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 $112

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

Frontier Airlines
Tue, Jul 28 - Tue, Aug 11
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jul 28 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $112 just found
Frontier Airlines
Wed, Sep 23 - Tue, Sep 29
MCO
Orlando Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 17 hours ago
$120
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $120 found 17 hours ago
Frontier Airlines
Sat, Jun 13 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 13 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jun 16, priced at $137 found 1 day ago
Frontier Airlines
Thu, May 28 - Fri, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Fri, May 29, priced at $141 found 4 days ago
United
Wed, Sep 23 - Tue, Sep 29
MCO
Orlando Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 17 hours ago
$171
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Sep 23 from Orlando Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $171 found 17 hours ago
Delta
Tue, Sep 22 - Wed, Oct 7
MCO
Orlando Intl.
MDW
Midway Intl.
$197 Roundtrip, found 17 hours ago
$197
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 22 from Orlando Intl. to Midway Intl., returning Wed, Oct 7, priced at $197 found 17 hours ago
Delta
Tue, Sep 1 - Tue, Sep 8
FLL
Fort Lauderdale - Hollywood Intl.
MDW
Midway Intl.
$217 Roundtrip, found 17 hours ago
$217
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Midway Intl., returning Tue, Sep 8, priced at $217 found 17 hours ago
Bargain Flight
Tue, Oct 27 - Tue, Nov 17
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 14 hours ago
$219
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Tue, Oct 27 from Austin-Bergstrom Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $219 found 14 hours ago
Frontier Airlines
Wed, Jul 29 - Wed, Aug 12
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$240 Roundtrip, found 17 hours ago
$240
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Jul 29 from Austin-Bergstrom Intl. to Midway Intl., returning Wed, Aug 12, priced at $240 found 17 hours ago
Frontier Airlines
Tue, Jun 16 - Tue, Jun 23
OKC
Will Rogers World
ORD
O'Hare Intl.
$264 Roundtrip, found 14 hours ago
$264
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Tue, Jun 16 from Will Rogers World to O'Hare Intl., returning Tue, Jun 23, priced at $264 found 14 hours ago
Bargain Flight
Wed, Aug 12 - Mon, Aug 17
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$265 Roundtrip, found 1 day ago
$265
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Aug 12 from Seattle - Tacoma Intl. to O'Hare Intl., returning Mon, Aug 17, priced at $265 found 1 day ago
Frontier Airlines
Tue, Jun 23 - Tue, Jun 30
OKC
Will Rogers World
MDW
Midway Intl.
$275 Roundtrip, found 1 day ago
$275
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 23 from Will Rogers World to Midway Intl., returning Tue, Jun 30, priced at $275 found 1 day ago
Delta
Tue, Oct 13 - Sat, Oct 17
DAL
Love Field
MDW
Midway Intl.
$301 Roundtrip, found 17 hours ago
$301
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 13 from Love Field to Midway Intl., returning Sat, Oct 17, priced at $301 found 17 hours ago
Delta
Wed, Sep 16 - Sat, Sep 19
DAL
Love Field
ORD
O'Hare Intl.
$301 Roundtrip, found 17 hours ago
$301
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Sep 16 from Love Field to O'Hare Intl., returning Sat, Sep 19, priced at $301 found 17 hours ago
Alaska Airlines
Wed, Aug 12 - Mon, Aug 17
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$380 Roundtrip, found 1 day ago
$380
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Aug 12 from Seattle Paine Field Intl. Airport to O'Hare Intl., returning Mon, Aug 17, priced at $380 found 1 day ago
Delta
Mon, Jun 8 - Fri, Jun 19
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$447 Roundtrip, found 3 days ago
$447
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jun 8 from Seattle - Tacoma Intl. to Midway Intl., returning Fri, Jun 19, priced at $447 found 3 days 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 July, 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 $112, 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 $112 right now, why wait?

Oswego Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$112

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! (914 reviews)
"Room was great for the price, but like most hotels since Covid, breakfast is not up to par. I know it’s free, but at least make it tasty, enticing and a variety, not just pork, some of us don’t eat beef or pork. But overall good rooms and stay was great."

Reviewed on May 25, 2026

Get rates
Best Western Oswego Hotel
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! (2,756 reviews)
"Great staff and spotless rooms."

Reviewed on May 26, 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! (1,566 reviews)
"Good and spacious was very quick and easy from the highway"

Reviewed on May 25, 2026

Get rates
Chicago Club Inn & Suites
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! (1,583 reviews)
"The room was clean, the bed was very comfortable. The weekend we went there was a lot of kids at the hotel. They were running around and screaming uncontrollably which was a bit frustrating. The housecleaner cleaned our room but left dirty glasses and didn't restock the coffee area. The walls of ..."

Reviewed on May 26, 2026

Get rates
Embassy Suites by Hilton Chicago Lombard Oak Brook
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 (1,123 reviews)
"Room size is too small and restroo.s are not clean.Not good for family"

Reviewed on May 26, 2026

Get rates
Red Roof Inn PLUS+ Chicago - Willowbrook
Hilton Chicago/Oak Brook Hills Resort & Conference Center

Hilton Chicago/Oak Brook Hills Resort & Conference Center

4 out of 5
3500 Midwest Road Oak Brook IL
Book a stay at this spa resort in Oak Brook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,009 reviews)
"The location is terrific. The restaurant on site and the restaurant staff excellent."

Reviewed on May 25, 2026

Get rates
Hilton Chicago/Oak Brook Hills Resort & Conference Center
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
Book a stay at this boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,526 reviews)
"Great little hidden gem for couples"

Reviewed on May 26, 2026

Get rates
The Champagne Lodge & Luxury Suites
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
70 Yorktown Center Lombard IL
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (1,267 reviews)
"Requested a room with a walk in shower as I have a broken foot and am wearing a walking boot. Was told none were available but online through the hotels own website it showed they were and were bookable for my entire stay. Rude front desk staff. Probably will never stay there again. This hotel has ..."

Reviewed on May 25, 2026

Get rates
The Westin Chicago Lombard
See all 612 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.