10 days in Chicago, Osage & Branson Itinerary

10 days in Chicago, Osage & Branson Itinerary

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Route & dates

10 days in Chicago, Osage & Branson Itinerary

Start: Bangor
Fly:  4​h 30​min
1
Chicago
— 3 nights
Drive:  6​h
2
Osage
— 2 nights
Drive:  8​h 15​min
3
Branson
— 3 nights
Fly:  6​h 30​min
End: Bangor

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Popular historic sites such as Millennium Park and Fourth Presbyterian Church are in your itinerary. Get some cultural insight at The Magnificent Mile and The Art Institute of Chicago. The adventure continues: get curious at Museum of Science and Industry, make a trip to Cloud Gate, take some stellar pictures from Tilt, and observe the fascinating underwater world at Shedd Aquarium.

To see where to stay, maps, photos, and more tourist information, refer to the Chicago itinerary maker tool .

Bangor to Chicago is an approximately 4.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Bangor to Chicago. Plan for somewhat warmer nights when traveling from Bangor in October since evenings lows in Chicago dip to 49°F. Finish your sightseeing early on the 22nd (Tue) to allow enough time to travel to Osage.

Things to do in Chicago

Museums Neighborhoods Shopping
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile
Museum of Science and Industry ©
Museum of Science and Industry

2
nights
Osage

Osage ©
Osage is a city in Mitchell County, Iowa, United States. Kick off your visit on the 22nd (Tue): steep yourself in history at Stockman House Museum and then appreciate the extensive heritage of Music Man Square. Get ready for a full day of sightseeing on the next day: wander the streets of Cedar Falls Main Street and then admire the landmark architecture of Historic Park Inn Hotel.

To see reviews, ratings, maps, and other tourist information, you can read our Osage driving holiday site .

You can drive from Chicago to Osage in 6 hours. Alternatively, you can do a combination of flight and car. Traveling from Chicago in October, plan for little chillier nights in Osage, with lows around 42°F. Wrap up your sightseeing on the 24th (Thu) early enough to travel to Branson.

Things to do in Osage

Historic Sites Neighborhoods Fun & Games

Side Trips

Mason City, Diamond Jo Casino, St. Augustine's Catholic Church, Cedar Falls Main Street
Highlights from your plan
Stockman House Museum ©
Stockman House Museum
Historic Park Inn Hotel ©
Historic Park Inn Hotel

3
nights
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Deepen your sense of the past at sights like Our Lady of the Lake Catholic Church and Wilderness Chapel. Satisfy your inner culture vulture at Titanic Museum and Stone Hill Winery. And it doesn't end there: get in on the family fun at Silver Dollar City, look for gifts at Pepper Palace- Branson, take a stroll through Historic Downtown Branson, and get great views at 165 Scenic Overlook.

Take the guesswork out of planning a Branson vacation by using our trip itinerary maker.

You can drive from Osage to Branson in 8.5 hours. Another option is to do a combination of car and flight. Prepare for a bit warmer weather when traveling from Osage in October: high temperatures in Branson hover around 71°F and lows are around 50°F. Cap off your sightseeing on the 27th (Sun) early enough to travel back home.

Things to do in Branson

Theme Parks Historic Sites Shopping
Highlights from your plan
Our Lady of the Lake Catholic Church ©
Titanic Museum ©
Titanic Museum
Stone Hill Winery ©
Stone Hill Winery

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