The fun never stops in Chicago. The Windy City celebrates year-round with festivals like Lollapalooza, Taste of Chicago, and the Magnificent Mile Lights Festival. 


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Night of 1,000 Jack-o’-Lanterns

Chicago Botanic Garden 1000 Lake Cook Rd, Glencoe, IL

The Chicago Botanic Garden gets in the Halloween spirit with 1,000+ hand-carved, glowing Jack-o’-Lanterns placed throughout the gardens. This is a ticketed event. 2021 Dates: October 13 – 17 and 20 – 24, 2021

WhiskyFest Chicago

Hyatt Regency 151 E Wacker Dr, Chicago, IL

Do you take your whisky neat or on the rocks? Either way, you’ll sample more than 300 whiskeys from across the globe at this boozy festival.

JASC Holiday Delight

4427 N. Clark St Chicago, IL

This Japanese festival includes traditional holiday celebrations, visits from Santa, taiko drumming, and more for all ages.

Christkindlmarket Chicago

Daley Plaza 50 W Washington St, Chicago, IL

This festival brings the German tradition of Christkindlesmarkt to Chicago with endless vendors, food and beverage packages, and more.

The Skating Ribbon at Maggie Paley Park

Maggie Daley Park 337 E Randolph St, Chicago, Illinois

Nothing says ‘white Christmas’ more than a snow-filled ice skating session at one of Chi-town’s best ice skating rinks. The Skating Ribbon at Maggie Paley Park is unique in that its curved serpentine structure makes it twice the length of a traditional ice skating rink.

Zoo Lights at Lincoln Park Zoo

Lincoln Park Zoo 2001 N Clark St, Chicago

When: Select dates November 19-January 2nd, 2022 Bright lights + Zoo animals = perfection! Get ready to witness the glow of millions of twinkling lights at one of Chi-town’s most beloved Holiday events. Zoo Lights at the Lincoln Park Zoo is a shining LED fueled extravaganza featuring hundreds of luminous displays, seasonal experiences, and an 18 foot Christmas Tree. This […]


Magnificent Mile Lights Festival

Magnificent Mile North Michigan Ave, Chicago, IL

Watch Magnificent Mile light up with holiday decorations and activities including a parade, tree lighting, and performances.

Light Up The Lake at Navy Pier

Navy Pier 600 E Grand Ave, Chicago, IL

Light up the Lake (formerly Winter Wonderfest) is Chicagoland's biggest indoor holiday festival this year. From ice skating to family-friendly activities, it’s impossible to be a Scrooge at this Navy Pier festival. Indoor attractions include an Arctic Express Train, the Candy Cane Lighthouse, the Chicago Blackhawks Ice Skating Rink, a Giant Decorated Tree, Winter Rules Mini Gold, and a visit […]

Twas’ The Night Before…

The Chicago Theatre 175 N State St, Chicago, Illinois

Twas’ The Night Before Christmas and all through the house, not a creature was stirring, not even an acrobatic mouse! Introduce children to the magic of Cirque du Soleil through their thrilling retelling of this classic Christmas tale.  Twas’ The Night Before offers splashy acrobatic spectacle, colorful artistry, and a sleigh full’s worth of good old-fashioned holiday cheer. Theatergoers of […]

Caroling at Cloud Gate

Millenium Park 201 E Randolph St, Chicago, IL

Participate in one of Chicago’s top holiday traditions by going caroling at Cloud Gate in Millennium Park.

One of a Kind Show and Sale

theMART 222 W Merchandise Mart Plaza, Chicago

As Chicago’s premier shopping event, this festival features 600+ makers, artists, and vendors.

Polar Express Train Ride

Chicago Union Station 225 S Canal St, Chicago, Illinois

All aboard, next stop, the North Pole! For all of those who still believe and those who have never stopped, now is your time to recreate the spellbinding enchantment of the Polar Express. The Chicago Union Station Polar Express Train Ride is an interactive theatrical experience that guarantees unforgettable festive memories.  Related Post: Most Festive Things to Do in Chicago […]

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