14 days in California, Wyoming & South Dakota Itinerary

14 days in California, Wyoming & South Dakota Itinerary

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Route & dates

14 days in California, Wyoming & South Dakota Itinerary

Start: Chicago
Fly:  6​h 15​min
1
San Diego
— 1 night
Drive:  2​h 15​min
2
Los Angeles
— 2 nights
Fly:  3​h 45​min
3
San Francisco
— 3 nights
Fly:  4​h 15​min
4
Jackson Hole
— 1 night
Drive:  2​h
5
Yellowstone National Park
— 4 nights
Drive + Fly:  6​h 15​min
6
Keystone
— 1 day
Fly:  4​h 45​min
End: Chicago

1
night
San Diego

San Diego ©
Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
Start off your visit on the 14th (Sun): stroll through La Jolla Cove. Here are some ideas for day two: examine the collection at Maritime Museum of San Diego and then meet the residents at San Diego Zoo.

To find more things to do and tourist information, read our San Diego day trip planner.

Chicago to San Diego is an approximately 6.5-hour flight. You can also drive; or take a train. Due to the time zone difference, you'll gain 2 hours traveling from Chicago to San Diego. Traveling from Chicago in June, expect nights in San Diego to be about the same, around 64°F, while days are little chillier, around 73°F. Finish your sightseeing early on the 15th (Mon) so you can drive to Los Angeles.

Things to do in San Diego

Parks Zoos & Aquariums Outdoors
Highlights from your plan
La Jolla Cove ©
La Jolla Cove
San Diego Zoo ©
San Diego Zoo
Maritime Museum of San Diego ©
Maritime Museum of San Diego

2
nights
Los Angeles

Los Angeles ©
Surrounded by mountain ranges, forests, valleys, beaches, and deserts, the metropolitan area of Los Angeles is home to over 17 million people.
Start off your visit on the 16th (Tue): make an unforgettable trip to Disneyland Park. Get ready for a full day of sightseeing on the 17th (Wed): immerse yourself in nature at Santa Monica State Beach, then enjoy the sand and surf at Venice Beach and Boardwalk, and then wander the streets of El Pueblo de Los Angeles.

To find maps, reviews, photos, and more tourist information, you can read our Los Angeles road trip tool .

Traveling by car from San Diego to Los Angeles takes 2.5 hours. Alternatively, you can take a bus; or fly. While traveling from San Diego, expect somewhat warmer days and about the same nights in Los Angeles, ranging from highs of 79°F to lows of 62°F. Finish up your sightseeing early on the 17th (Wed) so you can travel to San Francisco.

Things to do in Los Angeles

Theme Parks Outdoors Beaches

Side Trips

Disneyland Park, Santa Monica State Beach
Highlights from your plan
Disneyland Park ©
Disneyland Park
Venice Beach and Boardwalk ©
Venice Beach and Boardwalk
Santa Monica State Beach ©
Santa Monica State Beach

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Your inner history buff will appreciate Alcatraz Island and Twin Peaks. Get outdoors at Fort Funston National Park and Lincoln Park. There's lots more to do: take in the waterfront at Fisherman's Wharf, get curious at Exploratorium, take a stroll through Union Square, and snap pictures at Golden Gate Bridge.

To see traveler tips, other places to visit, where to stay, and more tourist information, you can read our San Francisco day trip website .

Fly from Los Angeles to San Francisco in 4 hours. Alternatively, you can do a combination of flight and train; or drive. In June, San Francisco is a bit cooler than Los Angeles - with highs of 71°F and lows of 55°F. Finish up your sightseeing early on the 20th (Sat) so you can travel to Jackson Hole.

Things to do in San Francisco

Neighborhoods Shopping Parks
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Golden Gate Bridge ©
Golden Gate Bridge
Fort Funston National Park ©
Fort Funston National Park

1
night
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.
On the 21st (Sun), take your sightseeing to a higher altitude at Grand Teton. Here are some ideas for day two: hike along Cascade Canyon Trail, then trek along Taggart Lake, and then identify plant and animal life at Blacktail Ponds Overlook.

For reviews, ratings, traveler tips, and other tourist information, read our Jackson Hole vacation planner.

Traveling by flight from San Francisco to Jackson Hole takes 4.5 hours. Alternatively, you can drive. You'll lose 1 hour traveling from San Francisco to Jackson Hole due to the time zone difference. Plan for a bit cooler nights when traveling from San Francisco in June since evenings lows in Jackson Hole dip to 39°F. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Yellowstone National Park.

Things to do in Jackson Hole

Parks Wildlife Nature

Side Trip

Grand Teton National Park
Highlights from your plan
Grand Teton ©
Grand Teton
Cascade Canyon Trail ©
Cascade Canyon Trail
Taggart Lake ©
Taggart Lake

4
nights
Yellowstone National Park

Yellowstone National Park ©
An exceptionally diverse landscape and varied wildlife have made Yellowstone National Park one of America's most popular parks.
Step out of the city life by going to Artist Point and Grand Canyon of the Yellowstone. There's still lots to do: explore the activities along Yellowstone Lake, take in the natural beauty of Grand Prismatic Spring, admire the sheer force of Gibbon Falls, and identify plant and animal life at Firehole Canyon Drive.

For where to stay, other places to visit, reviews, and more tourist information, read our Yellowstone National Park trip planner .

You can drive from Jackson Hole to Yellowstone National Park in 2 hours. Traveling from Jackson Hole in June, things will get slightly colder in Yellowstone National Park: highs are around 66°F and lows about 34°F. Wrap up your sightseeing on the 26th (Fri) to allow time to travel to Keystone.

Things to do in Yellowstone National Park

Parks Nature Outdoors
Highlights from your plan
Old Faithful ©
Old Faithful
Grand Canyon of the Yellowstone ©
Grand Canyon of the Yellowstone
Grand Prismatic Spring ©
Grand Prismatic Spring

1
day
Keystone

Keystone ©
Fewer than 400 people call Keystone home year-round, but the population explodes in summer when crowds flock to nearby Mount Rushmore.
Start off your visit on the 27th (Sat): take a memorable drive along Iron Mountain Road, then do a tasting at Prairie Berry Winery, and then explore and take pictures at Mount Rushmore National Memorial.

To see ratings, reviews, more things to do, and other tourist information, you can read our Keystone online tour itinerary planner .

You can do a combination of car and flight from Yellowstone National Park to Keystone in 6.5 hours. Other options are to drive; or do a combination of car, bus, and shuttle. Plan for a bit warmer temperatures traveling from Yellowstone National Park in June, with highs in Keystone at 73°F and lows at 48°F. Cap off your sightseeing on the 27th (Sat) early enough to travel back home.

Things to do in Keystone

Outdoors Scenic Drive Nature

Side Trips

Prairie Berry Winery, Iron Mountain Road
Highlights from your plan
Iron Mountain Road ©
Iron Mountain Road
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Prairie Berry Winery ©
Prairie Berry Winery

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