6 Best Illinois Towns For A Weekend Trip

If you have spent more time lately navigating a digital calendar than exploring new surroundings, it might be time for a weekend escape. The good news is that if you live in Illinois, a total change of pace is closer than you think! Whether you want to wander through rugged canyons and waterfalls or take a slower path with a horse-drawn carriage ride, these six towns are some of the best places to rest up and reconnect with a quieter side of life in 2026.

Ottawa

Travelers craving an escape into nature will love a trip to Ottawa, which is famously home to Starved Rock State Park. Established as a state park back in 1911, it is home to 18 canyons, 13 miles of trails, rain-fed waterfalls, and a wide variety of plant and animal life. Hiking, camping, boating, and fishing are a few of the most popular recreational activities. If you are not a big fan of camping, you can also opt to lodge at the Postcard Cabins Starved Rock, a collection of 58 upscale cabins with private firepits and forest views all around. In the area, there are some tremendous restaurants to visit, such as Hank's Farm Restaurant, which has been operating since 1941, known for its fried chicken and char-grilled steaks.

Macomb

If you are a fan of the game Monopoly, a weekend in Macomb is an absolute must. This small town is home to the world’s largest styled monopoly board, set right on Macomb’s Historic Courthouse Square! You can actually play a game here for yourself by downloading an app available on the town’s website, circling the square as if you were a Monopoly token. Macomb was also home to an important part of Abraham Lincoln’s legacy. Designated as an Abraham Lincoln National Heritage Area, there are ten sites to explore throughout the county, including the Living Lincoln Topiary Monument and the McDonough County Courthouse. You’ll find the Best Western Macomb Inn to be a comfortable place to spend the night, just minutes away from all the downtown action and offering amenities like a heated pool, a fitness center, and a complimentary breakfast in the morning.

Casey

If you are looking to spend a weekend in a fantastical world, you won’t find a place much better than Casey. With the motto “Big Things, Small Town,” Casey is known for its supersized attractions, home to landmarks like the World’s Largest Rocking Chair, World’s Largest Mailbox, World’s Largest Key, World’s Largest Wind Chime, and the World’s Largest Wooden Shoes, among many other giant, record-breaking objects. The downtown district is a great place to shop as well, with highlights including Casey's Candy Depot, a local candy shop housed in an old train depot, selling gourmet chocolates, fudge, popcorn, gummy candy, taffy, and more. You can round out your weekend by spending the night at the Eighteen-Ninety Sleepover, a boutique hotel set in a historic 1890 meeting hall with renovated rooms that will make you feel right at home.

Geneva

Situated along the Fox River, just an hour from downtown Chicago, Geneva is a lively town packed with gardens, history museums, and cultural festivals. The Fabyan Japanese Garden should be on the itinerary of all visitors, part of the Fabyan West Forest Preserve, and featuring about an acre of Japanese cultural structures and plant life. The Geneva History Museum, meanwhile, is a particularly interesting cultural institution. Its 3,000-square-foot main gallery chronicles the town’s history, while a smaller 950-square-foot space hosts rotating exhibits.

If you visit Geneva in June, you might be able to attend the town’s annual Swedish Days celebration, a five-day event that celebrates its Swedish heritage with nightly entertainment, a parade, a craft beer tent, and more. You won’t find a more beautiful place to spend the night than at the Herrington Inn & Spa, which sits on the Fox River, renowned for its European-style architecture, gabled roofs, and garden courtyard.

Nauvoo

With roots as a Native American village and a history shaped by the Church of Jesus Christ of Latter-day Saints, German immigrants, and Icarians, Nauvoo feels like a place where you are stepping back in time. You can kick off your weekend by signing up for a horse-drawn carriage ride, which takes visitors through different areas of the historic district, the Mormon Pioneer National Historic Trail, and other significant sites. The area’s nature is spectacular as well, largely preserved in Nauvoo State Park. Covering 148 acres, this park has a 13-acre lake, popular for fishing, boating, camping, and hiking. Some of the inns in town offer a historic experience as well, such as The Inn at Old Nauvoo, which has been renovated to offer comfortable amenities like an indoor heated pool and 10 different room types to accommodate every type of group.

Woodstock

Another great option for Chicagoans is Woodstock, situated just over an hour’s drive away. The town features a wonderful selection of cultural activities, including opera houses, antique malls, and apple orchards. The Woodstock Opera House has a great event calendar to check out year-round, hosting concerts, interactive performances, movie sing-alongs, and more. The perfect souvenir awaits you at the Roscoe Woodstock Antique Mall, which has over 70 vendors and 35,000 square feet of antiques to explore. In the fall, All Seasons Orchard draws in plenty of visitors as well, featuring apple picking, pumpkin picking, apple cider, and other festivities. The experience is excellently complemented with a night or two at The Cherry Tree Inn Bed and Breakfast, a house dating back to 1894 that has five guest rooms available for lodging.

Set Aside The Time For An Escape

Life is almost always going to feel busy, which is why it is so important to set aside time to relax. One of the best ways to do so is by planning a little weekend getaway every now and then, with Illinois offering plenty of potential. You can tailor your visit around history, culture, or the great outdoors, allowing you to return home at the end of the weekend feeling recharged and ready to face the world.