Luxury Vacation Rentals Oswego
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Best-rated
Pulaski Point Properties
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
The 6-room Pulaski Point Properties Chicago apartment features convenient proximity to such city attractions as Irving Park Lutheran Church, situated nearly 5 minutes' walk away. This apartment provides guests with amenities such as ironing facilities, a dishwasher to enhance their comfort during their stay.
Pulaski Point Properties
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Pulaski Point Properties
The 6-room Pulaski Point Properties Chicago apartment features convenient proximity to such city attractions as Irving Park Lutheran Church, situated nearly 5 minutes' walk away. This apartment provides guests with amenities such as ironing facilities, a dishwasher to enhance their comfort during their stay.
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Guest favorite
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
- Cookware/ Kitchen utensils
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts Chicago apartment boasts a convenient setting and in just an 8-minute walk from Gill Park. The apartment is situated about 8 km from Ogilvie Transportation Center train station and in close proximity to Addison & Clark bus station.
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
- Cookware/ Kitchen utensils
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts Chicago apartment boasts a convenient setting and in just an 8-minute walk from Gill Park. The apartment is situated about 8 km from Ogilvie Transportation Center train station and in close proximity to Addison & Clark bus station.
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Popular choice
5430 Happy Home
- Shared kitchen
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
5430 Happy Home Chicago apartment is located just 1 km from New Philadelphia Missionary Baptist Church and offers Wi-Fi for either business or leisure. The homestay is approximately 5 minutes' walk from Garfield underground station and about a 10-minute drive from Ogilvie Transportation Center railway station.
To stay fit, yoga instruction are provided for guests.
5430 Happy Home
- Shared kitchen
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
5430 Happy Home
5430 Happy Home Chicago apartment is located just 1 km from New Philadelphia Missionary Baptist Church and offers Wi-Fi for either business or leisure. The homestay is approximately 5 minutes' walk from Garfield underground station and about a 10-minute drive from Ogilvie Transportation Center railway station.
To stay fit, yoga instruction are provided for guests.
Cheap Vacation Rentals in Oswego Illinois
2F Chicago'S Little Italy Near West Loop & Downtown
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
- Laundry
Featuring a prime location a 6-minute walk from Arrigo Park, the spacious 2F Chicago'S Little Italy Near West Loop & Downtown Apartment accommodates up to 8 guests. This apartment is situated 2.1 km from Ogilvie Transportation Center train station and just steps from Ashland & Polk bus station.
2F Chicago'S Little Italy Near West Loop & Downtown
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
- Laundry
2F Chicago'S Little Italy Near West Loop & Downtown
Featuring a prime location a 6-minute walk from Arrigo Park, the spacious 2F Chicago'S Little Italy Near West Loop & Downtown Apartment accommodates up to 8 guests. This apartment is situated 2.1 km from Ogilvie Transportation Center train station and just steps from Ashland & Polk bus station.
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Suitable for 6 guests, The Avondale Guesthouse Chicago villa offers a location within a 300-metre distance of Algonquin Park and features a terrace and a picnic area.
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
The Avondale Guesthouse
Suitable for 6 guests, The Avondale Guesthouse Chicago villa offers a location within a 300-metre distance of Algonquin Park and features a terrace and a picnic area.
1F Cozy Home In Little Italy Near Downtown West Loop United Center
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
The spacious 1F Cozy Home In Little Italy Near Downtown West Loop United Center Chicago apartment is located 4 km from the premier natural-history Field Museum and 10 minutes' drive from the neon-lit 1926 theater "Cadillac Palace Theatre". The maximum occupancy at this apartment is 6 guests.
1F Cozy Home In Little Italy Near Downtown West Loop United Center
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
1F Cozy Home In Little Italy Near Downtown West Loop United Center
The spacious 1F Cozy Home In Little Italy Near Downtown West Loop United Center Chicago apartment is located 4 km from the premier natural-history Field Museum and 10 minutes' drive from the neon-lit 1926 theater "Cadillac Palace Theatre". The maximum occupancy at this apartment is 6 guests.
Pet Friendly Vacation Rentals Oswego
Classic Chicago Upstairs Apt Private Balcony
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
The 93 m² Classic Chicago Upstairs Apt Private Balcony is just a 7-minute walk from Park View Lutheran Church. Wi-Fi and a car park are also available at this 2-bedroom apartment.
