57 days in Illinois Itinerary

57 days in Illinois Itinerary

Created using Inspirock Illinois holiday planner

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Route & dates

57 days in Illinois Itinerary

Start: Guatemala City
Fly + Drive:  9​h
1
Crystal Lake
— 7 nights
Drive:  2​h 30​min
2
Galena
— 6 nights
Drive:  6​h 15​min
3
Cobden
— 6 nights
Drive:  3​h
4
Shelbyville
— 7 nights
Drive:  1​h 15​min
5
Springfield
— 8 nights
Drive:  2​h 15​min
6
Utica
— 7 nights
Drive:  1​h 45​min
7
Chicago
— 13 nights
Fly:  8​h 45​min
End: Guatemala City

7
nights
Crystal Lake

Crystal Lake ©
Crystal Lake is a city in McHenry County in the U.S. Satisfy your inner culture vulture at Prarie States Winery and Lynfred Winery. Escape the urban bustle at Red Oak Nature Center and Three Oaks Recreation Area. You'll find plenty of places to visit near Crystal Lake: Bloomingdale Golf Club (in Bloomingdale), Aurora (Phillips Park Zoo & Blackberry Farm) and Woodfield Mall (in Schaumburg). The adventure continues: tour the pleasant surroundings at Waukegan Municipal Beach, experience rural life at Stade's Farm and Market, glide through natural beauty at Veteran Acres Park, and look for gifts at Woodman's.

For ratings, other places to visit, where to stay, and other tourist information, read Crystal Lake itinerary planning app .

Guatemala City, Guatemala to Crystal Lake is an approximately 9-hour flight. Expect cooler temperatures when traveling from Guatemala City in November; daily highs in Crystal Lake reach 10°C and lows reach -1°C. Wrap up your sightseeing on the 12th (Mon) early enough to travel to Galena.

Things to do in Crystal Lake

Parks Outdoors Wildlife

Side Trips

Aurora, Stade's Farm and Market, The Arboretum of South Barrington, Woodfield Mall, Waukegan Municipal Beach
Highlights from your plan
Red Oak Nature Center ©
Red Oak Nature Center
Prairie States Winery ©
Prairie States Winery
Volo Bog State Natural Area ©
Volo Bog State Natural Area

6
nights
Galena

Galena ©
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. Your inner history buff will appreciate Ulysses S. Grant Home and Market House State Historic. Visiting Mississippi Palisades State Park and Morrison-Rockwood State Park will get you outdoors. You'll find plenty of places to visit near Galena: Oscar Taylor Home (in Freeport), Albany Mounds State Historic Site (in Albany) and Apple River Canyon State Park (in Apple River). Next up on the itinerary: do a tasting at Fergedaboudit Vineyard & Winery, look for gifts at Great American Popcorn Company, indulge your taste buds at Galena Cellars Winery, and contemplate the long history of Apple River Fort.

For other places to visit, photos, reviews, and other tourist information, refer to the Galena trip maker site .

Getting from Crystal Lake to Galena by car takes about 2.5 hours. In November, daily temperatures in Galena can reach 8°C, while at night they dip to -3°C. Finish your sightseeing early on the 18th (Sun) so you can travel to Cobden.

Things to do in Galena

Parks Outdoors Nature

Side Trips

Hanover, Ski Snowstar, Stockton Heritage Museum, Apple River Canyon State Park, Albany Mounds State Historic Site
Highlights from your plan
Mississippi Palisades State Park ©
Mississippi Palisades State Park
Blaum Bros. Distilling Co. ©
Blaum Bros. Distilling Co.
Stockton Heritage Museum ©
Stockton Heritage Museum

6
nights
Cobden

Cobden ©
Cobden is a village in Union County, Illinois, United States. Do some cultural sightseeing at Rustle Hill Winery and StarView Vineyards. Get in touch with nature at Ferne Clyffe State Park and Garden of the Gods. Explore the numerous day-trip ideas around Cobden: Little Mary's River Covered Bridge (in Chester), Annbriar Golf Course (in Waterloo) and Fort Massac State Park (in Metropolis). There's much more to do: appreciate the views at Little Grand Canyon, identify plant and animal life at Little Grassy Fish Hatchery, do a tasting at Owl Creek Vineyard, and get lost in a book at Marion Carnegie Library.

For maps, more things to do, traveler tips, and other tourist information, read Cobden day trip site .

Traveling by car from Galena to Cobden takes 7 hours. Alternatively, you can fly. Expect somewhat warmer temperatures when traveling from Galena in November; daily highs in Cobden reach 15°C and lows reach 1°C. Wrap up your sightseeing on the 25th (Sun) early enough to travel to Shelbyville.

