$64+ Cheap flights from Oklahoma to Chicago (CHI)
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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Sep 17 — Sep 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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 Oklahoma to Chicago
Cheapest
Best
Last-minute
One-way
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 August 18, 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 August 18, 2026.
This Southwest deal was found by Cheapflights users on 8/18. 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 9/195:05 am -
Nonstop1h 40m
Thu 9/248:55 pm -
Nonstop1h 55m
Deal found 8/18![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/106:23 pm -
Nonstop2h 17m
Thu 9/179:20 pm -
Nonstop2h 02m
Deal found 8/14![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/107:25 pm -
Nonstop2h 19m
Mon 9/1410:30 pm -
Nonstop2h 01m
Deal found 8/18![American Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 8/15. 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 11/35:30 am -
Nonstop1h 45m
Wed 11/47:05 am -
1 stop4h 10m
Deal found 8/15![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:05 pm -
1 stop6h 15m
Mon 9/148:55 pm -
Nonstop1h 55m
Deal found 8/17![Southwest logo]()
$187
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:48 pm -
Nonstop2h 43m
Sun 9/136:00 am -
Nonstop2h 41m
Deal found 8/13![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 10/11:23 pm -
1 stop10h 21m
Sat 10/36:25 am -
1 stop12h 18m
Deal found 8/13![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:16 pm -
Nonstop2h 29m
Sat 9/121:21 pm -
1 stop9h 38m
Deal found 8/13![Frontier logo]()
$189
This CheapOair deal was found by Cheapflights users on 8/13. 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.
Tue 9/84:16 pm -
1 stop6h 31m
Thu 9/1012:54 pm -
Nonstop2h 31m
Deal found 8/13![Frontier logo]()
$189
This CheapOair deal was found by Cheapflights users on 8/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:52 pm -
Nonstop2h 34m
Sun 10/2512:26 pm -
Nonstop2h 43m
Deal found 8/14![Frontier logo]()
$190
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:08 pm -
1 stop10h 35m
Mon 10/261:12 pm -
Nonstop2h 33m
Deal found 8/14![Frontier logo]()
$190
This Southwest deal was found by Cheapflights users on 8/13. 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 9/116:55 pm -
1 stop4h 55m
Fri 9/188:55 pm -
Nonstop1h 55m
Deal found 8/13![Southwest logo]()
$190
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 August 18, 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 August 18, 2026.
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 9/93:30 pm -
Nonstop1h 40m
Thu 9/105:55 am -
1 stop3h 55m
Deal found 8/18![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:49 pm -
1 stop6h 22m
Tue 11/36:30 am -
1 stop5h 34m
Deal found 8/14![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 10/86:00 am -
Nonstop2h 00m
Tue 10/138:00 pm -
Nonstop1h 59m
Deal found 8/16![United Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 11/59:57 pm -
1 stop12h 36m
Sun 11/88:37 pm -
1 stop9h 00m
Deal found 8/13![Multiple Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 8/16. 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.
Thu 9/104:40 pm -
1 stop6h 45m
Sat 9/126:05 pm -
Nonstop1h 55m
Deal found 8/16![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 8/16. 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.
Thu 11/55:00 am -
Nonstop1h 45m
Mon 11/910:15 am -
2 stops9h 00m
Deal found 8/16![Southwest logo]()
$192
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Thu 9/243:43 pm -
1 stop6h 21m
Fri 9/253:50 pm -
1 stop6h 54m
Deal found 8/14![American Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 8/13. 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 9/2211:19 am -
2 stops9h 37m
Wed 9/238:55 am -
1 stop5h 23m
Deal found 8/13![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 8/16. 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.
Tue 11/35:30 am -
Nonstop1h 45m
Fri 11/69:25 pm -
Nonstop2h 00m
Deal found 8/16![Southwest logo]()
$195
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Mon 9/212:40 pm -
Nonstop2h 08m
Mon 9/219:20 pm -
Nonstop2h 02m
Deal found 8/16![United Airlines logo]()
$257
This Delta deal was found by Cheapflights users on 8/13. 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 9/85:20 am -
1 stop7h 39m
Thu 9/106:10 am -
1 stop6h 21m
Deal found 8/13![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 8/13. 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 10/291:36 pm -
2 stops10h 16m
Sat 10/3110:55 am -
2 stops8h 24m
Deal found 8/13![Delta logo]()
$251
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Tue 11/246:26 pm -
Nonstop2h 04m
Fri 11/2712:29 pm -
Nonstop1h 58m
Deal found 8/17![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/13. 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 10/311:16 am -
2 stops11h 28m
Mon 10/51:19 pm -
2 stops10h 38m
Deal found 8/13![Delta logo]()
$251
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 11/233:10 pm -
Nonstop1h 55m
Fri 11/273:35 pm -
Nonstop2h 03m
Deal found 8/17![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
2 stops8h 10m
Mon 9/218:55 pm -
Nonstop1h 55m
Deal found 8/17![Southwest logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:57 pm -
1 stop12h 36m
Sun 11/158:37 pm -
1 stop9h 00m
Deal found 8/17![Multiple Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:45 pm -
2 stops6h 30m
Thu 9/175:25 am -
2 stops6h 55m
Deal found 8/17![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/13. 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 10/95:49 pm -
Nonstop2h 31m
Mon 10/128:10 pm -
Nonstop2h 21m
Deal found 8/13![United Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 12/25:30 pm -
1 stop5h 26m
Sat 12/511:28 am -
1 stop6h 46m
Deal found 8/15![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:40 am -
1 stop11h 59m
Sun 9/139:29 pm -
1 stop8h 12m
Deal found 8/17![Multiple Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 8/13. 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 9/263:00 pm -
2 stops8h 59m
Mon 9/283:55 pm -
1 stop6h 33m
Deal found 8/13![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 8/15. 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.
