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

View $197 flight on Wed, Dec 10, 2025Opens in a new window

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

Cheap Flights from Stillwater to Chicago (SWO-ORD)

Prices were available within the past 7 days and start at $197 for one-way flights and $415 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, Nov 17 - Tue, Nov 18
SWO
Stillwater
ORD
Chicago
$415 Roundtrip, found 1 day ago
$415
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Nov 17 from Stillwater to Chicago, returning Tue, Nov 18, priced at $415 found 1 day ago
American Airlines
Fri, Nov 14 - Sun, Nov 16
SWO
Stillwater
ORD
Chicago
$426 Roundtrip, found 4 days ago
$426
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 14 from Stillwater to Chicago, returning Sun, Nov 16, priced at $426 found 4 days ago
American Airlines
Wed, Dec 31 - Tue, Jan 13
SWO
Stillwater
ORD
Chicago
$446 Roundtrip, found 2 days ago
$446
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Dec 31 from Stillwater to Chicago, returning Tue, Jan 13, priced at $446 found 2 days ago
American Airlines
Thu, Dec 25 - Wed, Dec 31
SWO
Stillwater
ORD
Chicago
$454 Roundtrip, found 2 days ago
$454
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Dec 25 from Stillwater to Chicago, returning Wed, Dec 31, priced at $454 found 2 days ago
American Airlines
Mon, Nov 24 - Thu, Dec 11
SWO
Stillwater
ORD
Chicago
$463 Roundtrip, found 2 days ago
$463
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Nov 24 from Stillwater to Chicago, returning Thu, Dec 11, priced at $463 found 2 days ago
American Airlines
Thu, Dec 25 - Fri, Jan 9
SWO
Stillwater
ORD
Chicago
$471 Roundtrip, found 2 days ago
$471
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Dec 25 from Stillwater to Chicago, returning Fri, Jan 9, priced at $471 found 2 days ago
American Airlines
Wed, Dec 24 - Wed, Dec 31
SWO
Stillwater
ORD
Chicago
$476 Roundtrip, found 2 days ago
$476
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Dec 24 from Stillwater to Chicago, returning Wed, Dec 31, priced at $476 found 2 days ago
American Airlines
Sat, Feb 14 - Sun, Feb 22
SWO
Stillwater
ORD
Chicago
$483 Roundtrip, found 6 days ago
$483
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Feb 14 from Stillwater to Chicago, returning Sun, Feb 22, priced at $483 found 6 days ago
American Airlines
Sun, Nov 16 - Fri, Nov 21
SWO
Stillwater
ORD
Chicago
$485 Roundtrip, found 1 day ago
$485
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Nov 16 from Stillwater to Chicago, returning Fri, Nov 21, priced at $485 found 1 day ago
American Airlines
Sat, Nov 1 - Fri, Nov 21
SWO
Stillwater
ORD
Chicago
$493 Roundtrip, found 2 days ago
$493
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Nov 1 from Stillwater to Chicago, returning Fri, Nov 21, priced at $493 found 2 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $521
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $521
Flights from Stillwater (SWO) to Chicago (ORD)
Origin airport
Stillwater Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines
Roundtrip price
$414
Distance
635 mi

Stillwater to Chicago Flights

The cheapest times to fly from Stillwater to Chicago

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 Stillwater to Chicago are during the month of November. You can find some of the cheapest flights from Stillwater to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Stillwater to Chicago

Sunday is one of the best days to book for cheap flights from Stillwater to Chicago: 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 Stillwater to Chicago

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 Stillwater to Chicago 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 Stillwater to Chicago 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 Stillwater to Chicago 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 Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight from $197 or cheap return flight from $415 from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
Traveling in November is a good way to save, as it's the cheapest month for flights between SWO and ORD. You'll often find the lowest prices during the off-season.
Which airlines fly direct from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
You can't fly directly from Stillwater, OK (SWO-Stillwater Regional) to O'Hare Intl. Airport (ORD). However, you can find other airports that have nonstop flights. Hop on your plane at Will Rogers World Airport (OKC) and travel straight to Chicago without layovers.
What is the cheapest airline that flies from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from SWO to ORD. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
You'll have to hop on a flight with a layover when traveling from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from SWO to ORD?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, 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 Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Later departures are 22% more likely to be canceled.**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.
Is it cheaper to buy a plane ticket from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until right before your break to book a flight from SWO to ORD often results in higher prices. While you may come across some last-minute offers, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of snagging a bargain.
Is it cheaper to book a SWO to ORD flight and hotel package?
You'll typically save money by securing a SWO to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your ideal flights and accommodations, consider other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Stillwater Regional Airport (SWO) to O'Hare Intl. Airport (ORD)?
If you reserved your SWO to ORD flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

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*Available to One Key members.