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It’s no secret that the Uproxx crew loves a great American road trip. The freedom that comes with setting out on the open road is intoxicating. “Road trips are so good for us in the head, and the heart, and the spirit” — thus spoke a trending TikTok audio of Matthew McConaughey. But it’s not just a social media or film trope — the open road is a teacher. It takes us away from our ordinary and into the unknown.
If we let it, it’s a diversion from our lives that brings us closer to the lives of others. And that’s just what I set out to do – on the most famous road in America: Route 66.
Labeled the “Mother Road” by John Steinbeck in The Grapes of Wrath, the nearly 100-year-old road – winding over 2,400 miles from Chicago to Los Angeles – is legendary. What began as a transportation corridor during the Depression and World War II eventually became the poster child for freedom and optimism post-war. As the shortest year-round route between the Midwest and Los Angeles, families packed up their cars for long road trips to Disney, the Grand Canyon, and the storied American Southwest, stopping at roadside attractions, unique motels, and natural wonders along the way.
With the advent of Interstates in the later part of the century, many small towns and curiosities that made a trip on Route 66 so memorable were bypassed completely. Route 66 looked likely to become a string of ghost towns (this is pretty much the plot of the Disney movie, Cars, BTW). Luckily, various heritage groups sprung into action to preserve the iconic road, its local economies, and its place in American history.
In 1990, the US Congress passed a law recognizing that Route 66 had “become a symbol of the American people’s heritage of travel and their legacy of seeking a better life” — which led to the National Park Service Route 66 Corridor Preservation Program. With the 100th anniversary of the road coming in 2026, it’s the perfect time to revisit this storied road, get off the interstates, and take the long way. As an Illinois native, I was most interested in the beginning portion of this route, traveling between Chicago and St. Louis.
Here is my guide:
START IN CHICAGO
The official “beginning” of the road is in downtown Chicago in such an unassuming place that my Uber driver insisted I gave him the wrong address. But no, steps from Millenium Park at Adams Street and Michigan Avenue intersection lies the sticker-covered “Begin Route 66” sign where our journey launches.
Now, Chicago isn’t necessarily the sort of small-town vibe I envisioned when I decided to drive a portion of Route 66 solo, but as America’s “Second City” it would be a crime to touch down and not spend a couple of days exploring before hitting the road.
WHAT TO DO:
What can’t you do in Chicago, honestly? I’ve spent many weekends in the Windy City (and Uproxx has written plenty on it) and I’ve still never run out of things to do. For this trip, I decided to keep it somewhat “touristy” and check out some of the most famous landmarks, restaurants, and museums in town.
Is it a trip to Chicago if you don’t stop by “The Bean” in Millenium Park?
The art installation – officially named Cloudgate – has become an icon of the city. (Note: construction will limit access to Cloudgate until spring 2024) Stroll through this beautiful public park, stopping at The Bean, Lurie Garden, Crown Fountain, and catching a Jay Pritzker Pavillion show.
Head to The Second City for an unforgettable improv experience. The comedy theater is legendary, launching the careers of almost every notable comedian I can think of – John Belushi, Dan Aykroyd, Gilda Radner, Bill Murray, Tina Fey, Amy Poehler, Stephen Colbert, Steve Carell, Jordan Peele, and many others. There are several different shows to choose from – I opted for “The Best of The Second City: Chicago Style” on my last visit, and barely had time to sip my drink without spitting it out from laughter.
Stroll along the redeveloped Chicago Riverwalk, along the infamous Chicago River. Enjoy public art, eating, drinking, or people-watching. I loved sipping a glass of wine at City Winery while watching the boats pass me by.
For the adventurous, rent a kayak or head out on a guided kayak tour with Urban Kayaks, with locations along the Chicago Riverwalk and North Avenue Beach; there is an adventure for all skill levels. I loved kayaking downtown on the Chicago River for a sunset guided tour. It’s a great alternative to the popular architecture tours – if you’d like to get your heart pumping.
WHERE TO STAY:
I loved my stay at Arlo Chicago – just steps from Millenium Park and the start of Route 66. Formerly the Hotel Julian, the hotel has recently undergone a reopening and reimagining that is worth a look — with views of The Bean right from your window to a bustling bar and restaurant, impeccable service, and stylish but understated decor – it’s the perfect place to be if you want to get in the action of Michigan Avenue.
