’d suggest starting at the “World’s Largest Microbrewery” facility at the Lagunitas Brewery, then heading to Chicago’s most famous export after the Cubs themselves: the Goose Island Tap House. On to Revolution Brewery, and wrapping up with an ultra local option such as Haymarket or Burnt City or DryHop or Moody Tongue!
3. Favorite place to buy booze (liquor store or wine shop)?
Chicago is home to Binny’s, a chain of liquor superstores; there is bound to be one close to your hotel or Airbnb. I always stop into the location in the Lincoln Park neighborhood, where they stock 3,021 spirits, 6,151 wines, 2579 beers and 1,000 cigars through out 50,000 square feet- and tasting room too! As they say, “If you can’t find it at Binny’s, it isn’t worth drinking.”
4. Best bar/lounge to celebrate a special occasion?
When I am looking to take someone special to celebrate something as equally special as they are, I head towards Ada St. A bit off the beaten path, this hip lounge feels as isolated as it is inviting with low lights and high-end cocktails. If you get hungry, the food is pretty epic, but know that they don’t take reservations after 6pm.
5. Where would you take your parents for a glass of wine or cocktail?
When my folks are in town, we head straight to Chicago Pizza and Oven Grinder Company. While it’s not known for its drinks as much as its delicious “upside-down” pizzas and HUGE Italian grinder sandwiches, their bar is very full and very reasonable. Peroni on draft and bottles of Chianti for $20 seems extra appropriate here at the cash only CPOG. It’s located in an old row house just across the street from the prohibition era St. Valentines Day Massacre.
6. Best bottle service locale?
One of the things that I love about Chicago is that bottle service is just not necessary to have fun. Seven nights a week, there are hundreds of dives, juke joints, blues clubs, comedy shows, and dance halls that are all happening. If you are a true party animal, you can actually drink 24 hours a day in the Windy City! If you must buy bottles however, I’d either go with the place to see and be seen (Underground) or the place to dance until the money runs out (The Mid). Either spot will happily take your money, but both are more than capable to bring that bottle of Belvedere to your table with fireworks and ladies.