Itineraries, Museums & art
Chicago arts and culture weekend in the Loop
Take the ultimate Chicago culture trip to discover public art by the likes of Picasso and Chagall, art gallery districts exploding with fine art, incredible…
Classic Chicago itineraries
The can’t-miss things to see and do.
Itineraries
Spend the weekend in downtown Chicago
The Loop is Chicago’s vibrant urban and cultural hub, named for the distinctive elevated train tracks (called the ‘L’) that loop around it. You’ll find…
Itineraries
24 hours in downtown Chicago
With just one day to explore, you can make the most of your time with iconic, one-of-a-kind attractions and city experiences. Mix and match from…
Itineraries
Luxury Chicago weekend getaway
Live in the lap of luxury on your weekend escape in downtown Chicago. Bespoke tours, world-renowned restaurants, and couture shopping sprees are just the beginning.…
Family, Itineraries
Top 10 Chicago must-dos with teens or tweens
One thing teens and tweens will never call Chicago is boring. Whether they’re thrill-seekers, explorers, artists, shopaholics or knowledge hounds, these 10 must-dos will have…
Family, Itineraries
Spring break family fun in Chicago
Chicago is the perfect destination for a family-friendly spring escape. You can spend the day exploring hands-on exhibits at our interactive museums, boating through the…
Free & cheap, Itineraries
48-hour budget Chicago itinerary
Here’s the skinny on two days of budget-friendly Chicago sights and experiences, covering everything from beer tastings to neighborhood tours and attractions you won’t want…
Entertainment, Itineraries
Explore the Chicago World’s Fair
The Chicago World’s Fair in 1893 is one of the city’s most famous (and infamous) events. Often called “the fair that changed America”, the massive…
Itineraries
Explore Latino heritage in Chicago’s neighborhoods
Chicago is home to some of the most vibrant Latino communities in the country, including Pilsen, Little Village, and Humboldt Park. That’s where you’ll find…
Itineraries
Explore Asian culture in Chicago’s neighborhoods
Chicago is home to a melting pot of Asian cultures, from one of the oldest Chinese communities in the country to a vibrant mix of…
Itineraries
Explore Polish culture in Chicago’s neighborhoods
Chicago is home to a thriving Polish community that has been an integral part of our city’s culture for generations. The Polish population here is…
Itineraries
Explore Black culture and history in Chicago
Chicago’s African American community has had a lasting impact on our culture and history. The city’s first permanent settler was a Black man from Haiti,…
- 1
- 2
Explore hotels, flights, deals, and more
Plan your trip
