Best vacation spots near Chicago for adventurous travelers

It can be maddening when you’re itching to hit the road but are stumped on where to go. There is certainly no shortage of popular cities nearby but when you are looking for the best vacation spots near Chicago, digging through a list of 20 destinations will only add to decision fatigue. We’ll help you truly narrow your search: We chose the top three destinations near Chicago in two different categories — best lake towns and best places to hike — that offer variety and adventure for travelers seeking a memorable vacation.

3 best lake towns near Chicago

Chicago’s lakefront location provides locals and visitors with plenty of opportunities to get on and in the water. But even though access to Lake Michigan is convenient, sometimes you just need to get away. We consider these three destinations the best lake towns near Chicago because they each have a completely different vibe and plenty of water and non-water activities to add variety to your vacation.  

1. Chain O’Lakes, Illinois

Distance from Chicago: 55 miles (1 hours and 15 minutes)

What’s a better destination for a lakeside vacation than Lake County, Illinois? Chain O’Lakes is home to Illinois’ largest concentration of natural connected lakes, giving you plentiful options for water activities. A boat rental gives you the freedom to explore far and wide or to drop a line and try your hand at reeling in walleye, catfish, bluegill, largemouth bass and more. Step into a kayak to paddle along the banks of Fox River and spot resident wildlife. On days when you want a change of pace, the forested trails of Chain O’Lakes State Park are a top destination for hiking and biking. 

Away from the water, you’ll find the Lake County Libation Trail, which features dozens of craft breweries, wineries and distilleries welcoming visitors for tours and tastings.

2. Lake Geneva, Wisconsin

Distance from Chicago: 83 miles (1 hour and 45 minutes)

High-end resorts, world-class golf courses and postcard-worthy views are just some of the reasons that many Midwesterners consider Lake Geneva to be one of the best lake towns near Chicago. Soak up the sun at Riviera Beach, learn a new skill in a waterskiing class or soar above the water while parasailing. Board a classic boat with Lake Geneva Cruise Line for a scenic excursion or go on one of their themed adventures, like a cocktail cruise, U.S. mailboat tour or an ice cream social cruise.

There’s also plenty to do when you want a break from lake activities. Hike the trails at Big Foot Beach State Park, pick your own seasonal fruit at Apple Barn Orchard and Winery, fly above the treetops at Lake Geneva Ziplines & Adventures or pamper yourself at a spa, salon or wellness retreat.

3. Saugatuck, Michigan

Distance from Chicago: 146 miles (2 hours and 20 minutes)

There are plenty of destinations vying to be among the best Lake Michigan beaches near Chicago. Saugatuck ranks high in our book. Nearby Oval Beach, with its picturesque shoreline and plentiful activities, was recommended by Condé Nast Traveler as one of the “Perfect Lake Vacations Across America.” And Douglas Beach, Oval’s neighbor to the south, is just as welcoming but typically quieter — perfect for those seeking tranquility in their vacation days. What makes this lake town even more appealing is that the beaches face west, so you can grab your beach essentials, settle in and enjoy an unobstructed sunset every evening you’re there. 

When you aren’t lounging waterside, you’ll easily be drawn into Saugatuck’s thriving arts scene. There are dozens of studios, galleries and boutiques displaying pieces by local and nationally recognized painters, woodworkers, sculptors, ceramicists, crafters, mixed media artists and more. You may even be inspired to join a workshop and create your own art.

3 best places to hike near Chicago

Whether you’re on the hunt for a strenuous trail that will leave you breathless with rewarding views or an easy hike through a quiet forest covered with fresh snowfall, there are endless options within driving distance of Chicago. But if we had to choose where to start, it would be these three parks. Each one has its own unique claim to fame, so you can hike through them all without feeling déjà vu on the trail.

1. Indiana Dunes National Park

Distance from Chicago: 50 miles (50 minutes)

This national park’s proximity to Chicago makes it a local favorite. Interestingly, and perhaps a bit confusing, there is both a state and national park that cover the dunes system. Indiana Dunes State Park is flanked to the east and west by Indiana Dunes National Park. You’ll have a fantastic hiking experience no matter which park you choose, but the national park offers many more miles of trails than its counterpart — 50 miles versus 16. The national park features 15 trail systems that wind through a variety of biodiverse habitats, like wetlands, forests and the famous dunes, and range in difficulty from easy to moderate to rugged. 

2. Matthiessen State Park, Illinois 

Distance from Chicago: 96 miles (1 hour and 45 minutes)

Known for its caves, canyons, waterfalls and rock formations, Matthiessen State Park is a delight to explore, making it one of best places to hike near Chicago. There are five miles of well-marked trails for both novices and experienced hikers. Although that doesn’t sound like much, they are packed full of impressive natural sights that are also home to interesting plant life and a diverse array of birds, like nuthatches, cliff swallows, scarlet tanagers, red-tailed hawks and cedar waxwings. Aside from the Instagram-worthy views you’ll get year-round, Matthiessen State Park is stunning in the spring with its field of bright yellow sunflowers, and the display of colorful foliage in the fall is not to be missed. 

3. Devil’s Lake State Park, Wisconsin

Distance from Chicago: 192 miles (3 hours and 15 minutes)

If you’re looking for a weekend adventure, then the three-hour drive to Devil’s Lake State Park is worth it. The park boasts 29 miles of trails that take hikers through a living museum with remnants of ancient times. The 2.5-mile Steinke Basin Loop, rated as easy to moderate, cuts through an extinct glacial lake bed. Sauk Point, a 4.5-mile trail rated as medium to difficult, is part of the 1,000-mile National Scenic Ice Age Trail and brings hikers to great heights at 1,473 feet above sea level. The steep, difficult Potholes Trail — just 0.3 miles but can take two hours to complete — brings you past a series of depressions in rock face that were carved out by fast-moving water thousands of years ago. 

Get there with Avail

Whether you’re going to the lake or hitting the hiking trails, you’ll need a reliable rental car for your trip to the best vacation spots near Chicago. Avail car sharing has dozens of neighborhood locations across the city, making it convenient to pick up and return your car. Go ahead and add a second driver to share the wheel — you won’t be charged extra. And every trip is protected by Allstate insurance and 24/7 roadside assistance, so you can enjoy your adventure with peace of mind.