22 days in Illinois Itinerary

22 days in Illinois Itinerary

Created using Inspirock Illinois journey planner

Make it your trip
Fly
1
Chicago
— 11 nights
Drive
2
Rockford
— 4 nights
Drive
3
Galena
— 2 nights
Drive
4
Utica
— 2 nights
Drive
5
Springfield
— 1 night
Drive
6
Harrisburg
— 1 night
Drive

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Chicago

— 11 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Visiting Lakefront Trail and Indiana Dunes State Park will get you outdoors. For shopping fun, head to Lincoln Park or Chudnow Museum of Yesteryear. You'll find plenty of places to visit near Chicago: Chesterton (Coffee Creek Watershed Preserve & Cowles Bog), Milwaukee (Henry Maier Festival Park, Milwaukee Art Museum, &more) and Atwater Park & Beach (in Shorewood). The adventure continues: stroll through Silver Beach County Park, take in the architecture and atmosphere at Basilica of the Sacred Heart, take a stroll through The Loop, and find something for the whole family at Fox in a Box Chicago.

To see reviews, ratings, photos, and other tourist information, you can read our Chicago visit planner.

Pittsburgh to Chicago is an approximately 3-hour flight. You can also drive; or take a train. The time zone difference when traveling from Pittsburgh to Chicago is minus 1 hour. In June, daytime highs in Chicago are 81°F, while nighttime lows are 63°F. Wrap up your sightseeing on the 18th (Fri) to allow time to drive to Rockford.

Things to do in Chicago

Parks · Outdoors · Historic Sites · Museums

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. Step out of the city life by going to Geneva Lake Shore Path and Riviera Beach. Explore hidden gems such as Anderson Japanese Gardens and Rotary Botanical Gardens. Change things up with these side-trips from Rockford: Lake Geneva (Geneva National Resort & Club, Aerial Adventures, &more), Williams Bay (Williams Bay Beach & Kishwauketoe Conservancy) and Chocolate Museum (in Burlington). There's more to do: explore the landscape on two wheels at White River State Trail.

You can plan Rockford trip in no time by asking Inspirock to help create your itinerary.

Drive from Chicago to Rockford in 1.5 hours. Alternatively, you can take a bus; or do a combination of subway and bus. Expect a daytime high around 81°F in June, and nighttime lows around 60°F. Finish your sightseeing early on the 22nd (Tue) to allow enough time to drive to Galena.

Things to do in Rockford

Outdoors · Parks · Beaches · Golf

Side Trips

Galena

— 2 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. Start off your visit on the 23rd (Wed): indulge your taste buds at Massbach Ridge Tasting Room, get engrossed in the history at Galena / Jo Daviess County Historical Society and Museum, contemplate the long history of Dowling House, then relax and rejuvenate at some of the best spas, then contemplate the long history of Ulysses S. Grant Home, and finally deepen your understanding of the past and present with a heritage tour. On the 24th (Thu), you'll have a packed day of sightseeing: see the interesting displays at Savanna Train Car Museum, make a trip to Galena Veterans Memorial Park, then steep yourself in history at Belvedere Mansion, then fly down the slopes at Chestnut Mountain Resort, and finally stop by Jamie's Wine Studio.

To see ratings, reviews, traveler tips, and other tourist information, use the Galena sightseeing planning tool.

You can drive from Rockford to Galena in 2 hours. Alternatively, you can do a combination of taxi and bus; or take a bus. In June, daily temperatures in Galena can reach 79°F, while at night they dip to 59°F. Finish your sightseeing early on the 24th (Thu) to allow enough time to drive to Utica.

Things to do in Galena

Historic Sites · Museums · Tours · Parks

Side Trip

Utica

— 2 nights
North Utica, often known as Utica, is a village in Utica Township, LaSalle County, Illinois. Start off your visit on the 25th (Fri): see the interesting displays at Westclox Museum, immerse yourself in nature at Matthiessen State Park, admire the majestic nature at Starved Rock State Park, then stop by Mix's Trading Post, and finally walk around Allen Park. On your second day here, admire the majestic nature at Illini State Park, then see the interesting displays at IL Route 66 Association Hall of Fame & Museum, then immerse yourself in nature at Buffalo Rock State Park, and finally walk around LaSalle Rotary Park.

To find other places to visit, traveler tips, ratings, and more tourist information, you can read our Utica holiday maker app.

Traveling by car from Galena to Utica takes 3.5 hours. Alternatively, you can do a combination of flight, shuttle, and taxi; or do a combination of bus and taxi. June in Utica sees daily highs of 81°F and lows of 61°F at night. Finish your sightseeing early on the 26th (Sat) so you can drive to Springfield.

Things to do in Utica

Parks · Nature · Shopping · Museums

Side Trips

Springfield

— 1 night

Flower City

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Kick off your visit on the 27th (Sun): steep yourself in history at Dana-Thomas House, ponder the world of politics at Old State Capitol, see the interesting displays at Illinois State Museum, don't miss a visit to Lincoln Tomb & War Memorials, then take an in-depth tour of Union Station - Lincoln from History to Hollywood, and finally walk around Sugar Creek Covered Bridge.

To see reviews, more things to do, ratings, and more tourist information, read our Springfield trip planner.

You can drive from Utica to Springfield in 2.5 hours. Alternatively, you can do a combination of taxi, bus, and train; or do a combination of taxi, shuttle, and flight. In June, plan for daily highs up to 85°F, and evening lows to 65°F. Finish up your sightseeing early on the 27th (Sun) so you can travel to Harrisburg.

Things to do in Springfield

Historic Sites · Museums · Parks

Side Trip

Harrisburg

— 1 night
Harrisburg is a city in and the county seat of Saline County, Illinois, United States. Kick off your visit on the 28th (Mon): explore the stunning scenery at Little Grand Canyon and then tour the pleasant surroundings at Garden of the Gods.

To find other places to visit, where to stay, traveler tips, and more tourist information, you can read our Harrisburg trip itinerary planner.

Getting from Springfield to Harrisburg by car takes about 3.5 hours. June in Harrisburg sees daily highs of 85°F and lows of 65°F at night. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow time for travel back home.

Things to do in Harrisburg

Parks · Wildlife · Nature

Side Trip

Highlights from your trip

Illinois travel guide

4.4
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.