1. Explore the country’s largest magic museum
Driving time from Chicago: About three hours
You'll find everything from obscure conjuring tomes to equipment used in Harry Houdini's most famous escape acts at the American Museum of Magic in Marshall, Michigan, home to the biggest collection of magic ephemera in the United States. With more than 350,000 artifacts onsite, there's more than enough magical entertainment to fill an afternoon: Take a self-guided tour through magic history, try to squeeze into a replica of Houdini's Milk Can Escape or book an appointment at the museum's Lund Memorial Library to pore over archival materials.
2. Spot bison at Midewin National Tallgrass Prairie
Driving time from Chicago: About one hour
Want to get a firsthand look at why Illinois is nicknamed the Prairie State? Take a trip southwest of the city to Will County, where a herd of bison roam the 9,000-acre expanses of the Midewin National Tallgrass Prairie as part of an ongoing habitat restoration project (the area once housed the Joliet Army Ammunition Plant and bunkers still remain). Spotting the herd isn't a sure thing—it's a massive park, after all—so you're best off bringing a pair of binoculars and starting at the Iron Bridge Trailhead, which puts you closest to the bison pasture area. From there, a three-mile round trip hike will lead you to an overlook point outfitted with viewing scopes and benches to rest on.
3. Go spelunking inside Cave of the Mounds
Driving time from Chicago: About three hours
Wander among soda straws, flowstones, helictites and other stunning geological formations inside of Cave of the Mounds, a natural limestone cave near Blue Mounds, Wisconsin. Once home to a limestone quarry, the cave is now open for guided (or self-guided) tours through mineral deposits in shades of white, reddish brown, black, purple and gray. Fun fact: Whether you're visiting on a hot summer day or during the frigid depths of winter, the subterranean expanse is always a cool 50 degrees, so be sure to dress accordingly.
4. See the Batmobile (and tons of other famous cars) at the Volo Auto Museum
Driving time from Chicago: About an hour and a half
Don't think that you're a car person? A visit to the Volo Auto Museum just might change your mind. Throughout this suburban attraction's 33 exhibits, you can ogle everything from '50s-era Thunderbirds and Oldsmobiles (Vintage Cars), to Britney Spears' 2006 Mercedes-Benz and Elvis Presley's 1974 Cadillac (Cars of the Rich and Famous), to Scooby Doo's Mystery Machine and the Subaru driven by Paul Walker in Fast & Furious 7 (TV and Movie Cars). There's even an entire exhibition dedicated to different iterations of the Batmobile. Plus, if you're really hoping to find some artifacts that aren't car-related, check out the museum's collection of planes, antique card games, animatronics and music machines, or shop for new home decor at the nearby Volo Antique Malls.
5. Tour modernist architecture in Columbus, IN
Driving time from Chicago: About four hours
Thanks to a highly successful funding program in the mid-20th century, the small-ish town of Columbus, Indiana is home to some of the Midwest's most stunning examples of Modern buildings, structures and public art, with works by Eero Saarinen, I.M. Pei, Richard Meier and other architectural luminaries dotting its downtown thoroughfares. You can pay for a guide to lead you through the highlights, but the town also offers a free audio tour app that leads listeners through 18 of the most prominent buildings in the area.
6. Paddle along the African American Heritage Water Trail
Driving time from Chicago: About 40 minutes
Chicagoans who love active, experiential learning can take an impactful day trip of paddling through history along the Little Calumet River, a waterway which, along with others, connects Lake Michigan with the Mississippi River. In a span of just seven miles, experience nearly two centuries of African American history, from the underground railroad and civil rights to the birth of environmental justice. Beginners can join an organized group paddle during the summer season while experienced water recreationists can follow a self-guided paddle outlined on the Openlands website.
7. Hike around the iconic Farnsworth House
Driving time from Chicago: About an hour and a half
Located in Plano, Illinois at the banks of the Fox River, the glass-walled Farnsworth House—designed by Bauhaus architect Ludwig Mies van der Rohe as a weekend retreat for Dr. Edith Farnsworth—is both a National Historic Landmark and one of the area's foremost examples of Modernist architecture. Though the house has been besieged by floods throughout its 70-year history, ongoing preservation efforts have kept it in tip-top condition. Book a docent-led tour through the building (the summertime moonlight tours, which commence at dusk and loop around a lighted exterior path, are an especially beautiful option) and take some time to soak in the natural beauty of the home's 60-acre wooded grounds.
