$127+ Cheap flights from Oklahoma to Chicago (CHI)
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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Oklahoma to Chicago 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
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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 Oklahoma to Chicago
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Cheapest flights from Oklahoma to ChicagoExplore the most affordable flight options available from Oklahoma to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Oklahoma to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:19 pm -
1 stop28h 02m
Mon 11/166:30 am -
1 stop12h 54m
Deal found 10/19![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:19 pm -
1 stop28h 02m
Tue 11/106:30 am -
1 stop12h 54m
Deal found 10/19![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:19 pm -
1 stop28h 02m
Tue 11/176:30 am -
1 stop12h 54m
Deal found 10/16![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:29 pm -
1 stop28h 25m
Mon 12/77:25 am -
1 stop12h 08m
Deal found 10/16![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:19 pm -
1 stop28h 02m
Wed 11/116:30 am -
1 stop12h 54m
Deal found 10/17![Frontier logo]()
$230
This CheapOair deal was found by Cheapflights users on 10/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:44 pm -
1 stop10h 29m
Sat 11/146:30 am -
1 stop12h 54m
Deal found 10/16![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:19 pm -
1 stop28h 02m
Mon 11/98:30 pm -
2 stops22h 54m
Deal found 10/15![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/158:29 pm -
2 stops19h 01m
Thu 12/177:00 am -
1 stop12h 34m
Deal found 10/19![Frontier logo]()
$251
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1410:15 am -
Nonstop2h 10m
Wed 12/1612:55 pm -
Nonstop2h 14m
Deal found 10/19![United Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:05 pm -
Nonstop1h 55m
Wed 12/168:45 pm -
Nonstop2h 00m
Deal found 10/19![Southwest logo]()
$253
This American Airlines deal was found by Cheapflights users on 10/19. 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 12/1410:47 am -
Nonstop2h 16m
Wed 12/163:11 pm -
Nonstop2h 13m
Deal found 10/19![American Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:30 am -
Nonstop1h 45m
Sat 12/56:20 pm -
Nonstop2h 00m
Deal found 10/19![Southwest logo]()
$265
Best flights from Oklahoma to ChicagoDiscover carefully curated flight deals from Oklahoma to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Oklahoma to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:30 pm -
Nonstop1h 55m
Tue 12/158:50 pm -
Nonstop2h 10m
Deal found 10/15![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1410:00 am -
Nonstop2h 20m
Tue 12/157:55 pm -
Nonstop2h 29m
Deal found 10/15![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 am -
1 stop4h 55m
Mon 11/235:30 am -
1 stop7h 08m
Deal found 10/15![Delta logo]()
$309
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 11/103:16 pm -
1 stop7h 59m
Tue 11/176:59 am -
1 stop7h 47m
Deal found 10/15![American Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 10/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:20 am -
Nonstop2h 00m
Thu 12/1010:15 am -
Nonstop2h 10m
Deal found 10/16![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/231:27 pm -
Nonstop2h 16m
Wed 12/301:30 pm -
Nonstop2h 42m
Deal found 10/16![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:59 pm -
1 stop7h 54m
Fri 12/46:20 am -
2 stops9h 45m
Deal found 10/15![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:45 pm -
Nonstop2h 00m
Mon 11/239:25 pm -
Nonstop2h 20m
Deal found 10/15![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:33 pm -
Nonstop2h 26m
Sun 11/229:25 pm -
Nonstop2h 29m
Deal found 10/16![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 10/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:15 am -
Nonstop1h 55m
Wed 12/309:45 pm -
Nonstop2h 25m
Deal found 10/16![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 10/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:59 pm -
2 stops8h 36m
Wed 12/163:47 pm -
2 stops8h 08m
Deal found 10/16![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:10 pm -
1 stop9h 35m
Mon 11/239:25 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:25 am -
Nonstop2h 05m
Sat 1/28:45 am -
Nonstop2h 30m
Deal found 10/19![United Airlines logo]()
$345
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:30 am -
Nonstop1h 45m
Fri 12/48:45 pm -
Nonstop1h 55m
Deal found 10/15![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
Nonstop1h 45m
Mon 11/99:25 pm -
Nonstop2h 05m
Deal found 10/14![Southwest logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/213:21 pm -
1 stop7h 12m
Sun 11/226:59 am -
1 stop7h 52m
Deal found 10/16![American Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:14 pm -
1 stop6h 40m
Wed 11/252:44 pm -
2 stops7h 49m
Deal found 10/19![Delta logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:33 pm -
Nonstop2h 02m
Sun 1/36:50 am -
1 stop6h 13m
Deal found 10/19![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:55 am -
1 stop6h 25m
Thu 11/1210:20 am -
Nonstop2h 15m
Deal found 10/15![Southwest logo]()
$299
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/33:16 pm -
1 stop7h 14m
Sat 11/78:30 am -
1 stop6h 16m
Deal found 10/19![American Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:56 pm -
1 stop5h 03m
Sat 1/210:30 am -
2 stops7h 37m
Deal found 10/19![Delta logo]()
$440