Classic Chicago Upstairs Apt Private Balcony
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Classic Chicago Upstairs Apt Private Balcony
The 93 m² Classic Chicago Upstairs Apt Private Balcony is just a 7-minute walk from Park View Lutheran Church. Wi-Fi and a car park are also available at this 2-bedroom apartment.
Lincoln Park 3 Bedroom Penthouse
- Cookware/ Kitchen utensils
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Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Offering a sun deck, a picnic area, and a golf course, the 2-room Lincoln Park 3 Bedroom Penthouse Chicago apartment is located in Lincoln Park with a unique mix of bars, restaurants, and entertainment spots, around a 5-minute walk from Rosa's Lounge. At the 3-bedroom apartment, Wi-Fi and parking are also provided.
Lincoln Park 3 Bedroom Penthouse
- Cookware/ Kitchen utensils
-
Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Lincoln Park 3 Bedroom Penthouse
Offering a sun deck, a picnic area, and a golf course, the 2-room Lincoln Park 3 Bedroom Penthouse Chicago apartment is located in Lincoln Park with a unique mix of bars, restaurants, and entertainment spots, around a 5-minute walk from Rosa's Lounge. At the 3-bedroom apartment, Wi-Fi and parking are also provided.
Chicago Charm
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Ironing facilities
The spacious 3-bedroom Chicago Charm Apartment features convenient proximity to such city attractions as Saint Henry Catholic Church, situated approximately a 5-minute walk away. At the apartment, Wi-Fi and a car park are also provided.
Chicago Charm
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Ironing facilities
Chicago Charm
The spacious 3-bedroom Chicago Charm Apartment features convenient proximity to such city attractions as Saint Henry Catholic Church, situated approximately a 5-minute walk away. At the apartment, Wi-Fi and a car park are also provided.
Oswego Vacation Rentals Oceanfront
Avenir West Loop Penthouses With Iconic City Views
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Car park
US$ 50 per day
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Terrace
The 6-room Avenir West Loop Penthouses With Iconic City Views Chicago apartment provides easy access to various city attractions, such as Chicago Dramatists Theatre, situated nearly a 5-minute walk away. The apartment offers private car parking for USD 50 per day on site.
After a day full of activities, relaxing by a swimming pool is a perfect option.
Avenir West Loop Penthouses With Iconic City Views
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Car park
US$ 50 per day
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
- Terrace
Avenir West Loop Penthouses With Iconic City Views
The 6-room Avenir West Loop Penthouses With Iconic City Views Chicago apartment provides easy access to various city attractions, such as Chicago Dramatists Theatre, situated nearly a 5-minute walk away. The apartment offers private car parking for USD 50 per day on site.
After a day full of activities, relaxing by a swimming pool is a perfect option.
Fulbrix Bright Designer Apartments With West Loop Views
- BBQ facilities
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Car park
US$ 50 per day
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Situated within 2 km of Skydeck Chicago, the 6-room Fulbrix Bright Designer Apartments With West Loop Views Chicago also boasts easy access to Ogilvie Transportation Center train station which is nearly a 20-minute walk away. Guests can take advantage of an outdoor swimming pool or a fitness room while staying just steps from Johnny's Ice House East Hockey Rink.
Take advantage of fitness classes at the apartment to elevate your leisure experience.
Fulbrix Bright Designer Apartments With West Loop Views
- BBQ facilities
-
Car park
US$ 50 per day
- 24-hour reception
- Air conditioning
- Fitness centre
- Outdoor swimming pool
Fulbrix Bright Designer Apartments With West Loop Views
Situated within 2 km of Skydeck Chicago, the 6-room Fulbrix Bright Designer Apartments With West Loop Views Chicago also boasts easy access to Ogilvie Transportation Center train station which is nearly a 20-minute walk away. Guests can take advantage of an outdoor swimming pool or a fitness room while staying just steps from Johnny's Ice House East Hockey Rink.
Take advantage of fitness classes at the apartment to elevate your leisure experience.
Chicago Condo W/ Balcony: Walk To Cta Stations!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Accommodating up to 3 guests, the 2-bedroom Chicago Condo W/ Balcony: Walk To Cta Stations! villa offers a prime location 2.7 km from such educational tourist attractions as the public research University of Illinois at Chicago. Located around 15 minutes by car from the 35-acre beautifully landscaped Lincoln Park Zoo, this accommodation provides Wi-Fi and a car park.
