$180+ Cheap flights from Redmond (RDM) 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
mai 31 — juin 71
Round-trip
1 adult, Economy
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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 mai 1, 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 mai 1, 2026.
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/277:00 am
RDM
- ORD
1 stop9h 50m
Alaska Airlines
mer. 6/39:00 am
ORD
- RDM
1 stop14h 37m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/28. 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.
mer. 6/171:25 pm
RDM
- ORD
1 stop8h 14m
Delta
mar. 6/237:37 pm
ORD
- RDM
1 stop6h 22m
Delta
Deal found 4/28![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/276:10 am
RDM
- ORD
2 stops10h 40m
Delta
mer. 6/36:20 pm
ORD
- RDM
1 stop6h 32m
Delta
Deal found 4/27![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/276:10 am
RDM
- ORD
2 stops10h 40m
Delta
mar. 6/27:12 am
ORD
- RDM
1 stop7h 23m
Delta
Deal found 4/27![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/281:59 pm
RDM
- ORD
1 stop8h 31m
American Airlines
mar. 6/23:22 pm
ORD
- RDM
1 stop9h 34m
American Airlines
Deal found 4/30![American Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 4/28. 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.
mer. 6/171:25 pm
RDM
- ORD
1 stop8h 14m
Delta
lun. 6/226:55 am
ORD
- RDM
1 stop7h 50m
Delta
Deal found 4/28![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 4/29. 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.
ven. 5/296:10 am
RDM
- ORD
2 stops13h 40m
Delta
mar. 6/27:45 pm
ORD
- RDM
1 stop5h 59m
Delta
Deal found 4/29![Delta logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
jeu. 5/281:53 pm
RDM
- ORD
1 stop7h 06m
Alaska Airlines
lun. 6/17:59 pm
ORD
- RDM
1 stop17h 38m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/277:20 pm
RDM
- MDW
2 stops11h 23m
Delta
mer. 6/31:22 pm
MDW
- RDM
2 stops11h 30m
Delta
Deal found 4/27![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 4/29. 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.
ven. 7/107:25 pm
RDM
- ORD
2 stops11h 10m
Delta
jeu. 7/166:55 am
ORD
- RDM
1 stop7h 40m
Delta
Deal found 4/29![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 7/17:25 pm
RDM
- MDW
2 stops11h 12m
Delta
dim. 7/51:49 pm
MDW
- RDM
2 stops12h 10m
Delta
Deal found 4/27![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 4/30. 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.
ven. 7/35:20 am
RDM
- MDW
2 stops10h 58m
Delta
mer. 7/81:18 pm
MDW
- RDM
2 stops12h 40m
Delta
Deal found 4/30![Delta logo]()
$479
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 mai 1, 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 mai 1, 2026.
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/276:10 am
RDM
- ORD
2 stops10h 40m
Delta
mer. 6/36:20 pm
ORD
- RDM
1 stop6h 32m
Delta
Deal found 4/27![Delta logo]()
$362
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
sam. 5/231:53 pm
RDM
- ORD
1 stop8h 06m
Alaska Airlines
dim. 5/247:40 am
ORD
- RDM
1 stop7h 19m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 4/29. 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.
mer. 6/171:25 pm
RDM
- ORD
1 stop8h 14m
Delta
lun. 6/226:55 am
ORD
- RDM
1 stop7h 50m
Delta
Deal found 4/29![Delta logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
jeu. 7/307:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
mer. 8/57:20 am
ORD
- RDM
1 stop6h 19m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 4/30. 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.
lun. 6/17:20 pm
RDM
- ORD
2 stops11h 16m
Delta
sam. 6/612:47 pm
ORD
- RDM
1 stop7h 47m
Delta
Deal found 4/30![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 4/29. 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.
ven. 5/296:10 am
RDM
- ORD
2 stops13h 40m
Delta
mar. 6/27:45 pm
ORD
- RDM
1 stop5h 59m
Delta
Deal found 4/29![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 4/29. 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.
jeu. 7/305:20 am
RDM
- ORD
2 stops11h 09m
Delta
mer. 8/56:55 am
ORD
- RDM
1 stop7h 35m
Delta
Deal found 4/29![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 4/28. 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.
mer. 6/176:26 am
RDM
- ORD
2 stops13h 31m
Delta
mar. 6/237:37 pm
ORD
- RDM
1 stop6h 22m
Delta
Deal found 4/28![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/277:20 pm
RDM
- MDW
2 stops11h 23m
Delta
mer. 6/31:22 pm
MDW
- RDM
2 stops11h 30m
Delta
Deal found 4/27![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 4/30. 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.
