One of America's biggest bike rides, Bike the Drive offers participants the chance to enjoy a morning of car-free riding on Chicago's Lake Shore Drive. Participants can choose from three different routes on which to enjoy the unique experience.
Memorial Day Parades have graced the Windy City since 1871. Chicago's annual event is one of the largest and most spectacular tributes to veterans in the USA. More than 10,000 participants travel down State Street from Lake to Van Buren.
Annually screening upwards of 30 features and more than 100 shorts, the Chicago Underground Film Festival is held each year at the Gene Siskel Film Center. The programme also takes in videos, animation, documentaries and experimental cinema.
The lakefront in Grant Park is packed out for the Chicago Blues Festival. Big names appear in the Petrillo Music Shell at Jackson and Columbus, but there are also six other stages. Past headliners have included legendary blues guitarist BB King.
The Windy City hosts a month-long programme of social, sporting, cultural and political events for Gay Pride. The grand finale is the Chicago Pride Parade, featuring more than 250 floats, attracting an expected crowd of 375,000.
Race to the Taste is a 5km run, or two-mile walk, annually attracting more than 3000 people to Chicago. It starts at the corner of Columbus and Balbo, wends its way through the south loop and returns to Grant Park.
The city known for its prime rib steaks and deep-pan pizzas hosts the annual Taste of Chicago in Grant Park. The festival features menu highlights from more than 70 restaurants that showcase their cooking in colourful pavilions throughout the park.
The annual Chicago Folk and Roots Festival at Welles Park celebrates music and cultural expressions rooted in the traditions of diverse American and global communities. Welcoming local and international musicians, the festival features a Kids' Tent and hosts sing-along sessions.
Chicago's Pioneer Court becomes an outdoor art gallery for three days during the annual North Michigan Avenue Art Festival. Hosted by the Chicago Tribune, the festival sees more than 200 sculptors, painters, potters, glass-workers and photographers displaying their work.
The north section of Lincoln at Addison, Chicago comes alive for the annual Rock Around the Block festival. The music, food and arts festival attracts 40,000 people over two days.
Venetian Night transforms Chicago's Lakefront between the Shedd Aquarium at Roosevelt Road, into a romantic vision of light and sound. A fleet of boats decked in twinkling lights sail along the lakeside. Music and fireworks are other highlights.
Residents of Chicago's Gold Coast neighbourhood open their garden gates to visitors during this annual festival. This pleasant day out includes many beautiful gardens on Dearborn, State, Astor and LaSalle Streets and Sandburg Terrace, between Division Street and North Avenue.
For the best emerging and established indie rock bands, head to the annual Pitchfork Music Festival. The three-day event hosted by the popular (and achingly cool Pitchfork website) is held at Chicago's Union Park and boasts a line-up for coinnoiseurs.
Fast-paced straight-aways and 90-degree turns are all part of the Chicago Criterium bike race, held in Grant Park. Professional teams from around the world compete and there are sponsor booths and vendors on hand to keep the crowd happy.
Lollapalooza presents a wonderful array of live music in Chicago's Grant Park and is one of the country's biggest and best festivals. The brainchild of Jane's Addiction frontman Perry Farrell, it offers an eclectic mix of rock, hip-hop and alternative music.
The annual Arlington Million takes place at Chicago's Arlington Park and is one of the world's richest and most famous horse races. Inaugurated in 1981, this was the first race to offer a million-dollar prize.
Northalsted Market Days is a two-day affair attracting around 300,000 people to Chicago's Halsted gay district. As sure as there'll be local beer, there'll be someone cooling you down with a water pistol, an ongoing feature of the event.
The Second City Tennis Classic gay and lesbian tournament is held annually at the Lakeshore Athletic Club - Lincoln Park and the Mid-Town Tennis Club in Chicago. Singles and doubles draws are offered for each of five divisions.
The Chicago Air & Water Show presents two fun-packed days of spectacular air and watercraft demonstrations on Lincoln Park's lakefront, with North Avenue Beach as its focal point. Highlights include jets performing in a renowned delta formation.
Tens of thousands of people picnic on the grass and enjoy the music at the annual Chicago Jazz Festival, held in Chicago's Millennium Park and Grant Park. The festival offers a consistently attractive blend of familiar acts and up-and-coming talent.
Chicago's idyllic Garfield Park Conservatory presents the old-fashioned County Fair in a grand urban setting. The annual event features food, live music, from pulsating salsa tunes to mellow jazz sets, and includes competitions for the best garden produce.
The annual Chicago Summerdance provides an hour's worth of dance lessons to taped music, followed by free live music and dancing. The festival is held from Thursday to Sunday throughout the summer at the Spirit of Music Garden in Chicago's Grant Park.
