Title: Oswego Vacation Packages & Trips 2025/2026 from CA $493 | Expedia.ca [Hotels in Oswego](https://expedia.ca/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Vacation Rentals in Oswego](https://expedia.ca/Oswego-Vacation-Rentals.d142441.Travel-Guide-VacationRentals)[Flights to Oswego](https://expedia.ca/Cheap-Flights-To-Oswego.d142441.Travel-Guide-Flights)[Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide) ![](https://images.trvl-media.com/place/142441/b120e67f-cbdd-4376-a78c-263755ddd72d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oswego Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Anthony Martinez - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### Your Oswego Vacation Our vacation packages to Oswego offer countless opportunities to enjoy new sights, sounds and smells. And with all of the travel arrangements taken care of, you can breathe easy and enjoy your city escape in the way that you deserve. [Aurora University](https://www.expedia.ca/Aurora-University-Aurora.d6129538.Vacation-Attraction), [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) and [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) are just a few of the many attractions worth checking out during your trip to Oswego. Expedia is here to help you escape your routine. Tailor your vacation to Oswego to suit your travel style, whatever that may be! ## Top Oswego Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $493 per person Nov 24 - Nov 26 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvvPkafPx3PErDTDcz2OojvIcWHMjThkCqAigW8thoqJ5) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $706 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRu_CsNSoP-S_j5GrzVxLQqw3Dufdwb1IhwRe3sQl1_se) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,300 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRpJrZmpT9nkK4P1Esm1i5PJ2CeJq1VOvW6TfgRe7iXQT) ![Hampton Inn & Suites Chicago Medical District UIC](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Chicago Medical District UIC Near West Side CA $721 per person Dec 31 - Jan 6 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.6/10 Exceptional! (246 reviews) Clean room comfy beds and pillows Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-06/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102236658&paandie=true&dealMarker=b2OfsQi-A1ChFWQvPjdl9x6rVSNMXmdu88OWPMpjTSXAFwhu4IS9WmUKjvPublrK) ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $645 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,004 reviews) Clean room, friendly staff, great location and within walking distance from all shops! Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRu_CsNSoP-S_j5GrzVxLQqxKX3h6IajOy2ntY5lQEslm) ## Ready to book your vacation to Oswego? Choose your dates ## Oswego Hotel Deals ![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/81e2d310_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay Plus Hotel by Best Western Chicago Lombard 222 E 22nd Street, Lombard, IL Fully refundableReserve now, pay when you stay CA $105 CA $117 total Oct 29 - Oct 30 includes taxes & fees 8.8/10 Excellent! (2,284 reviews) "Sheets were not changed daily nor bed made up." Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=10641&PinnedHotelID=10641&HadPinnedHotel=true®ionId=142441) ![Chicago Club Inn & Suites](https://images.trvl-media.com/lodging/1000000/10000/8500/8492/7c5f8bdd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Club Inn & Suites 630 Pasquinelli Dr, Westmont, IL Fully refundableReserve now, pay when you stay CA $101 CA $112 total Oct 13 - Oct 14 includes taxes & fees 7/10 Good! (1,267 reviews) "Very good location, convenient to Oakbrook shopping center and West Suburbs. Great value" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true®ionId=142441) ![The Champagne Lodge & Luxury Suites](https://images.trvl-media.com/lodging/2000000/1800000/1791800/1791716/dc9a0641_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Champagne Lodge & Luxury Suites 16 W 621 S. Frontage Rd, Willowbrook, IL CA $125 CA $167 total Oct 13 - Oct 14 includes taxes & fees 8.4/10 Very Good! (1,276 reviews) "Very nice room. In lowkey quiet area. Overly enjoyed my stay." Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=1791716&PinnedHotelID=1791716&HadPinnedHotel=true®ionId=142441) [See all 605 properties in Oswego](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®ionId=142441) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Oswego #### Fox Valley Winery You can enjoy a tasting or tour at Fox Valley Winery during your travels to Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries. [](https://expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) #### Hudson Crossing Park Explore the great outdoors at Hudson Crossing Park, a lovely green space in Oswego. Stroll along this family-friendly area's riverfront, or simply enjoy its breweries. [](https://expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental ### Lodging - [Farmstay in Aurora](https://www.expedia.ca/Aurora-Agritourism.d6186-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Aurora](https://www.expedia.ca/Aurora-Apart-Hotels.d6186-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Aurora](https://www.expedia.ca/Aurora-Bed-And-Breakfast.d6186-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Aurora](https://www.expedia.ca/Aurora-Castles.d6186-aaCastles.Travel-Guide-Accommodation) - [Chalets in Aurora](https://www.expedia.ca/Aurora-Chalets.d6186-aaChalets.Travel-Guide-Accommodation) - [Cruise Ships in Aurora](https://www.expedia.ca/Aurora-Cruise-Ships.d6186-aaCruiseShips.Travel-Guide-Accommodation) - [Guest Houses in Aurora](https://www.expedia.ca/Aurora-Guest-Houses.d6186-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Aurora](https://www.expedia.ca/Aurora-Holiday-Parks.d6186-aaHolidayParks.Travel-Guide-Accommodation) - 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[Inns in Aurora](https://www.expedia.ca/Aurora-Inns.d6186-aaInns.Travel-Guide-Accommodation) - [Lodges in Aurora](https://www.expedia.ca/Aurora-Lodges.d6186-aaLodges.Travel-Guide-Accommodation) - [Motels in Aurora](https://www.expedia.ca/Aurora-Motels.d6186-aaMotels.Travel-Guide-Accommodation) - [Pensions in Aurora](https://www.expedia.ca/Aurora-Pensions.d6186-aaPensions.Travel-Guide-Accommodation) - [Pousadas in Aurora](https://www.expedia.ca/Aurora-Pousadas.d6186-aaPousadas.Travel-Guide-Accommodation) - [Ranches in Aurora](https://www.expedia.ca/Aurora-Ranches.d6186-aaRanches.Travel-Guide-Accommodation) - [Resorts in Aurora](https://www.expedia.ca/Aurora-Resort-Hotels.d6186-aaResortHotels.Travel-Guide-Accommodation) - [Riads in Aurora](https://www.expedia.ca/Aurora-Riads.d6186-aaRiads.Travel-Guide-Accommodation) - [Townhomes in Aurora](https://www.expedia.ca/Aurora-Townhomes.d6186-aaTownhomes.Travel-Guide-Accommodation) - [Treehouses in Aurora](https://www.expedia.ca/Aurora-Treehouses.d6186-aaTreehouses.Travel-Guide-Accommodation) - [Hotels near Aurora University](https://www.expedia.ca/Aurora-University-Hotels.0-l6129538-0.Travel-Guide-Filter-Hotels) - [Cottages in Boulder Hill](https://www.expedia.ca/Boulder-Hill-Cottages.d553248635975872155-aaCottages.Travel-Guide-Accommodation) - [Vacation Homes in Boulder Hill](https://www.expedia.ca/Boulder-Hill-Private-Vacation-Homes.d553248635975872155-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Hotels.0-l6260166-0.Travel-Guide-Filter-Hotels) - [Hotels near Hollywood Casino](https://www.expedia.ca/Hollywood-Casino-Hotels.0-l6065135-0.Travel-Guide-Filter-Hotels) - [Farmstay in Montgomery](https://www.expedia.ca/Montgomery-Agritourism.d6156952-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Montgomery](https://www.expedia.ca/Montgomery-Bed-And-Breakfast.d6156952-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Hotels near Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Hotels.0-l553248621532658485-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Yorkville](https://www.expedia.ca/Yorkville-Hotels-Luxury-Hotel.0-0-d602761-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Yorkville