Title: Oswego Vacation Packages 2026 from $315 | 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 $315 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.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 $315 per person Apr 17 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Housekeeper left hair shedding in room but overall amazing hotel and great staff Reviewed on Feb 12, 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 Apr 16 - Apr 19 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 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago Save 100% on your flight $637 per person Apr 22 - Apr 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,266 reviews) Perfect location and wonderful staff Reviewed on Feb 8, 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago $476 per person May 1 - May 4 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Amazing hotel. Always stay here when I make a trip to Chicago. Reviewed on Feb 10, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel $538 per person May 4 - May 9 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 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/2026-03-13/2026-03-20/?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 Feb 15 - Feb 16 Total with taxes and fees 8.6/10 Excellent! (834 reviews) All was good this time i will be staying rhere again Reviewed on Feb 6, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true®ionId=142441) ![SureStay Plus Hotel by Best Western Chicago Lombard](https://images.trvl-media.com/lodging/1000000/20000/10700/10641/w3838h2556x2y3-00664b38_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 $72 nightly $80 total Feb 15 - Feb 16 Total with taxes and fees 9/10 Wonderful! (2,551 reviews) My favorite spot to stay for the Glazier Clinic football conference in Oak Brook. I usually stay here twice a year love the location and the amenities of the hotel. Their stay is always courteous and helpful. Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=10641&PinnedHotelID=10641&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 $137 nightly $144 total Feb 23 - Feb 24 Total with taxes and fees 8.4/10 Very Good! (1,397 reviews) The staff is so nice Reviewed on Feb 10, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%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=2%2F14%2F2026&endDate=2%2F15%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/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](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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