Oswego Holidays
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Top Flight + Hotel Deals in Oswego
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,511, price is now €1,008 per person
€1,008
per person
1 Feb - 6 Feb
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Great stay. Excellent location.
Reviewed on 23 Nov 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €955, price is now €664 per person
€664
per person
1 Feb - 6 Feb
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.4/10 Exceptional! (317 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 28 Oct 2025
Pendry Chicago
Downtown Chicago
Price was €940, price is now €672 per person
€672
per person
1 Feb - 6 Feb
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Really great spot in the city right in the middle like a five minute walk to to everything around you the staff was great. The rooms were beautiful.
Reviewed on 24 Nov 2025
Top hotels in Oswego
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is €71 per night from 30 Nov to 1 Dec
€71
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (771 reviews)
Very clean room and hotel, friendly staff, had all amenities needed.
Reviewed on 10 Nov 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 €70 per night from 26 Nov to 27 Nov
€70
26 Nov - 27 Nov
includes taxes & fees
8.8/10 Excellent! (2,387 reviews)
Staff, room clean and excellent service
Reviewed on 20 Nov 2025
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is €57 per night from 24 Dec to 25 Dec
€57
24 Dec - 25 Dec
includes taxes & fees
7/10 Good! (1,334 reviews)
The clean room and the amenities
Reviewed on 21 Nov 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.
Popular places to visit
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.
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