15 days in Wyoming, Montana & Midwest Itinerary

15 days in Wyoming, Montana & Midwest Itinerary

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Route & dates

15 days in Wyoming, Montana & Midwest Itinerary

Start: Winnipeg
Fly + Drive:  13​h 15​min
1
Cody
— 1 night
Drive:  3​h 45​min
2
Bozeman
— 3 nights
Fly:  4​h 45​min
3
Jackson Hole
— 2 nights
Fly:  6​h 15​min
4
Branson
— 1 night
Drive + Fly:  3​h 45​min
5
Saint Louis
— 2 nights
Fly:  3​h 15​min
6
Chicago
— 3 nights
Fly:  5​h 30​min
End: Winnipeg


Learn more about your trip

1
night
Cody

Cody ©
A genuine cowboy city, Cody is famous for its nightly rodeos and its proximity to the protected wilderness areas of the world's first national park, now designated as one of the country's World Heritage Sites.
Start off your visit on the 28th (Tue): see the interesting displays at Cody Firearms Museum, take an in-depth tour of Buffalo Bill Center of the West, and then steep yourself in history at Old Trail Town. Get ready for a full day of sightseeing on the 29th (Wed): get engrossed in the history at Heart Mountain Interpretive Center, then see the interesting displays at Homesteader Museum, then see the interesting displays at Cody Dug Up Gun Museum, and finally admire the masterpieces at Whitney Gallery.

To find ratings, more things to do, maps, and other tourist information, read Cody trip builder tool .

Winnipeg, Canada to Cody is an approximately 13.5-hour flight. You can also drive. Traveling from Winnipeg to Cody, you'll gain 1 hour due to the time zone difference. May in Cody sees daily highs of 19°C and lows of 6°C at night. Wrap up your sightseeing on the 29th (Wed) to allow time to drive to Bozeman.

Things to do in Cody

Museums Shopping Historic Sites

Side Trip

Powell
Highlights from your plan
Cody Firearms Museum ©
Cody Firearms Museum
Heart Mountain Interpretive Center ©
Heart Mountain Interpretive Center
Cody Dug Up Gun Museum ©
Cody Dug Up Gun Museum

3
nights
Bozeman

Bozeman ©
Bozeman is a city in and the county seat of Gallatin County, Montana, United States, in the southwestern part of the state. Let the collections at Museum of the Rockies and Yellowstone Gateway Museum capture your imagination. Give yourself a bit of retail therapy at Bozeman Public Library and Yellowstone Gifts & Sweets. Step out of Bozeman to go to Gardiner and see Horseback Riding Tours, which is approximately 1h 30 min away. There's much more to do: get to know the fascinating history of Downtown Bozeman, indulge your thirst for a good beer at Madison River Brewing, and take an in-depth tour of American Computer Museum.

For more things to do, maps, other places to visit, and other tourist information, read our Bozeman road trip planning site .

You can drive from Cody to Bozeman in 4 hours. Traveling from Cody in May, you can expect nighttime temperatures to be slightly colder in Bozeman, with lows of 3°C. Finish your sightseeing early on the 1st (Sat) to allow enough time to travel to Jackson Hole.

Things to do in Bozeman

Museums Historic Sites Outdoors

Side Trips

Gardiner, Yellowstone Gateway Museum, Madison River Brewing
Highlights from your plan
Museum of the Rockies ©
Museum of the Rockies
American Computer & Robotics Museum ©
Downtown Bozeman ©
Downtown Bozeman

2
nights
Jackson Hole

Jackson Hole ©
The Jackson Hole valley is approximately 97 km (60 mi) long and 24 km (15 mi) wide, encompassing the town of Jackson, Teton Village, and the northern section of Grand Teton National Park.
Start off your visit on the 2nd (Sun): shop like a local with Mangelsen Images of Nature, view the masterpieces at The Brookover Gallery, make a trip to Town Square, then steep yourself in history at Mormon Row Historic District, and finally contemplate in the serene atmosphere at Chapel of the Transfiguration. Here are some ideas for day two: explore and take pictures at Jackson Hole Rodeo, admire the masterpieces at National Museum of Wildlife Art, then view the masterpieces at Rare Jackson Hole Gallery, and finally stop by Hines Goldsmiths.

