31 days in Illinois Itinerary

31 days in Illinois Itinerary

Created using Inspirock Illinois tour itinerary planner
Make it your trip
1
Chicago
— 5 nights
Drive
2
Ottawa
— 1 night
Drive
3
Casey
— 2 nights
Drive
4
Makanda
— 2 nights
Drive
5
Alton
— 4 nights
Drive
6
Springfield
— 4 nights
Drive
7
Peoria
— 4 nights
Drive
8
Galena
— 4 nights
Drive
9
Rockford
— 4 nights
Drive

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Chicago — 5 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, admire nature's wide array of creatures at Lincoln Park Zoo, walk around Millennium Park, and get up close and personal with brilliant marine life at Shedd Aquarium.

For ratings, where to stay, more things to do, and tourist information, use the Chicago tour planning app.

Use the Route module to find suitable travel options from your home destination to Chicago. In August, daytime highs in Chicago are 83°F, while nighttime lows are 67°F. Wrap up your sightseeing on the 5th (Sun) early enough to drive to Ottawa.
Parks · Museums · Childrens Museums · Zoos & Aquariums

Ottawa — 1 night

Ottawa is a city located at the confluence of the navigable Illinois River and Fox River in LaSalle County, Illinois, United States. On the 6th (Mon), indulge in some personalized pampering at SaltTreeYoga, appreciate the history behind The Middle East Conflicts Wall Memorial, and then learn about winemaking at August Hill Winery & Illinois Sparkling Co. Tasting Room.

To find photos, ratings, maps, and more tourist information, read our Ottawa trip planner.

Traveling by car from Chicago to Ottawa takes 1.5 hours. Expect a bit cooler evenings in Ottawa when traveling from Chicago in September, with lows around 56°F. Wrap up your sightseeing on the 6th (Mon) early enough to travel to Casey.
Spas · Wineries
Side Trips

Casey — 2 nights

Casey is a city in Clark and Cumberland counties in the U.S. state of Illinois. On the 7th (Tue), make a trip to World Largest Wind Chime, don't miss a visit to World's Largest Rocking Chair, and then make a trip to World's Largest Mailbox. Here are some ideas for day two: do a tasting at Castle Finn Vineyard & Winery and then take an in-depth tour of Heath Candy Bar Museum.

To find ratings, reviews, traveler tips, and tourist information, refer to the Casey online trip builder.

Traveling by car from Ottawa to Casey takes 3.5 hours. Expect a daytime high around 80°F in September, and nighttime lows around 57°F. Finish your sightseeing early on the 8th (Wed) to allow enough time to travel to Makanda.
Museums · Childrens Museums · Wineries
Side Trips

Makanda — 2 nights

Makanda is a village in Jackson County, Illinois, United States. Start off your visit on the 9th (Thu): do a tasting at Hickory Ridge Vineyard, then learn about winemaking at Pomona Winery, and then hike along Shawnee Hills. Get ready for a full day of sightseeing on the next day: get a dose of the wild on Shawnee Bluffs Canopy Tour and then learn about winemaking at StarView Vineyards.

For more things to do, photos, where to stay, and other tourist information, read our Makanda online day trip planner.

You can drive from Casey to Makanda in 3 hours. In September, plan for daily highs up to 82°F, and evening lows to 58°F. Finish up your sightseeing early on the 10th (Fri) so you can travel to Alton.
Wineries · Outdoors · Tours · Wildlife
Side Trips

Alton — 4 nights

Alton is a city on the Mississippi River in Madison County, Illinois, United States, about 15mi north of St. Explore the numerous day-trip ideas around Alton: Braeutigam Orchards (in Belleville), Eversgerd’s Civil War Fort (in Germantown) and Henry's Rabbit Ranch (in Staunton). The adventure continues: take a memorable drive along Great Rivers Scenic Route, take an in-depth tour of The 1820 Colonel Benjamin Stephenson House, pause for some serene contemplation at First Unitarian Church, and explore the landscape on two wheels at Miner Park.

To find maps, other places to visit, traveler tips, and more tourist information, go to the Alton road trip planner.

Traveling by car from Makanda to Alton takes 2.5 hours. In September, daytime highs in Alton are 81°F, while nighttime lows are 57°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Springfield.
Museums · Outdoors · Parks · Historic Sites
Side Trips

Springfield — 4 nights

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Change things up with a short trip to Mount Pulaski Courthouse State Historic Site in Mount Pulaski (about 42 minutes away). The adventure continues: get advice or help at Abraham Lincoln Presidential Library and Museum, don't miss a visit to Lincoln Tomb & War Memorials, explore the galleries of Lincoln Home National Historic Site, and contemplate the long history of Dana-Thomas House.

For where to stay, maps, traveler tips, and other tourist information, go to the Springfield journey site.

You can drive from Alton to Springfield in 2 hours. In September, daytime highs in Springfield are 82°F, while nighttime lows are 58°F. Finish your sightseeing early on the 18th (Sat) to allow enough time to drive to Peoria.
Historic Sites · Museums · Wildlife · Parks
Side Trip

Peoria — 4 nights

Venture out of the city with trips to Rock Island Trail (in Wyoming), Hennepin Canal State Park (in Sheffield) and Pontiac (Livingston County Courthouse & Route 66 Shield Mural).

For maps, other places to visit, ratings, and tourist information, refer to the Peoria trip itinerary planner.

Getting from Springfield to Peoria by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 81°F in September, and nighttime lows around 59°F. Finish up your sightseeing early on the 22nd (Wed) so you can go by car to Galena.
Museums · Outdoors · Parks · Nature
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. Change things up with these side-trips from Galena: Fulton (Lock & Dam 13 Recreation Area & De Immigrant Windmill). There's lots more to do: sample the fine beverages at Blaum Bros. Distilling Co., pause for some photo ops at Galena Veterans Memorial Park, see the interesting displays at The Old Blacksmith Shop, and indulge your senses at Massbach Ridge Tasting Room.

For maps, reviews, and tourist information, refer to the Galena sightseeing planner.

Getting from Peoria to Galena by car takes about 3.5 hours. Other options: fly; or do a combination of bus, ferry, and car. Traveling from Peoria in September, things will get slightly colder in Galena: highs are around 75°F and lows about 54°F. Wrap up your sightseeing on the 26th (Sun) early enough to drive to Rockford.
Historic Sites · Parks · Nature · Wildlife
Side Trips

Rockford — 4 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. Explore the numerous day-trip ideas around Rockford: The Eagle's Nest Art Colony Collection (in Oregon), John Deere Historic Site (in Grand Detour) and Oscar Taylor Home (in Freeport). And it doesn't end there: examine the collection at Historical Auto Attractions, don't miss a visit to Old Settlers Memorial Cabin, and take in nature's colorful creations at Anderson Japanese Gardens.

For reviews, traveler tips, ratings, and other tourist information, refer to the Rockford itinerary planner.

Traveling by car from Galena to Rockford takes 2 hours. Alternatively, you can do a combination of bus and taxi; or take a bus. In September, daily temperatures in Rockford can reach 78°F, while at night they dip to 56°F. Finish your sightseeing early on the 30th (Thu) so you can drive back home.
Museums · Historic Sites · Parks
Side Trips

Illinois travel guide

4.3
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.