39 days in Illinois Itinerary

39 days in Illinois Itinerary

Created using Inspirock Illinois tour builder
Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Waukegan
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Waukegan
— 2 nights
Drive
2
Sycamore
— 1 night
Drive
3
Rockford
— 5 nights
Drive
4
Galena
— 4 nights
Drive
5
Rock Island
— 4 nights
Drive
6
Peoria
— 3 nights
Drive
7
Springfield
— 4 nights
Drive
8
Makanda
— 2 nights
Drive
9
Pontiac
— 2 nights
Drive
10
Utica
— 4 nights
Drive
11
Chicago
— 7 nights
Fly

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Waukegan — 2 nights

Waukegan is a city and the county seat of Lake County, Illinois, United States. Discover out-of-the-way places like Chicago Botanic Garden and Volo Auto Museum. Explore Waukegan's surroundings by going to Deer Grove Forest Preserve (in Palatine), Arlington Park (in Arlington Heights) and Baha'i House of Worship (in Wilmette). Next up on the itinerary: contemplate the waterfront views at Lake Michigan, tour the pleasant surroundings at Prairie Wolf Slough, and see what you can catch with WindyCitySalmon.

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

Barcelona, Spain to Waukegan is an approximately 13-hour combination of flight and car. Due to the time zone difference, you'll gain 7 hours traveling from Barcelona to Waukegan. Traveling from Barcelona in May, expect Waukegan to be little chillier, temps between 22°C and 9°C. Cap off your sightseeing on the 28th (Sat) early enough to travel to Sycamore.
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Parks · Wildlife · Outdoors · Tours
Side Trips

Sycamore — 1 night

Sycamore is a city in DeKalb County, Illinois, United States. Kick off your visit on the 29th (Sun): relax in the rural setting at Honey Hill, then do a tasting at Prairie States Winery, and then relax in the rural setting at Whiskey Acres Distilling Co..

To find other places to visit, where to stay, reviews, and tourist information, read our Sycamore trip maker.

You can drive from Waukegan to Sycamore in 1.5 hours. In May, plan for daily highs up to 24°C, and evening lows to 10°C. Finish your sightseeing early on the 29th (Sun) so you can travel to Rockford.
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Wineries · Breweries & Distilleries
Side Trips

Rockford — 5 nights

Rockford is the third largest city in the U.S. state of Illinois, the 171st most populous city in the United States, the largest city in Illinois outside of the Chicago metropolitan area, and the city of the 148th most populous metropolitan area in the United States. Step off the beaten path and head to Anderson Japanese Gardens and Discovery Center Museum. Change things up with these side-trips from Rockford: Oscar Taylor Home (in Freeport), Climbing Tours (in Baraboo) and Illinois Railway Museum (in Union). Next up on the itinerary: take in nature's colorful creations at Klehm Arboretum & Botanic Garden, examine the collection at Barnacopia, make a trip to Dixon's Railroad Street Arches, and tour the pleasant surroundings at Kishwaukee River Forest Preserve.

For where to stay, ratings, and tourist information, read Rockford online trip itinerary planner.

Traveling by car from Sycamore to Rockford takes an hour. In May, daytime highs in Rockford are 26°C, while nighttime lows are 11°C. Cap off your sightseeing on the 3rd (Fri) early enough to go by car to Galena.
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Parks · Museums · Outdoors · Classes
Side Trips

Galena — 4 nights

Galena is the largest city in and the county seat of Jo Daviess County, Illinois, with a population of 3,429 at the 2010 census. You'll explore the less-touristy side of things at Blaum Bros. Distilling Co. and Chestnut Mountain Resort. Explore Galena's surroundings by going to Fulton (Windmill Cultural Center, Lock & Dam 13 Recreation Area, &more). There's lots more to do: contemplate the long history of Ulysses S. Grant Home, take an in-depth tour of Galena / Jo Daviess County Historical Society and Museum, do a tasting at Galena Cellars Winery, and indulge your senses at some of the top wineries in the area.

For ratings, maps, reviews, and tourist information, use the Galena travel planner.

Traveling by car from Rockford to Galena takes 2 hours. Alternatively, you can do a combination of taxi and bus; or take a bus. In June, daily temperatures in Galena can reach 30°C, while at night they dip to 17°C. Cap off your sightseeing on the 7th (Tue) early enough to go by car to Rock Island.
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Historic Sites · Parks · Wildlife · Museums
Side Trip

Rock Island — 4 nights

Rock Island is a city in and the county seat of Rock Island County, Illinois, United States. Explore hidden gems such as Historic Nauvoo and Quad City Botanical Center. Explore the numerous day-trip ideas around Rock Island: Nauvoo (Nauvoo Temple, Brigham Young Home, &more). And it doesn't end there: try your luck at Jumer's Casino Rock Island, get a new perspective on nature at Fryxell Geology Museum, steep yourself in history at Butterworth Center & Deere-Wiman House, and see human ingenuity at work at Mississippi River Lock and Dam No. 16.

To find more things to do, traveler tips, photos, and other tourist information, you can read our Rock Island trip planner.

