$197 Cheap Flights from Chicago (ORD) to Stillwater (SWO)

View $197 flight on Tue, Dec 30, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Stillwater, OK (SWO-Stillwater Regional)

Cheap Flights from Chicago to Stillwater (ORD-SWO)

Prices were available within the past 7 days and start at $197 for one-way flights and $393 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Dec 29 - Thu, Jan 1
ORD
Chicago
SWO
Stillwater
$393 Roundtrip, found 14 hours ago
$393
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Mon, Dec 29 from Chicago to Stillwater, returning Thu, Jan 1, priced at $393 found 14 hours ago
American Airlines
Sat, Dec 13 - Mon, Jan 5
ORD
Chicago
SWO
Stillwater
$404 Roundtrip, found 3 days ago
$404
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Stillwater, returning Mon, Jan 5, priced at $404 found 3 days ago
American Airlines
Mon, Dec 29 - Thu, Jan 1
ORD
Chicago
SWO
Stillwater
$425 Roundtrip, found 14 hours ago
$425
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Mon, Dec 29 from Chicago to Stillwater, returning Thu, Jan 1, priced at $425 found 14 hours ago
American Airlines
Sat, Dec 13 - Mon, Jan 5
ORD
Chicago
SWO
Stillwater
$436 Roundtrip, found 2 days ago
$436
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Stillwater, returning Mon, Jan 5, priced at $436 found 2 days ago
American Airlines
Sat, Dec 13 - Mon, Jan 5
ORD
Chicago
SWO
Stillwater
$439 Roundtrip, found 3 days ago
$439
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Stillwater, returning Mon, Jan 5, priced at $439 found 3 days ago
American Airlines
Sat, Jan 17 - Tue, Jan 27
ORD
Chicago
SWO
Stillwater
$448 Roundtrip, found 5 days ago
$448
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 17 from Chicago to Stillwater, returning Tue, Jan 27, priced at $448 found 5 days ago
American Airlines
Mon, Dec 29 - Thu, Jan 1
ORD
Chicago
SWO
Stillwater
$457 Roundtrip, found 14 hours ago
$457
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Mon, Dec 29 from Chicago to Stillwater, returning Thu, Jan 1, priced at $457 found 14 hours ago
American Airlines
Sat, Dec 13 - Mon, Jan 5
ORD
Chicago
SWO
Stillwater
$460 Roundtrip, found 21 hours ago
$460
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Stillwater, returning Mon, Jan 5, priced at $460 found 21 hours ago
American Airlines
Mon, Dec 29 - Thu, Jan 1
ORD
Chicago
SWO
Stillwater
$463 Roundtrip, found 14 hours ago
$463
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Mon, Dec 29 from Chicago to Stillwater, returning Thu, Jan 1, priced at $463 found 14 hours ago
American Airlines
Sat, Dec 13 - Mon, Jan 5
ORD
Chicago
SWO
Stillwater
$471 Roundtrip, found 2 days ago
$471
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Dec 13 from Chicago to Stillwater, returning Mon, Jan 5, priced at $471 found 2 days ago

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Alternative airports near Stillwater

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Stillwater Regional SWO. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $495
SWO
Stillwater Regional
CheapestClosest
Average driving time to city center8 min
Flights from $495
Flights from Chicago (ORD) to Stillwater (SWO)
Origin airport
O'Hare Intl.
Destination airport
Stillwater Regional
Airlines serving
American Airlines
Roundtrip price
$392
Distance
635 mi

Chicago to Stillwater Flights

The cheapest times to fly from Chicago to Stillwater

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Stillwater are during the month of December. You can find some of the cheapest flights from Chicago to Stillwater with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Stillwater

Sunday is one of the best days to book for cheap flights from Chicago to Stillwater: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Stillwater

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Stillwater in 2025. You can also book with separate airlines for your outbound and return journeys, from $197 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Stillwater flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Stillwater airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO) cost?
Lock in a cheap one-way flight from $197 or cheap return flight from $393 from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO)?
The cheapest month to fly from ORD to SWO is December, when there's less demand. Off-peak months are typically when you'll find lower airfares between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from ORD to SWO. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
How many flights per day from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO)?
Direct flights from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to SWO?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO)?
Choose a flight from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO) that takes off before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Stillwater from O'Hare Intl. Airport (ORD)?
If you're on a direct flight from O'Hare Intl. Airport (ORD) to Stillwater, Will Rogers World Airport (OKC) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO) last-minute?
Holding off until just before your departure to book a ticket from ORD to SWO often results in higher prices. Although you may find some last-minute deals, they aren't always guaranteed. Be flexible with your itinerary for the best chance of getting a bargain.
Is it cheaper to book an ORD to SWO flight and hotel package?
Booking an ORD to SWO flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Select from our extensive range of stays and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Stillwater Regional Airport (SWO)?
Usually, it's possible to reschedule or cancel your ORD to SWO flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.