39 days in Chicago & Traverse City Itinerary

39 days in Chicago & Traverse City Itinerary

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Route & dates

39 days in Chicago & Traverse City Itinerary

Start: Chicago
1
Chicago
— 20 nights
subway + Fly:  3​h
2
Traverse City
— 18 nights
Fly + subway:  3​h
End: Chicago

20
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: Whiskey Acres Distilling Co. (in DeKalb), South Bend (Basilica of the Sacred Heart, University of Notre Dame, & more) and Racine (SC Johnson Headquarters & River Bend Nature Center). The adventure continues: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at Skydeck Chicago - Willis Tower, wander the streets of The Magnificent Mile, and laugh and play at Navy Pier.

For traveler tips, other places to visit, photos, and more tourist information, read our Chicago trip builder site .

The Route module can give you travel options from your home to Chicago. In October in Chicago, expect temperatures between 65°F during the day and 49°F at night. Wrap up your sightseeing on the 8th (Fri) early enough to travel to Traverse City.

Things to do in Chicago

Museums Historic Sites Parks

Side Trips

Milwaukee, Oak Park, Evanston, South Bend, Lake Geneva
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

18
nights
Traverse City

Traverse City might be well known for its huge cherry industry, but its position along Grand Traverse Bay in Lake Michigan endows it with fine scenery and a wealth of outdoor attractions.
You'll find plenty of places to visit near Traverse City: Empire (Pierce Stocking Scenic Drive, Sleeping Bear Dunes National Lakeshore, & more), Sleeping Bear Heritage Trail (in Glen Arbor) and Charlevoix (Mushroom House Tours of Charlevoix & Charlevoix Circle of Arts). And it doesn't end there: sample some tasty brews at a beer tour and tasting, explore the landscape on two wheels at Traverse Area Recreation and Transportation Trails, contemplate in the serene atmosphere at Cross In The Woods National Shrine, and tour the pleasant surroundings at Fred Meijer White Pine Trail State Park.

To see other places to visit, reviews, where to stay, and other tourist information, read Traverse City route builder .

You can do a combination of subway and flight from Chicago to Traverse City in 3 hours. Alternatively, you can do a combination of flight and car; or drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In November, plan for daily highs up to 46°F, and evening lows to 32°F. Wrap up your sightseeing on the 26th (Tue) early enough to travel back home.

Things to do in Traverse City

Parks Outdoors Wineries

Side Trips

Petoskey, Suttons Bay, Manistee, Empire, Charlevoix
Highlights from your plan
Beer Tastings & Tours
Sleeping Bear Dunes National Lakeshore ©
Little Traverse Wheelway ©
Little Traverse Wheelway

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