16. Maifest Chicago
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (773) 545-4800
Description: Lincoln Square embraces its German roots with this traditional welcoming of the arrival of spring. Along with the anticipated keg-tapping and crowning of the May Queen, it features live bands, German folk music, and dancing around the decked-out May Pole. Free.
City: Chicago, IL
Category: Annual Events & Festivals
Address: 200 Ravinia Park Rd.
18. Ribfest Chicago
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (773) 525-3609
Description: Carnivores converge on the Northcenter neighborhood for this finger-licking spread of the best ribs the city has to offer. With upwards of 50,000 hungry souls, you might have to fight for a bite, but don’t worry, with two dozen restaurants slinging out a total of about 50,000 pounds of ribs, there’s enough to go around. Plus, there are two stages of local and national live bands, a Kids Square with loads of activities for getting sillies out, and a celebrity-judged “Best Ribs” winner. $5 donation.
City: Chicago, IL
Category: Annual Events & Festivals
City: Chicago, IL
Category: Annual Events & Festivals
Address: 2401 N. Lake Shore Dr.
City: Chicago, IL
Category: Annual Events & Festivals
22. Chicago Summerdance
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (312) 742-4007
Address: 601 S. Michigan Ave.
Description: More than 100,000 people each summer shake their groove thing under the stars on the Spirit of Music Garden’s open-air dance floor (made of totally recycled materials, by the way) in Grant Park. They come in groups, as couples, and solo. They come early for free dance lessons in everything from tango to salsa, mambo to jitterbug. Then they stick around for the live bands to strut their newly learned stuff. The SummerDance schedule often includes stints at other parks throughout the city and at Navy Pier, and a WinterDance takes place at Millennium Park. Thurs through Sat 6 to 9:30 p.m., and Sun 4 to 7 p.m. Free.
23. Sheffield Garden Walk & Festival
City: Chicago, IL
Category: Annual Events & Festivals
Description: Chicago’s urban gardeners combine efficiency and artistry to give their small spaces big impact. This summertime festival shows off some of the best blooms of the city on a stroll through the charming, historic neighborhood around Sheffield Avenue. Pick up a guidebook with map and garden details and start exploring; if you’ve got the stamina for it, take a peek at all 100 private gardens, or just make your way to a handful. A Kids Corner features a mini Ferris wheel, petting zoo, pony rides, and more, while gardening experts are on hand to answer your growing questions. Live music from national and local bands, and food too. Donation $7; after 3 p.m. $10.
24. Taste Of Lincoln Avenue
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (773) 868-3010
Description: Going on nearly 30 years, this scaled-down little sis to the Taste of Chicago attracts more than 50,000 attendees and has raised over $1.5 million for its causes including helping to fund area parks and schools. Five stages feature musical acts all day, both local and national in name (Freddy Jones, Otis Clay, Soul Asylum, to name a few). A block-long Kids’ Carnival scores with inflatable slides, face-painting, petting zoo, magicians, singers, and more. In between all the action, there’s plenty of food to suit all tastes, as well as a wine garden. Donation $7 to $10.
25. Chicago Air & Water Show
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (312) 744-3315
Description: They soar, they spin, they fly in formation, they generally defy logic. Those are the pilots of this amazing show, the largest free show of its kind in the US, attracting upwards of 2.2 million wide-eyed attendees. Typically showing off their flying prowess are the US Air Force Thunderbirds, the US Army Parachute Team Golden Knights, the Aeroshell Aerobatic Team, Chicago Fire Department Air/Sea Rescue, and a powerful display of military aircraft. Free.
26. Northalsted Market Days
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (773) 868-3010
Description: The people-watching doesn’t get much better—or much wilder—than at this Boystown street fair where scandalously skimpy and flamboyantly fun outfits are the norm. But feel free to come casual because, spanning four city blocks, lined with more than 400 food and arts-and-crafts vendors, this 2-day event is welcoming no matter what you wear. Three stages of live entertainment have featured famous acts such as Gloria Gaynor and Lisa Lisa. Suggested donation.
27. 57th Street Children’s Book Fair
City: Chicago, IL
Category: Annual Events & Festivals
Description: The best in kid lit gets pulled together for this reading rainbow of booksellers and community organizations. Little ones can’t help but fall in love with books when they’re paired with a parade where story characters come to life in costume (in the past, there’s been Curious George, Clifford, Winnie the Pooh, and Madeline); live music and dance; arts and crafts activities; and a story room where authors chat about their books with an awed little audience. Free.
28. Chicago Jazz Festival
City: Chicago, IL
Category: Annual Events & Festivals
Description: The city’s longest-running music festival is now a Labor Day weekend tradition, featuring acts in three different locations that culminates with two days in Grant Park. International and local musicians have included Cassandra Wilson, Roy Hargrove, and Orbert Davis. Free.
29. World Music Festival
City: Chicago, IL
Category: Annual Events & Festivals
Description: The “world” part of this event is no euphemism—many of the performers travel just for this event from across the globe. In fact, since the ambitious festival began in 1999, it has showcased more than 500 music and dance artists and ensembles from more than 75 countries. Typically, there are close to 100 acts and nearly all are free. Check online for specific lineup and locations.
30. Chicago Marathon
City: Chicago, IL
Category: Annual Events & Festivals
Telephone: (312) 904-9800
Description: Whether aiming for your personal best or just to complete the course, the Bank of America Chicago Marathon is a favored one for its flatness factor, attracting participants from every state and more than 100 countries. With a route that weaves its way through 29 of Chicago’s neighborhoods, it’s quite a way to tour the city too. A pre-race pasta dinner and post-race party add an enormous social element. Not a runner? Pick a spot along the course and cheer on the throngs as they pass—the website gives a good general rule of thumb as to when the runners reach each mile marker and where to stand for good viewing.