23 days in Chicago and Beyond Itinerary

Venture out of the city with trips to Chicago Botanic Garden (in Glencoe), Moraine Hills State Park (in McHenry) and Baha'i House of Worship (in Wilmette).

For more things to do, reviews, where to stay, and more tourist information, go to the Waukegan sightseeing planner.

Bremen, Germany to Waukegan is an approximately 15.5-hour combination of flight and car. Due to the time zone difference, you'll gain 7 hours traveling from Bremen to Waukegan. While traveling from Bremen, expect somewhat warmer days and about the same nights in Waukegan, ranging from highs of 27°C to lows of 15°C. Wrap up your sightseeing on the 5th (Tue) to allow time to drive to Kankakee.

On the 6th (Wed), look for all kinds of wild species at Midewin National Tallgrass Prairie, then don't miss a visit to Gemini Giant, and then examine the collection at Exploration Station...a children's museum. On the 7th (Thu), you'll have a packed day of sightseeing: get engrossed in the history at French Heritage Museum at The Stone Barn, admire the landmark architecture of B. Harley Bradley House, then examine the collection at Kankakee County Museum, and finally discover the deep blue sea with Haigh Quarry.

To find reviews, other places to visit, photos, and more tourist information, you can read our Kankakee trip maker tool.

Getting from Waukegan to Kankakee by car takes about 2 hours. September in Kankakee sees daily highs of 30°C and lows of 15°C at night. Finish your sightseeing early on the 7th (Thu) to allow enough time to drive to Chicago.

Explore the numerous day-trip ideas around Chicago: Wheaton (Cantigny Park, First Division Museum at Cantigny, &more). There's still lots to do: explore the world behind art at The Art Institute of Chicago, take in panoramic vistas at 360 Chicago Observation Deck, take in the waterfront at Navy Pier, and get a new perspective on things with Boat Tours & Water Sports.

For maps, traveler tips, more things to do, and more tourist information, go to the Chicago tour builder tool.

Getting from Kankakee to Chicago by car takes about 1.5 hours. Other options: drive. Traveling from Kankakee in September, you can expect nighttime temperatures to be somewhat warmer in Chicago, with lows of 19°C. Finish your sightseeing early on the 18th (Mon) so you can drive to Rockford.

Venture out of the city with trips to Dixon's Railroad Street Arches (in Dixon), Edwards Apple Orchard (in Poplar Grove) and Freeport (Jane Addams Recreation Trail, Krape Park, &more).

To find other places to visit, maps, reviews, and other tourist information, refer to the Rockford road trip app.

Traveling by car from Chicago to Rockford takes 1.5 hours. Alternatively, you can drive; or take a bus; or do a combination of subway and bus. Traveling from Chicago in September, expect a bit cooler with lows of 15°C in Rockford. Wrap up your sightseeing on the 24th (Sun) to allow time to travel back home.