WHERE TO EAT AND DRINK:
I opted for a food tour of classic Chicago restaurants on this visit, to go complete tourist. And I was not disappointed. The Chicago Favorites Walking Tour, with Bobby’s Bike Hike, was a great way to learn some Chicago history and enjoy classic Chicago dishes while meeting new people worldwide. We made stops at Lou Malnati’s for classic Chicago deep-dish, the SNL famous Billy Goat Tavern for a Chicago-style hotdog (always hold the ketchup), an Italian Beef, and a brownie for dessert.
Add a craft beer package at three stops, or buy drinks for a boozy and filling trip.
ABOUT LAST KNIFE
I was lucky to visit About Last Knife, the restaurant at Arlo Chicago, on the first days of their new menu for dinner and breakfast. My seared tuna appetizer was incredible, followed by truffle pasta with short ribs cooked to perfection – I loved it so much that I opted for a short rib hash the following day for breakfast. The vibe is hip without being overdone, with a great mix of travelers and locals.
There always seems to be a street festival in The Windy City, and it’s the perfect excuse to try new dishes. I headed to the Tacos Y Tamales Festival in Pilsen for some tamales (obviously), a churro ice cream sandwich, and some brews.
Before I left Chicago to embark on the next leg of my Route 66 road trip, I had to stop at the iconic Lou Mitchell’s for breakfast. The classic American diner, located right near the beginning of Mother Road, has been serving travelers and locals for 100 years. Before hitting the road, come early to get a table and enjoy classic diner fare, complimentary donut holes, and homemade ice cream.
LEG 2: CHICAGO TO PONTIAC, IL — TWO HOURS
The first leg of the trip winds from Chicago to Pontiac, Illinois. The town of just over 11,000 people is home to the Route 66 Museum, countless murals, and small-town vibes.
WHERE TO STOP:
TOUR OLD JOLIET PRISON
On the way to Pontiac, I stopped at the Old Joliet Prison for a tour – as historic prisons are always one of my favorite roadside attractions. The iconic former State Penitentiary housed inmates for over 150 years, appearing in The Blues Brothers, and was a filming location for the show Prison Break. These days, you can take self-guided or guided tours of the massive property and learn about its history and famous inmates.
VISIT THE ROUTE 66 MUSEUM
After your slightly macabre morning, drive into downtown Pontiac to spend an hour (or three) at the massive Route 66 Hall of Fame and Museum. The sprawling museum showcases an incredible amount of paraphernalia from all along the route, including — my favorite — the van and converted art school bus (the Road Yacht) of legendary artist and environmentalist Bob Waldmire. Spending much of his life traveling back and forth along Route 66 from Illinois to Arizona, Waldmire sold pen and ink drawings and told stories of life on the road.
Waldmire is beloved in the Route 66 community and was even the inspiration for Fillmore in the movie Cars. I loved seeing his vehicles, photos, and art on display in the museum. After your visit, explore downtown Pontiac for an impressive amount of murals and quaint small-town charm.
GRAB A BITE AT ACRESINN
Just steps away from the Route 66 Hall of Fame and Museum lies the locally-owned cafe, restaurant, and market ACRESinn. I loved the fried Korean BBQ sandwich with Korean BBQ, slaw, and kimchi mayo with a side of potatoes.
ENJOY A FLIGHT AT PK UNKORKED
After a long day, I loved finding PK Unkorked Wine Shop and Tasting Room. I settled in for a tasting with my book while local performers got ready to play. It was not fussy but offered great wine and a community feel.
LEG 3: PONTIAC TO SPRINGFIELD, IL — 2 HOURS
The second leg of my trip took me to Springfield — the capital of Illinois. As someone who grew up in Central Illinois, I know Springfield well — mostly through school field trips — so I was excited to explore some old haunts again — this time with a drink.
WHERE TO STOP:
WALK THROUGH LEGENDS NEON PARK
One of the coolest stops I made was Legends Neon Park at the Illinois State Fairgrounds. Walk through the park at dusk or later when iconic neon signs from Route 66 are illuminated on a path that takes you from Chicago to St. Louis. The attention to detail is impressive, and it’s kitschy fun to see all of the neon signs.