To see ratings, traveler tips, other places to visit, and more tourist information, read Jackson Hole trip planner .

Getting from Bozeman to Jackson Hole by flight takes about 5 hours. Other options: drive; or do a combination of bus and car. Prepare for a bit cooler weather when traveling from Bozeman in June: high temperatures in Jackson Hole hover around 26°C and lows are around 4°C. Wrap up your sightseeing on the 3rd (Mon) early enough to travel to Branson.

Things to do in Jackson Hole

Museums Shopping Historic Sites

Side Trip

Grand Teton National Park
Highlights from your plan
National Museum of Wildlife Art ©
National Museum of Wildlife Art
Chapel of the Transfiguration ©
Chapel of the Transfiguration
Mormon Row Historic District ©
Mormon Row Historic District

1
night
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
On the 4th (Tue), take some stellar pictures from 165 Scenic Overlook, contemplate the waterfront views at Table Rock Lake, then buy something for everyone on your list at Branson Landing, and finally stop by Dick's Oldtime 5 & 10. On your second day here, get engrossed in the history at Veterans Memorial Museum, then look for all kinds of wild species at Shepherd of the Hills Fish Hatchery, and then wander the streets of Historic Downtown Branson.

To see maps, other places to visit, traveler tips, and more tourist information, go to the Branson vacation maker website .

Fly from Jackson Hole to Branson in 6.5 hours. Alternatively, you can do a combination of flight and car; or drive. Traveling from Jackson Hole to Branson, you'll lose 1 hour due to the time zone difference. When traveling from Jackson Hole in June, plan for a bit warmer days and much warmer nights in Branson: temperatures range from 34°C by day to 21°C at night. Finish your sightseeing early on the 5th (Wed) to allow enough time to travel to Saint Louis.

Things to do in Branson

Parks Shopping Wildlife

Side Trip

Table Rock Lake
Highlights from your plan
Branson Landing ©
Branson Landing
Veterans Memorial Museum ©
Veterans Memorial Museum
165 Scenic Overlook ©
165 Scenic Overlook

2
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
On the 6th (Thu), explore the world behind art at Saint Louis Art Museum, tour the pleasant surroundings at Forest Park, and then appreciate the extensive heritage of St. Charles Historic District. On the 7th (Fri), you'll have a packed day of sightseeing: engage your brain at Saint Louis Science Center and then pause for some serene contemplation at Cathedral Basilica of Saint Louis.

For where to stay, more things to do, and more tourist information, use the Saint Louis trip planning site .

You can do a combination of car and flight from Branson to Saint Louis in 4 hours. Other options are to drive; or take a bus. June in Saint Louis sees daily highs of 36°C and lows of 22°C at night. Finish your sightseeing early on the 7th (Fri) so you can travel to Chicago.

Things to do in Saint Louis

Museums Childrens Museums Parks

Side Trip

St. Charles Historic District
Highlights from your plan
Cathedral Basilica of Saint Louis ©
St. Charles Historic District ©
St. Charles Historic District
Saint Louis Art Museum ©
Saint Louis Art Museum

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Museum-lovers will get to explore The Art Institute of Chicago and Museum of Science and Industry. Do your shopping at The Magnificent Mile and Chicago Cultural Center. There's still lots to do: get to know the fascinating history of Millennium Park, make a trip to Cloud Gate, try your luck at Horseshoe Hammond, and explore and take pictures at Wrigley Field.

To see more things to do, maps, where to stay, and other tourist information, read Chicago online travel route planner .

Traveling by flight from Saint Louis to Chicago takes 3.5 hours. Alternatively, you can drive; or take a bus. Traveling from Saint Louis in June, you will find days in Chicago are a bit cooler (32°C), and nights are about the same (20°C). Wrap up your sightseeing on the 10th (Mon) early enough to travel back home.

Things to do in Chicago

Museums Shopping Neighborhoods

Side Trip

Horseshoe Hammond
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
The Magnificent Mile ©
The Magnificent Mile
Chicago Cultural Center ©
Chicago Cultural Center

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