8. Check out Amish Country in Shipshewana, IN
Driving time from Chicago: About two and a half hours
Escape the bustle of city life among the placid streets of Shipshewana, a teeny town nestled in the center of northern Indiana's Amish Country. Kick off your day with a tour of Menno-Hof—a museum dedicated to Amish and Mennonite history—or book a sight-seeing expedition aboard a horse and buggy, then fuel up with traditional Amish eats at family-style restaurants like A Taste of of Shipshewana (where you'll also find live cooking and quilting demonstrations). In the market for antiques and tchotchkes? Plan a visit on Tuesdays or Wednesdays from May through September, when the town hosts the Midwest's largest flea market.
9. Wander through a Tudor-style castle in Oregon, IL
Driving time from Chicago: About two hours
Back in the late 1920s, Chicago Daily News publisher and owner Walter A. Strong began construction on a Tudor-style manor to serve as his family's summer home. The end result—a 10-bedroom, 8-bathroom behemoth with a couple of secret passages to boot—can be explored in the present day through an hour-long tour, which covers the history of the Strong family, the castle's architecture and a brief history of medieval life. If you're got time after the tour, head to the nearby Castle Rock State Park (unaffiliated with the aforementioned castle, in case you were wondering) to hike among gorgeous sandstone bluffs.
10. See the Great Pyramids without leaving Illinois
Driving time from Chicago: About one hour and five minutes
One of the most unexpected I-94 sights is the Gold Pyramid House, a 1970s-era family compound featuring replicas of the Great Pyramid of Giza, a 55-foot statue of Ramses II and King Tutankhamun’s tomb. Full of objects and decor leaning from kitschy to cult-like, visitors can meander the grounds and attend events, and even take home Gold Pyramid Water and Gold Pyramid Vodka as souvenirs, though it’s unclear whether either were on sale in ancient Egypt. House tours on select Saturdays and by appointment only.
11. Meander through an English-style village next to the largest inland oil refinery
Driving time from Chicago: About 35 minutes
Marktown Historic District may not be one of the seven wonders of the world, but it's certainly a marvel of Northwest Indiana. Built in 1917 as a planned worker community by renowned architect Howard Van Doren Shaw—10 years after the last home was sold in nearby planned community Pullman—Marktown became famous after its appearance in Ripley's Believe It or Not! for being the only town in North America where cars park on the sidewalk and neighbors walk on the streets. Today, the quaint Tudor revival-style homes with bright colors and cheerful window boxes are in eerie contrast to the surrounding heavy industry. Learn about architecture and the area’s history in steel on a self-guided tour. Then, refuel at Hegewisch favorite Pudgy’s Pizza before heading home.
12. Ride a vintage train at the Illinois Railway Museum
Driving time from Chicago: About an hour and a half
The country's largest railway museum sits just outside the Chicago metropolitan area in Union, Illinois, where you can check out a massive collection of antique train cars and hop aboard working streetcars, steam and diesel trains that loop around the 100-acre campus. Plan for an entire day of exploration: The museum's buildings house all kinds public transportation artifacts, including an 1859 horse-drawn streetcar, every kind of CTA 'L' car and a display of working railroad signs and signals.
13. Take a nature walk through Cantigny Park
Driving time from Chicago: About 45 minutes
This verdant Wheaton park—formerly the estate of the publishers of the Chicago Tribune—offers 29 acres of gardens and 160,000 plants, complete with two and a half miles of nature paths perfect for a leisurely afternoon stroll among the flowers. Military history buffs will also want to check out the First Division Museum on the park's grounds, which chronicles U.S. military history from World War I to the present.
