Title: Oswego Vacation Packages 2026 from $289 | 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 $289 ## 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. ![Illinois Beach Hotel](https://images.trvl-media.com/lodging/84000000/83570000/83567200/83567194/bc5aabfe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Illinois Beach Hotel $289 per person May 19 - May 23 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8/10 Very Good! (503 reviews) Pool was out of commission. Front desk was welcoming. Reviewed on Mar 5, 2026 ![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 $297 per person May 13 - May 15 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy. Reviewed on Mar 9, 2026 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago Save 100% on your flight $1,172 per person May 13 - May 20 found 6 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,323 reviews) Room was nice and clean, decent view. Perfect location. Close to shopping and nice restaurants. Staff was amazing; Myron in particular was so kind and accommodating. Reviewed on Mar 8, 2026 ![Hilton Chicago/Oak Brook Suites](https://images.trvl-media.com/lodging/1000000/20000/19500/19455/a848dc0d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago/Oak Brook Suites Yorkfield Save 100% on your flight $325 per person Jun 1 - Jun 6 found 23 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 7.8/10 Good! (1,004 reviews) Front desk customer service was poor. At front desk with no line, clerk(s) did not greet us but one whom had the audacity to ask us to step aside and allow the women getting off the elevator to be helped first… Talked with them for 15mins about their check in, when we approached the desk first for the same thing. Clerk assisting him just shuffled around behind him, as if he didn’t want to help neither his coworker or us. Did not check us in until I got out of line from behind the first set of mentioned women & asked if he was able to check us in. Also everything I handed the second clerk he never returned in my hand only in front of me on the counter, very disrespectful in my opinion. First clerk: male, bald, with glasses. Second clerk: male, silver shoulder length hair & glasses. Reviewed on Mar 6, 2026 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare $625 per person May 13 - May 17 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.4/10 Very Good! (2,217 reviews) Very convenient loved the restaurant. Food and staff was amazing. Reviewed on Mar 8, 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/2026-04-09/2026-04-16/?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/1000000/430000/424400/424318/4e4a11b7_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 15 - Mar 16 Total with taxes and fees 8.8/10 Excellent! (853 reviews) Rooms were clean Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%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 $77 nightly $85 total Mar 10 - Mar 11 Total with taxes and fees 7.2/10 Good! (1,471 reviews) The building caught fire while staying there. Every terrifying experience. Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%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 16 - Mar 17 Total with taxes and fees 6.4/10 (1,066 reviews) Parking was great; it was very easy to find a parking spot. They have a lot of spots for you to park, both in the back and front. Reviewed on Mar 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true®ionId=142441) [See all 611 properties in Oswego](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F10%2F2026&endDate=3%2F11%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 [](https://expedia.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.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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