VISIT THE LINCOLN PRESIDENTIAL MUSEUM AND LINCOLN HOME
You can’t visit Springfield without visiting some Abraham Lincoln attractions — they’re everywhere, and for good reason. Although the 16th President was not born in Illinois (despite it being known as the Land of Lincoln), he spent much of his life there from practicing law to becoming elected as President. I had visited Lincoln’s Home — a National Park Service Historic Site — many times but loved having a private tour with a park ranger on this visit before heading over to the impressive Lincoln Presidential Library and Museum.
The museum is surprisingly engaging and interactive – doing a great job of leading visitors through Lincoln’s life from birth to death — including a great exhibit set at my alma mater that I am, of course, partial to.
STEP BACK IN TIME, STAYING AT THE BRESSMER
I stayed right Downtown in Springfield at The Bressmer, a historic victorian style home with each floor available to rent. My ground floor suite was like stepping back in time — and was enormous. I had three bedrooms, two bathrooms, a kitchen, dining room, and office to relax in after a day exploring.
ORDER A HORSESHOE AT OBED AND ISAACS
Just down the street from The Bressmer is a Springfield classic — Obed and Isaacs Microbrewery. I popped in for dinner and ordered the Springfield-originated classic Horseshoe — an open-faced sandwich of toast layered with protein, cheese sauce, or gravy and topped with french fries — with one of their craft brews before heading next-door to 7th Street Cidery for some taster pours on the large patio.
GRAB LUNCH AND A LOCAL BREW AT LA PIAZZA
Just steps from the State Capital lies La Piazza where I enjoyed a salad, warm bread, and a local Cannibal Cupcake brew from local Anvil & Forge Brewing and Distilling. It’s a great place to sit outside and people-watch.
GRAB A COFFEE AND PASTRY AT CUSTOM CUP
Before leaving Springfield I stopped by Custom Cup Coffee for a lavender latte and pastries. The micro-roastery specializes in custom, small-batch, roasted-to-order coffees right in the heart of the city.
LEG 4: SPRINGFIELD TO ALTON, IL 1.5 HOURS
The next leg of the trip took me from Springfield to Alton, Illinois — on the banks of the Mississippi River. The historic town, along with the nearby Pere Marquette State Park have long been a stopping point for travelers heading West.
WHERE TO STOP:
There are plenty of Route 66 attractions on each leg of the trip, but I loved the kitschiness of those on this leg the most. Stop in the massive Pink Elephant Antique Mall, Shea’s Gas Station Museum, Route 66 Motorhead’s Bar and Grill, and the original historic Route 66 brick road, listed on the National Register of Historic Places.
RIDE THE ALPINE COASTER AT AERIE’S RESORT BEFORE DINNER WITH A VIEW
Head to Aerie’s Resort in nearby Grafton to take the gondola up for a great view over the Mississippi, with an alpine coaster (the first in Illinois), zip-lining, great food, and a great wine selection. You’ll feel like you’ve stepped out of the midwest and into the mountains.
WAKE UP OVER THE RIVER AT THE CRACKER FACTORY
I loved staying in downtown Alton at the Cracker Factory, a converted historic building with upscale suites to rent. I was lucky to have the Penthouse all to myself with two bedrooms, a huge great room, amazing large terraces with views of downtown and the river. It’s perfectly situated in downtown Alton with lots of eclectic shops nearby.
LEG 5: ALTON TO STATE LINE AND ST. LOUIS, MISSOURI — 30 MINUTES
The last leg of Route 66 in Illinois is from Alton to nearby St. Louis, Missouri. From there you can head into STL to explore or continue on Route 66 all the way to California.
WHERE TO STOP:
CAHOKIA MOUNDS STATE HISTORIC SITE
A visit to Cahokia Mounds, a UNESCO World Heritage Site, is essential if you’re anywhere near St. Louis. Named after the nearby modern-day community of Cahokia, the State Historic Site preserves the remains of an ancient Native American city that was once the largest and most sophisticated settlement in pre-Columbian North America. With more than 70 earthen mounds of varying sizes and purposes, it is recognized as one of the most important archaeological sites in the United States.
WORLD’S LARGEST CATSUP BOTTLE
I lived in Illinois outside of St. Louis as a kid for a few years, and one of my greatest memories is driving by the “Worlds Largest Catsup Bottle” on the way to school. A quirky Route 66 landmark and photo-op, the 170-ft water tower has been a staple for Route 66 travelers since its construction in 1949.