3 days in San Mateo & Chicago Itinerary

3 days in San Mateo & Chicago Itinerary

Created using Inspirock United States trip planner

Make it your trip
Drive
1
San Mateo
— 1 night
Drive to San Francisco International Airport, Fly to Chicago
2
Chicago
— 1 night
Fly

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San Mateo

— 1 night
San Mateo is a city in San Mateo County, California, located in the high-tech enclave of Silicon Valley in the San Francisco Bay Area. On the 15th (Fri), cruise along Peninsula and then enjoy the scholastic atmosphere at Stanford University.

For maps, reviews, and tourist information, you can read our San Mateo online trip itinerary maker.

San Francisco to San Mateo is an approximately half hour car ride. In October in San Mateo, expect temperatures between 73°F during the day and 56°F at night. Finish your sightseeing early on the 16th (Sat) to allow enough time to travel to Chicago.

Things to do in San Mateo

Scenic Drive · Outdoors

Side Trip

Highlights from your trip

Chicago

— 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 16th (Sat): engage your brain at Museum of Science and Industry and then get a new perspective on things with Boat Tours & Water Sports. On the 17th (Sun), you'll have a packed day of sightseeing: meet the residents at Shedd Aquarium, then make a trip to Millennium Park, then explore the world behind art at The Art Institute of Chicago, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see traveler tips, ratings, where to stay, and other tourist information, read Chicago day trip planner.

Use the Route module to find suitable travel options from San Mateo to Chicago. Traveling from San Mateo to Chicago, you'll lose 2 hours due to the time zone difference. Prepare for little chillier weather when traveling from San Mateo in October: high temperatures in Chicago hover around 65°F and lows are around 49°F. Finish your sightseeing early on the 17th (Sun) to allow enough time to fly back home.

Things to do in Chicago

Museums · Parks · Childrens Museums · Tours