MAY
May 7-8
Rockin’ de Mayo
Blues Traveler, Fountains of Wayne and Howie Day headline the summer’s first street fest. $10. Elston Avenue and Division Street, 773-777-1700.
May 15-16
Windy City Hemp Fest
Includes live music, presentations, food vendors, drum circles and literature. Free. Montrose Park, 4400 N. Lake Shore Drive, 847-293-4862.
May 21-23
Lakeview Mayfest
Features live music from local bands, arts and crafts and food vendors. $5. Ashland and Barry Avenues, 773-665-4682.
May 28-31
Gaelic Park Irish Fest
Five covered stages and seating areas with 40 hours of Irish bands. $12. 6119 W. 147th St., Oak Forest, 708-687-9323.
May 30
Bike the Drive
Cyclists take to Lake Shore Drive–shut down to auto traffic–for this 15- or 30-mile non-competitive ride. $20-$35. Register at bikethedrive.org. Columbus and Balbo Drives, 312-427-3325.
JUNE
June 4-6
Chicago Gospel Music Festival
More than 40 performances from some of the top gospel acts in the world. Free. Grant Park, 300 S. Columbus Drive, 312-744-3370.
June 5-6
Belmont/Sheffield Music Festival
Features bands Urban Funk Ordinance, Hairbanger’s Ball and Underwater People. $5. Belmont and Sheffield Avenues, 773-868-3010.
Printers Row Book Fair
The largest free literary event in the Midwest features new, used, antiquarian and specialty books for sale, plus readings from authors Augusten Burroughs, Ana Castillo and more. Free. Dearborn Street, between Congress Parkway and Polk Street, 312-222-3986.
57th Street Art Fair
More than 300 artists showcase paintings, sculpture, photography, ceramics and more at the 57th annual fair, one of the oldest and largest in Illinois. Free. 57th Street and Kimbark Avenue, 773-493-3247.
June 10-13
Chicago Blues Festival
The largest free outdoor blues event in the world includes performances by Hubert Sumlin, Lonnie Brooks, Otis Clay, Willie Clayton, Robert Jr. Lockwood, David Honey Boy Edwards, Homesick James and others. Free. Grant Park, 300 S. Columbus Drive, 312-744-3370.
June 12-13
Andersonville Midsommarfest
Food, arts and crafts, and live music and dancing on three stages. $5. Foster Avenue and Clark Street, 773-665-4682.
Wells Street Art Festival
More than 260 national artists showcase their work. Also features live music and a silent auction. $5. Wells Street, between North Avenue and Division Street,
773-868-3010.
Old Town Art Fair
The country’s oldest juried outdoor art fair features 250 artists. Also includes a garden walk and live and silent auctions. $5. Triangle Gallery of Old Town/Old Town Art Center, 1763 N. North Park Ave. 312-337-1938.
June 17-Aug. 29
Chicago SummerDance Festival
The 11-week festival features one-hour dance lessons followed by live music and dancing. Free. Thursdays-Sundays. Grant Park, Spirit of Music Garden, 601 S. Michigan Ave. 312-742-4007.
June 18-20
Taste of Randolph Street
Features food from neighborhood restaurants, live bands, cooking demonstrations, art vendors and more. $6-$10. Randolph Street and Racine Avenue, 312-458-9401.
June 19-20
Lincoln Park Festival
Live blues and rock music from Calexico, Waco Brothers and more. $7. Clark Street and Armitage Avenue, 773-868-3010.
Backyard Bash
Live music by national and local artists, plus food and beverages. $5. Roscoe Street between Lincoln and Ashland Avenues, 773-665-4682.
June 24-July4
Milwaukee Summerfest
Features Prince with New Power Generation, Blink-182, Christina Aguilera, Britney Spears, Nickelback, 3 Doors Down and John Mayer. $33.75-$73.75. Marcus Amphitheater, 200 N. Harbor Drive, Milwaukee, 414-273-2600.
June 26-27
Chicago Country Music Festival
Performers include Willie Nelson and Brad Paisley. Free. Grant Park, 300 S. Columbus Drive, 312-744-3370.
June 26
Pride Fest
The Northalsted Area Merchants Association hosts the second annual GLBT community celebration a day before Pride Parade, featuring DJs, live music and food and drink. $5. Halsted Street and Waveland Avenue, 773-868-3010.
June 27
Gay and Lesbian Pride Parade
Starting at Halsted Street and Belmont Avenue, this wild parade features floats, bands and politicians. Free. 773-348-8243.
