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Stillwater

$393+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWO
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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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 February 12, 2026.

This American Airlines deal was found by Cheapflights users on 2/9. 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 3/144:49 pm
ORD
-
SWO
1 stop6h 10m
American Airlines
Sun 3/222:26 pm
SWO
-
ORD
1 stop5h 14m
American Airlines
Deal found 2/9$393
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 3/138:25 am
ORD
-
SWO
1 stop5h 31m
American Airlines
Tue 3/246:00 am
SWO
-
ORD
2 stops14h 07m
American Airlines
Deal found 2/9$428
This American Airlines deal was found by Cheapflights users on 2/11. 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 2/268:26 am
ORD
-
SWO
1 stop5h 10m
American Airlines
Mon 3/22:25 pm
SWO
-
ORD
1 stop6h 15m
American Airlines
Deal found 2/11$457
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 3/139:20 am
ORD
-
SWO
1 stop4h 36m
American Airlines
Sat 3/216:00 am
SWO
-
ORD
1 stop7h 04m
American Airlines
Deal found 2/9$463
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Wed 2/253:45 pm
ORD
-
SWO
1 stop7h 14m
American Airlines
Sun 3/16:00 am
SWO
-
ORD
1 stop5h 03m
American Airlines
Deal found 2/10$467
This American Airlines deal was found by Cheapflights users on 2/11. 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 5/73:07 pm
ORD
-
SWO
1 stop7h 46m
American Airlines
Sat 5/93:06 pm
SWO
-
ORD
1 stop7h 14m
American Airlines
Deal found 2/11$541
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Sun 3/156:54 am
ORD
-
SWO
2 stops16h 05m
American Airlines
Tue 3/246:00 am
SWO
-
ORD
2 stops14h 07m
American Airlines
Deal found 2/9$567
This American Airlines deal was found by Cheapflights users on 2/10. 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 2/144:49 pm
ORD
-
SWO
1 stop6h 10m
American Airlines
Sun 2/152:25 pm
SWO
-
ORD
1 stop7h 00m
American Airlines
Deal found 2/10$581
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 2/136:00 am
ORD
-
SWO
1 stop7h 36m
American Airlines
Sun 2/156:00 am
SWO
-
ORD
1 stop7h 04m
American Airlines
Deal found 2/9$589
This American Airlines deal was found by Cheapflights users on 2/9. 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.
Fri 3/138:25 am
ORD
-
SWO
1 stop5h 31m
American Airlines
Mon 3/236:00 am
SWO
-
ORD
2 stops14h 02m
American Airlines
Deal found 2/9$591

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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$393
(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 February 12, 2026.
Use the filters below to find and compare flights from Chicago to Stillwater that are best for you.

Fly from

Chicago

Fly to

Stillwater

Route

Depart

Return

Price

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sun 3/15

6:10 am-1:56 pm

1 stop7h 46m

Stillwater Searcy Fld

Tue 3/24

6:00 am-8:07 pm

2 stops14h 07m

$428

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Fri 3/13

8:25 am-1:56 pm

1 stop5h 31m

Stillwater Searcy Fld

Tue 3/24

6:00 am-8:07 pm

2 stops14h 07m

$428

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Thu 2/26

8:26 am-1:36 pm

1 stop5h 10m

Stillwater Searcy Fld

Mon 3/2

2:25 pm-8:40 pm

1 stop6h 15m

$457

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sun 3/15

6:10 am-1:56 pm

1 stop7h 46m

Stillwater Searcy Fld

Fri 3/20

2:26 pm-9:25 pm

1 stop6h 59m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sun 3/15

6:10 am-1:56 pm

1 stop7h 46m

Stillwater Searcy Fld

Mon 3/23

2:26 pm-7:40 pm

1 stop5h 14m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sun 3/15

6:10 am-1:56 pm

1 stop7h 46m

Stillwater Searcy Fld

Sun 3/22

2:26 pm-8:40 pm

1 stop6h 14m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sat 3/14

9:20 am-1:56 pm

1 stop4h 36m

Stillwater Searcy Fld

Mon 3/23

2:26 pm-9:25 pm

1 stop6h 59m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Fri 3/13

7:00 am-1:56 pm

1 stop6h 56m

Stillwater Searcy Fld

Mon 3/23

2:26 pm-7:40 pm

1 stop5h 14m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Fri 3/13

8:25 am-1:56 pm

1 stop5h 31m

Stillwater Searcy Fld

Fri 3/20

2:26 pm-8:40 pm

1 stop6h 14m

$463

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

Sat 3/14

7:20 am-1:56 pm

1 stop6h 36m

Stillwater Searcy Fld

Tue 3/24

2:26 pm-7:40 pm

1 stop5h 14m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 12 results
1
2
  • 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

What is the cheapest month to book a flight from Chicago to Stillwater?

Currently, December is the cheapest month in which you can book a flight from Chicago to Stillwater (average of $163). Flying from Chicago to Stillwater in June is currently the most expensive (average of $274). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 7h 46m. 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.

  • What is the cheapest month to book a flight from Chicago to Stillwater?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Stillwater (average of $163). Flying from Chicago to Stillwater in June is currently the most expensive (average of $274). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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