5 Adorable Towns Near Chicago Perfect For Solo Trips, Per The Internet

Chicago is the perfect destination for solo travelers with easy access to the well-integrated "El" train and bus system, which takes visitors and residents alike to the city's diverse neighborhoods. However, what Chicago offers in bustling, big-city energy, it often lacks in quaint charm. Those traveling on their own can feel overwhelmed in the booming metropolis of over 2.7 million residents.

Luckily, Chicago's proximity to other states — like Michigan, Wisconsin, and Indiana — presents a great opportunity to explore new places without the hassle of a long journey. This cosmopolitan hub is seated between a handful of Midwestern gems that are no more than a few hours away, making them easily accessible to those who don't have a driving buddy for the trip.

If you're traversing the Windy City on your own, check out its neighboring towns. There are activities for every style of traveler, from those curious to discover rolling dunes off the majestic Lake Michigan to those itching to peruse a holiday market in a historic town center. Whatever your vibe, one of these towns should speak to you.

A storybook harbor city on Michigan's Art Coast, Saugatuck is a popular solo escape from Chicago. Nestled along Lake Michigan's shoreline and near a coveted state park, it boasts a walkable and historic downtown center. The town is just over a two-hour drive from the heart of Chicago, making it an ideal weekend excursion or a simple day trip. The internet has deemed the Saugatuck Dune Rides its top attraction, with a 4.9 rating from nearly 5,000 TripAdvisor reviews. 

With a population just under 1,000 residents, Saugatuck is a tight-knit area. That said, the town features many attractions and lodging options designed to accommodate visitors and make them feel right at home. Throughout the year, a handful of community events (such as the Venetian Festival and Oktoberfest) welcome travelers and locals. This distinctly creative region has a high concentration of galleries, art fairs, and studio visit opportunities which give solo sightseers a chance to connect with local artisans.

Additionally, it's hard to beat Saugatuck's access to nature. Nearby Saugatuck Dunes State Park lets visitors wander 2.5 miles of sandy shores along Lake Michigan with 300 forested acres of hiking trails inland. Meanwhile, the historic Saugatuck Chain Ferry (in operation since 1838 and currently running during the summer months) is available to take guests across the Kalamazoo River. From there, hikers can follow a walking trail to Oval Beach (aka one of the best Great Lakes beaches in America), beloved by visitors on TripAdvisor.

Galena is a cozy, historic, and underrated town that takes travelers out of the hustle and bustle of Chicago. Just under three hours away from the city by car, it lulls visitors into the slower pace of scenic northwest Illinois. The tight-knit community of 3,200 residents is preserved in time with roughly 62% of its buildings considered historic landmarks, according to The City of Galena. Paired with rolling hills and valleys off the nearby Mississippi River, this destination is regularly touted for its breathtaking scenery and positive travel experiences.

A surprising number of museums fall within the town's relatively small boundaries. The collection includes spots such as the Chicago Great Western Railway Depot Museum and Elizabeth History Museum, both of which are perfect for history buffs seeking a deeper understanding of the area. These attractions also let you take a peek into over a century of local industrial history.

Of course, the main attraction for many visitors is the Galena River which runs through the town's center and helps shape its layout. It's easy to enjoy while exploring historic buildings and small local shops, but nature enthusiasts can experience its banks more closely along the Galena River Trail. This 8.8-mile route starts just minutes from downtown and is perfect for biking, hiking, and cross country skiing in winter months. Additionally, one Reddit user advises visitors to "check out Horseshoe Mound" for "great views of Galena" and stop by Casper Bluff, "a really cool prairie just outside of Galena that has cool Thunderbird Effigy Mounds and loads of history."

The resort town of Lake Geneva is often referred to as the Hamptons of the Midwest and has been a popular destination for respite to Chicagoans for over a century. It's a 90-minute drive away into the state of Wisconsin, making it one of the best day trips near the Windy City for solo travelers who want a retreat. The area's beaches are its main draw, with Riviera Beach being a popular choice. For laid back options best for solo travelers avoiding crowds, visit neighboring Fontana and Williams, which boast beaches that beat the crowds while offering calm, warm water in summer months.

