8 days in Midwest Itinerary
Created using Inspirock Midwest attractions planner
Start: New York City
Fly
1
Empire
— 1 night
Drive
2
Hart
— 1 night
Drive
3
Chicago
— 5 nights
Fly
End: New York City
Fri, Sep 9 - Fri, Sep 16
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Empire — 1 night
Empire is a village in Leelanau County in the U.S. state of Michigan. On the 9th (Fri), learn about winemaking at Longview Winery and then enjoy the sand and surf at Lake Michigan Beach Park. Here are some ideas for day two: explore the wealth of natural beauty at Sleeping Bear Dunes National Lakeshore.
To see ratings, more things to do, where to stay, and other tourist information, read our Empire day trip tool.
New York City to Empire is an approximately 4-hour flight. You can also drive; or do a combination of bus and taxi. Expect little chillier temperatures when traveling from New York City in September; daily highs in Empire reach 71°F and lows reach 53°F. Finish your sightseeing early on the 10th (Sat) so you can drive to Hart.
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To see ratings, more things to do, where to stay, and other tourist information, read our Empire day trip tool.
New York City to Empire is an approximately 4-hour flight. You can also drive; or do a combination of bus and taxi. Expect little chillier temperatures when traveling from New York City in September; daily highs in Empire reach 71°F and lows reach 53°F. Finish your sightseeing early on the 10th (Sat) so you can drive to Hart.
Side Trip
Highlights from your trip
Hart — 1 night

Hart is a city in the U.S. state of Michigan. Start off your visit on the 11th (Sun): ride a horse along Stony Lake Stables and then stroll around Silver Lake State Park Pedestrian Dune Access.
For photos, more things to do, traveler tips, and other tourist information, you can read our Hart tour site.
Traveling by car from Empire to Hart takes 2 hours. In September, plan for daily highs up to 72°F, and evening lows to 52°F. Wrap up your sightseeing on the 11th (Sun) early enough to drive to Chicago.
more
For photos, more things to do, traveler tips, and other tourist information, you can read our Hart tour site.
Traveling by car from Empire to Hart takes 2 hours. In September, plan for daily highs up to 72°F, and evening lows to 52°F. Wrap up your sightseeing on the 11th (Sun) early enough to drive to Chicago.
Side Trip
Highlights from your trip
Chicago — 5 nights

Windy City
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.Satisfy your inner culture vulture at The Art Institute of Chicago and Field Museum. Popular historic sites such as Ernest Hemingway Birthplace and Pleasant Home are in your itinerary. Next up on the itinerary: wander the streets of The Magnificent Mile, admire the landmark architecture of Frank Lloyd Wright Home and Studio, contemplate in the serene atmosphere at Frank Lloyd Wright's Unity Temple, and try to win big at Horseshoe Hammond.
To see where to stay, ratings, photos, and more tourist information, use the Chicago holiday maker tool.
You can drive from Hart to Chicago in 4 hours. The time zone difference when traveling from Hart to Chicago is minus 1 hour. Traveling from Hart in September, expect Chicago to be somewhat warmer, temps between 78°F and 61°F. Finish up your sightseeing early on the 16th (Fri) so you can catch the flight back home.
Side Trips
Highlights from your trip