Cheap flights To Oswego (CHI) from $42
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Cheap Flights to Oswego from $42 One Way, $55 Round Trip
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$55 Roundtrip, found 13 hours ago
$55
Roundtrip
found 13 hours ago
DEN
Denver Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$84 Roundtrip, found 6 days ago
$84
Roundtrip
found 6 days ago
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$85 Roundtrip, found 6 days ago
$85
Roundtrip
found 6 days ago
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 10 hours ago
$100
Roundtrip
found 10 hours ago
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$126 Roundtrip, found 11 hours ago
$126
Roundtrip
found 11 hours ago
PHL
Philadelphia Intl.
MDW
Midway Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
LGA
LaGuardia
MDW
Midway Intl.
$164 Roundtrip, found 18 hours ago
$164
Roundtrip
found 18 hours ago
LGA
LaGuardia
ORD
O'Hare Intl.
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Oswego Flight Information
Traveling To | Oswego |
|---|---|
Destination Airport IATA Code | CHI |
Number of Airlines Serving | |
Airlines | Frontier Airlines |
Flight Price | $55 |
Earliest Departing Flight | |
Latest Departing Flight |
Book Your Flight & Hotel Together & Save
- Economy Flight + Hotel Deals
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- First Class Flight + Hotel Deals
Oswego economy flight packages
Price found within the past 48 hours. Click for updated prices.
Oswego premium economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (5,174 reviews)
Oct 23 - Oct 27
4 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,510, price is now $1,002 per person
$1,002
per person
found 1 day ago
Had to request towels three times throughout the day before brought up. Thermostat stopped working, maintenance came and “fixed”, it stopped again in the middle of night spent a stuffy, hot night’s sleep. Shower drain clogged, informed front desk, maintenance never came that day. Glad we checked out the next day before anything else went wrong.
Spend your $ somewhere else!
Reviewed on Sep 18, 2026
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,512 reviews)
Oct 23 - Oct 27
4 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,352, price is now $922 per person
$922
per person
found 1 day ago
Overall great place to stay; the only odd thing was housekeeping knocked on our door at 9:15 at night which we weren't expecting. Otherwise it was quiet, comfortable and a great location to get to everything.
Reviewed on Sep 17, 2026
Oswego business class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Chez Hotel Arlington Heights
9/10 Wonderful! (806 reviews)
Oct 18 - Oct 21
3 night stay
Phoenix (PHX) to Chicago (ORD)
Frontier Airlines • Roundtrip • BusinessClass
Price was $775, price is now $682 per person
$682
per person
found 24 hours ago
Gym equipment was broken and TV did not have a remote.
Reviewed on Sep 17, 2026
Oswego first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (5,174 reviews)
Nov 7 - Nov 11
4 night stay
Philadelphia (PHL) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Chicago (ORD) to Philadelphia (PHL)
American Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $1,307, price is now $870 per person
$870
per person
found 1 day ago
Had to request towels three times throughout the day before brought up. Thermostat stopped working, maintenance came and “fixed”, it stopped again in the middle of night spent a stuffy, hot night’s sleep. Shower drain clogged, informed front desk, maintenance never came that day. Glad we checked out the next day before anything else went wrong.
Spend your $ somewhere else!
Reviewed on Sep 18, 2026
5.0-star property
Trump International Hotel & Tower Chicago
9.6/10 Exceptional! (1,995 reviews)
Nov 7 - Nov 11
4 night stay
Philadelphia (PHL) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Chicago (ORD) to Philadelphia (PHL)
American Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $2,001, price is now $1,262 per person
$1,262
per person
found 1 day ago
4.5-star property
Kimpton Gray Hotel by IHG
9.4/10 Exceptional! (1,010 reviews)
Nov 7 - Nov 11
4 night stay
Philadelphia (PHL) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Chicago (ORD) to Philadelphia (PHL)
American Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $1,639, price is now $1,140 per person
$1,140
per person
found 1 day ago
Oswego
Save money on your flights to Oswego as well as on hotel and car packages.
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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.