Oswego Vacations from NT$17,071
Book a Hotel + Flight or Car together to unlock savings
Photo by Anthony Martinez
- Plan, book, travel with confidence
Better together
Save up to NT$5,067 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
The Latest Oswego Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$28,064, price is now NT$17,071 per person
NT$17,071
per person
Dec 23 - Dec 28
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean room, mazing breakfast
Reviewed on 2025/10/7
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was NT$48,634, price is now NT$20,538 per person
NT$20,538
per person
Dec 23 - Dec 28
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.
Reviewed on 2025/10/2
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$56,154, price is now NT$33,360 per person
NT$33,360
per person
Dec 23 - Dec 28
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on 2025/10/6
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$30,307, price is now NT$18,960 per person
NT$18,960
per person
Dec 23 - Dec 28
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on 2025/10/7
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was NT$27,044, price is now NT$17,138 per person
NT$17,138
per person
Dec 23 - Dec 28
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 2025/10/4
Find the Best Oswego Vacation Packages
Oswego Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is NT$2,469 per night from Oct 8 to Oct 9
NT$2,469
NT$2,740 total
Oct 8 - Oct 9
includes taxes & fees
8.8/10 Excellent! (2,269 reviews)
"Great price, great motel and staff was great."
Reviewed on 2025/10/2
Chicago Club Inn & Suites
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is NT$2,195 per night from Oct 19 to Oct 20
NT$2,195
NT$2,435 total
Oct 19 - Oct 20
includes taxes & fees
7/10 Good! (1,267 reviews)
"Very good location, convenient to Oakbrook shopping center and West Suburbs. Great value"
Reviewed on 2025/10/6
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is NT$2,725 per night from Oct 13 to Oct 14
NT$2,725
NT$3,652 total
Oct 13 - Oct 14
includes taxes & fees
8.4/10 Very Good! (1,273 reviews)
"The staff was friendly, room was perfect for the occasion."
Reviewed on 2025/10/5
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.
Discover the most popular places to visit in Oswego
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.
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.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
