January
Light Nights on the Magnificent Mile - Every Saturday night at 6:30 from January 8 to February 27, a spectacular fireworks and music show occurs above the Chicago River. Pioneer Court at 401 Michigan Avenue offers perfect views of the show, free holographic viewing glasses and prize giveaways.

February
Chicago Auto Show - This annual event is the largest auto show in the nation with more than 1.2 million square-feet of automobile perfection. More than 1,000 cars and trucks are on display for every car fan to drool over. But this show isn't just for gawking. Test tracks allow you to experience the rush of actually driving your ultimate fantasy ride. This is unlike any auto show on the planet.

Chicago Maritime Festival - Held at the Chicago History Museum, this festival lets you see live demonstrations and maritime exhibits and enjoy live music and presentations by seamen and historians.

March
St. Patrick's Day Parade - The procession begins from Dearborn Street and Wacker Drive. Be sure to check out the Chicago River, dyed a bright green for the holiday.

Chicago International Documentary Festival - This 10-day event features screenings of short and feature-length documentary films from around the world.

April
Green Apple Music Festival - Celebrate Earth Day at venues around the city, featuring live concerts by local, regional and nationally recognized musicians. The festival also includes children's activities at the Peggy Notebaert Nature Museum.

May
Chicago Mayfest - Celebrate spring with live music, arts and crafts, and food and beer vendors. The festival also features a pet parade and the crowning of Miss Mayfest.

Great Chicago Places and Spaces - This festival honors Chicago's architecture and design. Design experts and famous architects give tours of various structures and buildings throughout the city. Activities for the entire family include tours, building workshops and scavenger hunts. To name just one of Chicago's many architectural wonders, the Carson, Pirie, Scott and Company Building at 1 South State Street, inside the Chicago "Loop," was built around 1900 by famed architect Louis H. Sullivan. The department store still operates, and has been designated as a Chicago landmark.

June
Chicago Blues Festival - The largest free blues festival in the country has been held at Grant Park in June for the past 20 years. It features local Chicago bands as well as famous musicians from around the globe performing blues and swing music to a crowd of millions.

Artists of the Wall Festival - More than 100 artists of all ages gather at Loyola Park Beach to work together on a 600-foot mural. Anyone can come to watch artists join together in perfect harmony, or to enjoy the many shops and restaurants in the area.

Old Town Art Fair - More than 250 artists will display oil paintings, acrylics, sculptures, jewelry and more as patrons eat delicious food, participate in live auctions, stroll through a scenic garden walk and even play with their kids in an exciting children's play area.

July
Taste of Chicago - Grant Park is shut down for 10 days as millions of people chow down on gourmet food from more than 100 restaurants and food distributors, participate in fun activities and rides and listen to live music on several stages. It all leads up to one spectacular Fourth of July celebration.

Chicago Folk & Roots Festival - This festival at Welles Park features live local, regional and national musicians.

Venetian Night Boat Parade - Chicago's oldest event is modeled after a boat parade in Venice, Italy. The annual event is kicked off by a live concert at 8:30 and capped off by a musical-themed fireworks show at 9:30. In between that hour is a parade of spectacularly decorated and brilliantly lit boats sailing down Lake Michigan.

August
Chicago Air and Water Show - Two million people flock to a free two-day-long air and water show involving some of the most daring aerial and aquatic acrobatics ever seen. While the event is viewable from many locations, the best view is over North Avenue Beach. From there you can see the Chicago skyline in the background as the world- famous Blue Angels dazzle you with dizzying aerodynamic delights.

JazzFest Heritage Music Weekend - This festival at the South Shore Cultural Center features a black-tie-award gala and a "Battle of the High School Bands." Enjoy live music including blues, Latin, classical and contemporary jazz, as well as shopping, food and family picnics.

September
World Music Festival - The World Music Festival is a massive, sprawling event incorporating all the museums, stores and restaurants in downtown Chicago, as well as dozens of stages built specifically for the festival. Sixty featured performers representing more than 30 countries perform live as fun and educational workshops occur in Chicago museums, parks, theaters, bookstores and more. It's musical, it's emotional, it's fun and it's educational.

October
Chicagoween - Daley Plaza becomes "Pumpkin Plaza" in celebration of Halloween. This event features a haunted village, circus performers, pumpkin decorating and storytelling. Don't miss the adorable children's costume parade.

November
Chicago Chevy Vette Festival - More than 50,000 Corvettes from the 50s to the present will be on display and sale at the largest Chevrolet Corvette show and sale in the world. Car fans will be treated to classic cars, customs tuners, prototype vehicles, new parts and accessories at discounted prices and much more.

Christkindlmarket - A four-week-long Christmas celebration with more than a million visitors a day, Christkindlmarket is the main reason many tourists flock to Chicago in November. Inspired by the German Christmas Market in Nürnberg, this event starts after the parade on Thanksgiving Day and goes strong until three days before Christmas.

More than 65 traditional timber booths, walk-in cottages, and vendor pavilions are built so that vendors from Europe can set up shop and sell everything from "German holiday delicacies and chocolates such as the famous Nürnberger Lebkuchen [ginger bread cookies] or the Christmas Stollen [fruit cake] to original German holiday ornaments, from artistic glass, pewter and straw decorations to wooden toys and nutcrackers, from cuckoo clocks to beer steins, from delicate lace products and hand-knit sweaters to candles, jewelry and music" - (Source - http://www.weihnachtsmarkt-deutschland.de/weihnachtsmarkt-chicago.html)

Christmas Around the World - Starting on November 24 the Museum of Science and Industry has a display of more than 50 Christmas trees decorated in the Christmas styles of Puerto Rico, Poland, Germany, Iceland, India, Italy and other countries.

Zoolights Festival - No one brings the Christmas spirit to children better than the Lincoln Park Zoo. In November they start adorning the zoo with gigantic animal sculptures that illuminate the night with beautiful arrays of light, putting ear-to-ear smiles on any child who sees the display. Who knew that the Christmas spirit could be encapsulated in a giant red giraffe?

Magnificent Mile Lights Festival - The event begins with a tree lighting festival similar to that at Rockefeller Center in New York City. But instead of one large tree, all the trees along Michigan Avenue are lit up.

Every day is something different during the festival. One day you will find Disney characters performing live on a specially made stage. Another will show that Main Street has been turned into a magical winter walk complete with carolers, cider stands and many holiday festivities.

The main event involves a parade of Disney characters in extravagant floats as Mickey himself lights 1 million white lights from Oak Street to Wacker Drive. One of the biggest fireworks shows you will ever witness marks the end of the festivities, leaving Christmas morning to look forward to.

Sources:
(http://www.chicagotraveler.com)

(http://www.chicago-travel-services.com/)

(http://www.lonelyplanet.com)