Route 66 in Chicago, Illinois

Last updated on May 2nd, 2024 at 12:01 pm

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Established in 1926, Route 66, otherwise known as “The Mother Road,” has long served as the ultimate path for anyone taking a great American road trip. The journey spans around 2,448 miles through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. And, at the start of it all, is Route 66 in Chicago, Illinois.

In 1926, Route 66 officially stretched its asphalt legs, connecting Chicago to Santa Monica, California. Although where exactly that starting point was changed numerous times throughout the years. The original Route 66 alignment had Jackson Boulevard and Michigan Avenue as the iconic starting point for what would become an iconic road, where hopeful adventurers and families piled into their cars, chasing dreams westward. After the 1933 World’s Fair, the highway’s eastern boundary was extended to Grant Park at Jackson and Lake Shore Drive. In the 1950s, the official Chicago starting point shifted to Adams Street and Michigan Avenue due to traffic changes, after Jackson Drive became an east-facing one-way street.

With the completion of the Interstate Highway System in the mid-1970s, Route 66’s days as the main artery of cross-country travel were numbered. Although the road wouldn’t be officially decommissioned until 1985, the final official Chicago Route 66 highway marker was taken down in January 1977.

That could have easily been the end for Route 66 in Chicago. But, nearly twenty years later, a resurgence of nostalgia for the popular route began to emerge. In 1995 the Illinois Route 66 Association spearheaded an initiative to erect new historical markers along the original path. These brown signs with a shield designated the route as “Historic Route 66.” This project helped revitalize interest in the historic highway and paved the way for further preservation efforts.

Today you will find multiple Route 66 Begin signs on Adams, between Michigan Avenue and Wabash. Start your Route 66 journey there and then continue traveling west on Adams (or Jackson to stop for a pre-road-trip breakfast at Lou Mitchell’s) before turning onto W Ogden Ave/Old Rte 66 and continuing your Route 66 road trip across the rest of Illinois.

Want to make the most of your time on Route 66 in Chicago, Illinois? Explore the essential stops, find more things to do, and book the perfect pre-road trip hotel below.

Route 66 in Chicago, Illinois

Essential Route 66 Chicago Stops

While Chicago marks the start of Route 66, the city doesn’t hold much fanfare for the famed road. You won’t find many businesses or attractions that capitalize on their location. Still, there are a few must-experience places that have become synonymous with The Mother Road and the start of the journey. Here are some essential Route 66 Chicago stops to add to your itinerary.

Historic Route 66 Begin Sign in Chicago, Illinois - Route 66 Road Trip Attraction

Historic Route 66 Begin Sign

Every great Route 66 road trip starts here: the Historic Route 66 Begin Sign in Chicago, Illinois.

You can actually find three Route 66 start signs in downtown Chicago: one on a post above the stoplight at the northwest corner of Adams and Michigan Avenue (right across the street from the Art Institute of Chicago), one across the street in the middle of the block on Adams (probably the most-stopped and photographed), and another, often covered in stickers, at the small park at the corner of Adams and Wabash, underneath the el.

For those traveling east, find the Historic Route 66 End Sign at E. Jackson Blvd and S. Michigan Ave.

Pancakes and bacon at Lou Mitchell’s Restaurant in Chicago, Illinois Route 66 Diner

Lou Mitchell’s Restaurant

Start your Route 66 road trip off right with a good breakfast at Lou Mitchell’s restaurant in Chicago, Illinois.

Lou Mitchell’s opened in 1923 and its location at the start of Route 66 made it a quintessential stop before traveling the Mother Road. Choose from an impressive menu that hasn’t changed much from the start. Pancakes, waffles, and skillets are offered alongside the “world’s best” coffee, homemade bread, pastries, and fresh-squeezed orange juice.

Lou Mitchell’s is known as being “the first stop on the Mother Road” and was listed on the National Register of Historic Places in 2006.

Old St. Patrick’s Church

Built in 1856, St. Patrick’s Church is the oldest church in Chicago. It is also one of the few local buildings that survived the 1871 Chicago Fire. Located on the Adams alignment, motorists would stop before their travels to pray for a safe journey west.

The Berghoff Restaurant in Chicago, Illinois

The Berghoff Restaurant

Having opened in 1898, The Berghoff Restaurant in Chicago is older than The Mother Road itself. Herman Berghoff opened the restaurant after seeing the success of his beer stand at the 1893 World’s Fair and it has been (almost) continually operating ever since.

Located right on Route 66, The Berghoff became a popular destination for both locals and travelers alike. Stop in for some tasty German food and an ice-cold beer (or famous frosty root beer).

The Art Institute of Chicago

The Art Institute of Chicago

Founded in 1879, The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It’s located right at the start of Route 66, across the street from the famous begin sign. The museum hosts special exhibits alongside an impressive permanent collection featuring revered works like and Vincent van Gogh’s The Bedroom, Edward Hopper’s Nighthawks, Grant Wood’s American Gothic, and Georges Seurat’s A Sunday on La Grande Jatte.

Castle Car Wash

Castle Car Wash was a castle-shaped car wash built in 1925 by Louis Ehrenberger. While the business is no longer in operation, you can still pull over for photos of this historical landmark.

More Things to Do in Chicago

Depending on how much time you plan to spend in the city, your stop in Chicago might take you beyond the typical Route 66. Many travelers choose to spend an extra day, or extra week, in The Windy City to make the most of what Chicago has to offer has to offer. And there is no shortage on things the city has to offer. Here are some more things to do in Chicago to add to your Route 66 road trip itinerary.

