Oswego Holidays from NZ$2,045
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The Latest Oswego Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was NZ$2,596, price is now NZ$2,045 per person
NZ$2,045
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel staff was great from the door men to front desk staff everyone was great.
Reviewed on 23 Sept 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was NZ$4,661, price is now NZ$3,143 per person
NZ$3,143
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!
Reviewed on 23 Sept 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$2,946, price is now NZ$2,122 per person
NZ$2,122
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on 21 Sept 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NZ$3,179, price is now NZ$2,500 per person
NZ$2,500
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Close to the riverwalk
Reviewed on 23 Sept 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NZ$2,963, price is now NZ$2,347 per person
NZ$2,347
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Great view and a great staff!
Reviewed on 22 Sept 2025
Oswego Holiday
Our pick of the best Oswego Hotel Deals
Best Western Oswego Hotel
2055 Wiesbrook Dr, Oswego, IL
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 29 Sept to 30 Sept
NZ$162
29 Sept - 30 Sept
includes taxes & fees
8.6/10 Excellent! (738 reviews)
"Favorite hotel"
Reviewed on 16 Sept 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 NZ$153 per night from 25 Sept to 26 Sept
NZ$153
25 Sept - 26 Sept
includes taxes & fees
8.8/10 Excellent! (2,265 reviews)
"Very good place to stay."
Reviewed on 19 Sept 2025
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is NZ$202 per night from 29 Sept to 30 Sept
NZ$202
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very Good! (1,249 reviews)
"Cheap and has all the amenities"
Reviewed on 15 Sept 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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
