15 days in Chicago & Big Sur Itinerary

15 days in Chicago & Big Sur Itinerary

Created using Inspirock United States tour builder

Plan created by another user. Make it yours
1
Chicago
— 8 nights
Fly
2
Big Sur
— 6 nights
Fly

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8
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, wander the streets of The Magnificent Mile, and admire the striking features of 360 Chicago Observation Deck.

You can plan Chicago trip in no time by asking Inspirock to help create your itinerary.

The Route module shows you all the different ways you can get to Chicago. In October, daily temperatures in Chicago can reach 65°F, while at night they dip to 49°F. Wrap up your sightseeing by early afternoon on the 11th (Sun) to allow time for travel to Big Sur.

Things to do in Chicago

Parks · Museums · Childrens Museums · Zoos & Aquariums

Side Trips

Highlights from your trip
Millennium Park
Must see
Millennium Park
4.8

6
nights
Big Sur

Big Country of the South

A sparsely populated area with stunning views, Big Sur attracts artists and tourists traveling California’s scenic Highway 1.
Venture out of the city with trips to Balconies Cliffs Trails (in Soledad), Bear Gulch Caves (in Paicines) and Carmel Valley (Parsonage Winery Tasting Room, Joyce Vineyards, &more). There's lots more to do: get great views at Rocky Creek Bridge, immerse yourself in nature at Andrew Molera State Park, take in the dramatic scenery at McWay Falls, and enjoy the sand and surf at Julia Pfeiffer Burns State Park.

To find traveler tips, more things to do, where to stay, and more tourist information, go to the Big Sur online road trip planner.

You can fly from Chicago to Big Sur in 11.5 hours. Other options are to drive; or do a combination of train and taxi. Due to the time zone difference, you'll gain 2 hours traveling from Chicago to Big Sur. In October, plan for daily highs up to 70°F, and evening lows to 52°F. Finish your sightseeing early on the 17th (Sat) to allow enough time to travel back home.

Things to do in Big Sur

Parks · Outdoors · Trails · Wineries

Side Trips

Highlights from your trip
Partington Cove ©
Hiking Trail
Partington Cove
4.9
Joullian Vineyards & Winery ©
Winery / Vineyard
Joullian Vineyards & Winery
5.0

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