Articles, Itineraries
24 hours in downtown Chicago
Only have one day to explore downtown Chicago? No problem. You can make the most of your time while still hitting the city’s most iconic…
Classic Chicago itineraries
The can’t-miss things to see and do.
Articles, Bucket list, Itineraries, Parks & outdoors
Things to do in Chicago in the spring
What’s spring like in Chicago? Tulips bloom along iconic Michigan Avenue, cherry blossoms fill the Japanese garden in Jackson Park, and the Lakefront Trail fills…
Family, Itineraries
Top Chicago must-dos with teens or tweens
A family vacation to Chicago will be anything but basic. And it’s an especially perfect destination if you have teens and tweens in tow. Chicago…
Family, Itineraries
30+ kid-friendly things to do in Chicago
Chicago is a place where kids’ imaginations soar, with endless things to do and see around every corner. From hands-on museums and sprawling parks to…
Family, Itineraries
Spring break family fun in Chicago
Chicago is the perfect destination for a family-friendly spring escape — and we’ve got some spring break ideas that are sure to be a hit…
Architecture & history, Itineraries
Your guide to Chicago’s iconic architecture
Chicago’s stunning cityscape has been shaped by some of the biggest names in architecture — Louis Sullivan, Frank Lloyd Wright, Mies van der Rohe, Jeanne…
Food & drink, Itineraries
Chicago neighborhoods for food lovers
No matter where you go in Chicago, you’ll find a diverse selection of places to eat and drink in every corner of our city. These…
Architecture & history, Itineraries
Chicago architecture tour: two-day itinerary
From Frank Lloyd Wright’s Prairie School to skyscraper cool, you’ll find architecture that’s just your style in Chicago. This self-guided architecture tour covers some of…
Itineraries
Great Chicago date night ideas
Chicago has something for every kind of date, from cozy bars perfect for a first date to romantic restaurants worthy of milestone anniversaries. Whether it’s…
Itineraries, Parks & outdoors
2 days, 2 Chicago waterfronts
The waterfront is a center of life in Chicago. It’s where discoveries are made and adventures begin. Dedicate one day each to exploring the Chicago…
Itineraries
Been to Chicago? Do this next time.
It only takes one trip to Chicago to fall in love. Our skyline, our food, our festivals, museums, neighborhoods, and so much more make it…
Itineraries
How to spend a romantic weekend in Chicago
Chicago is the perfect spot for a romantic weekend getaway. You and your sweetheart can enjoy a scenic bike ride along the lake, bucket-list fine…
- 1
- 2
Explore Chicago hotels, flights, deals, and more
Plan your trip
