Search Cheap Flights to
Oswego

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Oswego Flights as Low as $58

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, May 12 - Wed, May 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 20 hours ago
$58
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Denver Intl. to O'Hare Intl., returning Wed, May 13, priced at $58 found 20 hours ago
Frontier Airlines
Tue, May 12 - Tue, May 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$70 Roundtrip, found 5 hours ago
$70
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 19, priced at $70 found 5 hours ago
Frontier Airlines
Wed, Aug 19 - Wed, Aug 26
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 26, priced at $70 found 2 days ago
Frontier Airlines
Tue, Aug 18 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $76 found 1 day ago
Spirit Airlines
Thu, Apr 30 - Sat, May 2
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Apr 30 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Sat, May 2, priced at $107 found 2 days ago
Bargain Flight
Fri, Sep 18 - Mon, Sep 21
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Sep 18 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Sep 21, priced at $156 found 3 days ago
Sun Country Airlines
Fri, Sep 18 - Mon, Sep 21
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Fri, Sep 18 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Sep 21, priced at $157 found 3 days ago
Frontier Airlines
Thu, Apr 30 - Thu, May 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$161 Roundtrip, found 4 days ago
$161
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 7, priced at $161 found 4 days ago
Frontier Airlines
Sat, May 16 - Sat, May 30
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$174 Roundtrip, found 13 hours ago
$174
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 16 from Minneapolis - St. Paul Intl. to Midway Intl., returning Sat, May 30, priced at $174 found 13 hours ago
Delta
Tue, Jun 2 - Wed, Jun 3
DAL
Love Field
MDW
Midway Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 2 from Love Field to Midway Intl., returning Wed, Jun 3, priced at $183 found 3 days ago
Frontier Airlines
Tue, May 12 - Sat, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, May 12 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, May 30, priced at $185 found 4 days ago
Frontier Airlines
Wed, May 6 - Tue, May 12
DEN
Denver Intl.
MDW
Midway Intl.
$186 Roundtrip, found 3 days ago
$186
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, May 6 from Denver Intl. to Midway Intl., returning Tue, May 12, priced at $186 found 3 days ago
Delta
Wed, Jun 3 - Sat, Jun 6
DAL
Love Field
ORD
O'Hare Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 3 from Love Field to O'Hare Intl., returning Sat, Jun 6, priced at $199 found 1 day ago
Frontier Airlines
Wed, May 20 - Tue, May 26
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$200 Roundtrip, found 4 days ago
$200
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, May 20 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, May 26, priced at $200 found 4 days ago
Bargain Flight
Mon, May 25 - Thu, May 28
GSO
Piedmont Triad Intl.
ORD
O'Hare Intl.
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, May 25 from Piedmont Triad Intl. to O'Hare Intl., returning Thu, May 28, priced at $263 found 2 days ago
Delta
Sat, Jun 6 - Tue, Jun 23
GSO
Piedmont Triad Intl.
MDW
Midway Intl.
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 6 from Piedmont Triad Intl. to Midway Intl., returning Tue, Jun 23, priced at $285 found 1 day ago

Cheap Flights to Oswego

Fall in love at first flight with your vacation to Oswego by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Oswego on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Oswego, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Oswego

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Oswego with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Oswego?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Oswego are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Oswego?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Oswego.

What airport is best to fly into Oswego?

When you’re planning your trip to Oswego, convenience is the name of the game. Luckily, Oswego Dupage Airport is nearby so you can deplane and get going on checking off everything on your Oswego must-do list.

How much are flights to Oswego?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Oswego on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $58, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Oswego?

The trick to saving a stack of cash on your flight to Oswego? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $58 right now, why wait?

Oswego Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$57

Last Minute Hotel Deals in Oswego

Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
2055 Wiesbrook Dr Oswego IL
Book a stay at this business-friendly hotel in Oswego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (885 reviews)
Breakfast was delicious. Front desk receptionist

Reviewed on Apr 23, 2026

Get rates
Best Western Oswego Hotel
AmericInn by Wyndham Oswego

AmericInn by Wyndham Oswego

3 out of 5
1050 Douglas Road Oswego IL
Book a stay at this golf hotel in Oswego. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.2/10 Very Good! (559 reviews)
I believe the girl I spoke with was new. Either busy or just didn't care. We were attending a visitation. I asked if our driving time got us there before 3:00 could we check in. Abruptly she said '40.00' You have got to be kidding. The Manager told me this morning we could check in an hour early ...

Reviewed on Apr 20, 2026

Get rates
AmericInn by Wyndham Oswego
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (1,303 reviews)
Great front line people fora great property

Reviewed on Apr 24, 2026

Get rates
DoubleTree by Hilton Lisle Naperville
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,523 reviews)
Good standard hotel.

Reviewed on Apr 21, 2026

Get rates
Embassy Suites by Hilton Chicago Lombard Oak Brook
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (2,699 reviews)
The lighting was difficult to deal with. Those bulbs that are almost blue light emitting, not warm or soft at all. I had about 3 spiders that dropped down from the ceiling. The room seemed old, but was newly painted, in bright white. When I turned the heat unit on. It smelled like urine, but the ...

Reviewed on Apr 24, 2026

Get rates
SureStay Plus Hotel by Best Western Chicago Lombard
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
7.2/10 Good! (1,524 reviews)
Staff was great. There was mold in my bathroom. Good People working there though

Reviewed on Apr 24, 2026

Get rates
Chicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Stay at this hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.4/10 (1,094 reviews)
I am writing to express my extreme disappointment with my recent three-night stay. Despite reserving a non-smoking room, I was initially checked into a smoking room that smelled of stale smoke and had a leaking bathroom. Upon requesting a change, the second room provided also had a strong odor. Furthermore, ...

Reviewed on Apr 21, 2026

Get rates
Red Roof Inn PLUS+ Chicago - Willowbrook
Hyatt Place Chicago/Lombard/Oak Brook

Hyatt Place Chicago/Lombard/Oak Brook

3 out of 5
2340 South Fountain Square Drive Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,114 reviews)
The room was clean and the king-sized bed and pillows were very comfortable. What impressed me most was the highly insulated room; walls are thick and we did not hear any disturbances from the adjacent rooms. Breakfast offered many selections from fresh scrambled eggs, sausages, pancakes and even ...

Reviewed on Apr 24, 2026

Get rates
Hyatt Place Chicago/Lombard/Oak Brook
See all 614 properties in Oswego
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.