Chicago

We’ve compiled the best of the best in Chicago - browse our top choices for the top things to see or do during your stay.

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  • 1. Berlin Nightclub

    Lakeview | Dance Clubs

    A multicultural, pansexual dance club near the Belmont El station, Berlin has progressive electronic dance music and fun themed nights (Madonna...Read More

  • 2. Big Chicks

    Far North Side | Bars/Pubs

    In the Uptown area of the Far North Side, Big Chicks is a striking alternative to the Halsted strip, with a funky crowd that appreciates the...Read More

  • 3. Buddy Guy's Legends

    South Loop | Music Clubs

    Relocated from its original location a few doors down, Buddy Guy's Legends has a superb sound system, excellent sightlines, and more space to...Read More

  • 4. Chicago Blues Festival

    Music Clubs

    The Chicago Blues Festival leaves no doubt about it: Chicago still loves to sing the blues. Each June, the city pulses with sounds from the...Read More

  • 5. Gilt Bar

    River North | Bars/Pubs

    Vintage furnishings and cocktails like the Bee's Knees (gin, lemon, and honey) set the 1920s speakeasy scene at this low-lighted lounge. The...Read More

  • 6. Green Mill Cocktail Lounge

    Far North Side | Music Clubs

    A Chicago institution, the Green Mill in not-so-trendy Uptown has been around since 1907. Deep leather banquettes and ornate wood paneling line...Read More

  • 7. Hopleaf

    Far North Side | Bars/Pubs

    An anchor in the Andersonville corridor, Hopleaf continues the tradition of the classic Chicago bar hospitable to conversation (there's not...Read More

  • 8. House of Blues

    River North | Music Clubs

    Though its name implies otherwise, House of Blues actually attracts big-name performers of all genres, including jazz, roots, gospel, alternative...Read More

  • 9. Old Town Ale House

    Near North | Bars/Pubs

    Just a stone's throw from Second City, Old Town Ale House has attracted a diverse cast of characters since it opened in 1958, including comedy...Read More

  • 10. Old Town School of Folk Music

    Lincoln Square | Music Clubs

    Chicago's oldest folk-music school has served as folk central in the city since it opened in 1957. The welcoming spot in Lincoln Square hosts...Read More

  • 11. Rosa's Lounge

    Logan Square | Music Clubs

    On a given night at Rosa's Lounge, near Bucktown, you'll find Tony, the owner, working the crowd, and his mother, Rosa, behind the bar. What...Read More

  • 12. Second City

    Near North | Comedy Clubs

    An institution since 1959, Second City has served as a launching pad for some of the hottest comedians around. Alumni include Dan Aykroyd, Tina...Read More

  • 13. Signature Lounge

    Near North | Bars/Pubs

    When it comes to views, the Signature Lounge has no competition. Perched on the 96th floor of the John Hancock Center—above even the tower's...Read More

  • 14. Simon's Tavern

    Andersonville | Bars/Pubs

    This classic Andersonville bar honors the neighborhood’s Swedish roots with its signature drink, glögg —mulled Swedish wine, served hot in...Read More

  • 15. The Annoyance Theatre & Bar

    Lakeview | Comedy Clubs

    This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails . ...Read More

  • 16. The Empty Bottle

    Wicker Park | Music Clubs

    This place, in the Ukrainian Village near Wicker Park, may have toys and knickknacks around the bar (including a case of macabre baby-doll heads...Read More

  • 17. The Hideout

    Bucktown | Music Clubs

    The Hideout, which is literally hidden away in a North Side industrial zone, has managed to make country music hip in Chicago. Players on the...Read More

  • 18. The Matchbox

    Wicker Park | Bars/Pubs

    In West Town near Wicker Park, the Matchbox isn't much bigger than a you-know-what, but the hodgepodge of regulars don't seem to mind. In fact...Read More

  • 19. 3rd Coast Cafe & Wine Bar

    Near North | Cafes–Nightlife

    The oldest coffeehouse in the Gold Coast pleases just about everyone with a full menu served until midnight seven nights a week. The inviting...Read More

  • 20. 404 Wine Bar

    Lakeview | Wine Bars–Nightlife

    Enter through rowdy Jack's Bar & Grill to find the serene 404 Wine Bar, a romantic spot filled with cozy nooks. The librarylike back room...Read More

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