The Viva! Chicago Latin Music Festival in Millennium Park celebrates Latin music and culture, attracting around 150,000 people annually. Infectious rhythms, including merengue, ballads, mariachi and salsa reverberate. The festival also hosts food and drink vendors.
Dozens of artists from around the globe fill the stages of Chicago with an amazing variety of music during the Chicago World Music Festival. Performances take place at more than 20 venues.
Comiskey Park / US Cellular Field is home to the Chicago White Sox Major League Baseball team and stages regular games from April to September. The White Sox compete in the tough American League Central, which includes the Minnesota Twins.
Wrigley Field is home to the Chicago Cubs Major League Baseball team and stages regular games from April to October. The Cubs compete in the tough National League Central, which includes the St Louis Cardinals, and the Pittsburgh Pirates.
Founded in 1964, Chicago International Film Festival is America's oldest competitive film festival, screening over 100 features and shorts at The Chicago Theatre, Loews Cineplex and Music Box Theatre. It boasts distinguished juries and an impressive line-up of international films.
The Chicago International Children's Film Festival (CICFF) is the largest competitive festival of children's cinema in the US. The event annually screens around 200 features and short films at the Facets Multimedia and other venues in Chicago.
SOFA (Sculpture, Objects and Functional Art) is America's leading art fair for the gallery market, firmly established as a driving force in the contemporary fine and decorative art market in America. It's held annually at Chicago's Navy Pier Festival Hall.
Chicago hosts a wild three days of fetish fun during the annual Rubber Blowout Weekend, held at Cell Block and other venues around town. The programme includes cocktail parties, the annual Rubber Buddies Brunch and a two-day rubber/leather market.
The Chicago Humanities Festival is an annual celebration of the liberal arts that honours the power of ideas in human culture. A variety of presenters including journalists, historians, economists and professors speak and host discussions.
The American Indian Center of Chicago invites visitors to celebrate the rich heritage of Native American cultures at its Annual Powwow. Held at the city's Navy Pier, don't miss the colourful dance performances.
Chicagoans love a celebration and Chicago's Christmas Tree Lighting Ceremony is really something. The enormous tree illuminates Daley Plaza and festive crowds are entertained with a special programme of live music from local choirs and marching bands.
Dating back to 1934, the Chicago Thanksgiving Parade tempts 350,000 people onto the Chicago streets, with another 1.5 million watching on TV. In the nippy autumn air marchers proceed up State Street - from Congress Street north to Randolph Street.
Giant illuminated animal figures and a magical holiday glow descend on Chicago's Lincoln Park Zoo during the annual Zoolights Festival. Chicago boasts many fine light displays at Christmas time, but few can compete with this one.
The One of a Kind Show and Sale at Chicago's Merchandise Mart builds on a successful Toronto event. Hundreds of artisans sell their hand-crafted work, from jewellery, pottery, glass and woodwork to ironwork, clothing and visual art.
The annual Julmarknad Christmas Bazaar at the Swedish American Museum Center on Chicago's north side features Scandinavian and modern crafts. The Kaffestuga Christmas cafe, with open-faced sandwiches and glögg (hot punch), caters for hungry holiday revellers.
Professional ghost hunter Richard T Crowe leads spooky Chicago Supernatural Tours by bus, starting at the Goose Island Brewery. Haunted cemeteries, pubs and murder sites - no stone is left unturned. The Halloween specials are particularly popular...
The Chicago Bears play their NFL games at the legendary Soldier Field. The Bears have a glittering history having won numerous NFL titles and the team has been home to stars of the game like Richard Dent and Sid Luckman.
The centre of Chicago takes on some of the trappings of a typical German Christmas - with a rather better chance of snow - as Daley Plaza hosts the annual Christkindlmarket. Children can visit Santa's house.
Enjoy classic Yuletide films in a Christmas Singalong Double Feature at Chicago's Music Box Theatre. A holiday tradition, the event also welcomes Santa who, accompanied by the theatre's organist, leads the audience in singing Christmas carols before the screening.
The Feast of St Lucia begins with a procession at Chicago's Swedish American Museum Center and winds through Andersonville, returning to the museum for a programme featuring performances and Christmas songs. The Ebenezer Lutheran Church hosts the evening programme.
The annual Chicago Auto Show at McCormick Place is the biggest in the US - no mean feat in a nation populated by passionate car-lovers. It features numerous accessories and auto-related exhibits, plus displays of competition vehicles and antique automobiles.
The first St Patrick's Day parade in Chicago took place on 17 March, 1843. Now every year a magnificent procession of marching bands, floats and hundreds of citizens dressed in green thrills spectators in the downtown area of the city.
The Chicago Blackhawks play their NHL ice hockey games at the United Center. The regular season runs from October to April. Full details of this season's schedule are available on the Blackhawks' website.