4 days in Chicago, Washington DC & Philadelphia Itinerary

4 days in Chicago, Washington DC & Philadelphia Itinerary

Created using Inspirock United States tour builder

Plan created by another user. Make it yours
1
Chicago
— 1 day
Drive
2
Washington DC
— 1 day
Drive
3
Philadelphia
— 1 day
Drive
4
Chicago
— 1 day

S M T W T F S
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18
19
20
21
22
23

1
day
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 19th (Tue): observe the fascinating underwater world at Shedd Aquarium, then admire the masterpieces at The Art Institute of Chicago, then stroll around Millennium Park, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

For reviews, other places to visit, more things to do, and other tourist information, you can read our Chicago holiday maker.

The Route module can give you travel options from your home to Chicago. In January in Chicago, expect temperatures between 32°F during the day and 18°F at night. Finish up your sightseeing early on the 19th (Tue) so you can travel to Washington DC.

Things to do in Chicago

Parks · Museums · Zoos & Aquariums

1
day
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.
Kick off your visit on the 20th (Wed): ponder the world of politics at White House, pause for some photo ops at Washington Monument, pause for some photo ops at Lincoln Memorial, pause for some photo ops at Vietnam Veterans Memorial, then get engrossed in the history at United States Holocaust Memorial Museum, and finally appreciate the history behind Jefferson Memorial.

Quickly create a custom-made itinerary for Washington DC using our trip planner.

Traveling by flight from Chicago to Washington DC takes 4 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. Expect somewhat warmer temperatures when traveling from Chicago in January; daily highs in Washington DC reach 44°F and lows reach 29°F. Finish your sightseeing early on the 20th (Wed) to allow enough time to take a train to Philadelphia.

Things to do in Washington DC

Museums

1
day
Philadelphia

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S.
On the 21st (Thu), pause for some photo ops at Rocky Statue, examine the collection at The Franklin Institute, then browse the eclectic array of goods at Reading Terminal Market, then ponder the world of politics at Independence Hall, and finally take a stroll around Kimmel Center for the Performing Arts.

To find ratings, photos, more things to do, and more tourist information, refer to the Philadelphia trip maker website.

Traveling by train from Washington DC to Philadelphia takes 2.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 41°F in January, and nighttime lows around 26°F. Finish up your sightseeing early on the 21st (Thu) so you can travel to Chicago.

Things to do in Philadelphia

Museums · Shopping · Historic Sites · Nightlife

1
day
Chicago

Windy City

Kick off your visit on the 22nd (Fri): admire the landmark architecture of 360 Chicago Observation Deck, then admire the landmark architecture of Chicago Cultural Center, then try to win big at Horseshoe Hammond, and finally have some family-friendly fun at Fox in a Box Chicago.

To see where to stay, maps, other places to visit, and other tourist information, read Chicago road trip planning website.

Fly from Philadelphia to Chicago in 4.5 hours. Alternatively, you can drive; or take a bus. You'll gain 1 hour traveling from Philadelphia to Chicago due to the time zone difference. Plan for slightly colder temperatures traveling from Philadelphia in January, with highs in Chicago at 32°F and lows at 18°F.

Things to do in Chicago

Fun & Games · Casinos · Theme Parks · Shopping

Side Trip