60 days in Illinois Itinerary

60 days in Illinois Itinerary

Created using Inspirock Illinois trip planner
Make it your trip
Ferry to Billy Bishop Toronto City, Fly to Chicago
1
Chicago
— 13 nights
Drive
2
Makanda
— 6 nights
Drive
3
Alton
— 5 nights
Drive
4
Springfield
— 8 nights
Drive
5
Peoria
— 7 nights
Drive
6
Galena
— 8 nights
Drive
7
Rockford
— 7 nights
Drive
8
Waukegan
— 5 nights
Drive to Chicago O'Hare International Airport, Fly to Toronto

S M T W T F S
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Chicago — 13 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Graue Mill & Museum (in Oak Brook), Lizzadro Museum of Lapidary Art (in Elmhurst) and Wheaton (Cantigny Park & First Division Museum at Cantigny). There's lots more to do: admire the masterpieces at The Art Institute of Chicago, get up close and personal with brilliant marine life at Shedd Aquarium, admire the landmark architecture of Skydeck Chicago - Willis Tower, and engage your brain at Museum of Science and Industry.

To see ratings, photos, where to stay, and other tourist information, go to the Chicago online itinerary planner.

Toronto, Canada to Chicago is an approximately 5-hour combination of ferry and flight. You can also drive; or do a combination of train and car. Traveling from Toronto to Chicago, you'll gain 1 hour due to the time zone difference. In November, plan for daily highs up to 11°C, and evening lows to 1°C. Wrap up your sightseeing on the 8th (Wed) early enough to travel to Makanda.
Museums · Historic Sites · Parks · Childrens Museums
Side Trips

Makanda — 6 nights

Makanda is a village in Jackson County, Illinois, United States. Change things up with these side-trips from Makanda: Mound City National Cemetery (in Mound City), Cache River State Natural Area (in Belknap) and U.S. Custom House (in Cairo). And it doesn't end there: surround yourself with nature on Shawnee Bluffs Canopy Tour, hike along Pomona Natural Bridge, learn about winemaking at StarView Vineyards, and discover the deep blue sea with Mermet Springs Scuba.

To find photos, reviews, traveler tips, and tourist information, read Makanda tour itinerary planner.

You can drive from Chicago to Makanda in 5.5 hours. Alternatively, you can do a combination of flight and car. While traveling from Chicago, expect a bit warmer days and about the same nights in Makanda, ranging from highs of 9°C to lows of -1°C. Wrap up your sightseeing on the 14th (Tue) early enough to travel to Alton.
Outdoors · Parks · Wineries · Wildlife
Side Trips

Alton — 5 nights

Alton is a city on the Mississippi River in Madison County, Illinois, United States, about 15mi north of St. Get out of town with these interesting Alton side-trips: National Shrine of Our Lady of the Snows (in Belleville), Collinsville (Kruta Bakery & Cahokia Mounds State Historic Site) and Henry's Rabbit Ranch (in Staunton). There's still lots to do: cruise along Great Rivers Scenic Route, get engrossed in the history at The 1820 Colonel Benjamin Stephenson House, steep yourself in history at Eversgerd’s Civil War Fort, and examine the collection at National Great Rivers Museum.

To find photos, traveler tips, ratings, and tourist information, go to the Alton trip app.

Drive from Makanda to Alton in 2.5 hours. In December in Alton, expect temperatures between 6°C during the day and -3°C at night. Wrap up your sightseeing on the 19th (Sun) to allow time to drive to Springfield.
Historic Sites · Museums · Outdoors · Parks
Side Trips

Springfield — 8 nights

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
You'll find plenty of places to visit near Springfield: Mahomet (Museum of the Grand Prairie & Lake of The Woods County Park), Larry Kanfer Photography (in Champaign) and The Vault Art Gallery (in Tuscola). The adventure continues: get lost in a book at Abraham Lincoln Presidential Library and Museum, learn about all things military at Illinois State Military Museum, steep yourself in history at Dana-Thomas House, and don't miss a visit to Lincoln Tomb & War Memorials.