ven. 7/35:20 am
RDM
- MDW
2 stops10h 58m
Delta
mer. 7/81:18 pm
MDW
- RDM
2 stops12h 40m
Delta
Deal found 4/30![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 4/27. 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.
mar. 5/125:05 am
RDM
- MDW
2 stops11h 28m
Delta
mer. 5/139:22 am
MDW
- RDM
2 stops11h 18m
Delta
Deal found 4/27![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 4/29. 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.
jeu. 7/307:25 pm
RDM
- MDW
2 stops11h 12m
Delta
mer. 8/512:41 pm
MDW
- RDM
2 stops13h 07m
Delta
Deal found 4/29![Delta logo]()
$537
This Delta deal was found by Cheapflights users on 4/27. 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.
mar. 5/126:10 am
RDM
- MDW
2 stops9h 46m
Delta
sam. 5/161:22 pm
MDW
- RDM
2 stops10h 52m
Delta
Deal found 4/27![Delta logo]()
$539
This Delta deal was found by Cheapflights users on 4/28. 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.
sam. 5/236:10 am
RDM
- MDW
2 stops9h 46m
Delta
dim. 5/249:23 am
MDW
- RDM
2 stops11h 17m
Delta
Deal found 4/28![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 4/26. 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.
ven. 5/227:20 pm
RDM
- MDW
2 stops11h 23m
Delta
lun. 5/259:23 am
MDW
- RDM
2 stops11h 17m
Delta
Deal found 4/26![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 4/27. 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.
ven. 5/85:05 am
RDM
- MDW
2 stops11h 28m
Delta
sam. 5/91:22 pm
MDW
- RDM
2 stops10h 52m
Delta
Deal found 4/27![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 4/29. 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.
mer. 5/137:20 pm
RDM
- MDW
2 stops11h 22m
Delta
sam. 5/161:59 pm
MDW
- RDM
2 stops10h 55m
Delta
Deal found 4/29![Delta logo]()
$590
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated mai 1, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated mai 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
sam. 5/237:20 pm
RDM
- ORD
2 stops11h 25m
Delta
sam. 5/3012:47 pm
ORD
- RDM
1 stop7h 48m
Delta
Deal found 5/1![Delta logo]()
$362
This Delta deal was found by Cheapflights users on 4/28. 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.
sam. 5/236:10 am
RDM
- ORD
1 stop9h 03m
Delta
lun. 5/257:45 am
ORD
- RDM
1 stop5h 50m
Delta
Deal found 4/28![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” 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.
sam. 5/237:20 pm
RDM
- MDW
2 stops11h 23m
Delta
sam. 5/309:22 am
MDW
- RDM
2 stops11h 13m
Delta
Deal found 5/1![Delta logo]()
$397
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
sam. 5/239:55 am
RDM
- ORD
1 stop7h 08m
Alaska Airlines
mar. 5/262:10 pm
ORD
- RDM
1 stop9h 27m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$398
This Expedia deal was found by Cheapflights users on 4/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/277:00 am
RDM
- ORD
1 stop9h 50m
Alaska Airlines
mer. 6/39:00 am
ORD
- RDM
1 stop14h 37m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/276:10 am
RDM
- ORD
2 stops10h 40m
Delta
mar. 6/27:12 am
ORD
- RDM
1 stop7h 23m
Delta
Deal found 4/27![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 4/27. 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.
mer. 5/277:20 pm
RDM
- MDW
2 stops11h 23m
Delta
mer. 6/31:22 pm
MDW
- RDM
2 stops11h 30m
Delta
Deal found 4/27![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/281:59 pm
RDM
- ORD
1 stop8h 31m
American Airlines
mar. 6/23:22 pm
ORD
- RDM
1 stop9h 34m
American Airlines
Deal found 4/30![American Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 4/28. 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.
jeu. 5/286:10 am
RDM
- ORD
1 stop8h 39m
Delta
mar. 6/27:45 am
ORD
- RDM
2 stops12h 53m
Delta
Deal found 4/28![Delta logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
jeu. 5/281:53 pm
RDM
- ORD
1 stop7h 06m
Alaska Airlines
lun. 6/17:59 pm
ORD
- RDM
1 stop17h 38m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/281:53 pm
RDM
- ORD
1 stop8h 06m
Alaska Airlines
mar. 6/29:00 am
ORD
- RDM
2 stops14h 34m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 4/29. 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.
ven. 5/296:10 am
RDM
- ORD
2 stops13h 40m
Delta
mar. 6/27:45 pm
ORD
- RDM
1 stop5h 59m
Delta
Deal found 4/29![Delta logo]()
$373
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 mai 1, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated mai 1, 2026.
