Take the Scenic Route
Fall Break Road Trips in the Midwest
When the school calendar gives you a few extra days off, make the most of them with a fall road trip. Cooler temperatures, changing leaves and seasonal activities make autumn one of the best times to get behind the wheel and explore somewhere new.
Whether you're planning a long weekend with the family or squeezing one more getaway into the season, these Midwest road trips combine easy-to-reach destinations with plenty to see and do along the way.
Chicago to Chicagoland: A Quick Fall Escape
Short on vacation days? You don't have to go far to make fall break feel like a getaway.
Head outside Chicago for a scenic drive through Chicagoland and surrounding communities, where you'll find colorful landscapes, local farms, seasonal attractions and plenty of places to stop along the way. Spend the day exploring, grab a seasonal treat and make your way back to the city, or turn the drive into a weekend escape.
For more inspiration on where to experience the season's changing colors, explore our guide to the best fall foliage in the Midwest.
Where to Stay: Make Rosemont a stop on your list and stay at Loews Chicago O'Hare Hotel where you'll get to experience the local dining, entertainment and shopping just minutes from the hotel while tapping into the nostalgia of Route 66 with the hotel’s Route 66-inspired offerings.
Chicago to St. Louis: A Route 66 Fall Break
Turn fall break into an adventure along the historic Route 66. Start in Chicago and make your way southwest toward St. Louis, taking your time to discover the roadside attractions, local favorites and charming communities along the way.
Before hitting the road, spend a day exploring Chicago's fall offerings, from seasonal events and family-friendly attractions to neighborhood restaurants and shopping. Then, settle in for the drive and watch the landscape transform as autumn arrives across the Midwest.
Once you reach St. Louis, extend the adventure with a few days exploring the Gateway City. Spend time outdoors, discover local attractions, enjoy seasonal dining or simply slow down and enjoy a change of scenery.
Where to stay: Start your Route 66 adventure at the newly refreshed Loews Chicago Hotel, with easy access to the Mother Road’s iconic Chicago attractions and 2026 centennial celebrations, plus Route 66-inspired hotel experiences including a custom road-trip map, themed suites and guestroom packages and a nostalgic pop-up diner. Then, continue to Live! by Loews – St. Louis, where you can explore the Gateway City and celebrate the next chapter of your Route 66 journey with a stay in the heart of the action.
Kansas City: Extend the Road Trip West
If your fall break allows for a few more days, continue west toward Kansas City. The drive offers plenty of opportunities to make spontaneous stops and discover something new, while the destination itself gives you enough to fill an entire weekend.
Once there, explore the city's neighborhoods, museums, parks and food scene. Add a few seasonal activities to the itinerary, then leave some downtime for simply enjoying the crisp fall weather.
Where to stay: Stay in the heart of downtown at Loews Kansas City Hotel, where you'll be within walking distance of the Power & Light District, T-Mobile Center, Kauffman Center for the Performing Arts and the KC Streetcar. After a day on the road or exploring the city, unwind with an indoor saltwater lap pool, grab-and-go coffee or a meal at The Stilwell.
Make the Drive Part of the Getaway
The best fall break road trips aren't about rushing to the destination. They're about making the most of the days away from school and work and enjoying everything you find between here and there.
So pack the sweaters, load up the car and leave a little room for detours. From a Route 66 adventure connecting Chicago, St. Louis and Kansas City to a quick escape just outside the city, fall is the perfect time to take the scenic route.
Hit the road start planning your fall break getaway.
