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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,113, price is now CA $1,436 per person
CA $1,436
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
Reviewed on Jul 14, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,178, price is now CA $800 per person
CA $800
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
I wish the space was bigger. It was too tight for me and my young girls but the staff was so extra nice and welcoming.
Reviewed on Jul 14, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,920, price is now CA $1,335 per person
CA $1,335
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows.
In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week.
Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).
Reviewed on Jul 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,339, price is now CA $965 per person
CA $965
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Free beer no perfect everyone was great
Reviewed on Jul 15, 2026
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 9 to Aug 10
CA $123
CA $134 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (975 reviews)
"Very nice stay. Check in was easy, and the room was clean and comfortable. Nice breakfast in the morning, with many options. The staff is always helpful, especially Jenny at the front desk."
Reviewed on Jul 14, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 26 to Jul 27
CA $105
CA $117 total
Jul 26 - Jul 27
includes taxes & fees
7.2/10 Good! (1,652 reviews)
"The property has a lot of potential, but is pretty run down. Our room had a hole in the wall, trim across one entire side of the room that was detached/detaching from the wall, and there was quite a bit of mold in the tub/shower. Our key cards only worked intermittently. We had to get them rekeyed ..."
Reviewed on Jul 13, 2026
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Aug 9 to Aug 10
CA $136
CA $151 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (2,876 reviews)
"Clean!!"
Reviewed on Jul 15, 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.
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- Water Tower Place
- Wrigley Field
- Serena Vacations
- Morton Arboretum
- Centennial Beach
- Woodfield Mall
- Navy Pier
- Washington Square Park
- Willis Tower
- Algonquin Vacations
- Chicago Riverwalk
- Ottawa Vacations
- Visit Downtown Chicago
- Rosemont Vacations
- Sheridan Vacations
- Grant Park
- Ernest Hemingway Museum and House
- Downtown Chicago Vacations
- Starved Rock State Park
- Legoland® Discovery Center
- Visit The Loop
- Millennium Park
- Art Institute of Chicago
- Malta Vacations
- Garfield Park Conservatory
- Chicago Vacations
- 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.
