Oswego Vacations from ￥337,288
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The Latest Oswego Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Wade
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.
Reviewed on Mar 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥497,724, price is now ￥371,403 per person
￥371,403
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors.
Reviewed on Mar 27, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥437,268, price is now ￥349,207 per person
￥349,207
per person
May 14 - May 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥641,108, price is now ￥516,587 per person
￥516,587
per person
May 14 - May 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ￥475,226, price is now ￥383,552 per person
￥383,552
per person
May 14 - May 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026
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 ￥12,263 per night from Apr 12 to Apr 13
￥12,263
￥13,364 total
Apr 12 - Apr 13
includes taxes & fees
8.8/10 Excellent! (858 reviews)
All good
Reviewed on Mar 20, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ￥12,358 per night from Mar 29 to Mar 30
￥12,358
￥13,715 total
Mar 29 - Mar 30
includes taxes & fees
7.2/10 Good! (1,487 reviews)
Breakfast was nasty hotel overall was outdated and not clean hotel had a smell trash was in the hallway falling over staff was nice saw a roach by the pool do not book
Reviewed on Mar 27, 2026
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is ￥9,092 per night from Apr 10 to Apr 11
￥9,092
￥10,181 total
Apr 10 - Apr 11
includes taxes & fees
6.4/10 (1,077 reviews)
Old hotel
Reviewed on Mar 27, 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.
Discover the most popular places to visit in Oswego
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.
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
