60 days in Chicago & Whitefish Itinerary

60 days in Chicago & Whitefish Itinerary

Created using Inspirock United States holiday planner

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Chicago
— 46 nights
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Whitefish
— 13 nights

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46
nights
Chicago

Chicago ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore Chicago's surroundings by going to Patch 22 (in Wadsworth), Hobart (Deep River County Park & County Line Orchard) and Chapel of the Resurrection (in Valparaiso). There's much more to do: admire the masterpieces at The Art Institute of Chicago, walk around Millennium Park, get curious at Museum of Science and Industry, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

Before you visit Chicago, use our trip planner to discover what you can do and see there.

Charlotte 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 Charlotte to Chicago. Traveling from Charlotte in October, expect nights in Chicago to be about the same, around 49°F, while days are little chillier, around 65°F. Wrap up your sightseeing on the 16th (Mon) early enough to travel to Whitefish.

Things to do in Chicago

Side Trips

Find places to stay Oct 1 — Nov 16:
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

13
nights
Whitefish

Whitefish ©
Whitefish is a city in Flathead County, Montana, United States. You'll find plenty of places to visit near Whitefish: Libby (Libby Heritage Museum & McGinnis Meadows Cattle and Guest Ranch), Glacier National Park (Swiftcurrent Mountain, Iceberg Lake Trail, &more) and Bigfork (Eric Thorsen Art Studio & Howe’s Fishing – A Able/Mo Fisch Charters and Tours). Spend the 23rd (Mon) exploring nature at Glacier National Park. categoryPhrases.sentence.On_the_day_spend_an_exhilarating_day_on_the_slopes_at. There's much more to do: take a peaceful walk through Flathead National Forest, sample the tasty concoctions at Great Northern Brewing Company, grab your bike and head to The Whitefish Trail, and make a trip to Dick Idol Signature Gallery.

To see ratings, photos, reviews, and tourist information, read our Whitefish planner.

You can fly from Chicago to Whitefish in 6.5 hours. Other options are to drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Chicago to Whitefish. Traveling from Chicago in November, things will get a bit cooler in Whitefish: highs are around 40°F and lows about 24°F. Wrap up your sightseeing by early afternoon on the 29th (Sun) to allow enough time to travel back home.

Things to do in Whitefish

Parks · Outdoors · Nature · Trails

Side Trips

Find places to stay Nov 16 — 29:
Highlights from your plan
Iceberg Lake Trail ©
Iceberg Lake Trail
Glacier National Park ©
Glacier National Park
McGinnis Meadows Cattle and Guest Ranch ©
McGinnis Meadows Cattle and Guest Ranch

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