HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stillwater

$477+ Cheap flights from Chicago (CHI) to Stillwater (SWO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWO
May 19 — May 261
Tue 5/19
Tue 5/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Stillwater with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Stillwater

Cheapest flights from Chicago to Stillwater
Explore the most affordable flight options available from Chicago to Stillwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 19, 2026.

This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:45 am
ORD
-
SWO
1 stop4h 53m
American Airlines
Mon 5/43:08 pm
SWO
-
ORD
1 stop4h 49m
American Airlines
Deal found 4/15$477
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:53 pm
ORD
-
SWO
1 stop5h 55m
American Airlines
Wed 9/163:52 pm
SWO
-
ORD
1 stop7h 20m
American Airlines
Deal found 4/17$503
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/164:40 pm
ORD
-
SWO
1 stop6h 13m
American Airlines
Wed 5/203:06 pm
SWO
-
ORD
1 stop6h 39m
American Airlines
Deal found 4/18$514
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:53 pm
ORD
-
SWO
1 stop5h 55m
American Airlines
Fri 9/186:05 am
SWO
-
ORD
1 stop5h 06m
American Airlines
Deal found 4/17$530
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/184:44 pm
ORD
-
SWO
1 stop6h 04m
American Airlines
Fri 7/243:45 pm
SWO
-
ORD
1 stop5h 28m
American Airlines
Deal found 4/15$592
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/183:07 pm
ORD
-
SWO
1 stop7h 46m
American Airlines
Wed 5/203:06 pm
SWO
-
ORD
1 stop6h 08m
American Airlines
Deal found 4/18$649
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:40 am
ORD
-
SWO
2 stops11h 08m
American Airlines
Wed 9/163:52 pm
SWO
-
ORD
1 stop7h 20m
American Airlines
Deal found 4/17$712
This American Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:55 am
ORD
-
SWO
2 stops10h 58m
American Airlines
Tue 5/193:06 pm
SWO
-
ORD
1 stop6h 39m
American Airlines
Deal found 4/18$733
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:40 am
ORD
-
SWO
2 stops11h 08m
American Airlines
Fri 9/183:52 pm
SWO
-
ORD
1 stop6h 18m
American Airlines
Deal found 4/17$739

Find flight deals from Chicago to Stillwater

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Stillwater (SWO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$477
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Stillwater Searcy Fld flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Stillwater Searcy Fld flights.
Search Deals
From Chicago (CHI) to Stillwater Searcy Fld
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Stillwater that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 19, 2026.
Use the filters below to find and compare flights from Chicago to Stillwater that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Thu 4/30

9:45 am-2:38 pm

1 stop4h 53m

Stillwater Searcy Fld

Mon 5/4

3:08 pm-7:57 pm

1 stop4h 49m

$477

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Mon 9/14

4:53 pm-10:48 pm

1 stop5h 55m

Stillwater Searcy Fld

Wed 9/16

3:52 pm-11:12 pm

1 stop7h 20m

$503

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sat 5/16

9:45 am-2:36 pm

1 stop4h 51m

Stillwater Searcy Fld

Mon 5/18

3:06 pm-10:20 pm

1 stop7h 14m

$514

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sat 5/16

8:20 am-2:36 pm

1 stop6h 16m

Stillwater Searcy Fld

Tue 5/19

3:06 pm-9:14 pm

1 stop6h 08m

$514

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sun 5/17

8:20 am-2:36 pm

1 stop6h 16m

Stillwater Searcy Fld

Mon 5/18

3:06 pm-9:14 pm

1 stop6h 08m

$514

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Tue 9/15

8:20 am-2:54 pm

1 stop6h 34m

Stillwater Searcy Fld

Thu 9/17

6:05 am-11:11 am

1 stop5h 06m

$649

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Tue 9/15

11:40 am-10:48 pm

2 stops11h 08m

Stillwater Searcy Fld

Wed 9/16

3:52 pm-11:12 pm

1 stop7h 20m

$712

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Tue 9/15

11:40 am-10:48 pm

2 stops11h 08m

Stillwater Searcy Fld

Fri 9/18

3:52 pm-10:10 pm

1 stop6h 18m

$739

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Fri 5/8

4:40 pm-10:53 pm

1 stop6h 13m

Stillwater Searcy Fld

Sun 5/10

6:00 am-1:51 pm

2 stops7h 51m

$1,001

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Thu 5/7

6:57 am-2:36 pm

1 stop7h 39m

Stillwater Searcy Fld

Sun 5/10

6:00 am-1:51 pm

2 stops7h 51m

$1,003

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Chicago-Stillwater flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Stillwater flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Stillwater flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Stillwater flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Stillwater flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Stillwater

Have a flexible travel schedule? Discover the best time to fly to Stillwater from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Stillwater
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Stillwater. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Stillwater from Chicago?

    For a flight from Chicago to Stillwater, you will be flying into Searcy Fld. Stillwater Searcy Fld (SWO) is just 3.5 mi from the center of the city. Searcy Fld is the only Stillwater airport and it handles 0 inbound flights from Chicago per day. 0 airlines have flights to Stillwater Searcy Fld from Chicago on a regular basis.

  • How long is the flight from Chicago to Stillwater?

    Airlines like American Airlines fly from Chicago to Stillwater in about 4h 53m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago and Stillwater is about 635 mi.

  • Can I find deals for flights from Chicago to Stillwater that include hotel bookings?

    Yes. In addition to deals on Chicago to Stillwater flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Stillwater?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Stillwater.

  • Can I find deals for business class flights from Chicago to Stillwater?

    Yes. Cheapflights offers flight deals from Chicago to Stillwater by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Stillwater?

Book flights to Stillwater if you plan to visit one of these locations
Ponca City
Enid

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.