14 days in Illinois Itinerary

14 days in Illinois Itinerary

Created using Inspirock Illinois tour planner

Make it your trip
+2
Drive to Ronald Reagan Washington National Airport, Fly to Abraham Lincoln Capital Airport, Drive to Shelbyville
1
Shelbyville
— 1 night
Drive
2
Galena
— 2 nights
Drive
3
DeKalb
— 2 nights
Drive
4
Waukegan
— 2 nights
Drive
5
Chicago
— 6 nights
Fly

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Shelbyville

— 1 night
Shelbyville is a city in Shelby County, Illinois, along the Kaskaskia River. On the 16th (Wed), learn about winemaking at Willow Ridge Winery and then enjoy the sand and surf at Lake Shelbyville. Get ready for a full day of sightseeing on the next day: view the masterpieces at The Vault Art Gallery, then look for gifts at Beachy's Bulk Foods, and then do a tasting at Tuscan Hills Winery.

For traveler tips, other places to visit, photos, and tourist information, you can read our Shelbyville day trip app.

Washington DC to Shelbyville is an approximately 8.5-hour combination of car and flight. You can also drive. The time zone difference when traveling from Washington DC to Shelbyville is minus 1 hour. Traveling from Washington DC in June, you can expect nighttime temperatures to be little chillier in Shelbyville, with lows of 64°F. Finish up your sightseeing early on the 17th (Thu) so you can travel to Galena.

Things to do in Shelbyville

Shopping · Wineries · Outdoors · Beaches

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 18th (Fri): contemplate the long history of Ulysses S. Grant Home, then brush up on your knowledge of spirits at Blaum Bros. Distilling Co., and then get thoroughly spooked out with a ghost and vampire tour. Get ready for a full day of sightseeing on the 19th (Sat): tour the pleasant surroundings at Horseshoe Mound, get engrossed in the history at Galena / Jo Daviess County Historical Society and Museum, see the interesting displays at The Old Blacksmith Shop, then stop by Great American Popcorn Company, and finally shop like a local with River Bend Gallery.

To find where to stay, reviews, other places to visit, and other tourist information, read our Galena online route builder.

Drive from Shelbyville to Galena in 5 hours. Alternatively, you can do a combination of car and flight. Traveling from Shelbyville in June, expect Galena to be a bit cooler, temps between 79°F and 59°F. Finish your sightseeing early on the 19th (Sat) to allow enough time to travel to DeKalb.

Things to do in Galena

Museums · Historic Sites · Breweries & Distilleries · Tours

DeKalb

— 2 nights
DeKalb is a city in DeKalb County, Illinois, United States. Start off your visit on the 20th (Sun): learn about winemaking at Prairie States Winery and then sample the fine beverages at Whiskey Acres Distilling Co.. On your second day here, stroll around Washington Square Park, relax and rejuvenate at SaltTreeYoga, and then stop by Tom's Farm Market and Greenhouse.

To see other places to visit, maps, ratings, and other tourist information, go to the DeKalb tour itinerary planner.

You can drive from Galena to DeKalb in 2.5 hours. In June in DeKalb, expect temperatures between 79°F during the day and 59°F at night. Wrap up your sightseeing on the 21st (Mon) to allow time to travel to Waukegan.

Things to do in DeKalb

Wineries · Shopping · Spas · Breweries & Distilleries

Side Trips

Waukegan

— 2 nights
Waukegan is a city and the county seat of Lake County, Illinois, United States. Kick off your visit on the 22nd (Tue): kick back and relax at Glencoe Beach, then enjoy the sand and surf at Rosewood Beach, and then stop by Oh Olive. Keep things going the next day: enjoy the sand and surf at Waukegan Municipal Beach, then enjoy the sand and surf at Illinois Beach State Park, and then brush up on your knowledge of spirits at Copper Fiddle Distillery.

To see photos, more things to do, where to stay, and more tourist information, read our Waukegan driving holiday planner.

Getting from DeKalb to Waukegan by car takes about 1.5 hours. Expect a daytime high around 76°F in June, and nighttime lows around 56°F. Finish up your sightseeing early on the 23rd (Wed) so you can go by car to Chicago.

Things to do in Waukegan

Outdoors · Beaches · Parks · Nature

Side Trips

Chicago

— 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll enjoy a bit of beach vacationing at Centennial Beach and Ohio Street Beach. For shopping fun, head to The Magnificent Mile or Chicago Cultural Center. Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, get a new perspective on things with Boat Tours & Water Sports, and get up close and personal with brilliant marine life at Shedd Aquarium.

To find photos, maps, more things to do, and other tourist information, use the Chicago visit planner.

Getting from Waukegan to Chicago by car takes about 1.5 hours. Traveling from Waukegan in June, Chicago is somewhat warmer at night with lows of 63°F. Finish your sightseeing early on the 29th (Tue) to allow enough time to fly back home.

Things to do in Chicago

Parks · Outdoors · Beaches · Museums

Side Trips

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.