The perfect family vacation destination isn’t far from home. Hop in your car and experience the unmatched nostalgia of Route 66. The First Hundred Miles of the iconic Mother Road are lined with throwback diners, fascinating museums and some of the most popular tourist spots along this acclaimed route. To help get you started, we’ve assembled a pre-made road trip itinerary, featuring some of the best family-friendly photo-ops along The First Hundred Miles.
201 E Randolph St, Chicago, IL
Chicago’s sprawling Millennium Park, located just a short walk from the Route 66 starting sign, is home to some great family-friendly photo-ops and popular pieces of public art. You’ll spy the world renowned ‘Cloud Gate’, a large reflective sculpture that’s affectionately called ‘The Bean’, ‘Crown Fountain’, where you can see your face displayed on a 50-foot wall of video bricks, and the snake-like ‘Pedestrian Bridge’, which has been featured in numerous films and television shows. Just a short walk away at neighboring Grant Park, you’ll encounter the famous Buckingham Fountain. At the top of every hour, you can snap a picture of the fountain’s spectacular water show, or wait until the evening to catch a special presentation featuring choreographed lights and music.
Skydeck Chicago ‘The Ledge’
233 S Wacker Drive, Chicago, IL
Looking for something a little more exhilarating? Step out 1,353-feet in the air with nothing between you and the ground except a pane of tempered glass at Skydeck Chicago! This attraction, known as ‘The Ledge,’ lets you experience Chicago from a whole new perspective. Located near the top of the former Sears Tower, which held the record for tallest building in the world for several years, you can easily see up to four states with the naked eye on a clear day. Daily tickets are limited, advance purchase is strongly recommended to this ADA accessible attraction.
8400 W 31st St, Brookfield, IL
Located only 15 miles west of Chicago, this 200+ acre zoo is widely regarded as one of the best in the nation, thanks in no small part to its accessibility and amazing array of animals. Opened to the public in 1934, Brookfield’s unique design utilized moats in place of bars and cages resulting in an up-close experience, unlike anything visitors had seen before. Now, with over 450 species represented by more than 2,500 animals, everyone is sure to find one of their favorite creatures. Brookfield also features a variety of souvenir shops and on-site food venues, serving up everything from fried chicken and hot dogs to cool drinks and treats.
Joliet Area Historical Museum
204 N Ottawa St, Joliet, IL
Life-sized statues of The Blues Brothers ‘Joliet’ Jake and Elwood Blues are photo-ready at Joliet Area Historical Museum’s interactive and interpretative Route 66 Welcome Center kiosk. While there, you can also climb into the white drop-top convertible in the drive-in display, a photo display complete with classic car-hop and Route 66 signage. Don’t forget to visit the gift shop and load up on a great selection of Route 66 memorabilia.
The Gemini Giant
810 E Baltimore St, Wilmington, IL
The most iconic and instantly recognizable of the “Muffler Men’' statues that dot Route 66, the Launching Pad Drive-In’s Gemini Giant is a beloved institution on the Mother Road, and one of the most popular photo destinations along Route 66 in Illinois. Known for its unique space-age theming and quirky color palette, this goliath figure has been welcoming travelers since the mid-60′s. In 2017, Holly Barker and Tully Garrett purchased the Launching Pad and pledged to return the iconic giant to its former glory. Within a year, a beautifully restored Gemini Giant was unveiled on its original parking lot pedestal, ready for its close-up.
140 N Front St, Braidwood, IL
The Braidwood Zoo is a prime example of the vintage roadside kitsch that once peppered Route 66. Featuring a menagerie of animal sculptures built by late artist Jack Barker, who utilized scrap metal, wood and plastic to fashion the figures. After his passing, locals banded together to create this roadside attraction to highlight Barker’s folk art achievement. The “zoo” includes a band of about six animals, including a bright yellow giraffe, pink elephant and an impressive longhorn steer.
Route 66 Assoc. Museum And The Bob Waldmire Bus
110 W Howard St, Pontiac IL
Now permanently parked at the Route 66 Association of Illinois museum in Pontiac, you’ll find Bob Waldmire’s former modified school bus/living space on display outside the museum. Said to have inspired the character ‘Filmore’ from the classic Pixar film ‘Cars’, Waldmire was an itinerant artist and conservationist, a fixture of Route 66 who could be seen driving his deeply personalized art cars along the Mother Road for many decades. While at the museum, be sure to also grab a photo of his Volkswagen Minibus, and read about the history of this local legend who delighted the world with his art and love of Route 66.
World’s Largest Route 66 Shield
100 W Howard St, Pontiac, IL
Dubbed the ‘Quintessential Route 66 Photo Op’, this outdoor mural is known as the largest Route 66 Shield in the world, aptly painted on the back of the Route 66 Museum in Pontiac. Created by Diaz Sign Art in 2007, this signage has become a huge tourist attraction in its own right, and is an extremely popular photo-op for visitors and Route 66 travelers. You can even submit your photo at IL66assoc.org to join a growing archive of people that have stopped at this iconic modern mural.