5 days in Washington DC & Chicago and Beyond Itinerary

5 days in Washington DC & Chicago and Beyond Itinerary

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Route & dates

5 days in Washington DC & Chicago and Beyond Itinerary

Start: Toronto
Fly:  4​h 15​min
1
Washington DC
— 2 nights
Fly:  3​h 45​min
2
Chicago
— 2 nights
Fly + ferry:  4​h 30​min
End: Toronto

2
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Washington DC is known for museums, historic sites, nightlife, zoos & aquariums, and parks. Your plan includes some of its best attractions: see the interesting displays at National Air and Space Museum, admire the masterpieces at National Gallery of Art, get a sense of history and politics at White House, and pause for some photo ops at Vietnam Veterans Memorial.

For photos, where to stay, other places to visit, and more tourist information, refer to the Washington DC trip itinerary site .

Toronto, Canada to Washington DC is an approximately 4.5-hour flight. You can also do a combination of flight, bus, and subway; or drive. Traveling from Toronto in June, expect Washington DC to be somewhat warmer, temps between 35°C and 24°C. Finish your sightseeing early on the 4th (Thu) so you can travel to Chicago.

Things to do in Washington DC

Museums
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 5th (Fri): get curious at Museum of Science and Industry, observe the fascinating underwater world at Shedd Aquarium, then walk around Millennium Park, and finally pause for some photo ops at Cloud Gate. On the next day, take in panoramic vistas at 360 Chicago Observation Deck, ponder the design of Buckingham Fountain, then explore the world behind art at The Art Institute of Chicago, and finally enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To see maps, other places to visit, photos, and more tourist information, read our Chicago trip builder site .

You can fly from Washington DC to Chicago in 4 hours. Alternatively, you can do a combination of train and flight; or drive. You'll gain 1 hour traveling from Washington DC to Chicago due to the time zone difference. Expect a bit cooler temperatures when traveling from Washington DC in June; daily highs in Chicago reach 32°C and lows reach 20°C. Wrap up your sightseeing on the 6th (Sat) early enough to travel back home.

Things to do in Chicago

Museums Parks Childrens Museums
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

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