Chicago IL Events

Shamrocks, Christmas parades, and Weiner schnitzel, oh my! The rich diversity of Chicago IL events will keep visitors entertained from January to December. Winter, Spring, Summer, and Fall Chicago has an event for all.

Holidays in Chicago

Kick off the holiday season “Chicago Style.” No, we don’t mean deep dish with extra cheese. Be dazzled by millions of lights, parades, and live entertainment at the Magnificent Mile Lights Festival. This event spans two days and is filled with magic. First, catch the Chicago Christmas tree lighting ceremony. You won’t want to miss festive live entertainment and a photo opportunity with Santa Claus himself!

Next, gaze in awe at spectacular light displays while reveling in the beauty of over 200 Christmas trees. However, the can’t-miss grand finale is the Chicago Christmas Parade. Secure your spot along the route and watch as dozens of floats, marching bands, and musical performers jingle down Michigan Ave.

Ready to ring in the New Year? The hardest decision of that December evening is deciding where to party! We recommend starting at the famous Navy Pier. It’s the epicenter of NYE entertainment. Breathtaking fireworks, DJs, and dancing, along with gourmet appetizers and drinks galore, will ensure you leave the year behind with a bang! Interested in learning more? Check out our in-depth guide on Chicago NYE events.

Chicago Spring Events

As winter winds down and promises of spring are in the air, Chicago events continue to deliver. Does the Luck of the Irish run through your veins? Watch in awe as bright green swirls and spreads through the typically azure waters at the iconic dyeing of the Chicago river for St. Patrick’s Day.

Do you find yourself fascinated with all things flora and fauna? Submerse yourself in a sea of color, petals, Botanics, and a master gardener or two when you make time for the Chicago Flower Show at Navy Pier.

Summer Events in Chicago

Summer in Chi-town can only mean one thing… concerts! Catch live entertainment all over the Windy City at any of their world-class venues. Sit under the stars at an amphitheater while bobbing along to the sounds of your favorite artist. Or, sit on the mezzanine level in a historic theater to get a bird’s eye view. Is your favorite band an arena sell-out type? Make your way to Soldier Field or Wrigley Field to sing along with 50,000 of your fellow fans!

Chicago Fall Events

Is fall your favorite of all? Celebrate the changing leaves and crisp morning air with events like Apple Fest and Chicago German-American Oktoberfest! Chow down on the likes of apple pie, apple fritters, and apple dumplings while you peruse local artisans’ handmade goods, all while listening to live music.

Grab your lederhosen and head to Lincoln square to get your fill of authentic German treats, live music, and of course, beer! Witness the Von Steuben Parade, attend a German Mass, and help the kiddos win at fun carnival games.

Chicago Awaits

Need more activities to fill your time in the Windy City? Check out Tripster’s full lineup of discounted tickets to experiences like Legoland Chicago, Medieval Times Dinner Show, Blue Man Group, and Shoreline Sightseeing Boat Tours. Need a Chicago hotel? Keep that budget in check with a Chicago vacation or hotel package. As always, rest easy knowing you’re guaranteed our best rates online!

Events Chicago IL are endless. So what will you find to do in Chi-town?


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Written by Kelsi Johnson

Meet Kelsi, a Colorado-based writer and editor for Tripster. When she isn't behind the keyboard crafting engaging travel content, you'll find her hiking...


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