60 days in Chicago and Beyond Itinerary

60 days in Chicago and Beyond Itinerary

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Route & dates

60 days in Chicago and Beyond Itinerary

Start: Detroit
Fly:  4​h
— 12 nights
Drive:  1​h 15​min
Crystal Lake
— 12 nights
Drive:  1​h 15​min
Loves Park
— 10 nights
Drive:  1​h 15​min
— 12 nights
Drive:  3​h
— 13 nights
Drive + Fly:  5​h 45​min
End: Detroit


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get out of town with these interesting Chicago side-trips: Wheaton (Cantigny Park & First Division Museum at Cantigny) and Illinois Holocaust Museum & Education Center (in Skokie). The adventure continues: explore the world behind art at The Art Institute of Chicago, take in the waterfront at Navy Pier, get to know the resident critters at Lincoln Park Zoo, and learn more about the world around you at Field Museum.

To see traveler tips, reviews, other places to visit, and other tourist information, you can read our Chicago vacation maker app .

Detroit to Chicago is an approximately 4-hour flight. You can also do a combination of bus and flight; or drive. The time zone difference when traveling from Detroit to Chicago is minus 1 hour. In December, plan for daily highs up to 38°F, and evening lows to 26°F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Crystal Lake.

Things to do in Chicago

Museums Historic Sites Parks

Side Trips

Oak Park, Wheaton, Evanston, Illinois Holocaust Museum & Education Center
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
Museum of Science and Industry ©
Museum of Science and Industry

Crystal Lake

Crystal Lake ©
Crystal Lake is a city in McHenry County in the U.S. Explore Crystal Lake's surroundings by going to Arlington Heights (Shalom Memorial Park & Arlington International Racecourse), Sri Venkateswara Swami Temple (in Aurora) and DeKalb (Whiskey Acres Distilling Co. & Ellwood House Museum). The adventure continues: ski along the peaceful trails at Veteran Acres Park, make a trip to Marytown - The National Shrine of St. Maximilian Kolbe, get lost in a book at Fremont Public Library, and sample the tasty concoctions at ZumBier.

To see maps, reviews, photos, and other tourist information, read Crystal Lake trip itinerary maker website .

Drive from Chicago to Crystal Lake in 1.5 hours. Plan for slightly colder nights when traveling from Chicago in December since evenings lows in Crystal Lake dip to 21°F. Finish your sightseeing early on the 25th (Wed) to allow enough time to travel to Loves Park.

Things to do in Crystal Lake

Parks Breweries & Distilleries Museums

Side Trips

Geneva, Batavia, Schaumburg, Mundelein, Saint Charles
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
Veteran Acres Park ©
Veteran Acres Park
Fremont Public Library ©
Fremont Public Library

Loves Park

Loves Park ©
Loves Park is a city in Boone and Winnebago counties in the U.S. Explore the numerous day-trip ideas around Loves Park: Edwards Apple Orchard (in Poplar Grove) and Freeport (Oscar Taylor Home, Krape Park, & more). There's much more to do: take in nature's colorful creations at Anderson Japanese Gardens, examine the collection at Vintage Wings and Wheels Museum, steep yourself in history at Midway Village & Museum Center, and look for all kinds of wild species at Kishwaukee River Forest Preserve.

To see traveler tips, ratings, photos, and other tourist information, use the Loves Park online route planner .

You can drive from Crystal Lake to Loves Park in 1.5 hours. December in Loves Park sees daily highs of 34°F and lows of 21°F at night. Cap off your sightseeing on the 4th (Sat) early enough to travel to Dixon.

Things to do in Loves Park

Parks Museums Fun & Games

Side Trips

Rockford, Freeport, Cherry Valley, Roscoe, Poplar Grove
Highlights from your plan
Anderson Japanese Gardens ©
Anderson Japanese Gardens
Historical Auto Attractions ©
Historical Auto Attractions
Oscar Taylor Home ©
Oscar Taylor Home


Dixon ©
Dixon is a city and county seat of Lee County, Illinois, United States. Venture out of the city with trips to LaSalle (Hegeler Carus Mansion, Starved Rock Family Fun, & more), Weber House and Garden (in Streator) and Utica (August Hill Winery & Illinois Sparkling Co. Tasting Room, Matthiessen State Park, & more). There's still lots to do: don't miss a visit to Old Settlers Memorial Cabin, see the interesting displays at Loveland Community House, admire the majestic nature at White Pines Forest State Park, and take an in-depth tour of Veterans Memorial Park.

To see other places to visit, ratings, reviews, and other tourist information, read Dixon trip itinerary planner.

Drive from Loves Park to Dixon in 1.5 hours. In January, daily temperatures in Dixon can reach 30°F, while at night they dip to 14°F. Wrap up your sightseeing on the 16th (Thu) to allow time to travel to Nauvoo.

Things to do in Dixon

Parks Museums Nature

Side Trips

Utica, Ottawa, Oregon, LaSalle, Weber House and Garden
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Old Settlers Memorial Cabin ©
Old Settlers Memorial Cabin
The Next Picture Show ©
The Next Picture Show


Nauvoo ©
Nauvoo is a small city in Hancock County, Illinois, United States, on the Mississippi River near Fort Madison, Iowa. Change things up with these side-trips from Nauvoo: Quincy (9/11 Memorial, All Wars Museum, & more). Next up on the itinerary: get engrossed in the history at Rheinberger House Museum, deepen your understanding at Historic Nauvoo, take in the spiritual surroundings of Nauvoo Temple, and steep yourself in history at Joseph Smith Historic Site.

To see reviews, traveler tips, ratings, and tourist information, go to the Nauvoo trip planner .

You can drive from Dixon to Nauvoo in 3 hours. In January, daytime highs in Nauvoo are 35°F, while nighttime lows are 17°F. You'll set off for home on the 29th (Wed).

Things to do in Nauvoo

Historic Sites Museums Fun & Games

Side Trip

Highlights from your plan
Nauvoo State Park ©
Nauvoo State Park
Nauvoo Temple ©
Nauvoo Temple
Historic Nauvoo ©
Historic Nauvoo

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