Hotels](https://www.expedia.ca/Yorkville-Hotels.d602761.Travel-Guide-Hotels) ### Flights - [Flights to Aurora](https://www.expedia.ca/Cheap-Flights-To-Aurora.d6186.Travel-Guide-Flights) - [Flights to Yorkville](https://www.expedia.ca/Cheap-Flights-To-Yorkville.d602761.Travel-Guide-Flights) - [Flights from Yorkville](https://www.expedia.ca/lp/flights/602761/flights-from-yorkville) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [Arcada Theater](https://www.expedia.ca/Arcada-Theater-St-Charles.d6129548.Vacation-Attraction) - [Broadview Vacations](https://www.expedia.ca/Broadview.d7064.Destination-Travel-Guides) - [Cabela's](https://www.expedia.ca/Cabelas-Chicago.d553248635998039755.Vacation-Attraction) - [Cedardell Golf Club](https://www.expedia.ca/Cedardell-Golf-Club-Plano.d553248621532658481.Vacation-Attraction) - [Centennial Beach](https://www.expedia.ca/Centennial-Beach-Chicago.d553248621532658519.Vacation-Attraction) - [Elgin Vacations](https://www.expedia.ca/Elgin.d7817.Destination-Travel-Guides) - [Elmhurst Vacations](https://www.expedia.ca/Elmhurst.d7836.Destination-Travel-Guides) - [Farnsworth House](https://www.expedia.ca/Farnsworth-House-Plano.d553248621532658479.Vacation-Attraction) - [Fox Valley Winery](https://www.expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) - [Geneva Commons](https://www.expedia.ca/Geneva-Commons-Geneva.d6260155.Vacation-Attraction) - [Hillside Vacations](https://www.expedia.ca/Hillside.d8353.Destination-Travel-Guides) - [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) - [Hollywood Casino](https://www.expedia.ca/Hollywood-Casino-Aurora.d6065135.Vacation-Attraction) - [Hudson Crossing Park](https://www.expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) - [Joliet Vacations](https://www.expedia.ca/Joliet.d8116.Destination-Travel-Guides) - [Lewis University](https://www.expedia.ca/Lewis-University-Romeoville.d6146844.Vacation-Attraction) - [Morton Arboretum](https://www.expedia.ca/Morton-Arboretum-Chicago.d6238155.Vacation-Attraction) - [Now Arena](https://www.expedia.ca/NOW-Arena-Chicago.d6192396.Vacation-Attraction) - [Otter Cove Aquatic Park](https://www.expedia.ca/Otter-Cove-Aquatic-Park-St-Charles.d553248621532658533.Vacation-Attraction) - [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) - [Santa's Village](https://www.expedia.ca/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) - [Schaumburg Vacations](https://www.expedia.ca/Schaumburg.d8107.Destination-Travel-Guides) - [Seneca Vacations](https://www.expedia.ca/Seneca.d3000435306.Destination-Travel-Guides) - [Serena Vacations](https://www.expedia.ca/Serena.d3000346572.Destination-Travel-Guides) - [Sheridan Vacations](https://www.expedia.ca/Sheridan.d6085097.Destination-Travel-Guides) - [Silver Springs State Park](https://www.expedia.ca/Silver-Springs-State-Park-Illinois.d553248621532658480.Vacation-Attraction) - [Splash Country Waterpark](https://www.expedia.ca/Splash-Country-Waterpark-Aurora.d553248621532658496.Vacation-Attraction) - [Wheaton Vacations](https://www.expedia.ca/Wheaton.d7599.Destination-Travel-Guides) - [Yorktown Shopping Center](https://www.expedia.ca/Yorktown-Shopping-Center-Chicago.d6227539.Vacation-Attraction) - [Yorkville Vacations](https://www.expedia.ca/Yorkville.d602761.Destination-Travel-Guides) ### Cars - [Car rentals in Budget 1426 State Route 66 Ste 101](https://www.expedia.ca/Budget-at-1426-State-Route-66-Ste-101-Flagstaff-Arizona-USA.v6186.Car-Rental-Guide-Location) - [Car rental Aurora](https://www.expedia.ca/Car-Rentals-In-Aurora.d6186.Car-Rental-Guide) - [Car rental Yorkville](https://www.expedia.ca/Car-Rentals-In-Yorkville.d602761.Car-Rental-Guide) - [Hertz Rental Cars in Aurora](https://www.expedia.ca/Hertz-Car-Rentals-In-Aurora.d6186-c40.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Aurora Vacation Rentals](https://www.expedia.ca/Aurora-Vacation-Rentals.d6186.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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