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Upcoming Chicago Events

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Winterland, a Thrilling and One of a Kind Immersive Holiday Experience
Dec24
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Winterland, a Thrilling and One of a Kind Immersive Holiday Experience

Prepare to step into a whimsical world of festive enchantment at Winterland, where, from the moment guests arrive, they’re transported into a wonderland of holiday delights.  Experience…

Tuesday, December 24th
2:00 p.m.9:00 p.m.
Navy Pier
600 East Grand Avenue
Chicago Christmas Eve Premier Dinner Cruise on Lake Michigan
Dec24
Tours & Attractions

Chicago Christmas Eve Premier Dinner Cruise on Lake Michigan

An unforgettable celebration of holiday cheer and fine dining awaits on our Premier Chicago Christmas Eve Dinner Cruise. This festive evening on Lake Michigan features…

Tuesday, December 24th
6:00 p.m.10:00 p.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Christmas Eve Premier Plus Dinner Cruise
Dec24
Tours & Attractions

Christmas Eve Premier Plus Dinner Cruise

Come together with loved ones for a dazzling holiday celebration complete with fine dining, up-close skyline views, and unparalleled entertainment aboard our Premier Plus Chicago…

Tuesday, December 24th
7:00 p.m.10:00 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
Big Bus Tours’ Sunset Live Tour
Dec24
Tours & Attractions

Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available now through Oct.…

Tuesday, December 24th
7:30 p.m.9:00 p.m.
63 West Ontario Street Chicago, IL 60654
63 West Ontario Street
Summer & Fall Afterwork Sunset Cruises on Lake Michigan
Dec24
Tours & Attractions

Summer & Fall Afterwork Sunset Cruises on Lake Michigan

 Experience summer on Lake Michigan with our weekday evening cruises featuring fireworks*, sunsets, skyline views, and cocktails starting May 27th, 2024. Unwind after work with…

Tuesday, December 24th
7:30 p.m.10:00 p.m.
DuSable Harbor 200 N Breakwater Access
DuSable Harbor 200 N Breakwater Access
City Cruises Holiday Fireworks and Drone Dinner Cruises
Dec25
Tours & Attractions

City Cruises Holiday Fireworks and Drone Dinner Cruises

Embark on an unforgettable evening filled with magic on a Holiday Fireworks or Drone Dinner Cruise on Lake Michigan or the Chicago River. Savor the…

Wednesday, December 25th
12:00 a.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Flyover Chicago: Two Flying Journeys Under One Roof
Dec25
Tours & Attractions

Flyover Chicago: Two Flying Journeys Under One Roof

Flyover, one of the city’s most exciting attractions to open in 2024, has launched an exciting new double feature that pairs their immersive Believe Chicago…

Wednesday, December 25th
Navy Pier 600 East Grand Avenue Chicago, IL
600 East Grand Avenue
Dressed in History: A Costume Collection Retrospective
Dec25
Museums, Galleries & Exhibitions, Tours & Attractions

Dressed in History: A Costume Collection Retrospective

What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…

Wednesday, December 25th
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
BRICK-Tastic Spring Break at LEGOLAND Discovery Center Chicago
Dec25
Tours & Attractions

BRICK-Tastic Spring Break at LEGOLAND Discovery Center Chicago

Spring Break memories will last a lifetime at the ultimate indoor LEGO® playground! Jump into a world of creativity, color and playful learning at LEGOLAND…

Wednesday, December 25th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Brick-or-Treat: Monster Party!
Dec25
Tours & Attractions

Brick-or-Treat: Monster Party!

Chicagoland’s top family Halloween event is here! Daily from September 27th – October 31st, families can get into the Halloween spirit as LEGO® Monsters take over LEGOLAND Discovery…

Wednesday, December 25th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Homeschool Days at PEPPA PIG World of Play Chicago
Dec25
Tours & Attractions

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Wednesday, December 25th
10:00 a.m.5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
Holiday Bricktacular
Dec25
Tours & Attractions

Holiday Bricktacular

Build the best memories at Chicago’s top family holiday event, Holiday Bricktacular! Daily from November 29th – January 5th, families can enjoy a winter wonderland…

Wednesday, December 25th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Christmas Day Premier Plus Brunch Cruise on the Chicago River
Dec25
Tours & Attractions

Christmas Day Premier Plus Brunch Cruise on the Chicago River

Delight in the merriment on Christmas Day reveling in breathtaking skyline views and unforgettable moments with family on our Premier Plus Chicago Christmas Day Brunch…

