Chicago to St. Louis on Route 66: Best Stops & Tips

Chicago to St. Louis on Route 66: Best Stops & Tips

Begin Historic Route 66 sign on Adams Street in Chicago.

Trip Snapshot:

• Distance & Drive Time: ~300 miles (about 5 hours of driving). Plan for 2–3 days with stops to fully enjoy the sights.
• Best Time: April–October for mild temperatures, open attractions, and longer daylight.
• Ideal For: Families, history buffs, neon-sign hunters, and road-food lovers looking for a classic Americana drive.
• Route Summary: Start at downtown Chicago’s famous “Begin Route 66” sign on East Adams Street, then follow historic Route 66 (which parallels I‑55 through Illinois) south through Pontiac and Springfield all the way to St. Louis. You’ll mostly shadow I‑55 on old alignment roads for those photogenic small-town gas stations and diners.
• Top 3 Highlights: Kitschy Route 66 museums (and their Muffler Men statues), a tour of Abraham Lincoln’s home, and a tram ride up to the top of the St. Louis Gateway Arch.

Route Overview: This trip kicks off from O’Hare Airport (ORD) from there, ease onto the highway toward downtown Chicago. Once in the city, make your way to the “Historic Route 66 Begin” sign at Adams St. and Michigan Ave. for the ceremonial photo op marking the start of the Mother Road. With your snapshot secured, you’ll leave Chicago’s skyscrapers behind and favor the well-marked historic Route 66 byways that run alongside I‑55. These old road segments lead you through classic Illinois towns filled with retro gas pumps, roadside giants, and chrome diners straight out of the 1950s. In Springfield, park the car and stroll the walkable historic neighborhood around Lincoln’s home. Finally, continue down to the Mississippi River and roll into St. Louis, Missouri. There, you’ll end your journey by exploring the riverfront and ascending the Gateway Arch for a bird’s-eye view of your route’s end.

Driving notes: As you depart Chicago, be aware the initial highways have tolls. The Illinois Tollway system doesn’t take cash, so you’ll want an I‑PASS or E‑ZPass transponder, or you can pay online later via the Pay By Plate program. Once you’re on I‑55 heading south, though, it’s smooth sailing—Route 66/I‑55 has no tolls at all.

Top Stops & Experiences:(listed north to south)

• “Begin Route 66” Sign Chicago (IL)Family-friendly. You can’t start a Route 66 trip without a photo at the starting line! On East Adams Street (westbound), between Michigan Ave. and Wabash, a sign marks the official beginning of Route 66. Snap the classic shot with the sign in front of the Art Institute. (Tip: There’s a parking garage on Wabash Ave. nearby for a quick stop.) The kids will love knowing this is where the adventure truly kicks off.
• Pontiac Route 66 Hall of Fame & Museum Pontiac (IL)Family-friendly. Immerse yourself in Mother Road nostalgia. This free museum (donations appreciated) overflows with neon signs, old maps, and memorabilia from Route 66’s heyday. It’s housed in an old firehouse, and even the exterior is a draw with huge painted murals and a vintage Gulf gas pump out front. The museum is open seven days a week (shorter hours in winter), making it an easy detour any day of the week. Don’t forget to pose with the giant Route 66 shield mural on the back wall for another great photo op.
• Atlanta’s 19‑ft “Bunyon Giant” Atlanta (IL)Family-friendly. Just south of Pontiac in the small town of Atlanta stands one of Route 66’s most beloved “Muffler Men.” This 19-foot fiberglass giant a quirky Paul Bunyan lookalike holds an enormous hot dog in his arms, earning him the nickname “Bunyon Giant.” It’s a quick curbside stop on SW Arch Street, right across from the Palms Grill Café, so you can park easily and snap a fun family picture with the big guy. Kids won’t forget this towering statue (and neither will your Instagram followers!).
• Lincoln Home National Historic Site Springfield (IL)Family-friendly. Step back in time by visiting Abraham Lincoln’s preserved 1860s home and the four-block historic neighborhood around it. The National Park Service offers free, ranger-led tours of Lincoln’s home you just need to stop at the visitor center for a timed ticket. Tours are first-come, first-served, so in summer months plan to arrive early in the day as tickets can run out by afternoon. Stroll the wooden sidewalks of this lovingly restored street to imagine life when Lincoln lived here. (Bonus: the surrounding historic district is closed to traffic, so it’s safe for little ones to roam a bit.)
• Cozy Dog Drive In Springfield (IL)Family-friendly. Ready for a classic road food lunch? This no-frills diner claims to be the home of the original corn dog on a stick, known as the “Cozy Dog”. It’s quick, cheap, and delicious basically a must-stop for any Route 66 traveler. The corn dogs are made from the same batter recipe they’ve used since 1946, and the walls are full of Route 66 memorabilia to check out while you wait. Kids and picky eaters will be thrilled with the simple hot dogs and fries, and nostalgia buffs will appreciate the mid-century vibe.
• Old Chain of Rocks Bridge over the IL/MO borderFamily-friendly. As you approach St. Louis, don’t miss this peculiar piece of Route 66 history. The Old Chain of Rocks Bridge carried Route 66 traffic across the Mississippi until 1970, and it has a notable 22-degree bend right in the middle a truly unique engineering quirk! Today, the mile-long bridge is open only to pedestrians and cyclists, so park at the designated lot on the Illinois side and walk out over the river. The kids can literally stand in two states at once, and you’ll get a fantastic view of the Mississippi River and the distant St. Louis skyline. Interpretive signs share the bridge’s history (including why it bends to avoid riverbed rocks and a water intake tower). It’s a leisurely walk and an awesome photo spot.