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/223:51 pm
RDM
- ORD
1 stop7h 08m
United Airlines
Deal found 4/28![United Airlines logo]()
$180
This Delta deal was found by Cheapflights users on 4/30. 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.
mar. 6/236:26 am
RDM
- ORD
2 stops10h 32m
Delta
Deal found 4/30![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 4/28. 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.
mer. 7/227:25 pm
RDM
- MDW
2 stops11h 12m
Delta
Deal found 4/28![Delta logo]()
$185
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
dim. 6/147:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/254:00 pm
RDM
- ORD
1 stop11h 00m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 4/28. 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.
ven. 7/247:25 pm
RDM
- MDW
2 stops11h 12m
Delta
Deal found 4/28![Delta logo]()
$195
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/234:00 pm
RDM
- ORD
1 stop11h 00m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$218
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/157:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 4/30. 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.
mer. 6/176:26 am
RDM
- ORD
2 stops12h 05m
Delta
Deal found 4/30![Delta logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 5/1512:15 pm
RDM
- ORD
2 stops29h 36m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/142:50 pm
RDM
- ORD
1 stop7h 42m
American Airlines
Deal found 4/30![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 4/28. 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.
sam. 5/165:05 am
RDM
- ORD
2 stops13h 09m
Delta
Deal found 4/28![Delta logo]()
$244
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 mai 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Expedia) |
One-way from | $180 (United Airlines) |
Popular in | February |
Cheapest in | December |
Average price | $326 |
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 2,558,603 searches. Data last updated mai 1, 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 - ORD
RDMORD
Bend/Redmond
mer. 5/27
6:10 am-6:50 pm
2 stops10h 40m
Chicago O'Hare Intl
mer. 6/3
6:20 pm-10:52 pm
1 stop6h 32m
$362
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
sam. 5/23
1:53 pm-11:59 pm
1 stop8h 06m
Chicago O'Hare Intl
dim. 5/24
7:40 am-12:59 pm
1 stop7h 19m
$368
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
mer. 6/17
1:25 pm-11:39 pm
1 stop8h 14m
Chicago O'Hare Intl
lun. 6/22
6:55 am-12:45 pm
1 stop7h 50m
$369
Quickest round-trip
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
jeu. 7/30
7:49 pm-5:00 am
1 stop7h 11m
Chicago O'Hare Intl
mer. 8/5
7:20 am-11:39 am
1 stop6h 19m
$369
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
lun. 6/1
7:20 pm-8:36 am
2 stops11h 16m
Chicago O'Hare Intl
sam. 6/6
12:47 pm-6:34 pm
1 stop7h 47m
$373
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
ven. 5/29
6:10 am-9:50 pm
2 stops13h 40m
Chicago O'Hare Intl
mar. 6/2
7:45 pm-11:44 pm
1 stop5h 59m
$373
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
jeu. 7/30
5:20 am-6:29 pm
2 stops11h 09m
Chicago O'Hare Intl
mer. 8/5
6:55 am-12:30 pm
1 stop7h 35m
$374
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
mer. 6/17
6:26 am-9:57 pm
2 stops13h 31m
Chicago O'Hare Intl
mar. 6/23
7:37 pm-11:59 pm
1 stop6h 22m
$374
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
mer. 5/27
7:20 pm-8:43 am
2 stops11h 23m
Chicago Midway
mer. 6/3
1:22 pm-10:52 pm
2 stops11h 30m
$379
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
ven. 7/3
5:20 am-6:18 pm
2 stops10h 58m
Chicago Midway
mer. 7/8
1:18 pm-11:58 pm
2 stops12h 40m
$479
Showing 1-10 of 35 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 May.
| 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, May is the cheapest month in which you can book a flight from Redmond to Chicago (average of $125). Flying from Redmond to Chicago in September is currently the most expensive (average of $352). 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?
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 mai 1, 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.
Food
7.1
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Comfort
7.8
Overall
7.9
Entertainment
7.0
Boarding
8.1
Crew
8.5
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
Hammond
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 mai 1, 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 mai 1, 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 2,558,603 searches. Data last updated mai 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$262 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$308 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$368 | FlexibilityNo cancel fee | On-timeN/A |