Chicago Condo W/ Balcony: Walk To Cta Stations!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Chicago Condo W/ Balcony: Walk To Cta Stations!
Accommodating up to 3 guests, the 2-bedroom Chicago Condo W/ Balcony: Walk To Cta Stations! villa offers a prime location 2.7 km from such educational tourist attractions as the public research University of Illinois at Chicago. Located around 15 minutes by car from the 35-acre beautifully landscaped Lincoln Park Zoo, this accommodation provides Wi-Fi and a car park.
Oswego Vacation Rentals with Private Pool
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Beach access
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
Located nearly 25 minutes' walk from Devon Avenue, the 4-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago provides access to various tourist attractions in the vicinity. This Chicago villa hosts up to 9 guests and includes a games room for their entertainment.
A variety of outdoor activities such as badminton and darts can be enjoyed in the surroundings.
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Terrace
Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find
Located nearly 25 minutes' walk from Devon Avenue, the 4-bedroom Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find Villa Chicago provides access to various tourist attractions in the vicinity. This Chicago villa hosts up to 9 guests and includes a games room for their entertainment.
A variety of outdoor activities such as badminton and darts can be enjoyed in the surroundings.
Perfect Place To Enjoy The City Or Just Relax
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated nearly a 5-minute stroll from Kedzie underground station, the spacious 93 m² Perfect Place To Enjoy The City Or Just Relax Chicago apartment offers Wi-Fi for business or leisure needs. Enjoying a convenient setting, the 1-bedroom apartment lies 3.5 km from the 184-acre Garfield Park Conservatory and within a 7-km distance of Skydeck Chicago.
Perfect Place To Enjoy The City Or Just Relax
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Perfect Place To Enjoy The City Or Just Relax
Situated nearly a 5-minute stroll from Kedzie underground station, the spacious 93 m² Perfect Place To Enjoy The City Or Just Relax Chicago apartment offers Wi-Fi for business or leisure needs. Enjoying a convenient setting, the 1-bedroom apartment lies 3.5 km from the 184-acre Garfield Park Conservatory and within a 7-km distance of Skydeck Chicago.
Starved Rock & Ottawa Retreat Amazing Getaway Home
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
With the capacity to host 6 guests, the 2-bedroom Starved Rock & Ottawa Retreat Amazing Getaway Home is located approximately a 10-minute ride from such significant cultural landmarks as Ottawa Historical and Scouting Heritage Museum.
Starved Rock & Ottawa Retreat Amazing Getaway Home
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Terrace
Starved Rock & Ottawa Retreat Amazing Getaway Home
With the capacity to host 6 guests, the 2-bedroom Starved Rock & Ottawa Retreat Amazing Getaway Home is located approximately a 10-minute ride from such significant cultural landmarks as Ottawa Historical and Scouting Heritage Museum.
Bucktown Private Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Patio
The spacious 2-bedroom Bucktown Private Condo Chicago lies 4.8 km from the skyscraper 360 Chicago Observation Deck and nearly 10 minutes' walk from Damen tube station. This 106 m² apartment is situated within a 6-km distance of Ogilvie Transportation Center train station and right around the corner from Armitage & Damen bus station.
Bucktown Private Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Patio
Bucktown Private Condo
The spacious 2-bedroom Bucktown Private Condo Chicago lies 4.8 km from the skyscraper 360 Chicago Observation Deck and nearly 10 minutes' walk from Damen tube station. This 106 m² apartment is situated within a 6-km distance of Ogilvie Transportation Center train station and right around the corner from Armitage & Damen bus station.
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Top location
This Is Not An Hotel But A Quiet Place
- Cookware/ Kitchen utensils
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Mini-bar
To enjoy your vacation in Bolingbrook, stay at the 2-room This Is Not An Hotel But A Quiet Place Bolingbrook, which is approximately a 15-minute drive from Whalon Lake Dog Park and within a 3-km distance of Pelican Harbor Indoor Water Park.
The apartment also offers a kitchenette on its balcony.
