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Stillwater

$207+ Cheap flights from Chicago (CHI) to Stillwater (SWO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWO
jul. 4 — jul. 111
sáb. 7/4
sáb. 7/11
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 junio 4, 2026.

This American Airlines deal was found by Cheapflights users on 6/2. 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.
jue. 7/23:49 pm
ORD
-
SWO
1 stop6h 58m
American Airlines
mar. 8/43:36 pm
SWO
-
ORD
1 stop5h 46m
American Airlines
Deal found 6/2$396
This American Airlines deal was found by Cheapflights users on 6/3. 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.
mié. 7/14:45 pm
ORD
-
SWO
1 stop6h 03m
American Airlines
mié. 7/83:45 pm
SWO
-
ORD
1 stop5h 37m
American Airlines
Deal found 6/3$407
This American Airlines deal was found by Cheapflights users on 6/3. 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.
vie. 7/38:30 am
ORD
-
SWO
1 stop6h 44m
American Airlines
dom. 7/53:45 pm
SWO
-
ORD
1 stop5h 37m
American Airlines
Deal found 6/3$413
This American Airlines deal was found by Cheapflights users on 5/31. 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.
mar. 6/168:19 am
ORD
-
SWO
1 stop6h 46m
American Airlines
sáb. 6/203:35 pm
SWO
-
ORD
1 stop7h 00m
American Airlines
Deal found 5/31$475
This American Airlines deal was found by Cheapflights users on 6/2. 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.
vie. 10/93:50 pm
ORD
-
SWO
1 stop6h 58m
American Airlines
dom. 10/113:52 pm
SWO
-
ORD
1 stop7h 20m
American Airlines
Deal found 6/2$597

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 junio 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$396
(American Airlines)

One-way from

$207
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Stillwater Searcy Fld flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Stillwater Searcy Fld flights.
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From Chicago (CHI) to Stillwater Searcy Fld
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One-way flight from Chicago (CHI) to Stillwater Searcy Fld
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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 junio 4, 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

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

jue. 7/2

3:49 pm-10:47 pm

1 stop6h 58m

Stillwater Searcy Fld

mar. 8/4

3:36 pm-9:22 pm

1 stop5h 46m

$396
Quickest round-trip

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

mié. 7/1

4:45 pm-10:48 pm

1 stop6h 03m

Stillwater Searcy Fld

mié. 7/8

3:45 pm-9:22 pm

1 stop5h 37m

$407

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

vie. 7/3

8:30 am-3:14 pm

1 stop6h 44m

Stillwater Searcy Fld

dom. 7/5

3:45 pm-9:22 pm

1 stop5h 37m

$413

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

mar. 6/16

8:19 am-3:05 pm

1 stop6h 46m

Stillwater Searcy Fld

sáb. 6/20

3:35 pm-10:35 pm

1 stop7h 00m

$475
Cheapest one-way
Quickest one-way

ChicagoStillwater

ORD - SWO

ORDSWO

Chicago O'Hare Intl

sáb. 9/12

3:50 pm-10:44 pm

1 stop6h 54m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

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 6h 58m. 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

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