The Skyline and Beyond: Toasting Through Illinois’ Most Vibrant City

Chicago is a beautiful city, offering one of the best downtown scenes in America. It has Old Style decor and signs swinging throughout, helping you recognize some of the favorite dive bars and lounges. Business people frequently open new watering holes for you to try on your next night out in Chicago. 

Many bars offer live music, events, and upscale experiences that anyone in your party will enjoy. A bar crawl in downtown Chicago will allow you to experience as many locations as possible. Learn more about some of the best places to stop on your next visit to Chicago below.

1. Kingston Mines

Chicago is famous for its history of blues music. Movies like “The Blues Brothers” were filmed in the city’s downtown area! Kingston Mines allows you to experience the rich musical history of Chicago. This location has live music Thursday through Saturday and stays open until 4:00 a.m. to give you a late-night experience. The Lincoln Park location is one of the most classic options in Chicago. It continues to hold many of its traditions from the last 30 years. Kingston Mines has several other locations throughout the city to give you added convenience on your bar crawl in Chicago.

2. Nine Bar

Nine Bar is in the middle of Chinatown in downtown Chicago. This location was the first cocktail bar opened in the Chinatown neighborhood. You can visit this classic speakeasy by entering through the Moon Palace Express. It has Asian-inspired cocktails to add to the cozy experience of the dark interior. One of the most popular drinks is a smoky rye cocktail. It has Chinese five-spice infused in the alcohol for a unique taste. Nine Bar has a live DJ every weekend to provide a premium nightlife experience for everyone who enters the door.

3. Osito’s Tap

Osito’s Tap is technically not a speakeasy, but the entrance can be fun to find. Walk through the second door of Moreno’s liquor store to get into the bar. The interior feels antique with the exposed brick walls and leather booths. Osito’s Tap has an affordable happy hour with daily specials. Draft beer is on tap at all times in the bar. Osito’s Tap also has unique cocktails, including the El Oscuro. The El Oscuro is an Old Fashioned with orange, chocolate, and ancho chile flavors. Every foot item on the menu has Mexican roots.

4. Milk Room

The Milk Room is a micro-bar in the heart of downtown Chicago. It resides in the back of the Chicago Athletic Association. Make a reservation for your bar crawl if you want to go to the Milk Room. The bar only has enough seating for eight customers! The Milk Bar has a two-hour experience option that lets you try several vintage cocktails and whiskeys. It includes alcohol from France from the early twentieth century. The food menu further adds to the luxurious experience with caviar and foie gras options. If you’re looking for a Halloween bar crawl in Chicago, the best way to crawl is with Bar Crawl Live.

5. Hopleaf

The last of the bars to visit in downtown Chicago is Hopleaf. This two-story location has multiple counters where you can order domestic and European beers, including craft options from the local area. Ask for the drinks on tap, or choose a bottle for an easy drinking experience. Hopleaf has over 60 drafts to give you the best experience you need. The bar has some wines available if you do not want a beer. Try to snag any rare option on the menu, as Hopleaf frequently changes its list!

Go Bar Crawling in Chicago

Chicago is a fun and upbeat city with some of the best nightlife in the world. You can go on a bar crawl to experience the most unique locations in the downtown area. Many bars on this list are in the back of other stores or on a corner, giving you a speakeasy-like experience. Visit Hopleaf for a more classic location. This two-story bar has over 60 drafts to ensure everyone in your party has something to enjoy! Remember, if you want to visit Milk Room on your bar crawl, you should make a reservation first! This location only has eight seats.


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