Our experienced guides focus on the most important and beautiful sights. Explore the best sights in Chicago with experienced guides.
Amazon offers products from hundreds of top brands at great prices. Shop low prices on holiday essentials. Free shipping, exclusive discounts, and more.
Search results
- Milwaukee, WI. Milwaukee is a big deal. This major city is located on the shores of western Lake Michigan in Wisconsin – just a 1.5 hour train ride or drive north of Chicago.
- South Bend, IN. South Bend has a different vibe as a university city on the St. Joseph River. It is fantastic if you are looking for a more sedate city experience.
- Madison, WI. Small Madison might not seem capital-worthy, but it is actually the capital city of Wisconsin, not the major, sprawling giant of Milwaukee.
- Starved Rock State Park, IL. Starved Rock State Park is one of the most popular attractions in Illinois. The park sits on the banks of the Illinois River and holds a collection of sandstone canyons amidst beautiful forests.
- 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.
- 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?
- 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.
- 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?
- Starved Rock State Park. Distance from Chicago: 91 miles/146 km. How Long it Takes: 1½ Hours. Settled along the Illinois River, Starved Rock State Park is an oasis teeming with seasonal waterfalls, towering sandstone canyons, thriving wildlife, and scenic hiking trails.
- Lake Geneva. Distance from Chicago: 83 miles/134 km. How Long it Takes: 1 Hour 45 Minutes. A resort city, Lake Geneva, was named “Newport of the West” after the American Civil War.
- Indiana Dunes National Park. Distance from Chicago: 39 miles/62 km. How Long it Takes: 1 Hour. One of the best day trips from Chicago, Indiana Dunes National Park is thriving with natural wonders with over 50 miles of scenic trails to observe these eye-catching features.
- Silver Beach County Park. Distance from Chicago: 98 miles/157 km. How Long it Takes: 1 Hour 45 Minutes. Bordering four states, Lake Michigan seeps into Illinois, Indiana, Michigan, and Wisconsin.
- Milwaukee, WI. Driving time from Chicago: One and half hours. Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half.
- Fennville, MI. Driving time from Chicago: Two hours and 20 minutes. Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking.
- South Bend, IN. Driving time from Chicago: One hour and 45 minutes. There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum, a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver.
- Madison, WI. Driving time from Chicago: Two and half hours. Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about.
- Gurnee, IL
- Cedarburg, WI
- Evanston, IL
- Kankakee County, IL
- Fairbury, IL
- South Bend, in
- Oak Park, IL
- Madison, WI
- Fennville, MI
- Oglesby, IL
With 23 million visitors making their way to Gurnee every year (including Chicagoans), you know you’re dealing with one of Illinois’s most popular tourist hubs. Sitting right off the I-94 and an hour’s drive away from Chicago, Gurnee is a hotspot, a regular feature on the list of Chicago day trips for those looking for world-class entertainment and...
Wichita’s Cedarburg is located just two hours away from Chicago—time slows down in this delightful town, so head here if you want a leisurely day of unwinding surrounded by small-town charm. In Cedarburg, friendly folks, rich culture, and gorgeous period architecture abound—you could spend your day here simply exploring and soaking all these in. If...
Want a break from the city but don’t want to travel too far, either? Evanston should feature among the options on your Chicago trips list, being that it’s only 33 minutes away. This little college town is home to gems such as the ethereal Baha’i House of Worship, one of only eight around the world and the oldest of the lot—the beautiful architectur...
If you’re looking for outdoor fun on your day trip, consider Kankakee County. Just an hour and a half away from Chicago, the land surrounding the Kankakee River served as home to many indigenous people through the centuries and is still revered ground for many. The Kankakee River State Park sits close to the river, sprawled across 4,000 acres of pr...
Foodies will enjoy a day out in Fairbury, home to the popular Slagel Family Farms and Kilgus Farmstead, both favorites among top chefs in the state. Fairbury sits at the heart of Illinois, two hours away from Chicago. Here, you can meet Kilgus’s lovely doe-eyed residents (of the human and Jersey variety!), get a 101 on milking, and even sample the ...
A little under two hours away from Chicago, South Bend itself may not ring a bell—most people only hear of it through the close-by Notre Dame University—but you should consider familiarizing yourself with the city if you adore culturally rich spots. Learn about the city at the History Museum, housed in inventor James Oliver’s Victorian manor, and i...
If you worship at the altar of Frank Lloyd Wright, Oak Park is a pilgrimage that you must make. Just 17 minutes away from downtown Chicago, Oak Park is a historic neighborhood whose primary identity is Lloyd Wright’s home and whose secondary identity is Ernest Hemingway’s home—a treat for architecture, art, and literature enthusiasts! Start with a ...
What could a capital city offer other than the usual capital-style entertainment, right? Well, that may also be the case with Madison, but the entertainment here is top-notch and definitely worth a visit for an urban getaway. Apart from its lovely cityscape, capitol-dotted skyline, and world-class beer, Madison offers visitors tons of attractions s...
Foodies don’t need much motivation to visit Michigan’s fruit belt, but if you do, petite Fennville might do the trick, with its excellent eateries that showcase the local bounty in manners that can have your tastebuds singing. Visit Fennville at the right time of the year and try your hand at picking ripe cherries and peaches, or get your fill of t...
Oglesby isn’t just another quiet, Illinois-Valley river town—it’s a haven for outdoor enthusiasts, with enough recreational activities to suit any adventurer’s palette. Sitting at the confluence of the Vermillion and Illinois rivers, Oglesby also sits close to the popular Starved Rock State Park (Illinois’s most visited) and Matthiessen State Park....
- Cole Evans
Mar 31, 2023 · If you’re going on a road trip from Cleveland to Chicago, we did the research for you and compiled some great stops along the way — with Sandusky, Toledo, South Bend, Saint Joseph, Michigan City, Put in Bay, and Port Clinton, as well as top places to visit like Rocky River Reservation and Findley State Park, or the ever-popular Castle Noel.
Jun 17, 2024 · 4. Geneva-on-the-Lake. Distance: 1 hour one-way. The beautiful Lake Erie. Located on the shore of Lake Erie in Ashtabula County, Geneva-on-the-Lake bills itself as “Ohio’s first summer resort,” and makes for a great getaway either just for the day, or for a weekend. 3 must-dos in Geneva-on-the-Lake: Go wine tasting.
People also ask
Where to go on a road trip from Cleveland to Chicago?
What are the best places to visit from Cleveland to Chicago?
Is Chicago a good place to go on a weekend getaway?
Is Cleveland a good city for a day trip?
What cities are between Cleveland & Chicago?
Which island should I visit from Cleveland?
