1. Chicago Blues Festival

    The raucous weekend-long Blues Festival kicks off summer in Chicago. An estimated 750,000 listeners converge on Grant Park for the world’s largest free blues event. The main stage line-up spans traditional bluesmen like Honey Boy Edwards, jazz interpreters such as Mose Allison, and blues-inflected popsters like Bonnie Raitt. Smaller side stages offer a more intimate audience experience.

    • 312 744 3315

    • Late May–early Jun

  2. Chicago Summer Neighborhood Festivals

    Chicago is a city of neighborhoods with upwards of 100 neighborhood festivals to prove it. Virtually every summer weekend features an event or three ranging from the gay-oriented North Halsted Market Days to the ethnic Korean Street Festival.

    • 312 744 3315

    • May–Sep

    Neighborhood festival in Chinatown
  3. Chicago Gospel Music Festival

    For three days Grant Park resounds with stirring choirs and impassioned soloists. Headliners have included R&B-star-turned-Memphis-preacher, Al Green.

    • 312 744 3315

    • Early Jun

  4. Old Town Art Fair

    This 50-year-old fair installs 250 artist booths along Old Town’s historic and leafy lanes. The artwork is supplemented by food vendors, kids’ entertainment, and garden tours.

  5. Ravinia Festival

    The summer home of the Chicago Symphony Orchestra, Ravinia stages concerts (classical, jazz, and pop) in suburban Highland Park. Sheltered seats are available but it’s more fun to pack a picnic and join the crowds on the lawn.

  6. Taste of Chicago

    Chicago’s signature foods including deep dish pizza star during the nearly two-week long Taste. Musical entertainers, a carnival with rides, and cooking demonstrations entertain at the sprawling Grant Park event.

    • 312 744 3315

    • Late Jun–early Jul

  7. Venetian Night

    On this night, boat owners dress up their ships and form a festive marine parade that culminates with fireworks over the lake. For the best views try Monroe Harbor at the lakefront.

    • 312 744 3315

    • Late Jul/early Aug

  8. Chicago Air & Water Show

    This massive display of military power features historic aircraft flybys, a staged amphibious attack, and precision flying teams. Prime beachfront viewing spots are from Oak Street to Montrose Beach.

    • 312 744 3315

    • Mid-Aug

  9. Chicago Jazz Festival

    Just as the Blues Fest ushers in summer, the smaller Jazz Fest caps it. Music fans are drawn to Grant Park for free concerts by a range of jazz greats like Branford Marsalis and Roy Hargrove.

    • 312 744 3315

    • Late Aug/early Sep (inc. Labor Day weekend)

  10. Magnificent Mile Holiday Lights Festival

    Merchants mark the start of the holiday season by lighting the shops, lampposts, and trees along Michigan Avenue. The parade and fireworks above the Chicago River on the Saturday night before Thanksgiving warrant braving the inevitable chill.

    • Mid Nov–end Dec

Top 10 Sports Teams & Events

  1. Chicago Cubs

    Despite the Cubbies’ losing streak, their baseball games are often sell-outs .

  2. Chicago White Sox

    The White Sox are renowned for their top-quality baseball.

  3. Chicago Bears

    A football team generating rabid fans and tailgate picnics on Soldier Field.


  4. Chicago Bulls

    Their basketball just hasn’t been the same since superstar Michael Jordan left.

  5. Chicago Blackhawks

    NHL ice hockey team sharing the United Center with the Bulls.

  6. Arlington Park

    Thoroughbreds race just north of Chicago.

  7. Chicago Fire

    Many local Latino soccer fans support the Fire.

  8. Chicago Wolves

    AHL’s Wolves have a better playoff record than NHL’s Blackhawks.

  9. Chicago Marathon

    40,000 entrants run through the city.

  10. Chicago Triathlon

    Over 6,000 run, bike, and swim in this one-dayer.

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