Oswego Vacation Packages
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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, Hollywood Casino Aurora and Raging Waves Waterpark 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!
Top Oswego Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,003
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The staff was very helpful, we loved the amenities, the breakfast was good, a lot of options every day
Reviewed on Aug 31, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,140
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
The staff was very friendly and the room was always clean and organized. I was a bit nervous what to expect as a solo traveler and it being my first time staying in Chicago but this was the perfect hotel for the trip. It always felt safe on property and very close to all the main things I wanted to see.
Reviewed on Aug 31, 2026
Holiday Inn Chicago North-Evanston by IHG
Downtown Evanston
CA $1,664
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,103 reviews)
This hotel is in a great location. You can’t ask for anything more central and with an easy walking distance to all of the public transit. The rooms were fine. The view was great, but the check-in process was not very easy. Arrived 15 minutes before 4 PM. Had to stand in line to check in only to find out the room was not ready. Had to wait another 15 minutes, the staff tried very hard, but had to wait on housekeeping.
Reviewed on Aug 30, 2026
Ready to book your vacation to Oswego?
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
CA $121
CA $132 total
Sep 6 - Sep 7
includes taxes & fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $78
CA $86 total
Sep 30 - Oct 1
includes taxes & fees
7.2/10 Good! (1,762 reviews)
"This place is really gross. So weird because its definitely in a rich area. We arrived and our toilet had poop in it. My husband went to talk to the staff and he laughed in his face, giving us a room that had the door already wide open. The new rooms hot tub was dirty so we didnt bother using it, ..."
Reviewed on Aug 31, 2026
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
CA $112
CA $125 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,986 reviews)
"Clean room and very nice staff"
Reviewed on Aug 31, 2026
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.
Stay near popular Oswego attractions
Hudson Crossing Park
6.0/10 (4 reviews)
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.
Fox Valley Winery
6.8/10 (5 reviews)
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.
Keller's Farmstand
Enjoy a fun-filled day at Keller's Farmstand as part of your trip to Oswego. While in this family-friendly area, you can enjoy the restaurants.
Frequently asked questions
How much does an Oswego vacation package cost?
Offering excellent value package deals from CA $1,003 on Expedia, you'll be surprised at how little a vacation to Oswego costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oswego?
January, February and November are great times to look for cheap Oswego vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on accommodations and flights.
How many days is enough for Oswego?
Usually, a few days is great for an Oswego vacation. With a carefully crafted itinerary, you can go to all the leading sights including Hollywood Casino, as well as discover some hidden gems along the way.
How to find the best Oswego package deals?
Start your search for an Oswego package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oswego package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oswego escape off to a flying start.
Is it cheaper to book an Oswego vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a personalized Oswego vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Oswego?
If you're considering an impromptu Oswego trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Oswego?
- Choose when to go: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Oswego.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Oswego.
- Decide how long to go away for: Now that you're up to speed on Oswego, you can figure out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Oswego vacation package.
Explore a world of travel with Expedia
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- Flights from Detroit (DTW) to Aurora (AUZ)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from San Diego (SAN) to Aurora (AUZ)
- Flights to Aurora
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights to Oswego
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from New Orleans (MSY) to Aurora (AUZ)
- Flights from London (YXU) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Vancouver (YVR) to Aurora (AUZ)
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Plainfield
- Flights from McAllen (MFE) to Aurora (AUZ)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Phoenix (PHX) to Aurora (AUZ)
- Flights to Yorkville
- Flights from Ottawa (YOW) to Chicago (ORD)
- Flights from Chicago (ORD) to Aurora (AUZ)
- Flights from Aurora Municipal
- Flights from Orlando (ORL) to Aurora (AUZ)
- Flights from O'Hare Intl.
- Flights from Providence (PVD) to Aurora (AUZ)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from Toronto (YYZ) to Aurora (AUZ)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Aurora (AUZ)
- Flights to Chicago
- Flights from Tampa (TPA) to Aurora (AUZ)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from Yorkville
- Flights to Plainfield
- Water Tower Place
- Wrigley Field
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- Morton Arboretum
- Centennial Beach
- Woodfield Mall
- Navy Pier
- Washington Square Park
- Willis Tower
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- Chicago Riverwalk
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- Sheridan Vacations
- Grant Park
- Ernest Hemingway Museum and House
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- Starved Rock State Park
- Legoland® Discovery Center
- Visit The Loop
- Millennium Park
- Art Institute of Chicago
- Malta Vacations
- Garfield Park Conservatory
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- Santa's Village
- Golf Vacations
- Lincoln Park Zoo
- Frank Lloyd Wright Historic District
- Unity Temple
- United Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
