$218+ Cheap flights from Redmond (RDM) 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Redmond 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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Cheapest flights from Redmond to ChicagoExplore the most affordable flight options available from Redmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
Explore the most affordable flight options available from Redmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:35 pm -
1 stop25h 15m
Sat 10/249:00 am -
1 stop10h 29m
Deal found 9/10![Alaska Airlines logo]()
$423
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:16 am -
2 stops15h 43m
Sat 12/59:00 am -
2 stops15h 08m
Deal found 9/15![Alaska Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 9/13. 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 10/206:10 am -
2 stops15h 37m
Tue 10/277:15 pm -
1 stop6h 44m
Deal found 9/13![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 9/12. 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 12/210:55 am -
1 stop9h 03m
Sat 12/55:00 am -
1 stop10h 17m
Deal found 9/12![American Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/131:52 pm -
1 stop7h 08m
Tue 10/2012:40 pm -
1 stop7h 32m
Deal found 9/13![United Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 9/13. 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 10/131:26 pm -
1 stop8h 08m
Tue 10/207:00 am -
2 stops13h 50m
Deal found 9/13![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/217:33 pm -
2 stops10h 08m
Tue 10/273:30 pm -
2 stops9h 36m
Deal found 9/13![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 9/13. 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 10/207:33 pm -
2 stops11h 11m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 9/12. 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 12/26:21 am -
2 stops9h 40m
Sat 12/51:41 pm -
2 stops11h 20m
Deal found 9/12![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 9/13. 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.
Mon 10/197:33 pm -
2 stops11h 59m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 9/13. 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 10/207:33 pm -
2 stops11h 59m
Mon 10/261:27 pm -
2 stops11h 39m
Deal found 9/13![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:05 am -
2 stops9h 42m
Tue 10/2010:12 am -
2 stops10h 38m
Deal found 9/11![Delta logo]()
$535
Best flights from Redmond to ChicagoDiscover carefully curated flight deals from Redmond to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
Discover carefully curated flight deals from Redmond to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/168:25 am -
1 stop13h 34m
Wed 1/206:57 pm -
1 stop16h 51m
Deal found 9/10![Alaska Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/217:33 pm -
2 stops11h 59m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$465
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/75:00 am -
1 stop8h 00m
Tue 10/207:00 am -
1 stop7h 50m
Deal found 9/12![United Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 9/15. 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 12/27:40 pm -
2 stops11h 57m
Sat 12/512:39 pm -
2 stops11h 30m
Deal found 9/15![Delta logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:22 pm -
2 stops22h 31m
Tue 11/32:07 pm -
1 stop6h 34m
Deal found 9/11![Alaska Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 10/301:26 pm -
1 stop8h 08m
Tue 11/312:30 pm -
2 stops11h 32m
Deal found 9/14![Delta logo]()
$506
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/238:25 am -
1 stop7h 34m
Wed 1/278:00 am -
2 stops9h 26m
Deal found 9/13![Alaska Airlines logo]()
$529
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 10/237:33 pm -
2 stops11h 11m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 9/13. 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 10/227:33 pm -
2 stops11h 11m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 12/76:21 am -
2 stops8h 29m
Sat 12/1212:39 pm -
2 stops11h 30m
Deal found 9/14![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 9/15. 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 10/227:33 pm -
2 stops11h 20m
Sun 10/256:35 am -
1 stop8h 11m
Deal found 9/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:33 pm -
2 stops10h 08m
Sun 10/186:35 am -
1 stop8h 11m
Deal found 9/10![Delta logo]()
$532
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:05 am -
2 stops9h 42m
Tue 10/2010:12 am -
2 stops10h 38m
Deal found 9/11![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 11/207:27 pm -
2 stops11h 37m
Mon 11/237:17 pm -
1 stop6h 39m
Deal found 9/14![Delta logo]()
$552
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 11/121:17 pm -
1 stop8h 42m
Mon 11/163:47 pm -
2 stops9h 10m
Deal found 9/14![Delta logo]()
$552
This Delta deal was found by Cheapflights users on 9/12. 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 10/237:33 pm -
2 stops10h 08m
Sun 11/17:35 am -
1 stop6h 10m
Deal found 9/12![Delta logo]()
$552
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 12/117:40 pm -
2 stops11h 57m
Sun 12/139:37 am -
2 stops11h 23m
Deal found 9/13![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 9/14. 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.
Wed 12/96:21 am -
2 stops8h 29m
Sun 12/139:37 am -
2 stops11h 23m
Deal found 9/14![Delta logo]()
$567
This Delta deal was found by Cheapflights users on 9/15. 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 10/157:33 pm -
2 stops11h 11m
Thu 10/2212:49 pm -
2 stops12h 17m
Deal found 9/15![Delta logo]()
$575
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:15 am -
2 stops10h 18m
Tue 9/299:29 am -
2 stops11h 15m
Deal found 9/11![Delta logo]()
$620
This Delta deal was found by Cheapflights users on 9/12. 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.
Sun 9/276:15 am -
2 stops10h 18m
Thu 10/11:19 pm -
2 stops12h 39m
Deal found 9/12![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/57:24 pm -
2 stops12h 08m
Thu 10/89:29 am -
2 stops11h 21m
Deal found 9/15![Delta logo]()
$644
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated September 15, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:20 am -
1 stop7h 45m
Tue 10/2012:40 pm -
1 stop7h 32m
Deal found 9/11![United Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/131:52 pm -
1 stop7h 08m
Tue 10/2012:40 pm -
1 stop7h 32m
Deal found 9/13![United Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 9/13. 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 10/131:26 pm -
1 stop8h 08m
Tue 10/207:00 am -
2 stops13h 50m
Deal found 9/13![Delta logo]()
$460
This Delta deal was found by Cheapflights users on 9/13. 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 10/137:33 pm -
2 stops11h 59m
Tue 10/2010:12 am -
2 stops10h 38m
Deal found 9/13![Delta logo]()
$466
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:26 pm -
1 stop8h 08m
Sun 10/186:35 am -
1 stop8h 11m
Deal found 9/10![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 9/13. 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.
Mon 10/197:33 pm -
2 stops11h 59m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$511
This Delta deal was found by Cheapflights users on 9/13. 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 10/206:10 am -
2 stops15h 37m
Tue 10/277:15 pm -
1 stop6h 44m
Deal found 9/13![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 9/13. 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 10/207:33 pm -
2 stops11h 11m
Tue 10/2712:27 pm -
2 stops13h 32m
Deal found 9/13![Delta logo]()
$465
This Delta deal was found by Cheapflights users on 9/13. 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 10/207:33 pm -
2 stops11h 59m
Mon 10/261:27 pm -
2 stops11h 39m
Deal found 9/13![Delta logo]()
$512
This Alaska Airlines deal was found by Cheapflights users on 9/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:35 pm -
1 stop25h 15m
Sat 10/249:00 am -
1 stop10h 29m
Deal found 9/10![Alaska Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/217:33 pm -
2 stops10h 08m
Tue 10/273:30 pm -
2 stops9h 36m
Deal found 9/13![Delta logo]()
$465
This Alaska Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:22 pm -
2 stops22h 31m
Tue 11/32:07 pm -
1 stop6h 34m
Deal found 9/11![Alaska Airlines logo]()
$478
One-way flights from Redmond to ChicagoSearch for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:52 pm -
1 stop9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:33 pm -
2 stops11h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$223
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:50 pm -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![American Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:21 am -
2 stops9h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Delta logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/232:46 pm -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 9/12. 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 12/166:21 am -
2 stops9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 9/231:44 pm -
1 stop8h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:24 pm -
2 stops11h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 10/181:26 pm -
1 stop8h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/2812:20 pm -
1 stop15h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:44 pm -
1 stop8h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:20 pm -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![United Airlines logo]()
$316
Find flight deals from Redmond to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Redmond (RDM) to Chicago (CHI). 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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $423 (Alaska Airlines) |
One-way from | $218 (United Airlines) |
Popular in | January |
Cheapest in | December |
Average price | $483 |
Cheapflights Fare Finder
Customize your flight search to find flights from Redmond 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 September 15, 2026.
Use the filters below to find and compare flights from Redmond to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Sat 10/10
7:33 pm-8:53 am
2 stops11h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$223
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Wed 12/16
6:21 am-6:06 pm
2 stops9h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$223
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Wed 12/16
6:21 am-6:01 pm
2 stops9h 40m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$265
Quickest round-trip
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Wed 9/23
1:44 pm-11:57 pm
1 stop8h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$266
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Wed 9/23
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$271
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Sun 10/4
7:20 pm-6:56 am
1 stop9h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$295
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Mon 9/28
1:44 pm-11:57 pm
1 stop8h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$315
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Sun 11/29
7:27 pm-8:50 am
2 stops11h 23m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$419
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Sat 1/16
8:25 am-11:59 pm
1 stop13h 34m
Chicago O'Hare Intl
Wed 1/20
6:57 pm-9:48 am
1 stop16h 51m
$423
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Wed 10/21
7:33 pm-9:32 am
2 stops11h 59m
Chicago Midway
Tue 10/27
12:27 pm-11:59 pm
2 stops13h 32m
$465
Showing 1-10 of 30 resultsSorted by cheapest first
Compare providers for flights from Redmond to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Redmond to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Redmond-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Redmond-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Redmond-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Redmond-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Redmond-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Redmond to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Redmond with our price prediction graph.
RDM-CHI
RDM-ORD
RDM-MDW
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 Redmond to Chicago
RDM-CHI
RDM-ORD
RDM-MDW
What is the cheapest month to book a flight from Redmond to Chicago?
Currently, November is the cheapest month in which you can book a flight from Redmond to Chicago (average of $320). Flying from Redmond to Chicago in February is currently the most expensive (average of $572). 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.
How much does it cost to fly round-trip from Redmond to Chicago?
Airfare is below average for this route at the moment.
Redmond to Chicago flights typically cost between $440 and $560 in October.The cheapest round-trip price found within the last 5 days was $423 on Alaska Airlines (Oct 21-Oct 24).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2026.
Read reviews from past customers who have flown Alaska Airlines,Delta, andUnited Airlines from Redmond to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Food
7.0
Boarding
8.1
Entertainment
7.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Redmond 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
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Other flights to Chicago
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Redmond and Chicago flights
Browse other Redmond and Chicago flight options. Last updated on September 15, 2026.
Other flights from Redmond
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Popular flight searches
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Top 3 airlines flying from Redmond to Chicago
Discover the top 3 airlines that operate flights from Redmond 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 September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$247 | Average$378 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$311 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$320 | Average$486 | FlexibilityNo cancel fee | On-time75% |