Route 66 Road Trip

 Get your Kicks on Route 66 in Chicagoland.

Begin your journey in Grant Park with the magnificent Buckingham Fountain, built in 1927 and designed to represent Lake Michigan with four sea horses symbolizing the four states that touch the lake: Wisconsin, Illinois, Indiana and Michigan.

Continue to the Art Institute of Chicago to see some of the most famous paintings in the world by van Gogh, Chagall, Dali, Matisse, Monet, Picasso, Rembrandt, and many others.

Next head to the Sears Tower, which opened in 1973 and is the highest observatory in Chicago. Get an amazing view of the Chicago and surrounding states!

On the other side of Union Station, at the intersection of Jackson and Jefferson, is Lou Mitchell’s Restaurant (1923), where you can get a great breakfast all day. Their unique traditions include a free box of milk duds for all guests.

Just west of the expressway is Chicago’s Greektown. Greektown is a great place to stop for lunch or dinner, with a huge variety of splendid Greek restaurants for your dining enjoyment. Park you car and walk several blocks along Halsted Street to experience Greektown firsthand, with Greek bakeries, shops, restaurants, and Greek taverns welcoming visitors from around the world.

Turn onto Ogden Avenue and pass by Castle Car Wash, built in 1925 as the automobile age was just beginning.


Stop in at Henry’s Drive-In for lunch or dinner. The hot dogs here are famous for being a meal in itself.

Berwyn: The Berwyn Route 66 Car Show is held annually in early September along Route 66 from Ridgeland to Oak Park Ave. Hundreds of gearheads and car enthusiasts come out to celebrate the spirit of Route 66.

Countryside: Drive by the old Wishing Well Motel. Currently closed, the motel reminds travelers as they drive along Route 66 of the past of this great Mother Road and the wonderment of the future.


Get Your Chicks on Route 66 at Dell Rhea’s Chicken Basket. Dating back to 1946 as a Blue Bird bus stop, all Route 66 ‘roadies’ make it a point to stop here.

Lemont: White Fence Farm has been open continuously since the 1920s and has some of the best fried chicken in Chicagoland. In addition to great food, White Fence Farm offers a petting zoo, musical entertainment and themed shows, a classic auto museum, and car shows during the summer months. Be sure to have your dinner in the Route 66 Room, one of twelve dining rooms in this popular restaurant.

Crest Hill

Opened in 1925, the Stateville Correctional Center was built to accommodate 1,506 inmates. The prison was designed around the panopticon cell house or “roundhouse”, which features an armed tower in the center of an open area surrounded by cells. Stateville has the only remaining “roundhouse” still in use in the United States.


The Joliet Area Historical Museum and Route 66 Welcome Center offers interactive exhibits for all ages. There’s also a unique gift shop, selling keepsakes, Route 66 memorabilia, games, toys, and more. The museum is located on the corner of Historic Route 66 & the Lincoln Highway. This is one of only 2 places in the nation that those two famous roads cross. Both are now National Scenic Byways.

The Rialto Square Theatre is now considered as one of the most beautiful theaters in the nation. Built in 1926, it is known as the “Jewel of Joliet” and originally conceived as “A Palace for the People”. Take in a show or schedule a tour on Tuesdays to see the Theatre that is noted to be one of the 10 most splendid theaters in the nation.


The 982 acre Abraham Lincoln Cemetery is located just south of Elwood. The cemetery was dedicated in 1999 by the United States Department of Veterans Affairs National Cemetery Administration. It was the 117th national cemetery dedicated under the administration and sits on the former Army Ammunition Plant site, also called the Joliet Arsenal.


No trip on Route 66 is complete without a stop at the Launching Pad Drive-In. It’s a must to have your picture taken with the Gemini Giant. He has welcomed Route 66 travelers since the 50’s.

Wilmington is also known as the antique capital of Will County. Don’t miss the Dinosaur on the roof of G & D’s tire shop that was an old Sinclair station. Stop along Water Street and browse the many antique shops. Some of them even have Route 66 relics.


The Polk-a-Dot-Diner, opened in 1956, offers appetizing meals and scrumptious desserts. This popular stop has a great Route 66 theme and a fantastic atmosphere. Be sure to visit with Elvis, Marilyn Monroe, James Dean, Betty Boop and the Blues Brothers while you’re there. Try a Turtle Sundae or their famous chili cheese fries. The first weekend in August hosts a huge cruise night with great music, food and fun.


Visit Bob & Peg, the owners of The Riviera, a historic 1928 speakeasy with cool “stalactite” décor over the bar. This is one of the most unique stops along your journey on Route 66. Bob or any of the bartenders are happy to share stories of prohibition, Al Capone, and the dumb waiter.

While at the Riviera make sure to step out back and see the old Streetcar Diner, an actual horse drawn streetcar that was moved to Gardner with the intention of converting it into a roadside diner in 1932. After the diner closed in 1939, it became a summer cottage, a children’s playhouse and a rental property for workers at the Joliet Arsenal in W.W. II.

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