Did Route 66 go through Chicago?

Yes. Chicago is the eastern end of Route 66. The road began downtown near Lake Michigan and left the city heading southwest toward Joliet.

What is there to see on Route 66 in Chicago?

We list 47 stops in and around Chicago, mostly museums, archaeological sites and parks and nature areas. The ones our trip planner rates highest are Berwyn Route 66 Museum, Lou Mitchell's and Navy Pier. Every stop is on the map above with a photo where one exists, and the distance from the old road.

How far is Chicago from the next towns on Route 66?

Chicago sits at about mile 0 of Route 66, counting from Chicago. It is the eastern end of the road. Heading west, Joliet, IL is about 40 miles on. Distances are measured along the road and rounded.

Is Chicago a good place to stay overnight on Route 66?

Yes. Our trip planner uses Chicago as one of its main overnight towns, so on a two-week trip a day often ends here. Plan the stops in town for the evening or the next morning.

Route 66 town guide · Illinois

Route 66 in Chicago, Illinois

Chicago is where Route 66 begins. The old highway started in the Loop, a few blocks from Lake Michigan, and ran southwest out of the city toward Joliet, about 41 miles down the road. That makes Chicago mile 0 on our map, and the place most travelers spend their first night or their last.

About mile 0 of 2,448 from Chicago
47 stops in and around Chicago
Main overnight town

Tap a dot to see that stop here.

Tap a dot for the photo and a link to the stop (the fork-and-knife markers are places to eat). Open Chicago on the full map to filter by kind or add stops to your trip.

Most of the stops we list in and around Chicago are museums, because the start of the road sits in the middle of a big city's museum district. The Art Institute of Chicago, home of American Gothic and Nighthawks, is a short walk from the starting point, and the Field Museum and the Adler Planetarium sit together on the lakefront. For a proper road-trip send-off, Lou Mitchell's is the classic diner where many Route 66 drivers eat breakfast before heading west.

The Mother Road itself shows up just beyond the city line: the Berwyn Route 66 Museum is a small nonprofit museum about the highway in Berwyn, just west of Chicago. Back downtown, the Chicago Water Tower survived the Great Fire of 1871, and Navy Pier is the city's long lakefront playground, packed with food, theaters and family attractions. South of the city, a handful of archaeological sites mark villages that stood here long before Chicago did.

Practical note: Chicago is a big-city start, with heavy traffic and paid parking. Many travelers see the sights on foot or by transit, then pick up the car and head for Joliet and the Illinois prairie. Our planner treats Chicago as a main overnight town, and the whole drive to Santa Monica runs about 2,448 miles.

Top 10 Route 66 attractions in and around Chicago

Berwyn Route 66 MuseumA small nonprofit museum about the Mother Road in Berwyn, just west of Chicago.
Lou Mitchell'sChicago's 1923 breakfast diner on Jackson Boulevard, long called the first stop on Route 66.
Navy PierA long lakefront pier packed with food, theaters, parks and family attractions, a Chicago favorite.
Chicago Water TowerThe Gothic Revival tower that survived Chicago's Great Fire in 1871, right on the Magnificent Mile.
Art Institute of ChicagoWorld-famous paintings like American Gothic and Nighthawks, a short walk from where Route 66 begins.
Chicago Harbor LightA working lighthouse from 1893 at the mouth of Chicago's harbor, best seen from Navy Pier.
Brookfield ZooThe Chicago area's largest zoo, famous since 1934 for showing animals behind moats instead of cages.
Field Museum of Natural HistoryOne of the world's great natural history museums, with fossils, world cultures and 24 million objects.
Hull HouseThe surviving home of Jane Addams's famous settlement house, now a National Historic Landmark museum.
Four Nineteen BuildingA 1928 Chicago gas station built to look like a small brick house, with a canopy and two garage bays.