29 days in Chicago & Great Smoky Mountains National Park Itinerary

29 days in Chicago & Great Smoky Mountains National Park Itinerary

Created using Inspirock United States holiday planner

Make it your trip
Drive
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Chicago
— 8 nights
Fly
2
Great Smoky Mountains National Park
— 20 nights
Drive

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Chicago

— 8 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Art Institute of Chicago and Frank Lloyd Wright Home and Studio. Take a break from the city and head to Boat Tours & Water Sports and Little Red Schoolhouse. Change things up with these side-trips from Chicago: Centennial Bike Trail (in Willow Springs), Prairie Wolf Slough (in Highland Park) and Skokie Lagoons (in Winnetka). There's much more to do: take a stroll through The Magnificent Mile, take in the spiritual surroundings of Fourth Presbyterian Church, contemplate the long history of Ernest Hemingway Birthplace, and get a new perspective on nature at Field Museum.

For where to stay, reviews, more things to do, and tourist information, use the Chicago attractions planner.

Bloomington to Chicago is an approximately 2.5-hour car ride. You can also drive. In May, plan for daily highs up to 71°F, and evening lows to 52°F. Wrap up your sightseeing on the 30th (Sun) early enough to travel to Great Smoky Mountains National Park.

Things to do in Chicago

Parks · Outdoors · Wildlife · Trails

Side Trips

Great Smoky Mountains National Park

— 20 nights

A Wondrous Diversity of Life

Great Smoky Mountains National Park contains some of the highest mountains east of the Mississippi River, but it's the ease of access that makes this national park the United States' most visited.
Get a sense of the local culture at Noah Bud Ogle Cabin and Little Greenbrier School. Get outdoors at Roaring Fork and Cades Cove. You'll find plenty of places to visit near Great Smoky Mountains National Park: Great Smoky Mountains National Park (Collins Creek Picnic Area & Cataloochee Valley). Next up on the itinerary: steep yourself in history at Walker Sisters' Cabin, identify plant and animal life at Sugarlands Valley Nature Trail, take your sightseeing to a higher altitude at Clingmans Dome, and take a memorable drive along Newfound Gap Road.

To find traveler tips, reviews, and other tourist information, read Great Smoky Mountains National Park journey builder tool.

Getting from Chicago to Great Smoky Mountains National Park by flight takes about 4.5 hours. Other options: drive; or do a combination of bus and subway. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. When traveling from Chicago in May, plan for somewhat warmer days and about the same nights in Great Smoky Mountains National Park: temperatures range from 79°F by day to 57°F at night. You will have some time to spend on the 19th (Sat) before leaving for home.

Things to do in Great Smoky Mountains National Park

Parks · Outdoors · Trails · Nature

Side Trips