Chicago Nightlife: Drinks and More

Turn on the news channel in any Chicago household and you will hear the police reporting yet another fatal shooting. It’s stories and events like these that make even the most fearless person running under their bedsheets when they think about going out at night in Chicago. Chicago natives know their way around their beautiful city, but travelers may not be as keen on the places to go that are not only safe, but fun and worth the trip.

Here are some fun, popular, and safe areas around the Chicago Loop:

  • Three Dots and a Dash (435 N Clark St, Chicago, IL 60654)

This tiki-inspired cocktail bar is hidden away in an alleyway where patrons could find the entrance after noting the ominous tiki torches that lights up the entrance to this underground bar. Although a hidden alleyway may seem scary, the entire neighborhood at night is reminiscent of NYC, with Uber drivers bustling on the roads and bars open throughout the streets. The drinks are served in a cool tiki-inspired cup and are absolutely delicious with interesting pairings, such as their signature Three Dots and a Dash drink with aged Guyana Rum and Never Say Die with aged Jamaican Rum. My advice is to call in advance, especially if you’re with a large group, so that way you would be able to skip the lines and have a lounge booth reserved instead of alternative high-top tables. The best drink of the five I tried: the signature Three Dots and a Dash.


(L to R) Three Dots and a Dash, Never Say Die, Too Many Chiefs, Caribbean Punch, and Royal Hawaiian


Never Say Die (L) and Too Many Chiefs (R)

  • Replay Chicago Lakeview (3439 N. Halsted Chicago, IL 60657)

Replay Bar is a fun arcade-themed bar with free games such as Pac-Man and Frogger. The inside is small, with a large bar counter serving free all-you-can-eat popcorn, even without a purchase of a drink, and several TV monitors playing music videos. The back of the bar opens up into an outdoor deck with another bar counter and several tables for seating. Replay has two locations – Andersonville and Lakeview, and both are great and safe areas to explore for nightlife.


Outdoor patio of Replay


Free all you can eat popcorn

  • Roscoe’s Tavern (3356 N Halsted St, Chicago, IL 60657)

Roscoe’s Tavern is a neighborhood gay and lesbian bar, and it is also one of the best bars in town. The reason being is that the drinks are not only good and cheap, but the entire space opens up into a lively dance floor that goes until 2-3 am. Looks are deceiving because as you enter Roscoe’s you see TV screens with popular pop music videos and a large, oval shaped center bar and a smaller bar to the side serving jello shots and tap beer. As you make your way further into the bar, a large dance floor underneath a hanging disco ball and light-up words spelling BRITNEY appears playing remixed versions of pop and EDM songs. While there is a cover charge at certain nights, Roscoe’s is definitely the place for anyone visiting to have a good time.

General tips for anyone in Chicago looking for a safe and enjoyable night out: 

  • If you’re taking the R-line train:
    • Get off at Belmont (Boystown) for Roscoe’s and Replay.
    • Get off at Addison for Wrigley Field, another safe area with your standard bars and Irish pubs.
    • Get off at Grand for Party Hut, an outdoor bar adjacent to the Chicago River popular on the weekends for drinks and outdoor games, and Three Dots and a Dash.
    • Don’t head more south than Cemak-Chinatown towards 95th/Dan Ryan as that area is known for street violence and may be unsafe.
  • As with all travel, know your area and become street smart. Even if an area isn’t known to be dangerous, be careful with your belongings and use your judgement when choosing to ride the train home versus taking an Uber.


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