8 days in Midwest Itinerary

Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, take a tour by water with Boat Tours & Water Sports, find something for the whole family at Navy Pier, and admire the striking features of 360 Chicago Observation Deck.

For ratings, reviews, other places to visit, and other tourist information, use the Chicago trip planner.

Sydney, Australia to Chicago is an approximately 23-hour flight. The time zone changes from Australian Eastern Standard Time to Central Standard Time, which is usually a -16 hour difference. Prepare for slightly colder weather when traveling from Sydney in October: high temperatures in Chicago hover around 21°C and lows are around 11°C. Wrap up your sightseeing on the 12th (Thu) to allow time to fly to Branson.

Start off your visit on the 13th (Fri): find something for the whole family at Silver Dollar City. On the next day, take an in-depth tour of Titanic Museum, head outdoors with Outdoor Activities, and then get great views at College of the Ozarks.

To find more things to do, traveler tips, other places to visit, and more tourist information, read our Branson trip itinerary planning app.

You can fly from Chicago to Branson in 3 hours. Alternatively, you can drive; or do a combination of train, bus, and taxi. Expect somewhat warmer weather when traveling from Chicago in October: highs in Branson hover around 25°C, while lows dip to 11°C. Finish your sightseeing early on the 15th (Sun) so you can fly back home.