Traveling by car from Galena to Rock Island takes 2 hours. Alternatively, you can take a bus. In June, daytime highs in Rock Island are 33°C, while nighttime lows are 19°C. Finish your sightseeing early on the 11th (Sat) so you can drive to Peoria.
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Historic Sites · Museums · Parks · Fun & Games
Side Trips

Peoria — 3 nights

You'll discover tucked-away gems like Grand View Drive and Wheels O' Time Museum. Get out of town with these interesting Peoria side-trips: Funks Grove Church & Chapel in the Trees (in McLean), Spring Lake Park (in Macomb) and Evergreen Memorial Cemetery (in Bloomington).

To see reviews, more things to do, traveler tips, and more tourist information, read Peoria driving holiday planner.

You can drive from Rock Island to Peoria in 2 hours. Another option is to take a bus. Expect a daytime high around 34°C in June, and nighttime lows around 20°C. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Springfield.
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Museums · Historic Sites · Parks · Outdoors
Side Trips

Springfield — 4 nights

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Explore hidden gems such as Dana-Thomas House and Lincoln Tomb & War Memorials. Explore the numerous day-trip ideas around Springfield: Lincolns New Salem State Park (in Petersburg), Great Rivers Scenic Route (in Alton) and Henry's Rabbit Ranch (in Staunton). The adventure continues: ponder the world of politics at Old State Capitol, tour the pleasant surroundings at Lincoln Memorial Garden, stroll the grounds of Camp Butler National Cemetery, and take an in-depth tour of Lincoln Home National Historic Site.

To find more things to do, where to stay, reviews, and more tourist information, refer to the Springfield trip itinerary builder.

Getting from Peoria to Springfield by car takes about 1.5 hours. Other options: take a bus. In June, daytime highs in Springfield are 34°C, while nighttime lows are 21°C. Finish your sightseeing early on the 18th (Sat) so you can travel to Makanda.
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Historic Sites · Museums · Outdoors · Scenic Drive
Side Trips

Makanda — 2 nights

Makanda is a village in Jackson County, Illinois, United States. On the 19th (Sun), immerse yourself in nature at Giant City State Park, then surround yourself with nature on Shawnee Bluffs Canopy Tour, and then hike along Pomona Natural Bridge. On the 20th (Mon), you'll have a packed day of sightseeing: see some colorful creatures with Mermet Springs Scuba, then stroll through Henry N Barkhausen Cache River Wetlands Center, and then trek along Shawnee Hills.

For where to stay, more things to do, reviews, and other tourist information, use the Makanda tour planner.

Traveling by car from Springfield to Makanda takes 3.5 hours. In June, plan for daily highs up to 35°C, and evening lows to 22°C. Finish your sightseeing early on the 20th (Mon) so you can travel to Pontiac.
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Outdoors · Parks · Wildlife · Tours
Side Trips

Pontiac — 2 nights

Pontiac is a city in Livingston County, Illinois, United States. Kick off your visit on the 21st (Tue): don't miss a visit to Route 66 Shield Mural, see the interesting displays at IL Route 66 Association Hall of Fame & Museum, then see the interesting displays at Pontiac-Oakland Automobile Museum, and finally stroll around Humiston Woods Nature Center. On the 22nd (Wed), you'll have a packed day of sightseeing: see the interesting displays at Museum of the Gilding Arts, make a trip to Ambler's Texaco Gas Station, Dwight, and then don't miss a visit to Two-Cell Jail.

To see more things to do, ratings, traveler tips, and other tourist information, use the Pontiac trip itinerary maker app.

You can drive from Makanda to Pontiac in 4.5 hours. Alternatively, you can do a combination of car and flight. In June, plan for daily highs up to 33°C, and evening lows to 19°C. Finish up your sightseeing early on the 22nd (Wed) so you can go by car to Utica.
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Museums · Parks
Side Trips

Utica — 4 nights

North Utica, often known as Utica, is a village in Utica Township, LaSalle County, Illinois. Step off the beaten path and head to Matthiessen State Park and Hegeler Carus Mansion. Change things up with these side-trips from Utica: Bureau County Soldiers and Sailors Monument (in Princeton), Sinnissippi Park (in Sterling) and Hennepin Canal State Park (in Sheffield). Next up on the itinerary: hike along Starved Rock State Park, indulge in some personalized pampering at SaltTreeYoga, stroll around LaSalle Rotary Park, and take in the waterfront activity at Heritage Harbor.

To find more things to do, photos, traveler tips, and other tourist information, use the Utica trip planner.

You can drive from Pontiac to Utica in 1.5 hours. June in Utica sees daily highs of 32°C and lows of 19°C at night. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Chicago.
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Parks · Nature · Outdoors · Spas
Side Trips

Chicago — 7 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step off the beaten path and head to Lakefront Trail and Buckingham Fountain. Explore Chicago's surroundings by going to Lizzadro Museum of Lapidary Art (in Elmhurst) and Riverwalk Lot (in Naperville). And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, appreciate the extensive heritage of Chicago Riverwalk, don't miss a visit to Frank Lloyd Wright Home and Studio, and take a stroll through The Magnificent Mile.

To see photos, more things to do, and other tourist information, you can read our Chicago trip maker site.

Getting from Utica to Chicago by car takes about 1.5 hours. Other options: do a combination of taxi and bus; or do a combination of taxi and train. In June, daytime highs in Chicago are 32°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 3rd (Sun) to allow time to fly back home.
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Museums · Parks · Historic Sites · Childrens Museums
Side Trips

Illinois travel guide

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Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.
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