5 days in Chicago & West Hollywood Itinerary

5 days in Chicago & West Hollywood Itinerary

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Route & dates

5 days in Chicago & West Hollywood Itinerary

Start: Chicago
1
Chicago
— 2 nights
Fly:  7​h
2
West Hollywood
— 2 nights
Fly:  7​h
End: Chicago

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, appreciate the history behind Cloud Gate, enjoy breathtaking views from Skydeck Chicago - Willis Tower, and learn about wildlife with up-close encounters at Lincoln Park Zoo.

To see traveler tips, reviews, other places to visit, and tourist information, read Chicago vacation planner.

The Route module can give you travel options from your home to Chicago. February in Chicago sees daily highs of 36°F and lows of 20°F at night. Cap off your sightseeing on the 12th (Wed) early enough to travel to West Hollywood.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Frank Lloyd Wright's Unity Temple
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

2
nights
West Hollywood

West Hollywood ©
West Hollywood, occasionally referred to locally as WeHo, is a city in Los Angeles County, California, United States. Start off your visit on the 13th (Thu): stroll through Santa Monica State Beach, take a leisurely stroll along Santa Monica Pier, then browse the eclectic array of goods at Santa Monica Farmers Market, and finally stop by Fred Segal. On your second day here, shop like a local with Third Street Promenade and then don't miss a visit to Montana Avenue.

To find ratings, other places to visit, where to stay, and more tourist information, read our West Hollywood journey planning website .

You can fly from Chicago to West Hollywood in 7 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Pacific Standard Time (PST) is minus 2 hours. Prepare for much warmer weather when traveling from Chicago in February: high temperatures in West Hollywood hover around 66°F and lows are around 51°F. Wrap up your sightseeing by early afternoon on the 14th (Fri) to allow enough time to travel back home.

Things to do in West Hollywood

Shopping Parks Beaches

Side Trip

Santa Monica
Highlights from your plan
Fred Segal ©
Fred Segal
Santa Monica Pier ©
Santa Monica Pier
Santa Monica State Beach ©
Santa Monica State Beach

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