This Southwest deal was found by Cheapflights users on 10/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/185:05 am -
Nonstop1h 45m
Sun 12/209:50 am -
Nonstop2h 00m
Deal found 10/16![Southwest logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 10/303:09 pm -
1 stop5h 29m
Tue 11/34:53 pm -
1 stop6h 00m
Deal found 10/15![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 10/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/11:40 pm -
1 stop6h 15m
Tue 12/17:45 pm -
Nonstop2h 11m
Deal found 10/16![United Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 10/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:11 am -
2 stops10h 06m
Sun 11/225:30 am -
1 stop6h 43m
Deal found 10/16![Delta logo]()
$453
This American Airlines deal was found by Cheapflights users on 10/14. 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 10/2712:41 pm -
Nonstop2h 19m
Wed 10/2811:45 am -
Nonstop2h 39m
Deal found 10/14![American Airlines logo]()
$525
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/183:05 pm -
Nonstop1h 50m
Wed 11/259:50 am -
Nonstop2h 00m
Deal found 10/19![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 10/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:01 pm -
1 stop5h 45m
Sun 11/228:43 am -
Nonstop2h 23m
Deal found 10/17![United Airlines logo]()
$455
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/16:00 am -
1 stop5h 05m
Thu 11/53:52 pm -
1 stop7h 25m
Deal found 10/16![American Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/145:40 am -
Nonstop1h 40m
Sun 1/1710:55 am -
Nonstop1h 55m
Deal found 10/15![Southwest logo]()
$342
Last-minute flights from Oklahoma to ChicagoDiscover last-minute flight deals from Oklahoma to Chicago. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Oklahoma to Chicago. Data last updated October 20, 2026 and is based on user searches.
This deal was found by Cheapflights users on 10/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop6h 08m
Mon 11/25:00 am -
1 stop5h 21m
Deal found 10/15![American Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:05 am -
Nonstop1h 55m
Mon 11/99:25 pm -
Nonstop2h 20m
Deal found 10/15![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 10/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
Nonstop1h 45m
Mon 11/95:20 am -
1 stop5h 10m
Deal found 10/14![Southwest logo]()
$299
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/65:43 pm -
Nonstop2h 22m
Mon 11/94:45 pm -
Nonstop2h 13m
Deal found 10/16![American Airlines logo]()
$289
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/1210:50 am -
Nonstop2h 02m
Thu 11/197:15 pm -
Nonstop2h 15m
Deal found 10/19![American Airlines logo]()
$253
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/1210:50 am -
Nonstop2h 02m
Mon 11/163:00 pm -
Nonstop2h 13m
Deal found 10/19![American Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:05 am -
Nonstop1h 55m
Mon 11/168:50 pm -
Nonstop2h 15m
Deal found 10/19![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:05 am -
Nonstop1h 55m
Sun 11/159:25 pm -
Nonstop2h 20m
Deal found 10/19![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:20 am -
Nonstop2h 00m
Mon 11/239:25 pm -
Nonstop2h 20m
Deal found 10/18![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:45 pm -
Nonstop2h 00m
Mon 11/239:25 pm -
Nonstop2h 20m
Deal found 10/19![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:00 am -
Nonstop1h 45m
Sun 11/229:25 pm -
Nonstop2h 05m
Deal found 10/19![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:05 am -
Nonstop1h 45m
Mon 11/239:25 pm -
Nonstop2h 05m
Deal found 10/18![Southwest logo]()
$280
One-way flights from Oklahoma to ChicagoSearch for one-way flight options from Oklahoma to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Oklahoma to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:30 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$127
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
Nonstop2h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:20 am -
Nonstop2h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:59 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$137
This Trip.com deal was found by Cheapflights users on 10/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:19 pm -
1 stop28h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:29 pm -
1 stop28h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:05 am -
Nonstop1h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$145
This American Airlines deal was found by Cheapflights users on 10/16. 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 12/231:37 pm -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$145
This United Airlines deal was found by Cheapflights users on 10/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
Nonstop2h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 10/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:59 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/101:00 pm -
2 stops6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$150
Find flight deals from Oklahoma to Chicago
Keep the following information in mind while searching for Oklahoma to Chicago flight deals. Data was last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $200 (Kiwi.com) |
One-way from | $127 (Southwest) |
Popular in | June |
Cheapest in | August |
Average price | $402 |
Good round-trip deal | $324 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oklahoma to Chicago 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 20, 2026.
