15 days in Los Angeles & Chicago Itinerary

15 days in Los Angeles & Chicago Itinerary

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Route & dates

15 days in Los Angeles & Chicago Itinerary

Start: New York City
Fly:  8​h 45​min
1
Los Angeles
— 8 nights
Fly:  7​h
2
Chicago
— 5 nights
Fly + bus:  4​h 45​min
End: New York City

8
nights
Los Angeles

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Deepen your sense of the past at sights like Santa Monica Pier and El Pueblo de Los Angeles. You'll find plenty of places to visit near Los Angeles: Anaheim (Disneyland Park & Disney California Adventure Park) and Ocean Avenue (in Santa Monica). Pack the 15th (Tue) with family-friendly diversions at Universal Studios Hollywood. There's much more to do: see the sky in a new way at Griffith Observatory, explore the different monuments and memorials at Hollywood Forever Cemetery, admire the striking features of Walt Disney Concert Hall, and tour the pleasant surroundings at Venice Beach and Boardwalk.

To see more things to do, maps, other places to visit, and other tourist information, you can read our Los Angeles trip planner .

New York City to Los Angeles is an approximately 9-hour flight. You can also do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 3 hours traveling from New York City to Los Angeles. In September in Los Angeles, expect temperatures between 85°F during the day and 66°F at night. Finish up your sightseeing early on the 21st (Mon) so you can travel to Chicago.

Things to do in Los Angeles

Theme Parks Historic Sites Museums

Side Trips

Anaheim, Santa Monica
Highlights from your plan
Santa Monica Pier ©
Santa Monica Pier
Hollywood Walk of Fame ©
Hollywood Walk of Fame
Ocean Avenue ©
Ocean Avenue

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Millennium Park and Ernest Hemingway Birthplace will appeal to history buffs. Explore the numerous day-trip ideas around Chicago: Spicer Lake County Park (in New Carlisle) and South Bend (University of Notre Dame, Basilica of the Sacred Heart, & more). The adventure continues: admire the masterpieces at The Art Institute of Chicago, take in the waterfront at Navy Pier, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and get to know the resident critters at Lincoln Park Zoo.

For maps, ratings, where to stay, and tourist information, you can read our Chicago visit planning tool .

Getting from Los Angeles to Chicago by flight takes about 7 hours. Other options: do a combination of bus and flight; or drive. The time zone difference moving from Pacific Standard Time to Central Standard Time is 2 hours. In September, Chicago is slightly colder than Los Angeles - with highs of 78°F and lows of 61°F. Finish up your sightseeing early on the 27th (Sun) so you can travel back home.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

South Bend, Oak Park, Spicer Lake County Park
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart

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