$68 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
MDW
Midway Intl.
$252 Roundtrip, found 5 days ago
$252
Roundtrip
found 5 days ago
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$344 Roundtrip, found 1 hour ago
$344
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$368 Roundtrip, found 1 hour ago
$368
Roundtrip
found 1 hour ago
LGA
LaGuardia
MDW
Midway Intl.
$371 Roundtrip, found 3 days ago
$371
Roundtrip
found 3 days ago
Airfares from $68 One Way, $135 Round Trip from New York to Oswego
Prices starting at $135 for return flights and $68 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.
LGA
New York
ORD
Chicago
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
LGA
New York
ORD
Chicago
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
LGA
New York
ORD
Chicago
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
LGA
New York
MDW
Chicago
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
EWR
New York
ORD
Chicago
$169 Roundtrip, found 4 days ago
$169
Roundtrip
found 4 days ago
Oswego economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
9.2/10 Wonderful! (512 reviews)
Aug 12 - Aug 16
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,153, price is now $798 per person
$798
per person
found 1 day ago
Location
Reviewed on Jul 10, 2026
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (3,764 reviews)
Aug 12 - Aug 16
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,458, price is now $1,028 per person
$1,028
per person
found 1 day ago
Probably the best hotel I ever stayed at next time. Make sure I get a room with a view of the lake for five stars.
Reviewed on Jul 12, 2026
5.0-star property
The Langham, Chicago
9.8/10 Exceptional! (1,003 reviews)
Aug 15 - Aug 19
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,236, price is now $1,682 per person
$1,682
per person
found 1 day ago
The Langham was one of my favorite hotels I've ever stayed at. The shower was incredible, the bed felt like heaven and the overall room set-up was amazing. I especially loved the vanity! I also highly recommend the hotel restaurant for breakfast. I had breakfast there every day of my stay and it was delicious! Can't wait to go back.
Reviewed on Jul 13, 2026
Oswego packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Sonesta Chicago O'Hare Airport Rosemont
8.8/10 Excellent! (1,642 reviews)
Aug 14 - Aug 17
3 night stay
New York (NYC) to Chicago (ORD)
JetBlue Airways • PremiumEconomy
Chicago (ORD) to New York (NYC)
Frontier Airlines • PremiumEconomy
Price was $763, price is now $678 per person
$678
per person
found 1 day ago
Clean room and convenient airport shuttle
Reviewed on Jul 12, 2026
3.5-star property
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
8.6/10 Excellent! (2,966 reviews)
Aug 14 - Aug 17
3 night stay
New York (NYC) to Chicago (ORD)
JetBlue Airways • PremiumEconomy
Chicago (ORD) to New York (NYC)
Frontier Airlines • PremiumEconomy
Price was $880, price is now $789 per person
$789
per person
found 1 day ago
Great room & breakfast. Just got back from Scotland & Ireland. US hotels need to up their game. I missed having free bottles of water in the refrigerator and cookies.
Reviewed on Jul 13, 2026
4.0-star property
Hyatt Regency O'Hare Chicago
8.8/10 Excellent! (2,757 reviews)
Aug 14 - Aug 17
3 night stay
New York (NYC) to Chicago (ORD)
JetBlue Airways • PremiumEconomy
Chicago (ORD) to New York (NYC)
Frontier Airlines • PremiumEconomy
Price was $801, price is now $723 per person
$723
per person
found 1 day ago
Nice ,clean ,staff was friendly
Reviewed on Jul 12, 2026
Oswego first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
8.2/10 Very Good! (2,809 reviews)
Aug 19 - Aug 23
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,213, price is now $911 per person
$911
per person
found 19 hours ago
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!
Reviewed on Jul 13, 2026
4.0-star property
Level Chicago – Old Town
9/10 Wonderful! (497 reviews)
Aug 20 - Aug 24
4 night stay
New York (JFK) to Chicago (ORD)
Delta • Roundtrip • FirstClass
Price was $1,757, price is now $1,291 per person
$1,291
per person
just found
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,566 reviews)
Aug 19 - Aug 23
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,764, price is now $1,306 per person
$1,306
per person
found 19 hours ago
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night
Reviewed on Jul 13, 2026
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.