The Old Chain of Rocks Bridge features a quirky 22° bend midway across the Mississippi River, a relic of its Route 66 days now enjoyed by pedestrians and cyclists.

• Gateway Arch National Park St. Louis (MO)Family-friendly. Cap off your road trip with the ultimate St. Louis icon. The Gateway Arch, towering 630 feet over the river, offers a tram ride to the top that’s a thrill in itself. (If you’re not claustrophobic, that is the tram pods are snug!) Plan about 45–60 minutes total for the round-trip tram experience. After a brief museum exhibit and intro video, you’ll board the tram for a 4-minute ride up the Arch’s interior. At the top, marvel at the panoramic views through small windows you can see up to 30 miles on a clear day! Note that time in the observation area is limited to around 7–10 minutes per group during busy times, which is usually enough to soak in the sights of downtown St. Louis on one side and the Mississippi River on the other. Back at ground level, don’t rush off the Gateway Arch’s modern underground museum (free admission) is full of great exhibits on American westward expansion and local history. Between the museum and the surrounding riverfront park (perfect for a walk or riverboat cruise), you can easily spend a half day here. (Pro tip: Arch tram tickets can sell out on peak weekends it’s wise to reserve your tram time online in advance.)

The view from the Gateway Arch observation deck offers a sweeping panorama of downtown St. Louis, including the historic Old Courthouse (with green dome) and Busch Stadium.

Where to Eat & Stay:

• Cozy Dog Drive In (Springfield) This was mentioned above as a must-stop, and it doubles as an ideal lunch spot. It’s quick counter service with retro charm. Grab a couple of the famous Cozy Dogs and a root beer, and enjoy at the picnic-style tables. Perfect for families on the go the kids can be back in the car and napping in no time, full of hot dogs and fries.
• Pappy’s Smokehouse (St. Louis) If you’re craving barbecue by the time you hit St. Louis, Pappy’s is the place to go. It’s a local legend known for dry-rubbed ribs smoked over apple and cherry wood. Be warned: they often sell out of ribs by early evening because they’re that popular. Aim to eat an early dinner or even lunch here. It’s casual, order-at-the-counter style. While it’s very family-friendly, barbecue aficionados (grown-ups) will especially appreciate pairing the tender ribs with a local craft beer. If you have room, try their barbecue nachos or fried corn on the cob, too.
• Arch Café (St. Louis) Conveniently located at the base of the Gateway Arch, this café is ideal if you need a quick bite or caffeine fix during your Arch visit. They serve sandwiches, salads, and kid-friendly options (like hot dogs and pretzels). It’s nothing fancy, but the convenience and location can’t be beat and it saves you from having to move the car and re-park in the city. Plus, sitting outside by the Arch grounds with an ice cream while riverboats cruise by is a nice way to relax after the tram ride.

Lodging: For this itinerary, many travelers choose to overnight in Springfield and then in St. Louis. In Springfield, consider staying in or near the historic downtown area (around 6th and Adams Street) that way you can walk to the Lincoln Home neighborhood and perhaps an evening meal at a local pub or the famous Maldaner’s restaurant. The downtown has a few modern hotels and restored historic inns, and you’ll enjoy the small-city charm after the day’s drive. In St. Louis, booking a hotel downtown near the Arch is a fantastic idea. You’ll be able to wander the illuminated Arch grounds at night (a beautiful sight) and easily visit other attractions like Busch Stadium or Ballpark Village if you have extra time. Waking up at a hotel with a view of the Arch or Mississippi River is a memorable finale for your trip. (Just be sure to reserve those Arch tram tickets ahead of time as mentioned they can coincide with lodging packages or be bought separately.)

