9 days in Illinois Itinerary

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.

Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, make a trip to Skydeck Chicago - Willis Tower, take a leisurely stroll along Navy Pier, and walk around Millennium Park.

To find where to stay, other places to visit, reviews, and more tourist information, use the Chicago online trip builder.

New York City to Chicago is an approximately 5-hour flight. You can also drive; or take a bus. The time zone difference when traveling from New York City to Chicago is minus 1 hour. Traveling from New York City in September, you can expect nighttime temperatures to be a bit cooler in Chicago, with lows of 61°F. Cap off your sightseeing on the 9th (Wed) early enough to go by car to Springfield.

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.

Kick off your visit on the 10th (Thu): get engrossed in the history at Abraham Lincoln Presidential Library and Museum, make a trip to Lincoln Tomb & War Memorials, and then relax in the rural setting at Apple Barn. On the next day, look for all kinds of wild species at Lincoln Memorial Garden, browse the exhibits of Lincoln Home National Historic Site, then steep yourself in history at Dana-Thomas House, and finally take in the architecture and atmosphere at Cathedral of the Immaculate Conception.

For ratings, maps, and other tourist information, read Springfield online tour planner.

Traveling by car from Chicago to Springfield takes 3.5 hours. Alternatively, you can fly; or do a combination of train and bus. Expect a daytime high around 82°F in September, and nighttime lows around 58°F. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Galena.

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. On the 12th (Sat), steep yourself in history at Ulysses S. Grant Home, then get thoroughly spooked out with The Haunted Galena Tour Company, then shop like a local with River Bend Gallery, and finally kick your exploration up a notch at Long Hollow Canopy Tours. Get ready for a full day of sightseeing on the 13th (Sun): sample the fine beverages at Blaum Bros. Distilling Co. and then learn about winemaking at Galena Cellars Vineyard.

To see reviews, other places to visit, traveler tips, and tourist information, use the Galena road trip planner.

Traveling by car from Springfield to Galena takes 4.5 hours. Alternatively, you can do a combination of bus, ferry, and car; or fly. When traveling from Springfield in September, plan for little chillier days in Galena, with highs around 75°F, while nights are about the same with lows around 54°F. Finish your sightseeing early on the 13th (Sun) to allow enough time to travel back home.