This Underrated Chicago Suburb Is A Riverfront Hub For Tourism With A Lively Downtown, Trails, And Seasonal Fun

It's easy to be drawn to the electrifying buzz of the Windy City — from under-the-radar Chicago gems that deserve to be on every itinerary to its hippest neighborhoods with artsy, trendy vibes and cobbled streets. As much as there's so much to see and do there, you shouldn't overlook its underrated suburbs. Oswego is a diamond in the rough, not too far from the bustling city noise. Here, you'll be walking the downtown streets in search of good eats and retail therapy; meanwhile, its parks make for wonderful picnic spots and leisurely strolls along the riverfront. Visit at the right time, and you just might catch one of Oswego's seasonal events that make this place all the more special.

Originally home to the Potawatomi, Ottawa, and Chippewa tribes, Oswego's location on the river was the primary reason for its establishment. The first settlers came to the area in the 1830s, which started a movement for more families to join. The village went by Hudson and Lodi before the community decided on the name "Oswego" in 1837. The Chicago suburb reaffirmed its strategic importance in regional transit — three state highways began there, and U.S. Route 34 connected it to broader networks. That, along with the residential constructions, further contributed to the village's growth. Nowadays, with the abundance of activities and year-round festivities, this is a great tourist destination to explore the road less traveled.

It only takes about an hour by car to get to Oswego from Chicago, while Rockford is an hour and 20 minutes away. Joliet is also close — just a short 40 minutes from the suburb. Regarding where to stay, your options include AmericInn by Wyndham Oswego and Best Western Oswego Hotel. You'll find relatively affordable accommodations on Airbnb as well, depending on how much you're willing to spend.

Trade the city lights for the beautiful simplicity of downtown Oswego, and you won't regret it. This part of the village is full of coffee shops, dessert spots, cute stores, and delicious eateries. 113 Main is the go-to restaurant for garlic mussels, smoked brisket poutine, prime rib Philly sandwiches, and hearty cheeseburger tacos. Order their grilled sirloin risotto, shrimp and scallops, and chicken pot pie for your main dish. Another must-visit for breakfast is Oswego Family Restaurant. Their menu features a variety of omelets, pancakes, waffles, French toast, and breakfast sandwiches. Mexican food lovers, on the other hand, can head to Mi Kozina.

But first, you need a good ol' cup of joe from Oak + Bean. Whether you get a classic cappuccino or opt for a specialty coffee like mango matcha, ube latte, or banana bread cold brew, the caffeine boost is exactly what you need. From there, make your way to My Sister's Lil Donut Shoppe to satisfy your sweet tooth the right way. Try their fruity pebble donuts, caramel espresso rings, and doughy goodness with apple filling. For nighttime unwinding, Fox Valley Winery is the place to be. From casual wine nights to live music events, this is where most people spend their weekends in Oswego.

Shopping is a part of the downtown experience. Bella-gia Boutique is the best store to find new pieces for your closet. The selection includes brands like Aloha Bags, Dear John, Steve Madden, Sorel, and more. Mod Stitch Company is another cool downtown shop, boasting snug sweaters, comfy cardigans, daring denim, and stylish sets. If you're looking to buy handmade self-care products, swing by Ginger Thomas Soap Company for souvenirs like honeysuckle bath bombs, coconut milk body butter, and raspberry vanilla soap.

There are plenty of outdoor spaces dotting Oswego, and you can access the Fox River Trail to traverse the 12.2-mile-long track. The point-to-point trail is multi-use — you'll see hikers and bikers sharing the path, as well as cross-country skiers during the colder months. From old railroad tracks to bridges, you'll pass by several quaint towns on your journey. The Waubonsie Trail is a much shorter hike. The 2.5-mile route takes you from Eagle Ridge to Jaycee Park, with stops at Northampton Greenway, Chesterfield Park, and Matena Greenway.

For a calmer walk, consider going to Marina Woods Park, which also connects to the Fox River Trail. Meander along the water, observe people catching and releasing fish, or have an afternoon picnic under the shade. The 6.2-acre Hudson Crossing Park is a local favorite, where people come to roam the pathways, admire the sculpture garden, and canoe along the river. If you want to practice playing basketball or baseball, you'll enjoy Washington Park. This 9-acre area is ideal for those who like to wear trainers over hiking boots. Prefer the latter? Violet Patch Park is the perfect starting point for tackling both the Fox River and Waubonsie Trails. Wormley Heritage Park provides several courts and fields for you to play baseball, sand volleyball, roller hockey, and basketball.

As for community events, the annual Wine on the Fox is a celebration of wine, craft beer, and live entertainment on the riverfront. Oswego Beats and Eats is also a beloved bash, with outdoor rock concerts, lots of beer, and good food. Not to mention, wintertime is when the Christmas Walk ushers in the holiday season. Not too far from Oswego is Glen Ellyn, a storybook train-stop town with annual festivals, boutique shops, and top dining.