Wed 9/1612:05 pm -
2 stops8h 40m
Wed 9/2310:10 am -
2 stops5h 55m
Deal found 8/15![Southwest logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/810:24 pm -
1 stop14h 55m
Sun 9/139:29 pm -
1 stop27h 25m
Deal found 8/16![Multiple Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Thu 9/101:27 pm -
Nonstop2h 21m
Mon 9/147:45 pm -
Nonstop2h 21m
Deal found 8/17![United Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/26:05 am -
1 stop7h 33m
Sun 9/69:40 am -
1 stop5h 29m
Deal found 8/18![American Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 8/16. 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.
Fri 10/164:31 pm -
1 stop6h 02m
Tue 10/206:04 am -
1 stop6h 00m
Deal found 8/16![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 8/13. 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 9/254:05 pm -
1 stop6h 15m
Sat 9/2610:25 am -
2 stops9h 55m
Deal found 8/13![Southwest logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Wed 9/2310:53 pm -
1 stop21h 46m
Sun 9/279:29 pm -
1 stop8h 12m
Deal found 8/13![Multiple Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 8/13. 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 10/87:15 am -
Nonstop2h 25m
Sun 10/118:10 pm -
Nonstop2h 21m
Deal found 8/13![United Airlines logo]()
$328
Last-minute flights from Oklahoma to ChicagoDiscover last-minute flight deals from Oklahoma to Chicago. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Oklahoma to Chicago. Data last updated August 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sat 9/512:05 pm -
2 stops10h 42m
Sat 9/121:06 pm -
Nonstop2h 32m
Deal found 8/15![Frontier logo]()
$190
This CheapOair deal was found by Cheapflights users on 8/13. 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.
Tue 9/84:16 pm -
1 stop6h 31m
Thu 9/1012:54 pm -
Nonstop2h 31m
Deal found 8/13![Frontier logo]()
$189
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:48 pm -
Nonstop2h 43m
Sun 9/136:00 am -
Nonstop2h 41m
Deal found 8/13![Frontier logo]()
$188
This United Airlines deal was found by Cheapflights users on 8/14. 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 9/106:23 pm -
Nonstop2h 17m
Thu 9/179:20 pm -
Nonstop2h 02m
Deal found 8/14![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 9/107:25 pm -
Nonstop2h 19m
Mon 9/1410:30 pm -
Nonstop2h 01m
Deal found 8/18![American Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:05 pm -
1 stop6h 15m
Mon 9/148:55 pm -
Nonstop1h 55m
Deal found 8/17![Southwest logo]()
$187
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:16 pm -
Nonstop2h 29m
Sat 9/121:21 pm -
1 stop9h 38m
Deal found 8/13![Frontier logo]()
$189
This Southwest deal was found by Cheapflights users on 8/13. 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 9/116:55 pm -
1 stop4h 55m
Fri 9/188:55 pm -
Nonstop1h 55m
Deal found 8/13![Southwest logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Sat 9/122:48 pm -
1 stop9h 35m
Wed 9/167:11 am -
1 stop14h 01m
Deal found 8/16![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 8/18. 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 9/195:05 am -
Nonstop1h 40m
Thu 9/248:55 pm -
Nonstop1h 55m
Deal found 8/18![Southwest logo]()
$177
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:36 am -
Nonstop2h 23m
Mon 9/2812:54 pm -
Nonstop2h 31m
Deal found 8/13![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 8/13. 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.
Sun 9/2710:16 pm -
Nonstop2h 29m
Tue 9/296:00 am -
Nonstop2h 41m
Deal found 8/13![Frontier logo]()
$190
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 August 18, 2026.
