$25 Cheap flight deals from New York (NYC) to Oswego (CHI)
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This Weekend's Flight Deals from New York to Oswego
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$142 Roundtrip, just found
$142
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$168 Roundtrip, found 7 hours ago
$168
Roundtrip
found 7 hours ago
LGA
LaGuardia
ORD
O'Hare Intl.
$179 Roundtrip, just found
$179
Roundtrip
just found
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$204 Roundtrip, just found
$204
Roundtrip
just found
Airfares from $25 One Way, $49 Round Trip from New York to Oswego
Prices starting at $49 for return flights and $25 for one-way flights to Oswego were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
EWR
New York
MDW
Chicago
$49 Roundtrip, found 18 hours ago
$49
Roundtrip
found 18 hours ago
JFK
New York
ORD
Chicago
$69 Roundtrip, found 5 hours ago
$69
Roundtrip
found 5 hours ago
EWR
New York
ORD
Chicago
$72 Roundtrip, just found
$72
Roundtrip
just found
LGA
New York
ORD
Chicago
$87 Roundtrip, just found
$87
Roundtrip
just found
LGA
New York
MDW
Chicago
$120 Roundtrip, found 18 hours ago
$120
Roundtrip
found 18 hours ago
Oswego economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Staybridge Suites, Lincolnshire by IHG
18/10 Exceptional! (1,000 reviews)
Dec 28 - Jan 2
5 night stay
New York (NYC) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to New York (NYC)
Frontier Airlines • Coach
Save 100% on your flight
Price was $539, price is now $364 per person
$364
per person
found 1 day ago
The breakfast was so fresh
Reviewed on Oct 26, 2025
4.5-star property
The Westin Michigan Avenue Chicago
17.6/10 Exceptional! (1,075 reviews)
Dec 22 - Dec 26
4 night stay
New York (LGA) to Chicago (ORD)
United • Coach
Chicago (ORD) to New York (LGA)
Spirit Airlines • Coach
Save 100% on your flight
Price was $1,377, price is now $716 per person
$716
per person
found 23 hours ago
Everything is EXCELLENT. But don’t consider the hotel for breakfast lunch or dinner
Reviewed on Oct 18, 2025
4.0-star property
The Hoxton Chicago
18/10 Exceptional! (1,001 reviews)
Dec 30 - Jan 4
5 night stay
New York (NYC) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $888, price is now $562 per person
$562
per person
found 7 hours ago
awesome area and hotel
Reviewed on Sep 1, 2025
Oswego packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn Chicago O'Hare – Rosemont by IHG
18/10 Exceptional! (2,591 reviews)
Jan 9 - Jan 11
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $439, price is now $381 per person
$381
per person
found 1 day ago
Clean, up to date, great location
Reviewed on Oct 13, 2025
4.0-star property
Hilton Chicago O'Hare Airport
16.4/10 Exceptional! (2,158 reviews)
Jan 9 - Jan 11
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $571, price is now $483 per person
$483
per person
found 1 day ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.
Reviewed on Nov 11, 2025
4.0-star property
DoubleTree by Hilton Chicago - North Shore Conference Center
17.6/10 Exceptional! (1,002 reviews)
Jan 9 - Jan 11
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $449, price is now $398 per person
$398
per person
found 1 day ago
Nice property and loved the free coffee bar !
Reviewed on Jun 9, 2025
Oswego first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Staybridge Suites Chicago O'Hare - Rosemont by IHG
18/10 Exceptional! (1,004 reviews)
Dec 25 - Dec 31
6 night stay
New York (NYC) to Chicago (ORD)
Delta • FirstClass
Chicago (ORD) to New York (NYC)
American Airlines • FirstClass
Price was $1,111, price is now $858 per person
$858
per person
found 9 hours ago
Clean and well kept.
Reviewed on Oct 14, 2025
4.0-star property
Hilton Chicago O'Hare Airport
16.4/10 Exceptional! (2,158 reviews)
Dec 25 - Dec 31
6 night stay
New York (NYC) to Chicago (ORD)
Delta • FirstClass
Chicago (ORD) to New York (NYC)
American Airlines • FirstClass
Price was $1,574, price is now $1,155 per person
$1,155
per person
found 9 hours ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.
Reviewed on Nov 11, 2025
5.0-star property
Trump International Hotel & Tower Chicago
18.8/10 Exceptional! (1,773 reviews)
Dec 26 - Dec 31
5 night stay
New York (NYC) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $2,110, price is now $1,564 per person
$1,564
per person
found 9 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
More About Flying To Oswego from New York
Route Information for Flights from New York to Oswego
Origin Airport IATA Code | NYC |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Oswego Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.