Oswego Holidays
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Top Flight + Hotel Deals in Oswego
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was €1,358, price is now €1,060 per person
€1,060
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was €1,960, price is now €1,281 per person
€1,281
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.
Reviewed on 9 Mar 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was €1,531, price is now €1,194 per person
€1,194
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.
Reviewed on 9 Mar 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was €1,748, price is now €1,370 per person
€1,370
per person
4 May - 9 May
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,873 reviews)
great area with lots of options nearby, close to the train & bus stop, and very safe!
Reviewed on 8 Mar 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,615, price is now €1,270 per person
€1,270
per person
16 Apr - 20 Apr
found 8 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed.
Reviewed on 3 Mar 2026
Top hotels in Oswego
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is €69 per night from 15 Mar to 16 Mar
€69
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (853 reviews)
Rooms were clean
Reviewed on 2 Mar 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is €70 per night from 10 Mar to 11 Mar
€70
10 Mar - 11 Mar
includes taxes & fees
7.2/10 Good! (1,471 reviews)
The building caught fire while staying there. Every terrifying experience.
Reviewed on 9 Mar 2026
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is €55 per night from 15 Mar to 16 Mar
€55
15 Mar - 16 Mar
includes taxes & fees
6.4/10 (1,066 reviews)
Parking was great; it was very easy to find a parking spot. They have a lot of spots for you to park, both in the back and front.
Reviewed on 8 Mar 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.
Popular places to visit
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
