3 days in Houston & Chicago Itinerary

3 days in Houston & Chicago Itinerary

Created using Inspirock United States trip itinerary maker

Make it your trip
1
Houston
— 1 day
Fly
2
Chicago
— 1 night
Fly

S M T W T F S
2
3
4
5
6
7
8

Houston

— 1 day

Bayou City

Although urban sprawl remains synonymous with Houston, most of the city's tourist attractions lie within the relatively small downtown area, surrounded by diverse neighborhoods housing the nation's biggest African-American, Asian-American, and Latino communities.
Start off your visit on the 6th (Thu): explore the different monuments and memorials at Glenwood Cemetery and then see the interesting displays at Space Center Houston.

To see where to stay and other tourist information, go to the Houston trip planner.

The Route module shows you travel options from your home to Houston. In May, daily temperatures in Houston can reach 84°F, while at night they dip to 68°F. Finish up your sightseeing early on the 6th (Thu) so you can catch the flight to Chicago.

Things to do in Houston

Museums · Historic Sites

Chicago

— 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 7th (Fri), admire the striking features of Skydeck Chicago - Willis Tower, admire the striking features of Reliance Building, stroll around Millennium Park, then explore the world behind art at The Art Institute of Chicago, and finally admire the striking features of Chicago Cultural Center. Here are some ideas for day two: get curious at Museum of Science and Industry, get up close and personal with brilliant marine life at Shedd Aquarium, then ponder the design of Buckingham Fountain, and finally admire the landmark architecture of Chicago Board of Trade Building.

To see maps, photos, reviews, and tourist information, read our Chicago day trip planning tool.

Getting from Houston to Chicago by flight takes about 4.5 hours. Other options: drive; or do a combination of bus and train. Traveling from Houston in May, things will get a bit cooler in Chicago: highs are around 71°F and lows about 52°F. Finish your sightseeing early on the 8th (Sat) to allow enough time to fly back home.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums