$220+ 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 11/30. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Nov 29 — Dec 61
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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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 Redmond to Chicago
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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 October 30, 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 October 30, 2026.
This Expedia deal was found by Cheapflights users on 10/26. 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.
Thu 12/103:38 pm -
1 stop6h 21m
Tue 12/156:00 am -
2 stops13h 01m
Deal found 10/26![Alaska Airlines logo]()
$467
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/267:59 pm -
1 stop7h 41m
Sun 1/37:00 am -
1 stop16h 41m
Deal found 10/28![Alaska Airlines logo]()
$494
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/267:59 pm -
1 stop7h 41m
Fri 1/18:59 pm -
1 stop14h 53m
Deal found 10/28![Alaska Airlines logo]()
$505
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/2512:20 pm -
1 stop15h 29m
Thu 12/314:08 pm -
2 stops21h 32m
Deal found 10/25![Multiple Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 10/28. 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 12/263:34 pm -
1 stop6h 25m
Sat 1/21:59 pm -
2 stops10h 52m
Deal found 10/28![Delta logo]()
$512
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/246:31 pm -
1 stop22h 23m
Sun 1/37:00 am -
1 stop16h 41m
Deal found 10/28![Alaska Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 10/28. 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 12/263:34 pm -
1 stop6h 25m
Thu 12/316:00 am -
1 stop16h 56m
Deal found 10/28![Delta logo]()
$515
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/267:59 pm -
1 stop7h 41m
Thu 12/316:00 am -
2 stops11h 21m
Deal found 10/28![Alaska Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 10/26. 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 12/106:21 am -
2 stops8h 29m
Tue 12/1510:24 am -
2 stops10h 36m
Deal found 10/26![Delta logo]()
$531
This Delta deal was found by Cheapflights users on 10/29. 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 12/107:40 pm -
2 stops11h 57m
Fri 12/181:41 pm -
2 stops11h 20m
Deal found 10/29![Delta logo]()
$555
This Delta deal was found by Cheapflights users on 10/29. 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 11/116:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops11h 26m
Deal found 10/29![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 10/29. 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 11/126:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops10h 32m
Deal found 10/29![Delta logo]()
$611
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 October 30, 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 October 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 1/162:41 pm -
1 stop7h 18m
Wed 1/208:00 am -
1 stop8h 01m
Deal found 10/28![Alaska Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 10/25. 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 12/2612:28 pm -
1 stop7h 59m
Fri 1/17:10 am -
2 stops9h 44m
Deal found 10/25![Delta logo]()
$547
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 2/38:25 am -
1 stop7h 34m
Sat 2/206:00 am -
1 stop8h 45m
Deal found 10/29![Alaska Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 10/29. 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 12/107:40 pm -
2 stops11h 57m
Fri 12/181:41 pm -
2 stops11h 20m
Deal found 10/29![Delta logo]()
$555
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/267:59 pm -
1 stop7h 41m
Fri 1/18:59 pm -
1 stop14h 53m
Deal found 10/28![Alaska Airlines logo]()
$505
This Delta deal was found by Cheapflights users on 10/29. 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 11/116:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops11h 26m
Deal found 10/29![Delta logo]()
$561
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 12/267:59 pm -
1 stop7h 41m
Thu 12/316:00 am -
2 stops11h 21m
Deal found 10/28![Alaska Airlines logo]()
$520
This Delta deal was found by Cheapflights users on 10/29. 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 11/126:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops10h 32m
Deal found 10/29![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 10/27. 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 11/107:27 pm -
2 stops11h 23m
Fri 11/1311:27 am -
2 stops14h 29m
Deal found 10/27![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 10/28. 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 12/246:06 am -
2 stops9h 18m
Fri 1/111:47 am -
2 stops12h 17m
Deal found 10/28![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 10/25. 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 11/96:20 am -
2 stops9h 44m
Fri 11/131:31 pm -
2 stops12h 25m
Deal found 10/25![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 10/27. 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 11/116:20 am -
2 stops9h 44m
Sun 11/159:30 am -
2 stops11h 17m
Deal found 10/27![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 10/28. 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 12/283:34 pm -
2 stops17h 27m
Fri 1/111:47 am -
2 stops12h 17m
Deal found 10/28![Delta logo]()
$716
This Delta deal was found by Cheapflights users on 10/25. 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 12/256:06 am -
2 stops9h 18m
Thu 12/3111:47 am -
2 stops11h 09m
Deal found 10/25![Delta logo]()
$913
This Delta deal was found by Cheapflights users on 10/26. 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 11/247:27 pm -
2 stops11h 23m
Sat 11/289:30 am -
2 stops11h 17m
Deal found 10/26![Delta logo]()
$992
This Delta deal was found by Cheapflights users on 10/28. 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 12/276:06 am -
2 stops9h 38m
Fri 1/19:58 am -
2 stops14h 06m
Deal found 10/28![Delta logo]()
$1,002
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/25. 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 11/96:20 am -
2 stops9h 44m
Fri 11/131:31 pm -
2 stops12h 25m
Deal found 10/25![Delta logo]()
$661
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/112:05 pm -
1 stop7h 22m
Sat 11/148:40 am -
1 stop6h 23m
Deal found 10/29![United Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 10/29. 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 11/111:20 pm -
1 stop8h 39m
Sat 11/143:47 pm -
2 stops9h 10m
Deal found 10/29![Delta logo]()
$556
This Delta deal was found by Cheapflights users on 10/29. 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 11/116:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops11h 26m
Deal found 10/29![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 10/27. 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 11/116:20 am -
2 stops9h 44m
Sun 11/159:30 am -
2 stops11h 17m
Deal found 10/27![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 10/29. 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 11/126:20 am -
2 stops9h 44m
Sat 11/141:31 pm -
2 stops10h 32m
Deal found 10/29![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 10/27. 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 11/125:15 am -
2 stops9h 24m
Fri 11/131:31 pm -
2 stops12h 25m
Deal found 10/27![Delta logo]()
$1,402
This Delta deal was found by Cheapflights users on 10/30. 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 11/181:20 pm -
1 stop8h 39m
Fri 11/203:47 pm -
2 stops9h 10m
Deal found 10/30![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 10/27. 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 11/2112:19 pm -
1 stop7h 28m
Fri 11/276:40 am -
1 stop7h 59m
Deal found 10/27![Delta logo]()
$559
This Delta deal was found by Cheapflights users on 10/27. 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 11/217:27 pm -
2 stops11h 23m
Fri 11/2711:05 am -
2 stops9h 52m
Deal found 10/27![Delta logo]()
$905
This Delta deal was found by Cheapflights users on 10/28. 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 11/231:20 pm -
1 stop8h 39m
Fri 11/276:40 am -
1 stop7h 59m
Deal found 10/28![Delta logo]()
$580
This Delta deal was found by Cheapflights users on 10/26. 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 11/247:27 pm -
2 stops11h 23m
Sat 11/289:30 am -
2 stops11h 17m
Deal found 10/26![Delta logo]()
$992
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 October 30, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/3012:20 pm -
2 stops25h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 10/25. 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 12/263:34 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$238
This WAYA deal was found by Cheapflights users on 10/25. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:20 am -
1 stop22h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$254
This Travelocity deal was found by Cheapflights users on 10/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:49 pm -
1 stop18h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 10/25. 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 12/286:50 pm -
1 stop8h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 10/25. 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 12/286:06 am -
2 stops12h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 10/25. 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 12/256:06 am -
2 stops9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$289
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:28 pm -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 10/29. 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 11/127:27 pm -
2 stops11h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 10/29. 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 11/127:27 pm -
2 stops11h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 10/25. 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 12/286:06 am -
2 stops9h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$371
This Alaska Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 11/294:17 pm -
1 stop18h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$415
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $450 (Expedia) |
One-way from | $220 (Kiwi.com) |
Popular in | October |
Cheapest in | December |
Average price | $719 |
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 October 30, 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
Quickest round-trip
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Sat 12/26
3:34 pm-11:59 pm
1 stop6h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$238
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Mon 11/30
12:20 pm-12:53 am
3 stops34h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$243
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Fri 12/25
5:15 am-5:59 pm
2 stops10h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$283
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Mon 11/30
7:49 pm-4:31 pm
1 stop18h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$283
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Mon 12/28
6:50 pm-4:57 am
1 stop8h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$284
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Mon 12/28
6:06 am-8:18 pm
2 stops12h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$289
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Fri 12/25
6:06 am-5:24 pm
2 stops9h 18m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$289
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Thu 11/12
12:28 pm-11:49 pm
1 stop9h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$326
RedmondChicago
RDM Bend/Redmond - ORD Chicago O'Hare Intl
RDMORD
Bend/Redmond
Thu 11/12
7:27 pm-9:04 am
2 stops11h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$331
RedmondChicago
RDM Bend/Redmond - MDW Chicago Midway
RDMMDW
Bend/Redmond
Thu 11/12
7:27 pm-8:50 am
2 stops11h 23m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$331
Showing 1-10 of 32 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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, December is the cheapest month in which you can book a flight from Redmond to Chicago (average of $339). Flying from Redmond to Chicago in November is currently the most expensive (average of $641). 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 typical for this route at the moment.
Redmond to Chicago flights typically cost between $434 and $735 in February.The cheapest round-trip price found within the last 5 days was $450 on Alaska Airlines (Feb 2-Feb 20).
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 October 30, 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.
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Food
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Food
7.0
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 30, 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 Redmond to Chicago by cabin class
Find flights from Redmond to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Redmond and Chicago flights
Browse other Redmond and Chicago flight options. Last updated on October 30, 2026.
Other flights from Redmond
Browse through other flights departing from Redmond. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$247 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$311 | Average$506 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$388 | Average$496 | FlexibilityNo cancel fee | On-time75% |