Oswego Trip
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Top Oswego Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ₹77,714, price is now ₹56,134 per person
₹56,134
per person
28 Jul - 30 Jul
found 3 hours ago
Return direct flight included
Cleveland (CLE) to Chicago (ORD)
9.4/10 Exceptional! (4,319 reviews)
Decent hotel overall. Major selling points are the cool rooftop and ideal location. Wouldn’t consider this a luxury experience though, so if that’s what you are expecting please curb your enthusiasm.
Reviewed on 8 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₹108,537, price is now ₹82,508 per person
₹82,508
per person
28 Jul - 30 Jul
found 3 hours ago
Return direct flight included
Cleveland (CLE) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on 6 Jun 2026
Arlo Chicago
Downtown Chicago
Price was ₹79,076, price is now ₹60,603 per person
₹60,603
per person
28 Jul - 30 Jul
found 3 hours ago
Return direct flight included
Cleveland (CLE) to Chicago (ORD)
9.4/10 Exceptional! (2,110 reviews)
Excellent location. Cleaner room. Double rooms look out at wall of building next door
Reviewed on 6 Jun 2026
River Hotel
Downtown Chicago
Price was ₹72,868, price is now ₹56,452 per person
₹56,452
per person
28 Jul - 30 Jul
found 3 hours ago
Return direct flight included
Cleveland (CLE) to Chicago (ORD)
8.8/10 Excellent! (5,221 reviews)
Close to the red line. Great for Cubs and W. Sox game visitors.
Reviewed on 30 May 2026
Top hotels in Oswego
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is ₹7,519 per night from 5 Jul to 6 Jul
₹7,519
₹8,195 total
5 Jul - 6 Jul
includes taxes & fees
8.8/10 Excellent! (926 reviews)
"The hotel decor is simple, but clean. Parking availability is almost all at the back. Not much they can do about it. But there is lots of spaces, just far enough away to make me a bit nervous walking from the car to the doorway. There is no one around. But it was fine. Breakfast is ok. Nice it’s ..."
Reviewed on 4 Jun 2026
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ₹8,734 per night from 21 Jun to 22 Jun
₹8,734
₹9,693 total
21 Jun - 22 Jun
includes taxes & fees
9/10 Wonderful! (2,790 reviews)
"Great affordable place to stay in Chicago area"
Reviewed on 7 Jun 2026
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
The price is ₹10,831 per night from 28 Jun to 29 Jun
₹10,831
₹12,020 total
28 Jun - 29 Jun
includes taxes & fees
8.2/10 Very Good! (1,616 reviews)
"Very nice staff. Great breakfast. Security to make you feel safe."
Reviewed on 7 Jun 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.
