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The Ultimate Route 66 Road Trip

The ultimate guide to seeing the best of the Mother Road from Illinois to California in one week

  • 69
  • 39:07
  • 2,183 mi
  • $358
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Created by Annette - March 16th 2023

Route 66, and its 2,500 miles, is known affectionately as "The Mother Road." It's the quintessential cross-country road trip experience. From Chicago through the beating heart of America, the route officially ends at the Santa Monica Pier. The road reached peak popularity in the late 1940s and early '50s before being officially removed from the U.S. Highway System in 1985. After a few years, travelers from around the country and beyond started feeling tinges of nostalgia, and by the end of the 1980s it was once again becoming one of the most popular road trip routes.

Looking for more tips for your Route 66 trip? We've got you covered.

Mauston, Wisconsin, United States

1
186mi 02h 52m

Beach Park, Illinois, United States

1
2
14mi 00h 27m

14245 W Rockland Rd, Libertyville, IL, US

Lambs Farm

2
3
19mi 00h 27m
Photo of Home Alone House
4.0

671 Lincoln Ave., Winnetka, IL, US

Home Alone House

3
4
24mi 00h 58m

1300 S Lake Shore Dr, Chicago, IL, US

Adler Planetarium

4
5
0mi 00h 07m

1410 S Museum Campus Dr, Chicago, IL, US

Soldier Field

5
6
0mi 00h 03m
Photo of Field Museum of Natural History
4.4

1400 S Lake Shore Dr, Chicago, IL, US

Field Museum of Natural History

6
7
0mi 00h 06m

1200 S DuSable Lake Shore, Chicago, IL, US

Shedd Aquarium

7
8
6mi 00h 12m

5700 S DuSable Lake Shore Dr, Chicago, IL, US

Museum of Science and Industry

8
9
8mi 00h 21m
Photo of Chicago Skyline
5.0

Chicago, IL, US

Chicago Skyline

9
10
5mi 00h 24m
Photo of Wrigley Field
4.5

1060 W Addison St, Chicago, IL, US

Wrigley Field

10
11
6mi 00h 16m
Photo of Buckingham Fountain
4.5

301 S. Columbus Dr, Chicago, IL, US

Buckingham Fountain

11
12
1mi 00h 09m

1200 S Lakeshore Dr, Chicago, IL, US

Museum Campus

12
13
5mi 00h 18m

2001 N Clark St, Chicago, IL, US

Lincoln Park Zoo

13
14
2mi 00h 12m
Photo of Centennial Fountain and Water Arc
4.6

North bank Chicago River at McClurg Court, Chicago, IL, US

Centennial Fountain and Water Arc

14
15
1mi 00h 07m
Photo of Daley Bicentennial Plaza
4.0

337 E Randolph St, Chicago, IL, US

Daley Bicentennial Plaza

15
16
0mi 00h 07m
Photo of Grant Park
4.5

337 E Randolph St, Chicago, IL, US

Grant Park

16
17
1mi 00h 06m
Photo of Chicago Riverwalk
4.5

100 E. Wacker Drive, Chicago, IL, US

Chicago Riverwalk

17
18
0mi 00h 07m
Photo of Cloud Gate
4.5

201 E Randolph St, Chicago, IL, US

Cloud Gate

18
19
1mi 00h 14m
Photo of Union Station
3.9

225 S Canal St, Chicago, IL, US

Union Station

19