Wednesday, December 25th
12:00 p.m.2:30 p.m.
City Cruises – River Esplanade
455 N Cityfront Plaza Dr
Winterland, a Thrilling and One of a Kind Immersive Holiday Experience
Dec25
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions, Tours & Attractions

Winterland, a Thrilling and One of a Kind Immersive Holiday Experience

Prepare to step into a whimsical world of festive enchantment at Winterland, where, from the moment guests arrive, they’re transported into a wonderland of holiday delights.  Experience…

Wednesday, December 25th
2:00 p.m.9:00 p.m.
Navy Pier
600 East Grand Avenue
Tropical Wednesdays
Dec25
Tours & Attractions

Tropical Wednesdays

Immerge yourself in a cultural experience as Latin dances come alive on Taylor street – Salsa, Bachata, Cumbia, and Cha Cha Cha with margarita!

Wednesday, December 25th
6:00 p.m.8:00 p.m.
Vintage Bar Chicago
1449 W. Taylor St.
Christmas Day Premier Dinner Cruise on Lake Michigan
Dec25
Tours & Attractions

Christmas Day Premier Dinner Cruise on Lake Michigan

An unforgettable celebration of holiday cheer and fine dining awaits on our Premier Chicago Christmas Day Dinner Cruise. This festive evening on Lake Michigan features…

Wednesday, December 25th
6:00 p.m.9:00 p.m.
Big Bus Tours’ Sunset Live Tour
Dec25
Tours & Attractions

Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available now through Oct.…

Wednesday, December 25th
7:30 p.m.9:00 p.m.
63 West Ontario Street Chicago, IL 60654
63 West Ontario Street
City Cruises Holiday Fireworks and Drone Dinner Cruises
Dec26
Tours & Attractions

City Cruises Holiday Fireworks and Drone Dinner Cruises

Embark on an unforgettable evening filled with magic on a Holiday Fireworks or Drone Dinner Cruise on Lake Michigan or the Chicago River. Savor the…

Thursday, December 26th
12:00 a.m.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United States
Flyover Chicago: Two Flying Journeys Under One Roof
Dec26
Tours & Attractions

Flyover Chicago: Two Flying Journeys Under One Roof

Flyover, one of the city’s most exciting attractions to open in 2024, has launched an exciting new double feature that pairs their immersive Believe Chicago…

Thursday, December 26th
Navy Pier 600 East Grand Avenue Chicago, IL
600 East Grand Avenue
Dressed in History: A Costume Collection Retrospective
Dec26
Museums, Galleries & Exhibitions, Tours & Attractions

Dressed in History: A Costume Collection Retrospective

What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…

Thursday, December 26th
9:30 a.m.4:30 p.m.
Chicago History Museum
1601 N. Clark St.
BRICK-Tastic Spring Break at LEGOLAND Discovery Center Chicago
Dec26
Tours & Attractions

BRICK-Tastic Spring Break at LEGOLAND Discovery Center Chicago

Spring Break memories will last a lifetime at the ultimate indoor LEGO® playground! Jump into a world of creativity, color and playful learning at LEGOLAND…

Thursday, December 26th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Brick-or-Treat: Monster Party!
Dec26
Tours & Attractions

Brick-or-Treat: Monster Party!

Chicagoland’s top family Halloween event is here! Daily from September 27th – October 31st, families can get into the Halloween spirit as LEGO® Monsters take over LEGOLAND Discovery…

Thursday, December 26th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
Homeschool Days at PEPPA PIG World of Play Chicago
Dec26
Tours & Attractions

Homeschool Days at PEPPA PIG World of Play Chicago

Join us for Homeschool Days at Peppa Pig World of Play Chicago, where preschool families can enjoy an OINKTASTIC discount! Experience the magic of Peppa…

Thursday, December 26th
10:00 a.m.5:00 p.m.
Peppa Pig World of Play Chicago
5 Woodfield Mall
Holiday Bricktacular
Dec26
Tours & Attractions

Holiday Bricktacular

Build the best memories at Chicago’s top family holiday event, Holiday Bricktacular! Daily from November 29th – January 5th, families can enjoy a winter wonderland…

Thursday, December 26th
10:00 a.m.5:00 p.m.
LEGOLAND Discovery Center Chicago
601 N. Martingale Road
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