Things to do in Cobden

Parks Wildlife Nature

Side Trips

Makanda, Little Grand Canyon, Ferne Clyffe State Park, Fort Massac State Park, Bald Knob Cross of Peace
Highlights from your plan
Garden of the Gods ©
Garden of the Gods
StarView Vineyards ©
StarView Vineyards
Cache River State Natural Area ©
Cache River State Natural Area

7
nights
Shelbyville

Shelbyville ©
Shelbyville is a city in Shelby County, Illinois, along the Kaskaskia River. Get some cultural insight at Sleepy Creek Vineyards and Thomas Lincoln Cemetery. Escape the urban bustle at Lake Shelbyville and Kickapoo State Recreation Area. Explore the numerous day-trip ideas around Shelbyville: Lincoln Trail State Park (in Marshall), Outlets at Tuscola (in Tuscola) and Fox Ridge State Park (in Charleston). There's still lots to do: experience rural life at Curtis Orchard & Pumpkin Patch, contemplate the waterfront views at Carlyle Sailing association, make a trip to Vandalia Statehouse State Historic Site, and stroll through Heron County Park.

Plan trip to Shelbyville with our itinerary maker to find out where to go and what to do.

Getting from Cobden to Shelbyville by car takes about 3 hours. Expect a daytime high around 13°C in November, and nighttime lows around 1°C. Finish up your sightseeing early on the 2nd (Sun) so you can travel to Springfield.

Things to do in Shelbyville

Parks Nature Outdoors

Side Trips

Urbana, Lincoln Trail State Park, Kickapoo State Recreation Area, Sleepy Creek Vineyards, Ludwig Farmstead Creamery
Highlights from your plan
Lake Shelbyville ©
Lake Shelbyville
Douglas-Hart Nature Center ©
Douglas-Hart Nature Center
Fox Ridge State Park ©
Fox Ridge State Park

8
nights
Springfield

Springfield ©
Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Step out of the city life by going to Lincoln Memorial Garden and Lake Lou Yaeger. Get some cultural insight at Lincoln Home National Historic Site and Abraham Lincoln Presidential Library and Museum. Explore the numerous day-trip ideas around Springfield: Melvin Price Locks and Dam (in East Alton), Pere Marquette State Park (in Grafton) and Collinsville (Willoughby Heritage Farms & Cahokia Mounds State Historic Site). There's much more to do: contemplate the long history of Dana-Thomas House, experience rural life at Apple Barn, get a sense of history and politics at Old State Capitol, and make a trip to Rees Memorial Carillon.

For photos, where to stay, more things to do, and other tourist information, read Springfield trip planner .

Traveling by car from Shelbyville to Springfield takes 1.5 hours. December in Springfield sees daily highs of 5°C and lows of -3°C at night. Cap off your sightseeing on the 10th (Mon) early enough to go by car to Utica.

Things to do in Springfield

Historic Sites Parks Outdoors

Side Trips

Collinsville, Sugar Creek Covered Bridge, Melvin Price Locks and Dam, Pere Marquette State Park, Danenberger Family Vineyards
Highlights from your plan
Lincoln Memorial Garden ©
Lincoln Memorial Garden
Lincoln Home National Historic Site ©

7
nights
Utica

Utica ©
North Utica, often known as Utica, is a village in Utica Township, LaSalle County, Illinois. Step out of the city life by going to Starved Rock State Park and Christ Apple Orchard. Change things up with these side-trips from Utica: The Sandwich Fair (in Sandwich), Shabbona Lake State Park (in Shabbona) and Dixon (Ronald Reagan Boyhood Home & The Next Picture Show). The adventure continues: immerse yourself in nature at Lowden State Park, make a trip to Standard Oil Gas Station, snap pictures at Red Covered Bridge, and explore and take pictures at Cedar Creek Ranch.

For other places to visit, where to stay, more things to do, and more tourist information, read Utica driving holiday website .

Drive from Springfield to Utica in 2.5 hours. Alternatively, you can do a combination of flight, shuttle, and taxi; or do a combination of bus, train, and taxi. Traveling from Springfield in December, expect nights in Utica to be about the same, around -5°C, while days are a bit cooler, around 2°C. On the 17th (Mon), wrap the sightseeing up by early afternoon so you can drive to Chicago.

Things to do in Utica

Parks Nature Trails

Side Trips

Dixon, Red Covered Bridge, Hennepin Canal State Park, Wildlife Prairie Park, Lowden State Park
Highlights from your plan
Starved Rock State Park ©
Starved Rock State Park
Hennepin Canal State Park ©
Hennepin Canal State Park
Ronald Reagan Boyhood Home ©
Ronald Reagan Boyhood Home

13
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Little Red Schoolhouse and Oak Street Beach. Get some cultural insight at The Magnificent Mile and Millennium Park. Explore the numerous day-trip ideas around Chicago: Centennial Beach (in Naperville), Bengtson's Pumpkin Farm (in Homer Glen) and Willowbrook Wildlife Center (in Glen Ellyn). There's much more to do: admire the masterpieces at The Art Institute of Chicago, tour the pleasant surroundings at Montrose Beach, enjoy the sand and surf at Kathy Osterman Beach, and explore the galleries of Ernest Hemingway Birthplace.

For traveler tips, other places to visit, ratings, and tourist information, refer to the Chicago trip planning tool .

Traveling by car from Utica to Chicago takes 2 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi and train. In December, daytime highs in Chicago are 3°C, while nighttime lows are -3°C. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.

Things to do in Chicago

Parks Outdoors Beaches

Side Trips

Oak Park, Illinois, Willowbrook Wildlife Center, Schaefer's Wines and Liquors, Centennial Beach
Highlights from your plan
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

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