16 days in Los Angeles, Chicago & Anchorage Itinerary

16 days in Los Angeles, Chicago & Anchorage Itinerary

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Route & dates

16 days in Los Angeles, Chicago & Anchorage Itinerary

Start: Auckland
Fly:  15​h 45​min
1
Los Angeles
— 4 nights
Fly:  7​h
2
Chicago
— 4 nights
Fly + Drive:  10​h
3
Anchorage
— 5 nights
Drive + Fly:  20​h
End: Auckland

4
nights
Los Angeles

Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Step out of the city life by going to Dolphin & Whale Watching and Crystal Cove. Do some cultural sightseeing at Ronald Reagan Presidential Library and Museum and Mission San Juan Capistrano. Venture out of the city with trips to Moonlight State Beach (in Encinitas), San Clemente Coastal Trail (in San Clemente) and Museum of Making Music (in Carlsbad). There's much more to do: examine the collection at The Nethercutt Collection, tour the pleasant surroundings at 26-Mile Bike Path, make a trip to The Wizarding World of Harry Potter, and get your bearings at The Huntington Library, Art Collections and Botanical Gardens.

To find ratings, maps, more things to do, and other tourist information, read Los Angeles trip builder site .

Auckland, New Zealand to Los Angeles is an approximately 16-hour flight. You can also do a combination of flight and bus; or do a combination of flight and train. The time zone changes from New Zealand Standard Time to Pacific Standard Time, which is usually a -20 hour difference. When traveling from Auckland in September, plan for much hotter days and somewhat warmer nights in Los Angeles: temperatures range from 34°C by day to 22°C at night. Wrap up your sightseeing on the 19th (Thu) to allow time to travel to Chicago.

Things to do in Los Angeles

Museums Parks Outdoors

Side Trips

The Huntington Library, Art Collections and Botanical Gardens, Moonlight State Beach, Crystal Cove, San Clemente Coastal Trail, Greystone Mansion and Park
Highlights from your plan
Dolphin & Whale Watching
Mission San Juan Capistrano ©
Mission San Juan Capistrano

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visiting Lakefront Trail and Kayaking & Canoeing will get you outdoors. Step off the beaten path and head to Starved Rock State Park and Chicago Riverwalk. You'll find plenty of places to visit near Chicago: Matthiessen State Park (in Utica), Cantigny Park (in Wheaton) and South Bend (University of Notre Dame, Grotto of Our Lady Lourdes, & more). There's still lots to do: admire the masterpieces at Milwaukee Art Museum, admire the landmark architecture of Holy Name Cathedral, examine the collection at Richard H. Driehaus Museum, and take in the spiritual surroundings of Basilica of St. Josaphat.

To find other places to visit, where to stay, reviews, and more tourist information, read our Chicago sightseeing planning app .

You can fly from Los Angeles to Chicago in 7 hours. Alternatively, you can do a combination of bus and flight; or drive. You'll lose 2 hours traveling from Los Angeles to Chicago due to the time zone difference. Traveling from Los Angeles in September, expect Chicago to be a bit cooler, temps between 30°C and 19°C. Finish your sightseeing early on the 24th (Tue) so you can travel to Anchorage.

Things to do in Chicago

Historic Sites Parks Museums

Side Trips

Milwaukee, South Bend, Utica, Cantigny Park, Baha'i House of Worship
Highlights from your plan
Basilica of the Sacred Heart ©
Basilica of the Sacred Heart
Starved Rock State Park ©
Starved Rock State Park
Lakefront Trail ©
Lakefront Trail

5
nights
Anchorage

Anchorage ©
Home to nearly half of Alaska's population, the port city of Anchorage covers a staggering area of over 4,900 sq km (1,900 sq mi) surrounded by mountains.
You'll explore the less-touristy side of things at Tony Knowles Coastal Trail and Portage Glacier. Take a break from the city and head to Flattop Mountain Trail and Friends of Eagle River Nature. Change things up with a short trip to Fishing Charters & Tours in Whittier (about 1h 20 min away). The adventure continues: explore the activities along Cook Inlet, examine the collection at Anchorage Museum at Rasmuson Center, look for all kinds of wild species at Star the Reindeer, and trek along Virgin Creek Falls Trail.

For traveler tips, ratings, and other tourist information, read our Anchorage trip planner .

Traveling by combination of flight and car from Chicago to Anchorage takes 10 hours. Alternatively, you can drive. The time zone difference when traveling from Chicago to Anchorage is minus 3 hours. Traveling from Chicago in September, you will find days in Anchorage are much colder (16°C), and nights are little chillier (7°C). Finish your sightseeing early on the 29th (Sun) so you can travel back home.

Things to do in Anchorage

Parks Outdoors Tours

Side Trip

Fishing Charters & Tours
Highlights from your plan
Tony Knowles Coastal Trail ©
Tony Knowles Coastal Trail
Friends of Eagle River Nature ©
Friends of Eagle River Nature
Portage Glacier ©
Portage Glacier

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