Detours & Extensions: If you have extra time in your schedule, there are a couple of worthwhile additions along or near this route:

• Meramec Caverns (Missouri): About 45 minutes west of St. Louis (in Stanton, MO, off I‑44) lies Meramec Caverns, one of Route 66’s classic roadside attractions. This extensive cave system was a famous tourist stop and even a legendary Jesse James hideout. Tours run about 1.5 hours, guiding you through dramatic underground formations with theatrical lighting. It’s an especially great detour on a hot summer day the cave stays a cool ~58°F year-round. If you’re headed further west on Route 66 after St. Louis, it’s an easy add-on.
• Chain of Rocks Bridge Greenway: If you loved the Old Chain of Rocks Bridge and want to stretch your legs more, you can explore the Madison County Transcontinental Bike Trail/Chain of Rocks Greenway that connects to the bridge area. There are easy walking and biking paths along both sides of the river here. On the Missouri side, the Riverfront Trail will give you a longer ride with views of the Mississippi. On the Illinois side, a nature trail follows the river and offers a peaceful break from driving. Even an extra 30-minute stroll to spot birds or watch barges on the water can be a refreshing addition.

Practical Tips:

• Tolls & Payment: As mentioned, when leaving Chicago you may encounter toll roads (especially if you hop on I‑294 or I‑90 briefly). Illinois Tollway roads are cashless, so have an I‑PASS/E‑ZPass or be prepared to pay online after using the tolls. The historic Route 66 route along I‑55 is toll-free, though, so if you stick strictly to that you’ll avoid tolls entirely once you’re past the Chicago metro area.
• Pace Yourself: The whole charm of a Route 66 road trip is enjoying the journey, not rushing to the destination. Plan for a leisurely pace. It’s easy to hop on I‑55 to make up time, but be sure to budget hours for the “old 66” alignments through the small towns. Those detours are where you’ll find restored diners, old service stations, and quirky roadside art. A 5-hour direct drive can pleasantly turn into two days of exploration and that’s the goal!
• Weather & Seasons: Midwest weather can be unpredictable. Summer days are long and great for driving, but they can get very hot and humid, and pop-up thunderstorms are common (keep an eye out for lightning and be ready to pull over if rain becomes torrential). Spring and fall are generally mild perfect for walking around sights but still pack a light rain jacket. If you’re attempting this drive in winter, be prepared for possible snow or ice, especially in Illinois. Always check the forecast and road conditions. Regardless of season, have a cooler with water and snacks in the car, and maybe a roadside emergency kit (jumper cables, etc.), just to be safe.
• Family Notes: This route is super family-friendly. Most attractions like the museums and Lincoln’s home are either free or low-cost. One thing to note: Lincoln Home tour tickets are first-come, and on busy days they can all be distributed by early afternoon. Try to get there in the morning if visiting in peak summer. For the Arch, strollers aren’t allowed up in the tram, but you can leave them with park staff. Restrooms are available both at Lincoln’s site and at the Arch facility (none at the very top of the Arch, though!). Keeping some coloring books or travel games for the kids during the longer stretches (like Springfield to St. Louis, about 1 hour 45 min drive) will help, though the frequent stops make this an easygoing trip for even younger children.

Rentals & Logistics: This road trip is a loop of cities and towns, so it’s easy to manage with a standard rental car. If you’re traveling with family or a larger group, consider renting a minivan at O’Hare. The sliding doors and extra space will be a godsend at frequent roadside stops (no bonking kids with doors in tight parking spots!), and you’ll have plenty of room for souvenirs. For couples or duos, a midsize SUV or roomy sedan will provide comfort and enough cargo space for your luggage and maybe a small cooler. When picking up your rental in Chicago, ask if they offer a toll transponder for I‑PASS it can simplify dealing with toll roads around Chicago (many rental companies in Illinois do offer this as an add-on). Also, request all-weather floor mats if available; you might track in sand, mud, or gravel from those old Route 66 stops, and mats make cleanup easier.

Finally, plan your timing to avoid Chicago rush hour when leaving (weekday mornings 7–9 AM are heavy traffic out of the city) and likewise be mindful of afternoon rush in St. Louis if you’re arriving at day’s end. Other than that, this trip is straightforward. Fuel up the car, queue up an oldies playlist (might we suggest “(Get Your Kicks on) Route 66”?), and get ready to create some unforgettable memories on America’s Mother Road!

Ready to kick off your Route 66 adventure? Start by picking the perfect ride for the journey. Reserve a minivan or SUV at Chicago O’Hare so you can hit the road with confidence the Mother Road is waiting for you!