20 days in Chicago and Beyond Itinerary

20 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond itinerary planner

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Route & dates

20 days in Chicago and Beyond Itinerary

Start: Bologna
Fly + Drive:  18​h 15​min
1
Rockford
— 5 nights
Drive:  3​h 15​min
2
Nauvoo
— 2 nights
Drive:  2​h 45​min
3
Utica
— 2 nights
Drive:  1​h 45​min
4
Chicago
— 8 nights
Fly:  21​h 45​min
End: Bologna

5
nights
Rockford

Rockford ©
Rockford is the third largest city in the U.S. Deepen your sense of the past at sights like Ronald Reagan Boyhood Home and Midway Village & Museum Center. Your cultural itinerary includes sights like Historic Auto Museum and Veterans Memorial Park. You'll find plenty of places to visit near Rockford: Dixon (Northwest Territory Historic Center, Veterans' Memorial Arch, & more), Castle Rock State Park (in Oregon) and Freeport (Jane Addams Recreation Trail, Oscar Taylor Home, & more). There's still lots to do: admire the natural beauty at Anderson Japanese Gardens, see the interesting displays at Frank Lloyd Wright's Laurent House, look for all kinds of wild species at Severson Dells Nature Center, and hike along Stone Bridge Trail.

To see where to stay, ratings, and tourist information, refer to the Rockford trip planner .

Bologna, Italy to Rockford is an approximately 18.5-hour flight. The time zone difference when traveling from Bologna to Rockford is minus 7 hours. While traveling from Bologna, expect a bit cooler days and about the same nights in Rockford, ranging from highs of 32°C to lows of 19°C. Cap off your sightseeing on the 11th (Sun) early enough to travel to Nauvoo.

Things to do in Rockford

Parks Museums Trails

Side Trips

Dixon, Freeport, Roscoe, Castle Rock State Park
Highlights from your plan
Anderson Japanese Gardens ©
Anderson Japanese Gardens
Discovery Center Museum ©
Discovery Center Museum
Ronald Reagan Boyhood Home ©
Ronald Reagan Boyhood Home

2
nights
Nauvoo

Nauvoo ©
Nauvoo is a small city in Hancock County, Illinois, United States, on the Mississippi River near Fort Madison, Iowa. On the 12th (Mon), contemplate in the serene atmosphere at Nauvoo Temple, then contemplate in the serene atmosphere at Nauvoo State Park, and then steep yourself in history at Historic Nauvoo. On your second day here, get engrossed in the history at Rheinberger House Museum, contemplate the long history of Brigham Young Home, then steep yourself in history at Joseph Smith Historic Site, and finally do a tasting at Baxter's Vineyards.

To see reviews, more things to do, traveler tips, and tourist information, read Nauvoo trip planner .

Traveling by car from Rockford to Nauvoo takes 4 hours. August in Nauvoo sees daily highs of 32°C and lows of 21°C at night. Cap off your sightseeing on the 13th (Tue) early enough to travel to Utica.

Things to do in Nauvoo

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

2
nights
Utica

Utica ©
North Utica, often known as Utica, is a village in Utica Township, LaSalle County, Illinois. Kick off your visit on the 14th (Wed): take in nature's colorful creations at Weber House and Garden, then admire the majestic nature at Matthiessen State Park, and then tour the pleasant surroundings at Starved Rock State Park. Get ready for a full day of sightseeing on the next day: admire the striking features of Farnsworth House, then take in the pleasant sights at Washington Square, then see the interesting displays at Ottawa Historical and Scouting Heritage Museum, and finally learn about winemaking at August Hill Winery & Illinois Sparkling Co. Tasting Room.

For other places to visit, reviews, and tourist information, refer to the Utica trip app .

You can drive from Nauvoo to Utica in 3 hours. August in Utica sees daily highs of 32°C and lows of 19°C at night. Finish your sightseeing early on the 15th (Thu) to allow enough time to drive to Chicago.

Things to do in Utica

Parks Nature Historic Sites

Side Trips

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

8
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get some cultural insight at Chicago Riverwalk and Riverwalk Lot. Cantigny Park and St. Charles History Museum and The Curious Fox Gift will appeal to history buffs. Explore the numerous day-trip ideas around Chicago: Naperville (Centennial Beach, Naper Settlement, & more), Rosewood Beach (in Highland Park) and Chicago Botanic Garden (in Glencoe). Next up on the itinerary: learn the secrets of beer at a beer tour and tasting, see the interesting displays at Kankakee County Museum, admire the striking features of Holy Name Cathedral, and contemplate the long history of Baha'i House of Worship.

To see photos, more things to do, traveler tips, and tourist information, read Chicago travel planner.

Getting from Utica to Chicago by car takes about 2 hours. Other options: do a combination of taxi and bus; or do a combination of taxi and train. In August in Chicago, expect temperatures between 33°C during the day and 22°C at night. Finish your sightseeing early on the 23rd (Fri) to allow enough time to travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Naperville, Kankakee, Rosewood Beach, Baha'i House of Worship, Chicago Botanic Garden
Highlights from your plan
Baha'i House of Worship ©
Baha'i House of Worship
Cantigny Park ©
Cantigny Park
Riverwalk Lot ©
Riverwalk Lot