Title: Oswego Vacation Packages 2026 from $328 | Expedia.com [Oswego Travel Guide](https://expedia.com/Oswego.dx142441)[Hotels in Oswego](https://expedia.com/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Vacation Rentals in Oswego](https://expedia.com/Oswego-Vacation-Rentals.d142441.Travel-Guide-VacationRentals)[Flights to Oswego](https://expedia.com/Cheap-Flights-To-Oswego.d142441.Travel-Guide-Flights)[Car Rentals in Oswego](https://expedia.com/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide) ![](https://images.trvl-media.com/place/142441/0f2c17dd-13ca-41e6-95b9-5e5017ce4f3e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oswego Vacations from $328 ## Book a Hotel + Flight or Car together to unlock savings ## 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.com/Aurora-University-Aurora.d6129538.Vacation-Attraction), [Hollywood Casino Aurora](https://www.expedia.com/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) and [Raging Waves Waterpark](https://www.expedia.com/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! ## The Latest Oswego vacation packages Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago Save 100% on your flight $328 per person May 11 - May 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) amazing staff and beautiful rooms and lobbies. i just loved the free breakfast Reviewed on Mar 1, 2026 ![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 Save 100% on your flight $444 per person May 11 - May 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on Jan 31, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight $481 per person May 11 - May 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Had a great stay!! Kelly at the front desk was so sweet Reviewed on Feb 22, 2026 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago Save 100% on your flight $334 per person May 11 - May 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) The staff was wonderful and the rooms were clean. Reviewed on Mar 1, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago Save 100% on your flight $349 per person May 11 - May 14 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,008 reviews) amazing stay 10/10 would recommend Reviewed on Feb 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Oswego [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-02/2026-04-09/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_142441) ### Discover the most popular places to visit in Oswego ![railway trestle bridge over wallkill river valley](https://images.trvl-media.com/place/553248621532658491/83afbe63-200d-4261-bc9e-ef33fb6ab5d6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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.com/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) #### 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.com/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) ## Oswego Hotel Deals ![Best Western Oswego Hotel](https://images.trvl-media.com/lodging/1000000/430000/424400/424318/7b695b40_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Oswego Hotel 2055 Wiesbrook Dr Oswego IL Fully refundableReserve now, pay when you stay $74 nightly $80 total Mar 8 - Mar 9 Total with taxes and fees 8.8/10 Excellent! (850 reviews) Rooms were clean Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true®ionId=142441) ![Chicago Club Inn & Suites](https://images.trvl-media.com/lodging/1000000/10000/8500/8492/02be5769_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Club Inn & Suites 630 Pasquinelli Dr Westmont IL Fully refundableReserve now, pay when you stay $74 nightly $82 total Mar 22 - Mar 23 Total with taxes and fees 7.2/10 Good! (1,458 reviews) Beautiful room !! Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&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 $114 nightly $119 total Mar 3 - Mar 4 Total with taxes and fees 8.6/10 Excellent! (1,426 reviews) The room had a weird smell… Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=1791716&PinnedHotelID=1791716&HadPinnedHotel=true®ionId=142441) [See all 616 properties in Oswego](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F3%2F2026&endDate=3%2F4%2F2026®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. ## Find the Best Oswego Vacation Packages ## Oswego Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 34,000 | | Max Temp Winter | 30ºF | | Max Temp Summer | 80ºF | | Top Sights | [Fox Valley Winery](https://www.expedia.com/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction), [Farnsworth House](https://www.expedia.com/Farnsworth-House-Plano.d553248621532658479.Vacation-Attraction) and [Hudson Crossing Park](https://www.expedia.com/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) | ## More vacations you might like ![](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.com/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 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does an Oswego vacation package cost? ### What are the cheapest months to go to Oswego? ### How many days is enough for Oswego? ### How to find the best Oswego package deals? ### Is it cheaper to book an Oswego vacation as a package? ### When to book a vacation package to Oswego? ### Does Expedia offer Book Now, Pay Later Oswego vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Hudson Crossing Park ](https://www.expedia.com/Hudson-Crossing-Park-Hotels.0-l553248621532658491-0.Travel-Guide-Filter-Hotels) - [Hotels near Fox Valley Winery ](https://www.expedia.com/Fox-Valley-Winery-Hotels.0-l553248621532658490-0.Travel-Guide-Filter-Hotels) - [Montgomery Hotels ](https://www.expedia.com/Montgomery-Hotels.d6156952.Travel-Guide-Hotels) - [Cabin Rentals in Montgomery ](https://www.expedia.com/Montgomery-Cabins.d6156952-aaCabins.Travel-Guide-Accommodation) - [5 Star Hotels in Montgomery ](https://www.expedia.com/5Star-Montgomery-Hotels.s50-0-d6156952.Travel-Guide-Filter-Hotels) - 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Savings not available on all packages.