For rustic paradise, travelers flock to Big Foot Beach State Park to take advantage of its 5 miles of hiking trails and well-equipped camping sites. In winter, cross-country skiing and snowshoeing dominate as the premier activities. The Geneva Lake Shore Path provides stunning water views over 26 miles as well as opportunities to examine historic estates up close. It's a popular solo activity with 775 visitors providing positive reviews on TripAdvisor which mention diverse scenic beauty as hikers traverse the trail. 

One visiting tourist gave curious travelers a snapshot of the meandering trail: "Every house must allow pedestrians to walk through their yard around the lake so they've all created unique little paths that connect. You get real up close and personal with some incredible mansions and get to enjoy lake views. It's a unique 'urban hiking' experience ... Plenty of places to cut off for lunch and drinks if you plan accordingly."

In just one hour, solo travelers can move from Chicago's industrial sprawl to the quaint, artsy town of Chesterton. With 15,000 residents in its boundaries, Chesterton is more bustling than other getaways on this list but still offers intimate charm with its tightly-knit downtown strip and easy access to nearby dunes and lakeshore views. 

It's a shopper's dream at Chesterton European Market which features artisanal bites and handcrafted goods from local vendors. The market's official Facebook page boasts over 24,000 followers and 1,200 positive reviews, demonstrating that its both a local and tourist favorite.  There are dozens of interesting shops along the town's center boasting antiques, classic wooden toys, Amish furniture, and hand wrapped cigars. With something for everyone, it's the perfect stroll for families and individual visitors of all kinds. Creatives can visit the Chesterton Art Center for outstanding art exhibitions as well as workshops for artists of all ages. 

Most visitors flock to Chesterton as a base for the Indiana Dunes National Park, a low-effort 2.5-mile drive from town. The park encompasses an impressive 16,000 acres, offers 50 miles of trails across sandy dunes, and 15 miles of coastline views. Visitors enjoy the surplus of natural diversity one can enjoy in a single day, with one outdoor enthusiast saying, "In under a 30-min hike, you can go from 100% typical sandy beach to beautiful sandy dune overlook to 100% forest where you see no sand or beach or lake."

Across the lake from Chicago, the under-the-radar Michigan resort town of New Buffalo is one of the closest tourist destinations to Chicago at just over an hour's drive away. The town is home to 1,700 residents and is perfect for visitors without a car since Amtrak's Wolverine train brings tourists directly to it's prized beaches. New Buffalo Beach has nearly 2,000 positive reviews on Google that mention its idyllic setting with plenty of amenities, perfect for solo travelers seeking convenience. 

The town is a 20-minute drive north of the popular Warren Dunes State Park, a shoreside attraction with 1,500 acres of rugged dunes that rise as high as 260 feet into the sky. There are 2 miles of coastline and 6 miles of hiking trails with campsites available for overnight guests.

Downtown New Buffalo is filled with plenty of cultural gems like the 1,500 seat Silver Creek Event Center and Harbor Country Museum of History + Rail, offering engaging educational experiences for travelers of all ages. On warm days, visitors can boat on Oselka Marina or stroll through the Galien River County Park's marshes on a 300-foot canopy walkway. Colder months make way for invigorating winter activities like cross country skiing, fat tire bike riding, and sledding on the Warren Dunes.

This list of solo trips was vetted and compiled by consulting real visitor and resident reviews as well as comments on Reddit with an emphasis placed on commentary reflecting expertise in the region. TripAdvisor, Facebook, and Google reviews revealed a broad interest in each town and we focused on attractions that are near-universally praised by visitors. Destinations were selected based on proximity to Chicago, popularity, and attraction density, with an emphasis on safety and accessibility for solo travelers. The selections are intentionally spread in different directions to provide readers with a diverse set of options depending on one's geographical, ecological, and cultural preferences. 

Tourism boards and local government sites were also referenced and our team meticulously vetted each destination for up-to-date data on the parks, activities, festivals, and cultural institutes mentioned above. Finally, we compiled census and Google Maps data for an accurate representation of the local communities as well as the distance between popular attractions.

If you're curious to explore even more places to travel on your own, check out these 13 underrated Central America destinations perfect for solo tourists. Or, read all about America's safest state for solo travel.