31 days in Illinois Itinerary

Created using Inspirock Illinois travel route planner
Make it your trip
Fly
1
Springfield
— 4 nights
Drive
2
Alton
— 4 nights
Drive
3
Makanda
— 5 nights
Drive
4
Galena
— 4 nights
Drive
5
Rockford
— 5 nights
Drive
6
Chicago
— 8 nights

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Springfield — 4 nights

Flower City

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: Rock Springs Conservation Area & Nature Center (in Decatur), Lake of the Woods Forest Preserve (in Mahomet) and Rooster in a Top Hat (in East Peoria). There's much more to do: get lost in a book at Abraham Lincoln Presidential Library and Museum, get a sense of history and politics at Old State Capitol, don't miss a visit to Lincoln Tomb & War Memorials, and identify plant and animal life at Lincoln Memorial Garden.

For ratings, more things to do, traveler tips, and other tourist information, you can read our Springfield planner.

Chicago to Springfield is an approximately 2.5-hour flight. You can also drive; or take a train. In May, daily temperatures in Springfield can reach 76°F, while at night they dip to 55°F. Finish your sightseeing early on the 5th (Fri) to allow enough time to drive to Alton.
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Historic Sites · Parks · Museums · Outdoors
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 Alton's surroundings by going to Litchfield Museum & Route 66 Welcome Center (in Litchfield), O'Fallon Community Park (in O'Fallon) and Silver Lake Park (in Highland). There's still lots to do: cruise along Great Rivers Scenic Route, make a trip to Haskell Playhouse, stroll around Gordon F. Moore Community Park, and tour the pleasant surroundings at Miner Park.

To find ratings, other places to visit, photos, and other tourist information, you can read our Alton day trip website.

Drive from Springfield to Alton in 2 hours. May in Alton sees daily highs of 74°F and lows of 54°F at night. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Makanda.
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Parks · Outdoors · Museums · Historic Sites
Side Trips

Makanda — 5 nights

Makanda is a village in Jackson County, Illinois, United States. Get out of town with these interesting Makanda side-trips: Cache River State Natural Area (in Belknap), Vienna (Mermet Springs Scuba & Tunnel Hill State Trail) and Mound City National Cemetery (in Mound City). And it doesn't end there: head outdoors with Shawnee Bluffs Canopy Tour, look for all kinds of wild species at Henry N Barkhausen Cache River Wetlands Center, immerse yourself in nature at Giant City State Park, and trek along Pomona Natural Bridge.

For ratings, maps, photos, and more tourist information, read our Makanda trip itinerary builder website.

You can drive from Alton to Makanda in 2.5 hours. In May, daily temperatures in Makanda can reach 76°F, while at night they dip to 56°F. Finish your sightseeing early on the 14th (Sun) to allow enough time to drive to Galena.
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Parks · Wineries · Outdoors · Wildlife
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: Stockton Heritage Museum (in Stockton), Fulton (De Immigrant Windmill, Lock & Dam 13 Recreation Area, &more) and Albany Mounds State Historic Site (in Albany). Next up on the itinerary: brush up on your knowledge of spirits at Blaum Bros. Distilling Co., look for gifts at Peace of the Past, steep yourself in history at The Old Blacksmith Shop, and get thoroughly spooked out with a ghost and vampire tour.

To see ratings, maps, and more tourist information, read our Galena trip itinerary builder.

Traveling by car from Makanda to Galena takes 7 hours. Traveling from Makanda in May, things will get little chillier in Galena: highs are around 69°F and lows about 48°F. Wrap up your sightseeing on the 18th (Thu) early enough to drive to Rockford.
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Historic Sites · Parks · Wildlife · Museums
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. You'll find plenty of places to visit near Rockford: Tom's Farm Market and Greenhouse (in Huntley), Whiskey Acres Distilling Co. (in DeKalb) and The Eagle's Nest Art Colony Collection (in Oregon). And it doesn't end there: admire the natural beauty at Anderson Japanese Gardens, make a trip to Old Settlers Memorial Cabin, walk around Krape Park, and examine the collection at Barnacopia.

To find traveler tips, more things to do, reviews, and tourist information, go to the Rockford trip itinerary maker tool.

You can drive from Galena to Rockford in 2 hours. Other options are to do a combination of bus and taxi; or take a bus. In May, daily temperatures in Rockford can reach 72°F, while at night they dip to 50°F. Finish your sightseeing early on the 23rd (Tue) to allow enough time to drive to Chicago.
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Parks · Museums · Nature · Shopping
Side Trips

Chicago — 8 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
When in Chicago, make a side trip to see Lilacia Park in Lombard, approximately Lombard away. The adventure continues: explore the world behind art at The Art Institute of Chicago, learn more about the world around you at Field Museum, get up close and personal with brilliant marine life at Shedd Aquarium, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

For where to stay, photos, maps, and tourist information, use the Chicago road trip planning website.

Traveling by car from Rockford to Chicago takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and subway. In May, plan for daily highs up to 71°F, and evening lows to 52°F. Finish up your sightseeing early on the 31st (Wed) so you can travel back home.
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Parks · Museums · Historic Sites · Childrens 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.
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