Search for one-way flight options from Oklahoma to Chicago. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/158:30 pm -
1 stop27h 53m
Deal found 8/13![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Wed 9/98:30 pm -
1 stop27h 53m
Deal found 8/13![Frontier logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/148:30 pm -
1 stop27h 53m
Deal found 8/17![Frontier logo]()
$74
This Southwest deal was found by Cheapflights users on 8/13. 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 9/55:05 am -
Nonstop1h 40m
Deal found 8/13![Southwest logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 11/101:56 pm -
1 stop20h 05m
Deal found 8/13![Frontier logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Wed 11/111:56 pm -
1 stop20h 05m
Deal found 8/13![Frontier logo]()
$77
This Frontier deal was found by Cheapflights users on 8/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:45 pm -
1 stop10h 31m
Deal found 8/17![Frontier logo]()
$79
This Expedia deal was found by Cheapflights users on 8/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:56 pm -
1 stop20h 05m
Deal found 8/16![Frontier logo]()
$85
This Trip.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/58:20 pm -
1 stop17h 16m
Deal found 8/13![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:27 pm -
1 stop27h 57m
Deal found 8/14![Frontier logo]()
$87
This Southwest deal was found by Cheapflights users on 8/15. 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 9/145:35 am -
Nonstop1h 40m
Deal found 8/15![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/175:41 pm -
Nonstop2h 15m
Deal found 8/14![American Airlines logo]()
$89
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 August 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $163 (Southwest) |
One-way from | $64 (Kiwi.com) |
Popular in | June |
Cheapest in | September |
Average price | $347 |
Good round-trip deal | $311 or less |
Good one-way deal | $227 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 2,558,603 searches. Data last updated August 18, 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 - MDW Chicago Midway
TULMDW
Tulsa
Wed 9/9
3:30 pm-5:10 pm
Nonstop1h 40m
Chicago Midway
Thu 9/10
5:55 am-9:50 am
1 stop3h 55m
$187
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Thu 9/10
4:40 pm-11:25 pm
1 stop6h 45m
Chicago Midway
Sat 9/12
6:05 pm-8:00 pm
Nonstop1h 55m
$187
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Thu 11/5
5:00 am-6:45 am
Nonstop1h 45m
Chicago Midway
Mon 11/9
10:15 am-7:15 pm
2 stops9h 00m
$192
Quickest round-trip
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Tue 11/3
5:30 am-7:15 am
Nonstop1h 45m
Chicago Midway
Fri 11/6
9:25 pm-11:25 pm
Nonstop2h 00m
$195
TulsaChicago
TUL Tulsa - ORD Chicago O'Hare Intl
TULORD
Tulsa
Tue 10/20
12:49 pm-7:11 pm
1 stop6h 22m
Chicago O'Hare Intl
Tue 11/3
6:30 am-12:04 pm
1 stop5h 34m
$197
DallasChicago
DFW Dallas/Fort Worth - ORD Chicago O'Hare Intl
DFWORD
Dallas/Fort Worth
Tue 9/22
11:19 am-8:56 pm
2 stops9h 37m
Chicago O'Hare Intl
Wed 9/23
8:55 am-2:18 pm
1 stop5h 23m
$234
DallasChicago
DFW Dallas/Fort Worth - ORD Chicago O'Hare Intl
DFWORD
Dallas/Fort Worth
Tue 9/8
5:20 am-12:59 pm
1 stop7h 39m
Chicago O'Hare Intl
Thu 9/10
6:10 am-12:31 pm
1 stop6h 21m
$241
DallasChicago
DFW Dallas/Fort Worth - ORD Chicago O'Hare Intl
DFWORD
Dallas/Fort Worth
Thu 10/29
1:36 pm-11:52 pm
2 stops10h 16m
Chicago O'Hare Intl
Sat 10/31
10:55 am-7:19 pm
2 stops8h 24m
$251
DallasChicago
DFW Dallas/Fort Worth - MDW Chicago Midway
DFWMDW
Dallas/Fort Worth
Sat 10/3
11:16 am-10:44 pm
2 stops11h 28m
Chicago Midway
Mon 10/5
1:19 pm-11:57 pm
2 stops10h 38m
$251
TulsaChicago
TUL Tulsa - MDW Chicago Midway
TULMDW
Tulsa
Sat 9/19
6:00 am-2:10 pm
2 stops8h 10m
Chicago Midway
Mon 9/21
8:55 pm-10:50 pm
Nonstop1h 55m
$255
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.
OKC-ORD
TUL-MDW
DFW-RFD
DFW-ORD
TUL-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
OKC-ORD
TUL-MDW
DFW-RFD
DFW-ORD
What is the cheapest month to book a flight from Oklahoma to Chicago?
Currently, September is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $339). 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 August 18, 2026.
It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 21% 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 August 18, 2026.
The most flights from USOK to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 $285 and $435 in September.The cheapest round-trip price found within the last 5 days was $261 on Southwest (Sep 26-Sep 28).
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 August 15, 2026.
Travelers seeking maximum savings on their Oklahoma to Chicago flight should consider departing on Wednesday afternoons 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
Lansing
Merrillville
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
Other flight options
Popular flights
Top destinations
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 August 18, 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 August 18, 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 4 airlines flying from Oklahoma to Chicago
Discover the top 4 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 2,558,603 searches. Data last updated August 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$166 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$384 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$427 | FlexibilityNo cancel fee | On-time63% |