June 25-July 4
Taste of Chicago
Find everything from hot dogs to haute cuisine at this annual food fest, featuring dishes from 70-plus restaurants, live music, cooking demonstrations and a wine garden. Free. Grant Park, 300 S. Columbus Drive, 312-744-3315.
JULY
July 3
Grant Park Fireworks
More than a million people flood the lakefront to see one of the country’s most spectacular fireworks displays, complete with an accompanying concert by the Grant Park Orchestra. Free. Grant Park, 300 S. Columbus Drive, 312-744-3315.
July 9-11
Chicago Tribune Magnificent Mile Art Festival
More than 200 painters, sculptors, potters, jewelry makers and photographers hawk their wares. Free. Chicago Tribune Pioneer Court, 435 N. Michigan Ave. 815-937-0920.
July 10-11
Rock Around the Block
More than 30 bands perform on three stages. $5. Intersection of Lincoln, Belmont and Ashland Avenues, 773-665-4682.
Lakeview’s Clark Street Fair
Live music and food from neighborhood restaurants. Price TBA. Clark and Addison Streets, 773-868-3010.
July 11
L.A.T.E. Ride
Bike 25 moonlit miles through downtown and North Side neighborhoods for the 16th annual “Long After Twilight Ends” ride. Snacks and a postride breakfast at Buckingham Fountain provided. Midnight registration; 1:30 a.m. ride. $35-$45. Registration: lateride.org. Buckingham Fountain, 500 S. Lake Shore Drive.
July 13-Aug. 24
Chicago Outdoor Film Festival
Grab a blanket, pack a picnic and spend Tuesday nights watching classic movies for free under the stars. Butler Field, Grant Park, 100 S. Lake Shore Drive, 312-744-3315.
July 16-17
Old St. Patrick’s World’s Largest Block Party
The 20th annual event–known for its hook-up potential–features live music, food, drinks and a raffle. 5-10:30 p.m. Price TBA. Madison Street and Des Plaines Avenue, 312-458-9401.
July 16-18
Benfest
Live music and food and drink. $5. Irving Park Road and Leavitt Street, 773-665-4682.
July 17-18
Sheffield Garden Walk
See more than 100 gardens in this historic neighborhood. $6. Webster and Sheffield Avenues, 773-929-9255.
July 18
Dearborn Garden Walk and Heritage Festival
Take a self-guided tour of more than 20 award-wining gardens. $30-$35. Dearborn and Goethe Streets, 312-632-1241.
July 24-25
Summer on Southport
Live music, food and craft vendors. $5. Southport Avenue and Grace Street, 773-665-4682.
July 31
Venetian Night
Lighted boat parade and fireworks. Free. Monroe Street at the lake, 312-744-3315.
AUGUST
Aug. 6-8
Gold Coast Art Fair
One of the city’s largest fairs, featuring more than 400 exhibitors in fine arts and crafts, live music, food and street performers. Free. LaSalle Boulevard and Huron Street, 847-444-9600.
Aug. 7-8
Northalsted Market Days
Annual Lakeview event is Chicago’s largest outdoor two-day festival, with fine art, food, entertainment and live music on three stages, including Buckwheat Zydeco and Shelby Lynne. Price TBA. Halsted Street between Belmont Avenue and Addison Street, 773-868-3010.
Aug. 14-15
Retro on Roscoe
This “flashback” weekend features an antique car and motorcycle show, craft vendors, ethnic food, games and live music. $5. Roscoe Street and Damen Avenue , 773-665-4682.
Aug. 20-22
The Chill on Kingsbury
Features live music by Violent Femmes (Friday), Los Lobos (Saturday) and more, beer, wine, food and craft booths. $6-$10. Kingsbury and Willow Streets, 312-458-9401.
Aug. 21-22
Chicago Air & Water Show
The oldest and largest air show of its kind. Free. Along the lakefront near North Avenue Beach, 312-744-3370.
Aug. 28-29
Bucktown Arts Fest
A celebration of performance, spoken and visual art. Browse paintings, sculpture, jewelry and photography, and see live music, theater, dance and poetry performances. Free. Senior Citizens Park, 2300 N. Oakley Ave. 312-409-8305.
Viva! Chicago Latin Music Festival
Listen to the sounds of cumbias, merengue, salsa and more at this festival of Latin music from around the world. Free. Grant Park, 300 S. Columbus Drive, 312-744-3370.
SEPTEMBER
Sept. 2-5
Chicago Jazz Festival
The city’s longest-running lakefront music festival features local, national and international performers on several stages. Free. Grant Park, 300 S. Columbus Drive, 312-744-3370.
