$280+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SWO
Nov 10 — Nov 171
Round-trip
1 adult, Economy
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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
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Best
Last-minute
One-way
Cheapest flights from Chicago to StillwaterExplore 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 October 11, 2026.
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 October 11, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 10/302:50 pm -
1 stop7h 56m
Sun 11/13:22 pm -
1 stop5h 50m
Deal found 10/10![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/242:50 pm -
1 stop7h 56m
Wed 10/283:09 pm -
1 stop7h 51m
Deal found 10/9![American Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/105:16 pm -
1 stop5h 30m
Tue 10/273:09 pm -
1 stop5h 24m
Deal found 10/7![American Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Fri 10/303:09 pm -
1 stop5h 29m
Deal found 10/7![American Airlines logo]()
$570
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Sat 10/316:05 am -
2 stops11h 54m
Deal found 10/7![American Airlines logo]()
$704
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Tue 10/273:09 pm -
2 stops15h 04m
Deal found 10/7![American Airlines logo]()
$728
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/109:40 am -
1 stop4h 59m
Fri 10/306:05 am -
2 stops11h 33m
Deal found 10/7![American Airlines logo]()
$738
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/105:16 pm -
1 stop5h 30m
Sun 11/16:00 am -
2 stops15h 00m
Deal found 10/7![American Airlines logo]()
$780
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Sun 11/16:00 am -
2 stops15h 00m
Deal found 10/7![American Airlines logo]()
$784
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/108:14 am -
1 stop6h 25m
Mon 10/263:09 pm -
2 stops15h 17m
Deal found 10/7![American Airlines logo]()
$788
Best flights from Chicago to StillwaterDiscover carefully curated flight deals from Chicago to Stillwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 11, 2026.
Discover carefully curated flight deals from Chicago to Stillwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 11, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 10/302:50 pm -
1 stop7h 56m
Sun 11/13:22 pm -
1 stop5h 50m
Deal found 10/10![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/242:50 pm -
1 stop7h 56m
Wed 10/283:09 pm -
1 stop7h 51m
Deal found 10/9![American Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 10/7. 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 11/199:00 am -
1 stop5h 51m
Fri 11/203:21 pm -
1 stop6h 51m
Deal found 10/7![American Airlines logo]()
$894
This American Airlines deal was found by Cheapflights users on 10/7. 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 11/186:59 am -
1 stop7h 53m
Fri 11/206:00 am -
2 stops10h 00m
Deal found 10/7![American Airlines logo]()
$1,002
Last-minute flights from Chicago to StillwaterDiscover last-minute flight deals from Chicago to Stillwater. Data last updated October 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Stillwater. Data last updated October 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Fri 10/303:09 pm -
1 stop5h 29m
Deal found 10/7![American Airlines logo]()
$570
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Sat 10/316:05 am -
2 stops11h 54m
Deal found 10/7![American Airlines logo]()
$704
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Tue 10/273:09 pm -
2 stops15h 04m
Deal found 10/7![American Airlines logo]()
$728
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/86:55 am -
1 stop7h 44m
Sun 11/16:00 am -
2 stops15h 00m
Deal found 10/7![American Airlines logo]()
$784
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/105:16 pm -
1 stop5h 30m
Tue 10/273:09 pm -
1 stop5h 24m
Deal found 10/7![American Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/109:40 am -
1 stop4h 59m
Fri 10/306:05 am -
2 stops11h 33m
Deal found 10/7![American Airlines logo]()
$738
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/105:16 pm -
1 stop5h 30m
Sun 11/16:00 am -
2 stops15h 00m
Deal found 10/7![American Airlines logo]()
$780
This American Airlines deal was found by Cheapflights users on 10/7. 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 10/108:14 am -
1 stop6h 25m
Mon 10/263:09 pm -
2 stops15h 17m
Deal found 10/7![American Airlines logo]()
$788
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/242:50 pm -
1 stop7h 56m
Wed 10/283:09 pm -
1 stop7h 51m
Deal found 10/9![American Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 10/302:50 pm -
1 stop7h 56m
Sun 11/13:22 pm -
1 stop5h 50m
Deal found 10/10![American Airlines logo]()
$506
One-way flights from Chicago to StillwaterSearch for one-way flight options from Chicago to Stillwater. Find affordable one-way fares based on user searches. Data last updated October 11, 2026.
Search for one-way flight options from Chicago to Stillwater. Find affordable one-way fares based on user searches. Data last updated October 11, 2026.
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/245:16 pm -
1 stop5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/256:55 am -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/9. 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 10/3010:50 pm -
2 stops15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Tue 10/278:10 am -
2 stops14h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$557
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Mon 10/269:41 pm -
2 stops16h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![American Airlines logo]()
$571
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 October 11, 2026.
Round-trip from | $506 (American Airlines) |
|---|---|
One-way from | $280 (American Airlines) |
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 7,457,451 searches. Data last updated October 11, 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
Cheapest round-trip
Quickest round-trip
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Sat 10/24
5:16 pm-10:46 pm
1 stop5h 30m
Stillwater Searcy Fld
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Fri 10/30
3:50 pm-10:46 pm
1 stop6h 56m
Stillwater Searcy Fld
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Wed 10/28
6:55 am-2:39 pm
1 stop7h 44m
Stillwater Searcy Fld
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$280
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Mon 10/26
3:50 pm-10:46 pm
1 stop6h 56m
Stillwater Searcy Fld
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$339
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Fri 10/30
2:50 pm-10:46 pm
1 stop7h 56m
Stillwater Searcy Fld
Sun 11/1
3:22 pm-9:12 pm
1 stop5h 50m
$506
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Sat 10/24
2:50 pm-10:46 pm
1 stop7h 56m
Stillwater Searcy Fld
Wed 10/28
3:09 pm-11:00 pm
1 stop7h 51m
$525
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Thu 11/19
9:00 am-2:51 pm
1 stop5h 51m
Stillwater Searcy Fld
Fri 11/20
3:21 pm-10:12 pm
1 stop6h 51m
$894
ChicagoStillwater
ORD Chicago O'Hare Intl - SWO Stillwater Searcy Fld
ORDSWO
Chicago O'Hare Intl
Wed 11/18
6:59 am-2:52 pm
1 stop7h 53m
Stillwater Searcy Fld
Fri 11/20
6:00 am-4:00 pm
2 stops10h 00m
$1,002
Sorted by cheapest first
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.
CHI-SWO
ORD-SWO
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
CHI-SWO
ORD-SWO
No data available for this route at this time. Please check back soon.
Related info for your journey
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