4 days in Chicago & San Antonio Itinerary

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

The Art Institute of Chicago and Richard H. Driehaus Museum will appeal to museum buffs. Your inner history buff will appreciate Chicago Riverwalk and Holy Name Cathedral. There's still lots to do: stroll through Lakefront Trail, contemplate the waterfront views at Chicago River, see the interesting displays at Money Museum at the Federal Reserve Bank, and take a tour by water with Boat Tours & Water Sports.

For other places to visit, photos, where to stay, and other tourist information, refer to the Chicago trip itinerary maker.

The Route module can give you travel options from your home to Chicago. In July, daytime highs in Chicago are 83°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 16th (Thu) early enough to travel to San Antonio.

As the state’s second largest city, San Antonio embodies Texas’ rich cultural heritage while maintaining the Old West charm of an oil town.

Kick off your visit on the 17th (Fri): steep yourself in history at The Alamo, then take an in-depth tour of Battle For Texas: The Experience, then take in the architecture and atmosphere at St Joseph Catholic Church, and finally pause for some serene contemplation at San Fernando De Bexar Cathedral.

For photos, ratings, other places to visit, and more tourist information, use the San Antonio sightseeing planner.

Traveling by flight from Chicago to San Antonio takes 6 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer temperatures when traveling from Chicago in July; daily highs in San Antonio reach 98°F and lows reach 75°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to travel back home.