Oswego real estate.

The community of Oswego is located in Kendall County, 50 miles southwest of the Chicago loop and 12 miles south of Aurora. Located on the Fox River, the residents of Oswego enjoy riverside views and boating recreation.

Oswego is located in a less densely populated area from the suburbs. Surrounding towns include Boulder Hill, Montgomery, Aurora, Yorkville, Sugar Grove, North Aurora, Plainfield, Plano.

Oswego is located halfway between interstate 55 and interstate 88 making it equally accessible by both highways and connected to other Chicago suburbs.

Populations (2000)
Total 13,326

White 93.5%
Black 1.8%
Asian 1.4%
Hispanic 5%
Other 3.3%

Source US Census

Oswego was used as a location in the TV show Prison Break episode “Manhunt” that marked the first episode of the second season of the hit TV show on the Fox Network.

Originally inhabited by local Potowatomi, Ottawa, and Chippewa tribes, Oswego was founded where the Fox River and the Waubonsie Creek join waters. In 1833, William Smith Wilson and his wife, Rebecca Wilson were the first American settlers in the Oswego area.

In only two years, more people came to the area looking to purchase property, and in 1842, the US Government sold the Oswego property at $1.25 per acre.

The town became a steadily populated village without much growth until the 1980’s when Naperville and Aurora began major development. Those developments began near Route 34 and eventually caught on in Owego.

Since the 1980’s, Oswego has continued to grow until the 2000 census recorded a population over 13,000 people. Another special census was conducted four years later finding a population total over 20,000 residents.

Today, Oswego is the biggest community in Kendall County, and the name Oswego is a Native American word meaning “mouth of the stream”.

Oswego homes have a median home value of 287,700, and 53.5% of homes were built after 2000 making many of the homes in Oswego newly built and more current architectural designs. Single family detached residences can range in price from nearly $2,000,000 to more affordable homes at $100,000.

More affordable homes include many cottage, ranch, and split level style homes with 3 or more bedrooms and spacious fenced in yards. More luxurious homes in Oswego are often neoecletic, colonial, and victorian style architecture. These homes are newer built and often contain hardwood floors, unique floorplans, large finished basements, three car garages, and many more comforts.

Oswego Condos are a very affordable option for residents looking to purchase property. Condos and townhomes in Oswego can be priced anywhere between $30,000 and $190,000. Many condos are small one bedrooms within complexes that include in-ground swimming pools, beautifully landscaped courtyards, and recreation rooms. Townhomes are newer constructed and include more spacious bedrooms and bathrooms, two car garages, and floral yards.

Median monthly rent for properties in Oswego is $1,400. Oswego apartments, condos, and townhomes for rent can cost anywhere from $700 and $1,500. Rental properties in Oswego offer comfortable and affordable homes.

Parking in Oswego is similar to most suburbs of Chicago- parking on village streets from 2am to 6am is not allowed. Exceptions to the overnight parking ban are made in some areas of Oswego in the hometown division and downtown areas. Temporary exemptions are also made for guests by calling the non-emergency police department at (630) 551-7300.

Oswego parking does not require parking permits or costly meters in all areas of the village, including downtown neighborhoods.

Like most suburbs, Oswego is a difficult area to live without a car. Downtown area of Oswego scores high on the Walk Score scale with a 77%, but the average score for the village is 49%.

The nearest commuter train station is the Aurora Metra station, about 6 miles from Oswego and a ten minute drive. The BNSF Railway offers fast and express trains to downtown Chicago and the

Pace Bus Route 907- Aurora - Oswego Metra Shuttle is a convenient and fast way to reach downtown Aurora and commuter trains to downtown Chicago.

Oswego schools and public education provide the community with safe and nurturing environments for fun and exciting education.

Waubonsee Community College provides affordable education for Oswego area students and the community. Whether looking for adult continuing education programs, certificate and career programs, as well as courses for transferring to four year universities. Academic departments include theatre, film studies, computers and technology, sciences, health care, and many more. 

Public Schools: Oswego Community Unit School District 308
Oswego High School (9-12) 4250 Route 71, Oswego, IL 60543 
Oswego East High School (9-12) 1525 Harvey Road, Oswego, IL 60543 
Churchill Elementary School (K-5) 520 Secretariat Lane, Oswego, IL 60543
Fox Chase Elementary School (K-5) 260 Fox Chase Drive North, Oswego, IL 60543
Hunt Club Elementary School (K-5) 4001 Hunt Club Drive, Oswego, IL 60543 
Old Post Elementary School (K-5) 100 Old Post Road, Oswego, IL 60543 
Prairie Point Elementary School (K-5) 3650 Grove Road, Oswego, IL 60543 
Southbury Elementary School (K-5) 820 Preston Lane, Oswego, IL 60543 
Plank Junior High School (6-8) 510 Secretariat Lane, Oswego, IL 60543 
Thompson Junior High School (6-8) 440 Boulder Hill Pass, Oswego, IL 60543 
Traughber Junior High School (6-8) 570 Colchester, Oswego, IL 60543 

Private Schools:
La Petite Academy (Early Childhood Education) 1260 Douglas Road, Oswego IL 60543 
Prairie Pals Christian Preschool 33 Stonehill Road, Oswego, IL 60543 

Oswego bars and restaurants offer fun, exciting, and sometimes relaxing atmospheres. Bars like Scoreboards Sports Pub and The Arena Bar & Grill offer a mixture of the Chicago Irish pub experience with a more modern sports bar including tv’s and great food.

