$30 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.
LGA
LaGuardia
ORD
O'Hare Intl.
$163 Roundtrip, just found
$163
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$181 Roundtrip, found 8 hours ago
$181
Roundtrip
found 8 hours ago
LGA
LaGuardia
MDW
Midway Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$201 Roundtrip, just found
$201
Roundtrip
just found
Airfares from $30 One Way, $58 Round Trip from New York to Oswego
Prices starting at $58 for return flights and $30 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.
JFK
New York
ORD
Chicago
$58 Roundtrip, found 3 days ago
$58
Roundtrip
found 3 days ago
EWR
New York
ORD
Chicago
$70 Roundtrip, found 15 hours ago
$70
Roundtrip
found 15 hours ago
EWR
New York
MDW
Chicago
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
LGA
New York
MDW
Chicago
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
JFK
New York
ORD
Chicago
$126 Roundtrip, found 5 days ago
$126
Roundtrip
found 5 days ago
Oswego economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Holiday Inn Chicago O'Hare – Rosemont by IHG
9/10 Wonderful! (2,591 reviews)
Feb 12 - Feb 16
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $411, price is now $291 per person
$291
per person
found 1 day ago
Very nice staff. Clean room, and nice restaurant and coffee bar in the lobby. I have stayed there several times. It's a convinient location as well.
Reviewed on Dec 29, 2025
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (447 reviews)
Feb 13 - Feb 17
4 night stay
New York (NYC) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $776, price is now $521 per person
$521
per person
found 1 day ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
3.5-star property
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
8.6/10 Excellent! (2,617 reviews)
Feb 12 - Feb 16
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $459, price is now $345 per person
$345
per person
found 1 day ago
Clean, comfortable although the bed is a little soft, helpful staff.
Reviewed on Jan 8, 2026
Oswego packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Royal Sonesta Chicago Downtown
9.4/10 Exceptional! (3,062 reviews)
Feb 12 - Feb 16
4 night stay
New York (NYC) to Chicago (ORD)
Delta • Roundtrip • PremiumEconomy
Price was $669, price is now $549 per person
$549
per person
found 1 day ago
The lady who checked us in (the countess) was very friendly and welcoming. Even though she was the only person working the front desk, she did not get frazzled or curt. She was great!
Room was beautiful and had an amazing view!
Reviewed on Dec 22, 2025
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (2,790 reviews)
Feb 14 - Feb 16
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $815, price is now $616 per person
$616
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful.
Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates!
The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods.
The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely.
I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month.
Kudos to all, and thank you for our wonderful stay!
Reviewed on Dec 28, 2025
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,773 reviews)
Feb 14 - Feb 16
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Delta • Non-stop roundtrip • PremiumEconomy
Price was $952, price is now $777 per person
$777
per person
found 1 day 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
Oswego first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Palmer House a Hilton Hotel
8.4/10 Very Good! (2,059 reviews)
Feb 26 - Mar 3
5 night stay
New York (LGA) to Chicago (ORD)
Delta • FirstClass
Chicago (ORD) to New York (LGA)
American Airlines • FirstClass
Price was $965, price is now $777 per person
$777
per person
found 21 hours ago
Our stay was absolutely perfect. The room was clean. The staff was amazing! The decorations were festive and the pool was spotless warm and very very family friendly!!
Reviewed on Dec 29, 2025
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (2,790 reviews)
Feb 12 - Feb 15
3 night stay
New York (LGA) to Chicago (ORD)
Delta • FirstClass
Chicago (ORD) to New York (LGA)
American Airlines • FirstClass
Price was $1,075, price is now $779 per person
$779
per person
found 21 hours ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful.
Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates!
The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods.
The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely.
I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month.
Kudos to all, and thank you for our wonderful stay!
Reviewed on Dec 28, 2025
5.0-star property
Trump International Hotel & Tower Chicago
9.4/10 Exceptional! (1,773 reviews)
Feb 12 - Feb 15
3 night stay
New York (LGA) to Chicago (ORD)
Delta • FirstClass
Chicago (ORD) to New York (LGA)
American Airlines • FirstClass
Price was $1,350, price is now $1,049 per person
$1,049
per person
found 21 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 |
New York to Oswego
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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.