The Most Fun Bars in Chicago - From an Experienced Bar Crawl Organizer
Ask a dozen Chicagoans what the best neighborhood is for nightlife and you’re sure to hear a dozen different answers. Some locals love Gold Coast for its high-end vibe and unbeatable happy hour convenience. Others swear by the youthful vibrancy of Boystown. Others still might say all the fun in Chicago is to be had west of the river.
Whatever the answer, you can bet Chicago is no stranger to fun and diverse nightlife experiences. It’s estimated there are over 3000 bars in the city alone! And that’s to say nothing of the suburbs and nearby cultural hubs like Evanston!
So, from that enormous stack of potential destinations, how are you and your friends supposed to decide where to go?
Let us be your guide as we walk you through seven of the top fun bars in Chicago, IL. Each is sure to offer a unique and fun experience for you and your fam.
1. Three Dots and a Dash
A night out is best with friends. And a night out with friends is best with comically enormous, shared drinks. Enter Three Dots and a Dash. This Polynesian-inspired bar on Clark (more on that later) is so much more than its kitsch would have you believe.
Enjoy a robust food menu, famously strong drinks, and bookable private spaces for parties and special events. Island time has come to Chicago. You and your friends may never want to depart.
2. Sidetrack
Situated just north of the Loop in the neighborhood of Boystown (near Wrigley Field), Sidetrack is an institution. It’s considered one of the premier gay bars in Chicago. And it’s been going strong for over 40 years, with an inclusive vibe, themed nights, and an inviting dance floor.
Whether you are looking for fun with your fam or just need a night out to express yourself, Sidetrack is it. And with over 4 stars on Yelp, other Chicagoans can confirm this spot is fire.
3. Emporium Arcade Bar
Channel your inner nerd as you enjoy great drinks and a broad selection of classic arcade games. Emporium is located in Wicker Park. This novel experience offers digital games and classic physical fun like pinball, air hockey, and more.
One extra note is while the games seem like family-friendly fun, Emporium is 21+. That’s what makes it one of the most fun bars in Chicago for young adults and the young at heart. So, leave the kiddos at home and enjoy an adults-only barcade that your 10-year-old self could only dream of!
4. Old Town Ale House
As its name might suggest, this spot is located just above River North in, you guessed it… Old Town! This watering hole is like a mainline for Chicago history.
Old Town Ale House has got that classic dive bar aesthetic but with a welcoming vibe. As a bonus, Second City is right across the street. And what could pair better than great drinks and even better improv comedy?
5. The Whistler
A live music bar all its own. The Whistler is Logan Square’s no-so-secret music lover’s dream. This is a place that just oozes a love of music. And the patrons fall right in step.
Expect novel experiences like Japanese vinyl nights and dance party weekends. With so many aural experiences to choose from, you’re sure to crave another night out at the Whistler.
6. Constellation
It doesn’t get much more “Chicago” than a jazz bar. And Constellation very well may be the best venue with a jazzy cocktail bar in the city.
Expect everything from prog jazz to improvisation. And expect everyone from local musicians to renowned touring artists. This is a place to luxuriate in a classic Chicago tradition.
It’s worth noting, though, you can also probably expect a slightly older demographic. Y’know, this being a jazz bar, and all…
7. How About a Self-Guided Pub Crawl?
You may have heard that Clark Street is the most famous bar street in Chicago. And those who let it loose didn’t lie.
Clark has over 200 bars along its neighborhood-spanning drag alone! And many of them are some of the most fun bars in downtown Chicago. So naturally, picking just one is sort of impossible.
But, if you and your friends are up for a legendary night, here are just a few spots to consider along the route:
- Fame Nightclub – A dark and swanky nightclub with high energy.
- Lore Nightclub – Just upstairs from Fame Nightclub.
- Electric Hotel Nightclub – If you love disco balls, this venue is for you.
- Y Bar Nightclub – A modern and vibrant nightclub.
- LiqrBox Nightclub – This nightclub is high energy. Huge artwork lines the walls and great music.
- The Handsome Speakeasy – A speakeasy that makes you feel like you are back in the prohibition era.
- Yours Truly Bar – The perfect bar to grab an oyster and a cocktail.
- Joy District Nightclub – This bar is the talk of the town.
- Hubbard Inn Nightclub – They have everything you could want in one place.
- Mother Hubbard's Pub – A traditional sports bar.
There are so many others to discover, so we recommend hitting the town and letting us know your favorites! Whether you prefer south of Millennium Park or well above Lincoln Park, there are sure to be bars that delight you.
Don't want to do the research? Just hit up one of our bar crawls during an upcoming holiday weekend! You’re sure to have the experience of a lifetime with us and discover the most fun bars in Chicago.