09/01/2011 03:16 pm ET Updated Oct 31, 2011

Chicago Labor Day Staycations: Be Your Own Chicago Tour Guide This Weekend

If you don't want to deal with snarls on the Interstate and crowded airports this Labor Day weekend, stay in Chicago. The city has a multitude of eclectic ways to entertain you, whether you want to head to the North, South or West sides or just hang out in the middle of Millennium Park. Here's what to pack into your Chi-Town staycation this Labor Day.

Commemorate Labor Day with a Bike Ride: Don't just revel in an extra day off on Labor Day. Honor its origins with a 30-mile bike ride. The Seventh Annual Pullman Labor Day Bike Ride begins on Monday in Pullman on the far South Side, site of the famed 1894 Pullman Strike, which labor unions started after the wages of workers were cut by the Pullman Palace Car Company. The strike resulted in several worker deaths and injuries after U.S. Army troops were brought in to break it up, and Labor Day was instituted shortly after the strike by President Grover Cleveland, partly to appease labor unions. To commemorate what occurred, the Pullman Civic Organization will host a bike ride that takes off from Historic Pullman, the town built by George Pullman to house workers, and wind through both nature and industry. The ride will cross through to Indiana and the southern portion of Lake Michigan and include stops at Marktown, Ind., a historic steel and industrial town, and continue to the site of the Memorial Day Massacre, where 10 unarmed protestors in a steel strike were killed when a confrontation with the Chicago Police Department turned violent. The ride ends with an included lunch at the Hotel Florence back in Historic Pullman. Registration costs $15 per person and includes lunch.
11111 S. Forrestville Ave.; 773-660-2341

Chicago Jazz Festival: When you think jazz, you immediately think New Orleans. Or Detroit. Or definitely Chicago. But China? At this year's 33rd Annual Chicago Jazz Festival, a Windy City Labor Day weekend tradition, Francis Wong brings his highly regarded saxophone skills. Wong, an Asian American from the Bay Area, will contribute to a one-hour rendition of Shanghai Stories, which lends a jazz-tinged interpretation to music that evokes the world's most populous nation. Joining Wong at the Claudia Cassidy Theater at the Chicago Cultural Center, 78 E. Washington Street, from 1:45 p.m. to 2:45 p.m. Thursday are Tatsu Aoki, Jeff Chan, Edward Wilkerson, Dashun Mosley, Yangqin Zhao and Tomeka Reid. Headlining the festival on opening night Thursday is Randy Weston and the Chicago Jazz Ensemble at the Jay Pritzker Pavilion; the Saxophone Summit with Joe Lovano, David Liebman and Ravi Coltrane at Pritzker on Friday; vocalist Cassandra Wilson at the Petrillo Music Shell in Grant Park on Saturday; and trumpet specialist Roy Hargrove at Petrillo on Sunday.

Go to the Races: To take some last gawks of the season at the Chicago area's most beautiful thoroughbreds (and win some cash), head to Arlington Park, which is hosting a series of Labor Day events throughout the weekend. Things get started on Thursday with live racing from 1 p.m. until about 5:30 p.m. with $6 admission and keep going on Friday with the racing season's last Miller Lite Party in the Park, which features the country rock-playing Local Favorite Band. Post times run from 3 p.m .to 7:05 p.m. that night, and the party keeps going even after the horses are ushered back into the stables. Food specials include $1 mini hot dogs, burgers and tacos. Festivities continue the next day with the last Miller Lite Saturday Summer Bash of the racing season, with music by Four Man Band and the Robbie Gold Band and post times starting at 1 p.m. The horses keep running on Sunday with Family Day, where kids ages 17 and younger are free, the first 3,000 people admitted snag American flags and pony rides and a petting zoo accompany the thoroughbred racing, which runs from 1 p.m. until about 5:15 p.m. The Labor Day racing marathon ends on Monday with the Jin & Tonic band and race times from 1 p.m. to 5:15 p.m.
2200 Euclid Avenue in Arlington Heights; 847-385-7500

Hit the Beach One Last Time: Perhaps nothing marks the unofficial end of summer more than the end of the city's beach season on Labor Day, but you still have an entire long weekend to get in one last tan in the sand. Hit the volleyball pits at North Avenue Beach, take in the sailboats from Montrose Beach, or check out the skyline from the sands of South Shore. Dogs can also go for a dip at Belmont Harbor and the north ends of Montrose and Foster Avenue Beaches. Swimming for humans is generally permitted at two dozen beaches between 11 a.m. and 7 p.m., when lifeguards are present.

Meander through Poland and Africa (with Tyrese and India.Arie): Two of Chicago's largest ethnic festivals hit up the Northwest and South Sides over Labor Day weekend. On Lawrence, the Taste of Polonia, with its five stages of music and endless supply of pierogi, potato poncackes, kielbasa and Polish beer should leave your stomachs and ears nearly bursting. Further South in Washington Park, African-tinged textiles, photos, clothing, photography, beauty products and sculpture will be on display and on sale from more than 300 artists and vendors at the 2011 African Festival of the Arts and its African Marketplace. R&B crooner Tyrese Gibson, author of "How to Get Out of Your Own Way," will be on hand from 1 p.m. - 3 p.m. at the festival's Author and Book Pavilion, and Bootsy Collins brings his funk to the main stage on Saturday, with India.Arie adding her soul to the stage on Monday. Awareness is also a main component of the festival, where those dropping by the African Heritage Pavilion can learn about newly created South Sudan and find out more about Chicago's first settler, Jean Baptiste Point du Sable.
Taste of Polonia, Copernicus Center, 5126 W. Lawrence Ave.; 5 p.m. - 11 p.m. Fri., noon - 11 p.m. Sat.-Sun., noon-10 p.m. Mon.; Suggested donation: $7 for adults, $3 for seniors 65 and older, free for kids 12 and younger.
African Festival of the Arts, 51st and Cottage Grove Avenue in Washington Park Fri.-Mon.; $10 for adults in advance; $15 for adults at the gate