60 days in Detroit & Chicago Itinerary

60 days in Detroit & Chicago Itinerary

Created using Inspirock United States vacation planner

Make it your trip
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1
Detroit
— 20 nights
Fly
2
Chicago
— 39 nights
Fly

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Detroit

— 20 nights

The Motor City

Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
Discover out-of-the-way places like Detroit Institute of Arts and The Ford Piquette Avenue Plant. Explore the numerous day-trip ideas around Detroit: Midland (The Tridge & Dow Gardens), Toledo (National Museum of the Great Lakes, Imagination Station, &more) and Sawyer Quarry Nature Preserve (in Perrysburg). There's still lots to do: take an in-depth tour of Detroit Historical Museum, contemplate the long history of Crossroads Village & Huckleberry Railroad, make a trip to University of Michigan, and take a leisurely stroll along Detroit RiverFront.

To find maps, reviews, ratings, and more tourist information, read Detroit travel planner.

New York City to Detroit is an approximately 3.5-hour flight. You can also drive; or take a bus. Traveling from New York City in November, expect Detroit to be slightly colder, temps between 48°F and 34°F. Wrap up your sightseeing on the 9th (Thu) early enough to fly to Chicago.

Things to do in Detroit

Museums · Historic Sites · Shopping · Parks

Side Trips

Chicago

— 39 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Discover out-of-the-way places like Holy Name Cathedral and Lake Michigan. Explore the numerous day-trip ideas around Chicago: SC Johnson Headquarters (in Racine), Milwaukee (Lakefront Brewery, Chudnow Museum of Yesteryear, &more) and South Bend (Basilica of the Sacred Heart, Grotto of Our Lady Lourdes, &more). Spend the 22nd (Wed) exploring nature at Indiana Dunes National Park. There's lots more to do: take a stroll through The Loop, admire the natural beauty at Garfield Park Conservatory, see the interesting displays at Money Museum at the Federal Reserve Bank, and contemplate the waterfront views at Chicago River.

To see photos, maps, more things to do, and other tourist information, read our Chicago trip itinerary maker app.

Traveling by flight from Detroit to Chicago takes 3 hours. Alternatively, you can drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Detroit to Chicago. In December, plan for daily highs up to 38°F, and evening lows to 26°F. Finish your sightseeing early on the 17th (Mon) so you can fly back home.

Things to do in Chicago

Museums · Parks · Historic Sites · Nature

Side Trips