21 days in Chicago and Beyond Itinerary

21 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond attractions planner

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Route & dates

21 days in Chicago and Beyond Itinerary

Start: Milan
Fly:  19​h 30​min
— 4 nights
Drive:  3​h 15​min
— 2 nights
Drive:  2​h 45​min
— 3 nights
Drive:  1​h 45​min
— 9 nights
Fly:  14​h 45​min
End: Milan


Rockford ©
Rockford is the third largest city in the U.S. Discover out-of-the-way places like Historic Auto Museum and Veterans Memorial Park. Do some cultural sightseeing at Discovery Center Museum and Northwest Territory Historic Center. Explore Rockford's surroundings by going to Vintage Wings and Wheels Museum (in Poplar Grove), Dixon (Loveland Community House & Veterans' Memorial Arch) and Freeport (Jane Addams Recreation Trail & Famous Fossil Winery). There's still lots to do: get a new perspective on nature at Burpee Museum of Natural History, take in nature's colorful creations at Anderson Japanese Gardens, admire the masterpieces at Rockford Art Museum, and take an in-depth tour of Ellwood House Museum.

For photos, ratings, maps, and more tourist information, refer to the Rockford online itinerary planner .

Milan, Italy to Rockford is an approximately 19.5-hour flight. The time zone difference when traveling from Milan to Rockford is minus 7 hours. Expect a daytime high around 32°C in August, and nighttime lows around 19°C. Wrap up your sightseeing on the 15th (Thu) to allow time to travel to Nauvoo.

Things to do in Rockford

Museums Parks Outdoors

Side Trips

Dixon, Freeport, Roscoe, Ellwood House Museum, Vintage Wings and Wheels Museum
Highlights from your plan
Discovery Center Museum ©
Discovery Center Museum
Historic Auto Museum ©
Historic Auto Museum
Burpee Museum of Natural History ©
Burpee Museum of Natural History


Nauvoo ©
Nauvoo is a small city in Hancock County, Illinois, United States, on the Mississippi River near Fort Madison, Iowa. On the 16th (Fri), steep yourself in history at Historic Nauvoo, then make a trip to Brigham Young Home, and then learn about winemaking at Baxter's Vineyards. On the 17th (Sat), you'll have a packed day of sightseeing: take an in-depth tour of Rheinberger House Museum, then make a trip to Joseph Smith Historic Site, then contemplate in the serene atmosphere at Nauvoo State Park, and finally pause for some serene contemplation at Nauvoo Temple.

To find ratings, more things to do, where to stay, and other tourist information, refer to the Nauvoo holiday builder tool .

You can drive from Rockford to Nauvoo in 4 hours. In August in Nauvoo, expect temperatures between 32°C during the day and 21°C at night. Cap off your sightseeing on the 17th (Sat) early enough to travel to Utica.

Things to do in Nauvoo

Historic Sites Museums Wineries
Highlights from your plan
Historic Nauvoo ©
Historic Nauvoo
Nauvoo State Park ©
Nauvoo State Park
Joseph Smith Historic Site ©
Joseph Smith Historic Site


Utica ©
North Utica, often known as Utica, is a village in Utica Township, LaSalle County, Illinois. Explore hidden gems such as Starved Rock State Park and Reddick Mansion and Gardens. Do some cultural sightseeing at Ottawa Historical and Scouting Heritage Museum and Farnsworth House. Change things up with a short trip to Weber House and Garden in Streator (about 36 minutes away). And it doesn't end there: immerse yourself in nature at Matthiessen State Park, stop by Mix's Trading Post, learn about winemaking at August Hill Winery & Illinois Sparkling Co. Tasting Room, and admire all the interesting features of Washington Square.

To see other places to visit, more things to do, ratings, and tourist information, you can read our Utica trip itinerary planner.

Getting from Nauvoo to Utica by car takes about 3 hours. August in Utica sees daily highs of 32°C and lows of 19°C at night. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Chicago.

Things to do in Utica

Parks Nature Museums

Side Trips

Ottawa, Weber House and Garden, Farnsworth House, Hegeler Carus Mansion
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Matthiessen State Park ©
Matthiessen State Park
Weber House and Garden ©
Weber House and Garden


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Let the collections at Chicago Cultural Center and Kankakee County Museum capture your imagination. Visiting Rosewood Beach and Cog Hill Golf & Country Club will get you outdoors. Explore Chicago's surroundings by going to Seven Bridges Golf Club (in Woodridge), Wheaton (Cantigny Golf Club & Cantigny Park) and Naperville (Centennial Beach & Naperville Historic District). There's much more to do: see the interesting displays at Exploration Station...a children's museum, take a stroll through Lincoln Park, view the masterpieces at Intuit: The Center for Intuitive and Outsider Art, and contemplate the long history of St. Charles History Museum and The Curious Fox Gift.

Plan my day in Chicago using traveler tips and tourist information provided by Inspirock.

You can drive from Utica to Chicago in 2 hours. Other options are to do a combination of taxi and bus; or do a combination of taxi and train. In August, daytime highs in Chicago are 33°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 29th (Thu) so you can travel back home.

Things to do in Chicago

Outdoors Golf Museums

Side Trips

Naperville, Wheaton, Aurora, Kankakee, Skokie Northshore Sculpture Park
Highlights from your plan
Cantigny Park ©
Cantigny Park
Volo Auto Museum ©
Volo Auto Museum
Holy Name Cathedral ©
Holy Name Cathedral