8 Can’t Miss Stops on Route 66 Chicago

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These are the best stops on Route 66 Chicago where you will bookend your epic Route 66 road trip!

route 66 chicago

Your Route 66 trip will either start or end in Chicago and it is the perfect city to bookend your road trip. This is where the original Route 66 started as people began to head west towards California. You can find a few fun stops directly related to Route 66 in town and we’ll cover them all here!

We took the entire Route 66 road trip from California to Chicago over the course of 10 days. It was a rushed trip for sure but we absolutely loved every second of it.

> Read our full Route 66 Road Trip Itinerary!

We’ll cover the best stops on Route 66 Chicago, Route 66 Chicago start point, Route 66 Chicago sign, Route 66 Chicago to Santa Monica, and more!

This post is all about the best stops on Route 66 Chicago!

Route 66 Chicago

Start of the Route Sign

Route 66 road trip

If you are starting your road trip in Chicago, there is no better place to start than at the “Begin” Sign. You can find it on the corner of Michigan Ave and Adams St. It’s a fairly nondescript sign on the side of the road. It looks almost identical to all the other Historical Route 66 signs you will see throughout your travels. But it’s a great place to stop as you begin your trip. This is especially true if you are traveling the entire length of Route 66 and ending at the End of the Trail sign in Santa Monica (a much better sign marker).

Pro Tip: Download the free Spot Hero App to find the best parking rates and availability in Chicago and other big cities in the US. It saved us over $50 while in Chicago for 2 days!

End of the Route Sign

route 66 chicago sign

If you are taking the opposite route from California to Chicago, be sure to check out the end of the route sign just one block south. It’s located on the corner of Jackson Blvd and Michigan Ave. I don’t recommend driving here and stopping to get the photo unless you can take it from the passenger window. It’s in the heart of Chicago and can be quite busy with no parking in sight. It’s small and put up with a bunch of other signs but still worth the stop to bookend your trip!

Grant Park

route 66 attractions

This massive park along the riverfront is a must-visit while in Chicago. It’s hard to miss and is just across from both the Route 66 signs. This iconic park is the historic start of Route 66. People would start up at Grant Park in Chicago and drive all 2,448 miles (3,939 km) to the ocean in Santa Monica. Again not a great place for driving though you will likely drive past it as you make your way into or out of Chicago. Grant Park is home to Buckingham Fountain and Millenial Park with “the Bean.”

The Berghoff Restaurant

This classic German restaurant seems like an odd stop on Route 66. However, this restaurant has been in business since 1898 and serving up steins of beer ever since. Its neon sign out front will certainly catch your eye and is one of the most iconic parts of this restaurant. Be sure to also check out the great beer that was famous at the World’s Fair in 1893!

Willis Tower

route 66 chicago start point route 66 chicago to california

No stop to Chicago is complete without the Willis Tower. You’ll easily be able to spot the tower in the skyline and see it looming above as you drive by. You can visit the tower and stand a glass box off of the side of the building. At 108 stories high, I am sure it is quite the thrill!

Lou Mitchell’s

route 66 chicago start

This diner has been feeding hungry road trippers since 1923! Stop in for some of their famous and hearty breakfast or lunch. This building is only one story with an awesome old-school sign on the roof and surrounded by high rises. There is some outdoor dining if you are coming during good weather!

Mercury Oil Gas Station

Most of Route 66 stops are restaurants or fun and kitschy stops (like the Blue Whale of Catoosa). Chicago is no exception. Your first kitschy stop out of Chicago is the old Mercury Oil Gas Station located at 1254 S Western Ave. Just a few minutes outside of town, this old Gas Station is now a GoodYear Tires but its architecture is what makes it iconic. It’s a small cottage-style building in the middle of industrial and commercial buildings, it stands out.

Castle Car Wash

The next kitschy stop is the Castle Car Wash. Although it is closed now, it’s exactly what it sounds like. A former car wash is located in a building that looks like a small castle. You can find this fun stop at 3801 Ogden Ave.

Dell Rhea’s Chicken Basket

We are now outside of Chicago but there are few stops to mention as you are leaving town and heading on to St. Louis, Missouri!. Just outside of town, about 45 min is Dell Rhea’s Chicken Basket. This is a great place to stop before heading into the crazy driving scene that is Chicago since the other restaurants in town don’t have great parking options. Dell Rhea’s is an iconic stop on Route 66 serving fried chicken and a great diner feel. The awesome neon sign is a must-see, even if you don’t get a chance to stop for food!

Route 66 Chicago Accommodations:

Budget | Hotel Versey Days Inn by Wyndham Chicago – this boutique hotel has a good location close to Wrigley Field and Michigan’s North Avenue. It’s full of art and culture and includes a free pass to LA Fitness next door.

Mid-Range | Majestic Hotel – This 1920’s building pulls you back in time and gives you an authentic, old-school Chicago vibe. With a great location and even a wood-burning fireplace in the lobby, this is a great spot for any trip to Chicago.

Luxury | Viceroy Chicago – This historic, luxury hotel has a great location, walking distance to all the main attractions. There is also a rooftop bar and lounge as well as a seasonal pool and panoramic city views.

> Find your perfect stay in Chicago with Booking.com!

This post was all about the best stops on Route 66 Chicago. We can’t wait to see all your adventures. Be sure to tag us @thepassportcouple on Instagram!

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We’re Alicia & Nate! We sold everything & quit our jobs to travel full time. On the road since 2020, we are traveling the world one bucket list item at a time. Join us on our epic journey!

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