6 days in North Carolina & Chicago Itinerary

6 days in North Carolina & Chicago Itinerary

Created using Inspirock United States trip itinerary maker

Make it your trip
— 1 night
— 4 nights



— 1 night

Land of the Sky

Asheville nestles between two major mountain ranges in the scenic western section of North Carolina.
On the 10th (Sun), experience rural life at Stepp's Hillcrest Orchard, experience rural life at Justus Orchard, and then grab your bike and head to Adventure Center of Asheville. Keep things going the next day: savor the flavors at Food & Drink, cruise along Blue Ridge Pkwy, and then view the masterpieces at New Morning Gallery.

To see ratings, photos, where to stay, and other tourist information, you can read our Asheville driving holiday website.

Chicago to Asheville is an approximately 3-hour flight. You can also drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In October, daytime highs in Asheville are 70°F, while nighttime lows are 47°F. Finish up your sightseeing early on the 11th (Mon) so you can catch the flight to Chicago.

Things to do in Asheville

Outdoors · Tours · Scenic Drive · Trails

Side Trips


— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, walk around Millennium Park, admire the landmark architecture of 360 Chicago Observation Deck, and take a tour by water with Boat Tours & Water Sports.

To find maps, ratings, where to stay, and other tourist information, use the Chicago trip planner.

Getting from Asheville to Chicago by flight takes about 3 hours. Other options: drive; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. When traveling from Asheville in October, plan for a bit cooler days in Chicago, with highs around 65°F, while nights are about the same with lows around 49°F. Finish your sightseeing early on the 15th (Fri) to allow enough time to travel back home.

Things to do in Chicago

Museums · Childrens Museums · Theme Parks · Parks

North Carolina travel guide

History Museums · Specialty Museums · Zipline
The Tar Heel State
A top destination for a holiday in nature, North Carolina provides a seemingly endless variety of outdoor activities, including hiking, mountain climbing, and skiing. While the state's rural regions offer a taste of traditional Appalachian music and culture, its increasingly diverse big cities feature modern skyscrapers, renowned museums, and historical neighborhoods perfect for sightseeing tours. The coastal region, famous for its year-round temperate climate, attracts millions of annual visitors, making North Carolina the sixth most-visited state in the country. Though it's hard to find a quiet time of year in coastal North Carolina, the state's inland areas retain many secluded corners where you can experience the laid-back Old South atmosphere.