The Field Museum in Chicago, Illinois.

Explore Chicago Museums

Chicago museums go beyond The Art Institute. Whether you want to learn more about science, history, sea life, or the stars, there’s a museum to add to your Route 66 itinerary. Here are some of the best museums in Chicago:

Planning on filling your vacation with Chicago museums? Consider getting a Chicago CityPASS, which offers significant savings on five major attractions and experiences.

Take an Architectural Boat Tour

Learn more about the city at the start of it all. In between the quintessential stops taking photos at the Begin Route sign and grabbing breakfast Lou Mitchell’s, there’s a whole city to explore. One of the best ways to get to know Chicago is by taking one of the architectural boat tours offered several times throughout the day. Climb aboard a cruise and get unobstructed views of and in-depth understanding of some of the best sights in the city. While it’s not a Route 66-specific activity, it is a cool experience you can only have in Chicago.

See Chicago From Above

Some of the best ways to see Chicago are from above. Take the elevator to the top of some of Chicago’s tallest buildings to get a bird’s eye view of the city and the start of Route 66. Both Skydeck Chicago at the top of Willis Tower and the 360 Chicago Observation Deck at the top of the John Hancock Building offer incredible views and unique experiences that allow you to step out over the city, if you’re not afraid of heights.

Get Outside

When the weather is nice, Chicago comes alive with outdoor activities. Take a walk and explore some of the best outdoor attractions in Chicago: Lincoln Park Zoo, Maggie Daley Park, the Magnificent Mile, the River Walk, Millennium Park (home of Cloud Gate/The Bean), Navy Pier, and Grant Park.

Explore Chicago Neighborhoods

Many Route 66 travelers choose to stay downtown and explore the area directly surrounding the start of The Mother Road. But Chicago is more than just downtown. If you’re tacking a Chicago vacation onto your Route 66 road trip, spend some time out of downtown and in the many neighborhoods of Chicago. Hop on the el and take in a Cubs game in Wrigleyville; try the many local restaurants, bars, and shops in Lakeview, Wicker Park, the West Loop, or Lincoln Square; see a theatre performance at Steppenwolf in Lincoln Park; walk through Bucktown, Humboldt Park, and Logan Square on the 606; or check out one of the many street fests or farmers markets that pop up throughout the city throughout the summer.

Route 66 Chicago Hotels

Chicago is the start (or end) of a full Route 66 journey. If you’re driving the entire route, you’ll start your journey at the Historic Route 66 Begin Sign at the corner of Adams Street and Michigan Avenue and continue west until you reach Los Angeles, California. If you’re beginning your Route 66 road trip in Chicago, you’ll probably need a place to spend a night or two.

While there aren’t many specific Route 66 hotels in Chicago, there are a lot of hotels with a history as long as the road. For a special start, book a room at one of these downtown hotels with a past.

Downtown Chicago hotels can be pricy, and they do not include parking (which is also pretty pricy). If you’re road tripping on a budget you might want to forgo spending the first night in Chicago and wait until you’re out of the city to find more budget-friendly accommodations with free parking lots.

But if you want to kick off your road trip with a night, or even a week, exploring Chicago, add one of these Chicago Route 66 hotels to your travel itinerary.

The Blackstone

Opened in 1910, The Blackstone was once known as “The Hotel of Presidents,” having hosted several heads of state (including Teddy Roosevelt and Jimmy Carter), along with a slew of celebrities, like the Rockefellers, the Vanderbilts, Lena Horne, Nat King Cole, Rudolph Valentino, and Al Capone. The historic landmark and architectural wonder has been renovated to appease the contemporary traveler and offers 335 accommodations

W Chicago

W Chicago is a contemporary Chicago hotel with a historic beginning. The Beaux-Arts building was commissioned in the 1920s to serve as a private club for businessmen. After the Great Depression the building was converted into a hotel. In 2001 W Hotels renovated the historic building bringing back its art deco charm and ornate decor that pay homage to its past.

Congress Plaza Hotel

Located near the start of Route 66, the Congress Plaza Hotel has been in operation since 1893 and is a welcoming stay for the beginning of your journey on the Mother Road.

Palmer House Hilton

Located just steps from Route 66, Palmer House Hilton is a luxurious historic hotel with all the modern conveniences you could desire alongside award-winning services. Palmer House was built in 1925 and was the city’s first hotel with elevators, electric light bulbs, and telephones in the guest rooms. The French neo-classical influences of the design give this landmark its distinctive charm.

The Gwen

521 N Rush St, Chicago, IL 60611

The Gwen is a luxury hotel in the heart of downtown Chicago with a historic facade crafted by sculptress Gwen Lux in 1928. The property offers two on-site restaurants, a rooftop terrace, a state-of-the-art fitness center, and modern rooms with large flat-screen TVs, free WiFi, and custom décor inspired by signature sculptures.

Freehand Chicago

Located in the River North neighborhood, just one mile from the beginning of Route 66, Freehand Chicago is a hip hotel featuring unique designs, a fun atmosphere, and happy hour specials at the on-site bar, Broken Shaker. Freehand is housed in a 1927 building that originally operated as the Devonshire Hotel.


Want more Chicago Route 66 hotels? Explore more here and peruse reviews.

Map of Route 66 in Chicago, Illinois

Use the map below to explore all the best things to do in Chicago, Illinois. Or, download our full Illinois Route 66 map to your phone!

Plan Your Route 66 Road Trip

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Last modified: May 2, 2024
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