Before you visit Springfield, use our trip planner to discover what you can do and see there.

Traveling by car from Alton to Springfield takes 2 hours. December in Springfield sees daily highs of 5°C and lows of -3°C at night. Wrap up your sightseeing on the 27th (Mon) to allow time to drive to Peoria.
Museums · Parks · Outdoors · Shopping
Side Trips

Peoria — 7 nights

You'll find plenty of places to visit near Peoria: Bureau County Soldiers and Sailors Monument (in Princeton), Atlanta (Atlanta Public Library & Memories: Route 66 Museum) and Starved Rock State Park (in Utica).

To see photos, reviews, more things to do, and other tourist information, use the Peoria travel route planner.

Traveling by car from Springfield to Peoria takes 1.5 hours. Alternatively, you can take a bus. In December, daily temperatures in Peoria can reach 4°C, while at night they dip to -5°C. Cap off your sightseeing on the 3rd (Mon) early enough to go by car to Galena.
Museums · Historic Sites · Outdoors · Shopping
Side Trips

Galena — 8 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. Get out of town with these interesting Galena side-trips: Fulton (Windmill Cultural Center, Lock & Dam 13 Recreation Area, &more), Stockton Heritage Museum (in Stockton) and Timber Lake Playhouse (in Mount Carroll). And it doesn't end there: brush up on your knowledge of spirits at Blaum Bros. Distilling Co., pause for some photo ops at Galena Veterans Memorial Park, take in the exciting artwork at Outside the Lines Art Gallery Galena, and steep yourself in history at Ulysses S. Grant Home.

For ratings, photos, more things to do, and tourist information, you can read our Galena road trip planning site.

Drive from Peoria to Galena in 3.5 hours. Alternatively, you can fly; or do a combination of bus, ferry, and car. Plan for a bit cooler temperatures traveling from Peoria in January, with highs in Galena at -3°C and lows at -14°C. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Rockford.
Museums · Shopping · Historic Sites · Parks
Side Trips

Rockford — 7 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. You'll find plenty of places to visit near Rockford: Prairie States Winery (in Genoa), White Pines Forest State Park (in Mount Morris) and Barnacopia (in Polo). The adventure continues: brush up on your knowledge of spirits at Whiskey Acres Distilling Co., stop by Tom's Farm Market and Greenhouse, don't miss a visit to Old Settlers Memorial Cabin, and see the interesting displays at McHenry County Historical Society.

For reviews, photos, other places to visit, and other tourist information, use the Rockford trip planning website.

You can drive from Galena to Rockford in 2 hours. Alternatively, you can do a combination of bus and taxi; or take a bus. January in Rockford sees daily highs of -1°C and lows of -12°C at night. Wrap up your sightseeing on the 18th (Tue) early enough to drive to Waukegan.
Museums · Parks · Outdoors · Historic Sites
Side Trips

Waukegan — 5 nights

Waukegan is a city and the county seat of Lake County, Illinois, United States. Change things up with these side-trips from Waukegan: Arlington International Racecourse (in Arlington Heights), Baha'i House of Worship (in Wilmette) and Chicago Botanic Garden (in Glencoe). There's still lots to do: contemplate the waterfront views at Lake Michigan, delve into the lush surroundings at Lake County Forest Preserves, get engrossed in the history at Grayslake Heritage Center & Museum, and head outdoors with WindyCitySalmon.

To find other places to visit, traveler tips, photos, and tourist information, go to the Waukegan trip itinerary maker website.

Drive from Rockford to Waukegan in 2 hours. January in Waukegan sees daily highs of -1°C and lows of -11°C at night. Finish your sightseeing early on the 23rd (Sun) so you can travel back home.
Parks · Nature · Wildlife · Museums
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.