4 days in Chicago & New Orleans Area Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Kick off your visit on the 25th (Thu): admire the landmark architecture of Skydeck Chicago - Willis Tower, then get up close and personal with brilliant marine life at Shedd Aquarium, then admire the masterpieces at The Art Institute of Chicago, and finally find something for the whole family at Fox in a Box Chicago.

For other places to visit, where to stay, maps, and more tourist information, you can read our Chicago trip builder.

Use the Route module to find suitable travel options from your home destination to Chicago. In February, daily temperatures in Chicago can reach 36°F, while at night they dip to 20°F. Wrap up your sightseeing on the 25th (Thu) early enough to fly to New Orleans.

Known for its Creole cuisine, rich musical tradition, and nearby swamps and plantations, New Orleans is one of the nation's oldest cities.

New Orleans is known for historic sites, nightlife, and museums. Your trip includes some of its best attractions: appreciate the extensive heritage of Jackson Square, take a stroll through Garden District, take in the architecture and atmosphere at St. Louis Cathedral, and examine the collection at Audubon Butterfly Garden and Insectarium.

To find other places to visit, maps, reviews, and more tourist information, read our New Orleans trip itinerary maker website.

Traveling by flight from Chicago to New Orleans takes 4 hours. Alternatively, you can drive; or take a train. Traveling from Chicago in February, expect nights in New Orleans to be much hotter, around 56°F, while days are somewhat warmer, around 56°F. Finish your sightseeing early on the 28th (Sun) so you can fly back home.