14. Find your zen in the Anderson Japanese Gardens
Driving time from Chicago: About two hours
Once you've thoroughly explored the lovely Garden of the Phoenix in Jackson Park, set your sights on a visit to the Anderson Japanese Gardens in Rockford. Designed by landscape architect Hoichi Kurisu, the 12-acre gardens feature trails, waterfalls, tranquil ponds, gravel gardens and an abundance of Japanese maples, among other plant life. Plan ahead and book the "Frank Lloyd Wright Meets 16th Century Japan Tour" that guides visitors through the garden's 16th century Sukiya-style tea house and the Laurent House, which has the distinction of being the only home Wright designed for a client with a physical disability.
15. Learn about America’s RVs at a niche museum
Driving time from Chicago: About two hours
Get inspired to embark on your version of the great American road trip as you browse permanent collections of trailers, motorhomes, housecars and more ranging from the 1910s to present at Elkhart’s RV/MH Hall of Fame (RV/MH stands for recreational vehicle and manufactured housing). Step back in time with Instagram-worthy vintage airstreams, Model T campers and motorhomes that look like they stepped off the set of Stranger Things. After your visit, explore the thousands of archives at the RV/MH Library, where you can glimpse into the recreational lives of North Americans in the 1960s issues of Trailer Life or 1980s issues of Camping Today.
16. Take a picture with a (smaller) Leaning Tower of… Niles
Driving time from Chicago: About 25 minutes
Sitting at a half the size its original at 94 feet tall and leaning 7.4 feet, the replica of the Leaning Tower of Pisa in suburban Illinois is an unlikely site and guaranteed out-of-the-box day trip. In the 1930s, a local businessman wanted to disguise a water tower and the answer was—obviously!—to craft a leaning tower. Taking an illusion photo holding up the tower is a must, and if you’re not too tired, head to nearby North Branch Trail and surrounding forest preserves for nature spotting or cozy up with your next great read at New Book Joy.
17. Watch an outdoor play at American Players Theatre
Driving time from Chicago: About three and a half hours
Spring Green, Wisconsin is perhaps best known as the home of Taliesin, Frank Lloyd Wright's Prairie style summer estate set amid the limestone outcroppings of Wisconsin's Driftless Area. You should make a stop at the house if you have time—Wright's estate offers a huge variety of guided tours—but the 1,089-seat outdoor ampitheater at American Players Theatre is an equally unbeatable summertime attraction. The company's repetoire is mostly classical, though you'll find more contemporary works on the lineup as well.
18. Celebrate Christmas in July at Santa’s Village
Driving time from Chicago: About an hour
Sure, Six Flags is fun, but there's only one suburban amusement park where you'll run into Santa Claus year-round, and that's Santa's Village Azoosment & Water Park in East Dundee. Despite its wintry theme, the family-friendly park is best visited in summer: Splash around in the Caribbean Christmas-themed Santa Springs water park—featuring two 300-foot, candy cane-colored slides—or take a spin on thrill rides like the Blizzard, which swings riders 40 feet in the air on a spinning pendulum.
19. Eat fried chicken on Historic Route 66
Driving time from Chicago: About 35 minutes
Fried chicken with a side of history? We’ll take it. At Dell Rhea’s Chicken Basket, you’ll be eating food that has been satisfying hangry travelers and folks simply looking for a good meal since 1946. This gas station lunch counter-turned-dining room is conveniently located off Route 66, its gleaming lights a beacon for those traveling to or from Chicago. Listed on the National Register of Historic Places, step into the nearly unchanged brick building and devour a Famous Fried Chicken Dinner, hand breaded and deep fried half chicken served with mashed potatoes and biscuits.
20. Say “prost” in Germantown, WI
Driving time from Chicago: About two hours
Despite its name, the Milwaukee suburb of Germantown, Wisconsin doesn't quite have the transportative qualities of other places in the Midwest that look like Europe. Still, there's a lot to love about this historically German settlement—sip a stein full of Krombacher Pils at the Von Rothenburg Bier Stube, check out more than 5,000 antique bells at the Sila Lydia Bast Bell Museum & Fire Hall or don your best lederhosen/dirndls for Maifest, the annual three-day festival held in honor of the beginning of spring.
