Chicago is a city that never runs out of things to do. But sometimes, a change of scenery is exactly what you need.
Whether you’re craving quiet nature trails, small-town charm, or lakeside relaxation, these road trips, which are all within a 1 to 5-hour drive, make for perfect weekend getaways. This summer, it’s time to get out of the city and explore some of these wonderful places that don’t require you to hop on a plane to explore.
1. Milwaukee, Wisconsin
Distance: 1.5 hours
Best for: Beer lovers, foodies, and lake views
Milwaukee is a quick and rewarding drive from Chicago. Renowned for its storied brewing heritage, this city is a haven for beer enthusiasts. Be sure to tour local favorites like Lakefront Brewery and Milwaukee Brewing Company, where you can enjoy tastings and learn about the city’s beer-making past.
Food lovers will appreciate the Milwaukee Public Market, where vendors offer everything from local cheeses and fresh seafood to bakery treats and wine. It’s also a great place to grab a casual lunch before heading over to the lakefront to explore the Milwaukee Art Museum. The museum itself is a visual landmark, with its wing-like design on the lakefront, which was designed by the renowned artist Santiago Calatrava.
Make time in your plans to walk along the RiverWalk or the shores of Lake Michigan, especially in the summer when the city hosts outdoor concerts and festivals. Don’t forget to hop aboard “The Hop,” Milwaukee’s free streetcar, to easily explore downtown without needing to repark (though parking throughout the city is pretty easy).
2. Starved Rock State Park, Illinois
Distance: 1.5 hours
Best for: Hikers and nature photographers
Located in Oglesby, Illinois, Starved Rock State Park is one of the most picturesque places in the state. It offers more than 13 miles of trails winding through canyons, sandstone bluffs, and waterfalls. Some waterfalls do dry up in the summer, so spring or fall is often the best time to visit if you want to see them flowing with water.
While you’re out hitting the trails, don’t miss spots like St. Louis Canyon or the panoramic views from Lover’s Leap Overlook. During the fall, the park becomes a riot of color as the leaves change.
Besides hiking, visitors can enjoy fishing, birdwatching, or picnicking near the Illinois River. For a longer trip, opt to stay overnight at the historic Starved Rock Lodge, which will add a rustic vibe to your trip.
3. Lake Geneva, Wisconsin
Distance: 1.5 hours
Best for: Summer relaxation and watersports
Lake Geneva is a laid-back resort town that comes alive in the midst of the summer. The 26-mile Geneva Lake Shore Path offers an up-close view of lakefront estates, many of which date back to the Gilded Age. It’s a beautiful area to walk, jog, or bike on a sunny Wisconsin summer day.
Downtown Lake Geneva has a quaint mix of art galleries, cafes, and local boutiques. When you’re ready for more adventure, Big Foot Beach State Park offers kayaking, swimming, and picnic spots right on the water.
Lake Geneva is also home to a lively summer events calendar, including boat tours, festivals, and farmers markets. In winter, the town transforms into a cozy escape with snowshoeing and holiday markets.
4. Indianapolis, Indiana
Distance: 3 hours
Best for: Families and sports fans
Indianapolis, the capital of Indiana, is perhaps best known for the Indianapolis Motor Speedway, home of the Indy 500. Motorsports fans can tour the track and explore the adjacent museum filled with classic race cars.
For families, the Children’s Museum of Indianapolis is a can’t-miss stop. It’s the largest children’s museum in the world, featuring hands-on exhibits that range from dinosaurs to space travel. The outdoor Sports Legends Experience is also a hit for kids, especially those who have already found a love of the game (any game, that is!).
Downtown Indy offers cultural experiences like the Indiana State Museum, the Indianapolis Zoo, and White River State Park. Cap off the visit with a climb to the top of the Soldiers and Sailors Monument in Monument Circle for sweeping views of the city.
5. Galena, Illinois
Distance: 3 hours
Best for: History and antiques
Galena is a beautifully preserved 19th-century town tucked into the hills of northwest Illinois. It’s the former home of Ulysses S. Grant, and you can tour his historic house along with the Galena History Museum.