For a fun and relaxing Irish pub night out, Riley Finn’s Sports Pub combines the setting of an Irish pub with the fun of watching sports. Riley’s is host to many charity events and other parties to celebrate St. Patrick’s Day, Mardi Gras, and other seasonal holidays. Riley’s is also a great spot for after work drinks and includes a full menu of foods and drink specials. 

Comedy Under the Tap hosts stand up comedy every week and a full bar. During all of the comedy shows, guests can order from the Tap House Grill menu and this is a great way to celebrate a birthday or any other special occasion. All guests must be over 21 and tickets are only $3. 

Mason Square Shopping Center provides Oswego residents with many retail shopping options and is located at Route 34 (Oswego Road) and Douglas Road. Shops and retail stores within and near the Shopping Center include Walmart, Target, Kohl’s, TJ Maxx, Shoe Carnival, Lowe’s Home Improvement, Ultra Saloon & Cosmetics, Lane Bryant, Dress Barn, and many more. 

The Chicago Premium Outlet Shopping Center is located in neighboring town of Aurora. Some of the outlet stores include designer and retail shops like Wilsons Leather, Calvin Klein, Hugo Boss, Coach, DKNY, and tons more. 

For the best cinema in Oswego, the Goodrich Kendall 10 Movie Theater is a large theater with multiple screens, party rooms, stadium seating, midnight releases, and all the new releases from Hollywood. 

Limelight Theatre Company is a youth-orientated theatre that the Oswegoland Park District sponsors. Past productions include the Odyssey, It’s a Wonderful Life, Harriet the Spy, West Side Story, Pride and Prejudice, A Midsummer Night’s Dream, Alice in Wonderland, and many other great theater productions. 

Dining in Oswego includes many restaurants featuring Mexican, Asian, pizza delivery or dine in, American, Barbeque, traditional diners, and fast food.

A favorite dining spot, the Tap House Grill Oswego offers a large menu with many different and unique creations while still serving affordable large portions of food. Regulars at the Tap House recommend trying the Kobe Burger, which uses American Wagyu Beef, a more tender meat worth the extra price. The menu also includes buffalo wings with ten different sauces, including the Leinenkugal BBQ, Firecracker Asian, and Screamer sauces. 

La Cabana D Oswego has the best authentic Mexican cuisine in the Oswego area. Their menu includes breakfast served until 11am, a small kids menu, Texas and Mexican style enchiladas, chicken flautas, daiquiris, margaritas, burritos, and fajitas. 

For the best authentic pizza in Oswego, Giordano’s offers some of Chicagoland’s best thin, stuffed, and deep dish pizzas. While the menu has plenty more to offer than pizza, stuffed pizza remains their most popular item on the menu along with delicious deserts like canoli and tiramisu. 

Smokey’s Wood Pit BBQ is a great place for some of the best Barbeque in the Oswego area. Using a wood pit to capture an authentic smoky flavor, a favorite item on the menu is the Pit Boss, a sandwich with beef brisket, pulled pork, onion rings, and coleslaw--all piled onto a bun together. Smokey’s also serves delicious ribs, BBQ chicken, homemade mashed potatoes, baked beans, coleslaw, and much more. 

Another must try restaurant is Southern Belle’s Pancake House. Anyone who values the occasional large breakfast will be an instant fan of Southern Belle’s menu. The menu includes six different varieties of eggs benedict; 17 different types of omelettes; a lunch menu; kids menu; 21 varieties of pancakes and waffles; very filling skillets; and specialities like the Banana Split Waffle or the Peach French Toast. 

Oswegoland Biking and Hiking Trails and Oswegoland Community Parks maintain natural and beautiful playgrounds throughout Oswego. With almost 50 neighborhood parks and bike trail, the Park District also upholds Oswego Community Gardens, Disc Golf at Eagle Ridge Park, Oswego Aquatic Park, Fox Bend Golf Course, and the Chesterfield Skate Park.

The main festival that attracts people to Oswego is the annual Prairie Fest. For over twenty years, the four day festival attracts approximately 44,000 people and features petting zoo, live music, children’s performances, pony rides, food vendors, and admission is free.

The Oswego High School sponsors the Festival of Brass every year and showcases a drum corps show. Tickets also benefit the Susan M. Kiley Memorial Scholarship Fund and Madison Scouts Drum & Bugle Corps.