This Is Not An Hotel But A Quiet Place
- Cookware/ Kitchen utensils
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Mini-bar
This Is Not An Hotel But A Quiet Place
To enjoy your vacation in Bolingbrook, stay at the 2-room This Is Not An Hotel But A Quiet Place Bolingbrook, which is approximately a 15-minute drive from Whalon Lake Dog Park and within a 3-km distance of Pelican Harbor Indoor Water Park.
The apartment also offers a kitchenette on its balcony.
Sinclair Suites - Boutique Hotel West Dundee
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Tea and coffee facilities
The 1-bedroom Sinclair Suites - Boutique Hotel West Dundee overlooks the city and is situated around a 5-minute stroll from Saint James Episcopal Church. Enjoying a prime setting, the apartment lies 2.8 km from Milk Pail Village Shopping Center and 2.6 km from the American Santa's Village Azoosment Park.
Sinclair Suites - Boutique Hotel West Dundee
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Tea and coffee facilities
Sinclair Suites - Boutique Hotel West Dundee
The 1-bedroom Sinclair Suites - Boutique Hotel West Dundee overlooks the city and is situated around a 5-minute stroll from Saint James Episcopal Church. Enjoying a prime setting, the apartment lies 2.8 km from Milk Pail Village Shopping Center and 2.6 km from the American Santa's Village Azoosment Park.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Oswego, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Pulaski Point Properties |
9.7 / 10 (177 Reviews) |
From 53$ | |
| Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts |
8.9 / 10 (364 Reviews) |
From 82$ | |
| 5430 Happy Home |
8.2 / 10 (562 Reviews) |
From 29$ | |
| 2F Chicago'S Little Italy Near West Loop & Downtown |
9.3 / 10 (225 Reviews) |
From 215$ | |
| The Avondale Guesthouse |
9.6 / 10 (122 Reviews) |
From 313$ |
Frequently Asked Questions
Which Oswego vacation rentals are best for families with kids?
Northside Famlynest Lincoln Sq and 5430 Happy Home are great options for families. They offer spacious living areas and easy access to parks.
Book a place with a kitchen so you can prepare meals for picky eaters without worrying about dining out every night.
Which vacation rentals in Oswego are near downtown attractions?
Double Play Wrigley and Avenir West Loop Penthouses are close to downtown attractions. You can walk to restaurants and entertainment quickly.
Choose a rental that provides easy walking access to stores like Mariano's and landmarks such as the Chicago Riverwalk.
Which Oswego vacation rentals have two bedrooms?
1F Cozy Home In Little Italy and Lincoln Park 3 Bedroom Penthouse offer two-bedroom accommodations. Ideal for families or groups traveling together.
Secure the two-bedroom rentals early, especially during summer months, as they tend to book quickly.
Are there pet-friendly vacation rentals in Oswego?
Look for options like Chicago Charm and 5430 Happy Home. They welcome pets for an additional fee.
Confirm pet policies before booking to ensure your furry friend meets size or breed restrictions.
Which Oswego vacation rentals are best for extended stays?
Chicago Condo W/ Balcony and Classic Chicago Upstairs Apt are suitable for extended stays. They provide essential amenities for comfort.
Inquire about discounts for longer bookings to save money on your stay.
Which vacation rentals near landmarks should I choose?
Consider rentals such as Chicago's Little Italy Near West Loop and Fulbrix Bright Designer Apartments. You'll be close to popular sites like Wrigley Field.
Set up a walking tour to explore nearby landmarks without the hassle of driving or finding parking.
Where can I find budget-friendly vacation rentals in Oswego?
Check out 5430 Happy Home and Pulaski Point Properties for economical stays. They offer essential services without high costs.
Book your rental during off-peak seasons like late fall for better deals.
What unique cultural experiences can I enjoy in Oswego?
Visit local events such as the Oswego East Festival or the annual Art & Artisan Fair. These showcase local talent and community spirit.
Plan your visit around local events for a chance to experience Oswego's art and culture more intimately.
How can I navigate Oswego and reach popular attractions?
Use a car or rideshare services for rapid transport. Public buses also connect key areas, making it easy to explore.
Check bus schedules in advance to plan your itinerary efficiently, especially for outings to the beach.
How long should I plan to stay in Oswego?
A 3-4 day stay is ideal to fully enjoy attractions and activities. This allows you to explore both Oswego and nearby cities.
Prioritize weekends for local festivals and markets, offering a unique taste of the area's culture.