Downtown Galena is charming and walkable, with cobblestone streets lined with boutiques, antique stores, and cozy cafes. It’s a great place to shop for vintage treasures or grab a slice of homemade pie.
Beyond history, Galena has some quirky outdoor offerings like the “Hoof It” goat hikes or relaxing strolls through its sculpture garden. For a guided overview of the town’s history, hop aboard the Galena Trolley Tour.
6. Mackinac Island, Michigan
Distance: 4.5 hours (plus ferry)
Best for: A car-free island escape
Mackinac Island is like stepping into a different era. After reaching Mackinaw City, leave your car behind and ferry to this car-free island. Horse-drawn carriages, bicycles, and walking are the only ways to get around.
Explore historic Fort Mackinac, shop for the island’s famous fudge, and wander streets lined with Victorian architecture. You can bike the 8-mile trail around the perimeter of the island or enjoy a private carriage ride through the interior.
Don’t miss Arch Rock or the Grand Hotel, both of which offer beautiful views and historic charm. It’s a true escape from the modern world.
7. Door County, Wisconsin
Distance: 4.5 hours
Best for: Coastal charm and cherry blossoms
Often called the Cape Cod of the Midwest, Door County, Wisconsin, is a peninsula with more than 300 miles of shoreline, five state parks, and a slew of charming small towns.
In spring and summer, the area blooms with cherry and apple orchards. Fish Creek and Ephraim are two of the most picturesque towns you’ll ever come across, offering art galleries, local food, and lakeside lodging.
Peninsula State Park is perfect for hiking or biking and features stunning views of Green Bay. Wine lovers can enjoy tastings at local vineyards, while others may opt for kayaking tours or fish boils, which is a Door County tradition that you have to take part in while you’re visiting.
8. Madison, Wisconsin
Distance: 2.5 hours
Best for: Culture and college town energy
Madison sits on the strip of lane, right in between Lake Mendota and Lake Monona, giving it a relaxed waterfront vibe from every angle. As Wisconsin’s capital and a university town, it offers a fun mix of political history and youthful creativity.
The Dane County Farmers’ Market around the Capitol Square is one of the best in the country. The Olbrich Botanical Gardens and Henry Vilas Zoo are free and make for relaxing afternoon visits.
Don’t miss the Chazen Museum of Art, or grab lunch at one of Madison’s many food trucks or casual cafes. The city is also known for its biking trails and lakefront paths, making it a pretty athletic city.
9. Indiana Dunes National Park, Indiana
Distance: 1 hour
Best for: Beaches and nature close to home
Just an hour from Chicago, Indiana Dunes offers an easy nature escape. The park stretches along 15 miles of Lake Michigan shoreline and features rugged sand dunes, prairies, and wetlands.
Hiking, swimming, and birdwatching are popular here. West Beach is great for families, while Mount Baldy and the Dune Succession Trail offer more challenging hikes.
Sunsets here are gorgeous here and if you visit in winter, the snowy trails offer a peaceful contrast to the summer crowds.
10. St. Louis, Missouri
Distance: 4.5 hours
Best for: Food, music, and monumental views
St. Louis is a lively city with a mix of historical and cultural attractions. Start your visit at the Gateway Arch, where you can ride to the top for panoramic views or just stroll through the parks that line the river.
Explore the city’s music roots at the National Blues Museum or walk through Forest Park, home to the Saint Louis Art Museum, the Missouri History Museum, and the Saint Louis Zoo (all free!).
Food lovers should try St. Louis-style ribs, toasted ravioli, and gooey butter cake. The city also has a growing craft beer scene, and neighborhoods like The Hill and Soulard are great for local eats.
11. Cedar Point, Ohio
Distance: 5 hours
Best for: Thrill-seekers
Located in Sandusky, Ohio, Cedar Point is one of the most iconic amusement parks in the country. It’s home to some of the tallest and fastest roller coasters in the world.
The park also offers live entertainment, a water park, and kid-friendly rides, making it a fun trip for all ages. Staying overnight at one of the park’s resorts gives you early access to rides.
If you visit during shoulder seasons, lines are shorter, and the weather is milder. Don’t forget to bring sunscreen, comfy shoes, and a sense of adventure.