33 days in Chicago & Los Angeles Itinerary

33 days in Chicago & Los Angeles Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Fly
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Chicago
— 14 nights
Fly
2
Los Angeles
— 18 nights
Fly

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Chicago

— 14 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Kline Creek Farm (in West Chicago), Naperville Historic District (in Naperville) and Wheaton (First Division Museum at Cantigny & Illinois Prairie Path). The adventure continues: admire the masterpieces at The Art Institute of Chicago, take a tour by water with Boat Tours & Water Sports, wander the streets of The Magnificent Mile, and engage your brain at Field Museum.

For maps, other places to visit, more things to do, and other tourist information, read our Chicago road trip planning site.

London, UK to Chicago is an approximately 12-hour flight. The time zone difference when traveling from London to Chicago is minus 6 hours. Prepare for somewhat warmer weather when traveling from London in September: high temperatures in Chicago hover around 30°C and lows are around 19°C. Finish your sightseeing early on the 30th (Thu) so you can fly to Los Angeles.

Things to do in Chicago

Parks · Museums · Historic Sites · Outdoors

Side Trips

Los Angeles

— 18 nights

City of Angels

Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Change things up with these side-trips from Los Angeles: Beverly Hills (Rodeo Drive & Mulholland Drive), The Getty Villa (in Malibu) and Anaheim (Guardians of the Galaxy – Mission: BREAKOUT!, Disneyland Park, &more). Pack the 13th (Wed) with family-friendly diversions at Universal Studios Hollywood. Next up on the itinerary: take a leisurely stroll along Santa Monica Pier, examine the collection at The Getty Center, see the sky in a new way at Griffith Observatory, and don't miss a visit to Two Rodeo Drive.

To find other places to visit, maps, more things to do, and tourist information, read our Los Angeles road trip planning tool.

Fly from Chicago to Los Angeles in 6 hours. Alternatively, you can drive; or do a combination of train and bus. The time zone difference when traveling from Chicago to Los Angeles is minus 2 hours. Traveling from Chicago in September, expect nights in Los Angeles to be about the same, around 22°C, while days are somewhat warmer, around 34°C. Finish your sightseeing early on the 18th (Mon) so you can fly back home.

Things to do in Los Angeles

Parks · Theme Parks · Museums · Outdoors

Side Trips