Title: Oswego Vacation Packages 2026 from $309 | 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 $309 ## 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 $309 per person May 8 - May 10 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) It was a wonderful visit with not one complaint about the amenities, cleanliness or staff! Reviewed on Mar 19, 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 $709 per person May 21 - May 25 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) There was no kitchen. Reviewed on Mar 18, 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 $812 per person May 21 - May 25 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,646 reviews) Nice room, fun rooftop bar, late to check in, room wasn’t ready but it was St Patty’s day so lots of revelers. Reviewed on Mar 18, 2026 ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago Save 100% on your flight $471 per person May 21 - May 24 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) The hotel was nice , and clean. The guy at the front desk was super nice. However , the rooms are small, the shower water splashes over on to floor so extra towels are needed for the bathroom floor, and every vending machine was either jammed and or out of water. Reviewed on Mar 17, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago Save 100% on your flight $717 per person May 1 - May 5 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago. Reviewed on Mar 14, 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/2026-04-19/2026-04-26/?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 Mar 29 - Mar 30 Total with taxes and fees 8.8/10 Excellent! (857 reviews) Second time at this hotel, it's a good value for the money. The staff is wonderful, very helpful and professional, good Wi-Fi and quiet for the most part. Super clean! There is a wide selection of breakfast choices (i wasnt impressed with the eggs) and a fitness room with a couple of cardio machines. ... Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%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 $70 nightly $78 total Mar 25 - Mar 26 Total with taxes and fees 7.2/10 Good! (1,480 reviews) Very dated. Needs a good overhaul and updating Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F25%2F2026&endDate=3%2F26%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 Mar 26 - Mar 27 Total with taxes and fees 6.4/10 (1,070 reviews) Had to leave, didn’t stay the night. Place was not clean , full of cockroaches, dirty towels, bedding Reviewed on Mar 18, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true®ionId=142441) [See all 607 properties in Oswego](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F20%2F2026&endDate=3%2F21%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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