3 days in Chicago & Southwest Michigan Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Kick off your visit on the 24th (Sat): admire the landmark architecture of Chicago Cultural Center, then admire the masterpieces at Richard H. Driehaus Museum, then hike along Lakefront Trail, and finally take a stroll through The Loop.

To find ratings, where to stay, more things to do, and other tourist information, you can read our Chicago travel route planner.

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. Finish your sightseeing early on the 24th (Sat) so you can drive to New Buffalo.

New Buffalo is a city in Berrien County in the U.S. Kick off your visit on the 25th (Sun): stroll around Washington Park Zoo, cross one thing off your bucket list with Skydive Windy City, and then immerse yourself in nature at Indiana Dunes State Park.

To see more things to do, maps, where to stay, and tourist information, go to the New Buffalo holiday builder.

You can drive from Chicago to New Buffalo in 1.5 hours. Traveling from Chicago in October, expect slightly colder with lows of 44°F in New Buffalo. Finish up your sightseeing early on the 25th (Sun) so you can go by car to Saugatuck.

Saugatuck is a city in Allegan County in the U.S. Start off your visit on the 26th (Mon): head off-road at Saugatuck Dune Rides, then kick back and relax at Oval Beach, and then trek along Kal Haven Trail.

For ratings, more things to do, other places to visit, and tourist information, use the Saugatuck attractions planner.

You can drive from New Buffalo to Saugatuck in 1.5 hours. Traveling from New Buffalo to Saugatuck, you'll lose 1 hour due to the time zone difference. In October, daily temperatures in Saugatuck can reach 63°F, while at night they dip to 45°F. Finish up your sightseeing early on the 26th (Mon) so you can go by car back home.