26 days in Chicago, Apple Valley & Silver Cliff Itinerary

26 days in Chicago, Apple Valley & Silver Cliff Itinerary

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Route & dates

26 days in Chicago, Apple Valley & Silver Cliff Itinerary

Start: Philadelphia
Fly:  4​h
1
Chicago
— 9 nights
Drive:  25​h
2
Apple Valley
— 9 nights
Drive:  11​h 30​min
3
Silver Cliff
— 5 nights
Drive + Fly:  10​h 30​min
End: Philadelphia

9
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Anderson Japanese Gardens (in Rockford) and Rotary Botanical Gardens (in Janesville). There's still lots to do: admire the masterpieces at The Art Institute of Chicago, take in the waterfront at Navy Pier, admire the striking features of Skydeck Chicago - Willis Tower, and get curious at Museum of Science and Industry.

To find maps, ratings, traveler tips, and other tourist information, read Chicago trip planning tool .

Philadelphia to Chicago is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. Traveling from Philadelphia to Chicago, you'll gain 1 hour due to the time zone difference. In October in Chicago, expect temperatures between 65°F during the day and 49°F at night. Cap off your sightseeing on the 28th (Mon) early enough to travel to Apple Valley.

Things to do in Chicago

Parks Museums Fun & Games

Side Trips

Oak Park, Anderson Japanese Gardens, Rotary Botanical Gardens, Horseshoe Hammond
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

9
nights
Apple Valley

Apple Valley ©
The Town of Apple Valley is located in the Victor Valley of San Bernardino County, in the U.S. Explore the numerous day-trip ideas around Apple Valley: Temecula (Old Town Spice & Tea Merchants & Wine Tours & Tastings), Joshua Tree National Park (Arch Rock, Split Rock, & more) and Redlands (Redlands Art Association & Redlands Bowl). There's lots more to do: explore the different monuments and memorials at Riverside National Cemetery, take in the architecture and atmosphere at Church of the Woods, have some family-friendly fun at Perris Indoor Skydiving, and explore the landscape on two wheels at Alpine Pedal Path.

To find ratings, other places to visit, maps, and tourist information, use the Apple Valley sightseeing planner.

You can drive from Chicago to Apple Valley in 28 hours. Traveling from Chicago to Apple Valley, you'll gain 2 hours due to the time zone difference. Traveling from Chicago in October, you will find days in Apple Valley are a bit warmer (79°F), and nights are about the same (49°F). Finish up your sightseeing early on the 7th (Thu) so you can travel to Silver Cliff.

Things to do in Apple Valley

Parks Outdoors Trails

Side Trips

Joshua Tree National Park, Big Bear Lake, Temecula, Redlands, Murtle the Turtle
Highlights from your plan
Ashwood Golf Course ©
Ashwood Golf Course
Wine Tours & Tastings
Redlands Bowl ©
Redlands Bowl

5
nights
Silver Cliff

Silver Cliff ©
Silver Cliff is a statutory town that is the most populous town in Custer County, Colorado, United States. Venture out of the city with trips to Mosca Pass Trail (in Great Sand Dunes National Park & Preserve), Bishop Castle (in Rye) and Mission: Wolf (in Gardner). There's much more to do: explore the stunning scenery at Poudre Canyon, admire the verdant scenery at Rabbit Valley, contemplate the waterfront views at Arkansas River, and see the interesting displays at Silver Cliff Museum.

For traveler tips, ratings, more things to do, and other tourist information, go to the Silver Cliff trip planning tool .

Traveling by car from Apple Valley to Silver Cliff takes 14.5 hours. The time zone difference when traveling from Apple Valley to Silver Cliff is 1 hour. You will leave for home on the 13th (Wed).

Things to do in Silver Cliff

Parks Nature Trails

Side Trips

Colorado, Mosca Pass Trail, Mission: Wolf, Bishop Castle
Highlights from your plan
Mission: Wolf ©
Mission: Wolf
Bishop Castle ©
Bishop Castle

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