Oswego Vacations from ￥266,174
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The Latest Oswego Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥304,722, price is now ￥266,174 per person
￥266,174
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on Nov 10, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥345,035, price is now ￥293,264 per person
￥293,264
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥320,001, price is now ￥275,657 per person
￥275,657
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Clean! Staff friendly and a great location.
Reviewed on Nov 11, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥309,020, price is now ￥274,304 per person
￥274,304
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
It was so relaxing and peaceful
Reviewed on Nov 9, 2025
Find the Best Oswego Vacation Packages
Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr, Oswego, IL
Fully refundableReserve now, pay when you stay
The price is ￥11,537 per night from Nov 18 to Nov 19
￥11,537
￥12,572 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (766 reviews)
Staff was great, clean, continental breakfast was good. Beds need some work, they were very hard.
Reviewed on Nov 2, 2025
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is ￥11,791 per night from Nov 12 to Nov 13
￥11,791
￥13,085 total
Nov 12 - Nov 13
includes taxes & fees
8.8/10 Excellent! (2,354 reviews)
I had a nice stay at the SureStay Plus Hotel in Lombard. The room was comfortable and clean, the breakfast had a good variety. When my room wasn’t cleaned one night, Patrick at the front desk was very helpful — he gave me fresh towels right away and confirmed that my room would be cleaned the next ...
Reviewed on Nov 7, 2025
Chicago Club Inn & Suites
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is ￥10,482 per night from Dec 11 to Dec 12
￥10,482
￥11,633 total
Dec 11 - Dec 12
includes taxes & fees
7/10 Good! (1,312 reviews)
Great!
Reviewed on Nov 9, 2025
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.
