Our Favorite Fall Getaways within 5 Hours of Chicago

Fall is nature's most elegant season, and if you're from the Chicago area you know it's been an incredible season this year! The sunshine and warm breezes combined with brilliant, golden colors have made fall an absolute spectacle, and it's not one to miss! That's why we've compiled a list of places where we think you might enjoy fall's beauty and elegance at its best.

The summer season may have come and gone, and the holiday season will be upon us soon, but there's still enough time to enjoy a few, last moments of fall's majesty with a weekend trip. In fact, now is the time perfect time for a journey - getting close with mother nature's changing beauty helps to reflect upon the year coming to an end and all that lies ahead. 

 So pack a bag, take a deep breath, let go, and enjoy! These fall getaways are all within a 5 hour drive of Chicago! 


1. Galena, IL

This quaint little town in northwest Illinois is a wonderful place to reflect and nurture the spirit. Beautiful autumn landscapes, 19th century history, small shops, and restaurants serving seasonal specialties provide the perfect combination of attractions to help you unwind. 

A few ways to explore FALL in Galena -

  • Take a walk through under a canopy of trees at Grant Park, located across the Galena River. Enjoy views of historic homes as you stroll through the park's walking paths.
  • Ride the Tri-State Trolley for a tour through the town's winding roads featuring all of Galena's fall colors.
  • Ride the ski lift for amazing views high above the Mississippi River at the Chestnut Mountain Resort. This is also an incredible place for a hike - the wooded trails provide breathtaking autumn scenery.  
  • President Ulysses S. Grant's home is not just an important historical site but also a great place to enjoy the local landscape and views of Galena from a distance. 

How to enjoy Galena's fall elegantly - 

Distance: 164 miles / 3 hours from downtown Chicago 


2. Brown County, Indiana

"Singing Winds" - On an autumn afternoon, with the breeze stirring the nodding heads of snapdragons and carrying the call of southbound geese, landscape artist T.C. Steele's wife, Selma, named this place. Sitting on the screen porch she noticed that "it sounded like the wind was singing us to sleep." And so, "Singing Winds" it was. 

One of America's first artist colonies, Brown County Indiana is one of the midwest's most unique fall destinations. Located just south of Indianapolis this 316 square mile area is 85% parks and forests. As autumn unfolds its golden colors, the views here become absolutely spectacular. Hiking and biking trails fill the deep woods, while backroads and highways provide an unforgettable fall weekend drive. The tranquil terrain is home to Brown County State Park, Yellowwood State Forest and parts of the Hoosier National Forest. Winding roads provide surprises at every turn bringing views of covered bridges and vistas transformed by fall's brush. There's plenty a site here to please the eye and fill the soul. 

How to make the best of Fall in Brown County: 

Where to find luxury and relaxation in Brown County: 

  • Spas, yoga and spiritual healing - book a massage or a healing session. Whichever your preference, it's sure to revitalize your body and soul and fill you with a feeling of serenity. 
  • Dive into the Arts - some of Brown County's first settlers (and visitors) were artists seeking repose and inspiration in the majesty of its nature. Whether you want to create art, browse galleries or purchase work of artists inspired by the beauty of Brown County, you're sure to find an opportunity for it all. 

Distance: 234 miles / 4 hours from downtown Chicago



3. Illinois River National Scenic Byway

Here you can get close with nature by taking the old routes of early French explorers! The Illinois River Road National Scenic Byway preserves the natural river country along the banks of the Illinois River. Biking historic canal towpaths, fishing, or hiking the numerous forest paths and canyons around Starved Rock are just some of the activities to be enjoyed. While exploring the area, visitors can experience beautiful wildlife habitats and learn about the rich history of the Illinois River Valley. 

How to explore the Illinois River National Scenic Byway:

Where to find luxury and relaxation: 

Distance: 201 miles / 3 hours from downtown Chicago


4. Lake Geneva, Wisconsin 

There is no better place to feel the elegance of fall than Lake Geneva! This resort city located in southeastern Wisconsin is not only surrounded by nature's beauty but also decorated with historic mansions built by wealthy Chicagoans in the early 20th century. It's both a place for beautiful, outdoor adventures as well as the best of class experiences.  

Where can you begin? 

How to explore Lake Geneva in luxury: 

Distance: 83 miles / 1.5 hours from downtown Chicago


5. Missouri Wineries 

You don't have to travel all the way to Napa Valley to experience some of the best American-produced wine. Missouri Wine country not only offers breathtaking autumn scenery but also a best of class vineyard experience! Take a stroll along rolling hills and enjoy award-winning wines at any of Missouri's top wineries. Missouri has over 125 wineries which have grouped together in areas to form 10 incredible wine trails.

They're all worth exploring but you'll find the closest group along the Route Du Vin Wine trail

Along the route you can experience various atmospheres - natural cave, quiet and elegant, comfortable and relaxed to fast paced and energetic. Each winery offers picturesque tours, great food, award winning wine experiences and weekend music. What an incredible way to enjoy autumn's elegance! 

Distance: approx. 370 miles / 5.5 hours from downtown Chicago