Use the filters below to find and compare flights from Oklahoma to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Mon 11/16
7:00 am-9:06 am
Nonstop2h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$127
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - MDW Chicago Midway
OKCMDW
Oklahoma City Will Rogers World
Wed 12/9
5:20 am-7:20 am
Nonstop2h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
Quickest round-trip
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - MDW Chicago Midway
OKCMDW
Oklahoma City Will Rogers World
Thu 12/10
3:30 pm-5:25 pm
Nonstop1h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - ORD Chicago O'Hare Intl
OKCORD
Oklahoma City Will Rogers World
Mon 11/23
8:29 pm-12:53 am
1 stop28h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Mon 11/16
4:20 pm-10:45 pm
2 stops6h 25m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$142
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - ORD Chicago O'Hare Intl
OKCORD
Oklahoma City Will Rogers World
Fri 11/20
7:00 am-9:18 am
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - ORD Chicago O'Hare Intl
OKCORD
Oklahoma City Will Rogers World
Mon 11/23
5:33 pm-7:59 pm
Nonstop2h 26m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - MDW Chicago Midway
OKCMDW
Oklahoma City Will Rogers World
Mon 11/23
5:05 am-7:00 am
Nonstop1h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Oklahoma CityChicago
OKC Oklahoma City Will Rogers World - ORD Chicago O'Hare Intl
OKCORD
Oklahoma City Will Rogers World
Sat 11/21
7:00 am-9:18 am
Nonstop2h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Fri 11/13
7:00 am-9:06 am
Nonstop2h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oklahoma to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oklahoma with our price prediction graph.
TUL-MDW
TUL-ORD
OKC-MDW
OKC-ORD
SWO-ORD
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 Oklahoma to Chicago
USOK-CHI
TUL-MDW
TUL-ORD
OKC-MDW
OKC-ORD
What is the cheapest month to book a flight from Oklahoma to Chicago?
Currently, April is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $352). Flying from Oklahoma to Chicago in July is currently the most expensive (average of $443). 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.
What is the cheapest time of day to fly from OK to CHI?
Find hourly flight availability from Oklahoma to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2026.
It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Oklahoma to Chicago
Explore weekly flight availability from Oklahoma to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 20, 2026.
The most flights from USOK to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Oklahoma to Chicago?
Airfare is below average for this route at the moment.
Oklahoma to Chicago flights typically cost between $318 and $548 in December.The cheapest round-trip price found within the last 5 days was $200 on Frontier (Dec 4-Dec 7).
How far ahead should I book a flight from Oklahoma to Chicago?
The price you pay for your flight from Oklahoma to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 77 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Oklahoma to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Oklahoma to Chicago. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Oklahoma to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Oklahoma to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
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Alternative routes for Oklahoma to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oklahoma to Chicago by cabin class
Find flights from Oklahoma to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oklahoma and Chicago flights
Browse other Oklahoma and Chicago flight options. Last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oklahoma to Chicago flights
Consider these flights traveling from Oklahoma to Chicago.
Top 3 airlines flying from Oklahoma to Chicago
Discover the top 3 airlines that operate flights from Oklahoma to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$177 | Average$412 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$394 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$408 | FlexibilityNo cancel fee | On-time63% |