19 days in Chicago & Santa Monica Itinerary

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

Get out of town with these interesting Chicago side-trips: Kneeland-Walker House (in Wauwatosa), Milwaukee (Milwaukee Art Museum & Harley-Davidson Museum) and The Apple Hut (in Beloit). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, meet the residents at Lincoln Park Zoo, laugh and play at Navy Pier, and get curious at Museum of Science and Industry.

To find reviews, other places to visit, where to stay, and more tourist information, you can read our Chicago trip itinerary maker site.

Alicante, Spain to Chicago is an approximately 14.5-hour flight. Traveling from Alicante to Chicago, you'll gain 7 hours due to the time zone difference. Expect little chillier temperatures when traveling from Alicante in August; daily highs in Chicago reach 33°C and lows reach 22°C. Finish your sightseeing early on the 28th (Mon) to allow enough time to fly to Santa Monica.

A famed resort town since the early 20th century, Santa Monica sits on the picturesque Santa Monica Bay, bordered on three sides by the city of Los Angeles.

Kick off your visit on the 30th (Wed): browse the different shops at Two Rodeo Drive, don't miss a visit to Rodeo Drive, stroll around Beverly Gardens Park, then enjoy the sand and surf at Santa Monica State Beach, and finally take in the waterfront at Santa Monica Pier.

To find ratings, traveler tips, other places to visit, and other tourist information, you can read our Santa Monica planner.

Fly from Chicago to Santa Monica in 6 hours. Alternatively, you can drive; or do a combination of train, bus, and tram. Traveling from Chicago to Santa Monica, you'll gain 2 hours due to the time zone difference. Expect a bit cooler weather when traveling from Chicago in August: highs in Santa Monica hover around 28°C, while lows dip to 21°C. Finish up your sightseeing early on the 30th (Wed) so you can travel back home.