Holidays
Your guide to Christkindlmarket Chicago
Christkindlmarket is one of Chicago’s most beloved holiday traditions. This free-admission outdoor market (recently featured in Hallmark Channel’s Holiday Touchdown: A Bears Love Story) brings…
Kelsey O'Connor
66 posts by Kelsey O'Connor
Festivals, Festivals & special events, Special events
Your guide to the Chicago Thanksgiving Parade 2026
Thursday, Nov. 26, 2026 State Street The Chicago Thanksgiving Parade, a local tradition for more than 90 years, kicks off the holiday season with a…
Festivals, Special events
The ultimate Chicago holiday itinerary: three days of festive fun
Chicago goes all out for the holidays, with something magical happening in every corner of the city. The season kicks off with the Christmas Tree…
Blog, Sports & recreation
A fall bucket list for sports fans in Chicago
It’s an incredible time to be a Chicago sports fan. Almost all of the city’s iconic sports teams are still playing, whether the season is…
Blog, Special events
Where to watch the Bank of America Chicago Marathon 2026: the ultimate spectator’s guide
One of just eight World Marathon Majors, the Bank of America Chicago Marathon is one of the planet’s most epic athletic events. Each year, more…
Architecture & history, Special events
16 unique places to discover during Open House Chicago 2026
Fall in Chicago is the best time of year for architecture lovers. The season brings top events like the annual Pullman House Tour, the Chicago…
Tours & attractions
9 of Chicago’s most haunted places
Chicago is a city with history — a whole lot of history, dating back to before the city’s founding in 1837. So it’s hardly surprising…
Articles, Holidays
Your guide to Chicago’s Arts in the Dark parade
The annual Arts in the Dark parade channels Chicago’s artistic spirit into a one-of-a-kind Halloween celebration. Packed with creative expression and spooky spectacle, Arts in…
Festivals & special events
Chicago House Music Festival and Conference
Aug. 27 – 30, 2026 Free admission • Millennium Park and beyond The Chicago House Music Festival is an annual celebration of Chicago house music…
Blog, Special events
Bud Billiken Parade 2026: Experience Chicago’s legendary South Side tradition
The 97th annual Bud Billiken Parade steps off Saturday, Aug. 8, 2026 at 10 a.m. on Dr. Martin Luther King Jr. Drive in Bronzeville, ending…
Blog, Hotels, Neighborhoods
Where to stay in Chicago: hotels and things to do by area
Chicago is a city of multitudes — skyscrapers and sparkling waterfronts, bustling city streets and sprawling green spaces, a cosmopolitan downtown and charming neighborhoods. And…
Articles, Museums & art
Free museums in Chicago
There are boundless opportunities to learn and explore at free museums in Chicago, from awe-inspiring art galleries to fascinating science exhibits to interactive hands-on experiences.…
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