Title: Oswego Vacation Packages 2026 from $791 | 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 $791 ## 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 $791 per person Jun 21 - Jun 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,688 reviews) This is a gem. The staff were caring, welcoming and accommodating. The property is at a perfect location with many eating and shopping options. The bus stop was feet away and access to the metro a couple blocks away. Breakfast was great; it had a great selection of food. Negative: I tried modifying my reservation a couple weeks prior my stay, after noticing a mistake made at the time of booking. However, I was unable to reach anyone at tye hotel, over the phone. Later, I was told by the site I booked my stay, that the hotel denied the request. I will definitely go back to this hotel! Reviewed on Apr 5, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago Save 100% on your flight $873 per person Jun 21 - Jun 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (2,096 reviews) Enjoyed our stay, will definitely be back Reviewed on Apr 5, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight $913 per person Jun 11 - Jun 16 found 13 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (453 reviews) Room was super clean. The view all the way down to the lake from balcony was nice. Reviewed on Apr 2, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight $1,076 per person Jun 21 - Jun 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,647 reviews) Clean room! The view was amazing Reviewed on Apr 6, 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago Save 100% on your flight $801 per person Jun 21 - Jun 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (3,357 reviews) Great location. Staff was welcoming. Room could have been cleaned better hair on sink, toilet and bed but overall not the worse I’ve seen. Would stay again for sure. Reviewed on Apr 5, 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/2026-05-06/2026-05-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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/1000000/430000/424400/424318/0af52ead_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Oswego Hotel 2055 Wiesbrook Dr Oswego IL Fully refundableReserve now, pay when you stay $77 nightly $84 total Apr 12 - Apr 13 Total with taxes and fees 8.8/10 Excellent! (866 reviews) The breakfast was awesome daily and the air worked GREAT!! Reviewed on Apr 3, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%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 $90 nightly $100 total Apr 7 - Apr 8 Total with taxes and fees 7.2/10 Good! (1,497 reviews) . Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F7%2F2026&endDate=4%2F8%2F2026&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true®ionId=142441) ![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/2539e456_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn PLUS+ Chicago - Willowbrook 7535 Kingery Highway Willowbrook IL Fully refundableReserve now, pay when you stay $57 nightly $64 total Apr 12 - Apr 13 Total with taxes and fees 6.4/10 (1,085 reviews) Yes Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true®ionId=142441) [See all 612 properties in Oswego](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F7%2F2026&endDate=4%2F8%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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