$207+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Aug 10 — Aug 171
Round-trip
1 adult, Economy
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Find cheap flights from Redmond to Chicago with Cheapflights
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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 Juli 11, 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 Juli 11, 2026.
This Trip.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 8/221:31 pm
RDM
- ORD
1 stop8h 28m
Alaska Airlines
Sa 8/296:00 am
ORD
- RDM
1 stop8h 34m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Mi 9/912:30 pm
RDM
- ORD
1 stop7h 22m
Delta
Sa 9/127:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/6![Delta logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Mi 10/78:31 am
RDM
- ORD
1 stop8h 22m
Alaska Airlines
Mo 10/127:16 pm
ORD
- RDM
1 stop19h 22m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Di 9/87:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Di 9/157:45 am
ORD
- RDM
1 stop6h 05m
Delta
Deal found 7/6![Delta logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Fr 9/111:33 pm
RDM
- ORD
1 stop8h 26m
Alaska Airlines
Mi 9/162:18 pm
ORD
- RDM
1 stop9h 20m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Di 9/87:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Sa 9/127:45 am
ORD
- RDM
2 stops12h 59m
Delta
Deal found 7/6![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Di 9/87:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Di 9/152:00 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 7/6![Delta logo]()
$423
This lol.travel deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 8/201:31 pm
RDM
- ORD
1 stop8h 28m
Alaska Airlines
Do 8/276:54 pm
ORD
- RDM
1 stop7h 04m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Mi 9/91:44 pm
RDM
- ORD
1 stop8h 13m
Delta
So 9/137:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/6![Delta logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Do 8/64:00 pm
RDM
- ORD
1 stop11h 00m
Alaska Airlines
Di 8/115:42 pm
ORD
- RDM
1 stop8h 17m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Fr 9/181:37 pm
RDM
- ORD
1 stop20h 30m
Alaska Airlines
Mo 9/217:00 pm
ORD
- RDM
1 stop16h 36m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 7/10. 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.
Do 9/101:33 pm
RDM
- ORD
1 stop8h 26m
Alaska Airlines
Mo 9/148:00 am
ORD
- RDM
1 stop27h 36m
Alaska Airlines
Deal found 7/10![Alaska Airlines logo]()
$436
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 Juli 11, 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 Juli 11, 2026.
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Mi 9/237:24 pm
RDM
- ORD
2 stops10h 33m
Delta
Sa 9/265:44 pm
ORD
- RDM
1 stop7h 09m
Delta
Deal found 7/7![Delta logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Do 9/106:17 pm
RDM
- ORD
1 stop10h 03m
Alaska Airlines
Mo 9/147:00 pm
ORD
- RDM
1 stop16h 36m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Di 9/2212:30 pm
RDM
- ORD
1 stop7h 22m
Delta
So 9/277:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/7![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Di 10/66:20 am
RDM
- ORD
1 stop8h 39m
Delta
So 10/116:55 am
ORD
- RDM
1 stop7h 51m
Delta
Deal found 7/7![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Do 9/107:24 pm
RDM
- MDW
2 stops11h 43m
Delta
Di 9/151:19 pm
MDW
- RDM
2 stops11h 49m
Delta
Deal found 7/6![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Mi 9/97:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Fr 9/119:59 am
MDW
- RDM
2 stops10h 45m
Delta
Deal found 7/8![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Fr 9/111:44 pm
RDM
- ORD
1 stop8h 13m
Delta
So 9/135:44 pm
ORD
- RDM
1 stop7h 24m
Delta
Deal found 7/6![Delta logo]()
$453
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Do 8/276:15 am
RDM
- ORD
2 stops10h 14m
Delta
So 8/305:56 pm
ORD
- RDM
1 stop7h 02m
Delta
Deal found 7/5![Delta logo]()
$458
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Mo 9/287:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Fr 10/22:00 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 7/8![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Fr 11/136:20 am
RDM
- MDW
2 stops8h 30m
Delta
Mo 11/161:00 pm
MDW
- RDM
2 stops11h 46m
Delta
Deal found 7/6![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Do 9/107:24 pm
RDM
- MDW
2 stops11h 43m
Delta
Mo 9/141:19 pm
MDW
- RDM
2 stops12h 39m
Delta
Deal found 7/9![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/10. 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.
Sa 12/55:55 am
RDM
- MDW
2 stops8h 55m
Delta
Mo 12/712:30 pm
MDW
- RDM
2 stops13h 10m
Delta
Deal found 7/10![Delta logo]()
$492
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Di 8/257:36 pm
RDM
- MDW
2 stops11h 41m
Delta
Do 8/271:25 pm
MDW
- RDM
2 stops11h 33m
Delta
Deal found 7/6![Delta logo]()
$504
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Do 10/157:26 pm
RDM
- MDW
2 stops11h 21m
Delta
So 10/181:28 pm
MDW
- RDM
2 stops11h 38m
Delta
Deal found 7/9![Delta logo]()
$507
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated Juli 11, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated Juli 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Sa 7/116:13 am
RDM
- MDW
2 stops9h 54m
Delta
Sa 7/189:19 am
MDW
- RDM
2 stops11h 24m
Delta
Deal found 7/9![Delta logo]()
$511
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Di 8/412:34 pm
RDM
- ORD
1 stop14h 26m
Alaska Airlines
Di 8/117:20 am
ORD
- RDM
1 stop10h 00m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Do 8/64:00 pm
RDM
- ORD
1 stop11h 00m
Alaska Airlines
Di 8/115:42 pm
ORD
- RDM
1 stop8h 17m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Mi 8/121:52 pm
RDM
- ORD
1 stop7h 07m
United Airlines
Do 8/208:50 am
ORD
- RDM
1 stop8h 05m
United Airlines
Deal found 7/9![United Airlines logo]()
$439
This lol.travel deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 8/201:31 pm
RDM
- ORD
1 stop8h 28m
Alaska Airlines
Do 8/276:54 pm
ORD
- RDM
1 stop7h 04m
Alaska Airlines
Deal found 7/6![Alaska Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Do 8/206:15 am
RDM
- ORD
1 stop8h 45m
Delta
So 8/237:48 am
ORD
- RDM
1 stop6h 03m
Delta
Deal found 7/6![Delta logo]()
$453
This Trip.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 8/221:31 pm
RDM
- ORD
1 stop8h 28m
Alaska Airlines
Sa 8/296:00 am
ORD
- RDM
1 stop8h 34m
Alaska Airlines
Deal found 7/7![Alaska Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Sa 8/222:30 pm
RDM
- ORD
1 stop7h 58m
American Airlines
Sa 8/291:40 pm
ORD
- RDM
1 stop8h 28m
American Airlines
Deal found 7/9![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Sa 8/221:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Sa 8/2911:22 am
ORD
- RDM
2 stops13h 36m
Delta
Deal found 7/7![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Di 8/251:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Do 8/277:44 pm
ORD
- RDM
1 stop6h 05m
Delta
Deal found 7/7![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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.
Di 8/257:36 pm
RDM
- MDW
2 stops11h 41m
Delta
Do 8/271:25 pm
MDW
- RDM
2 stops11h 33m
Delta
Deal found 7/6![Delta logo]()
$504
This Alaska Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” 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.
Do 8/277:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
So 8/306:00 am
ORD
- RDM
1 stop8h 34m
Alaska Airlines
Deal found 7/9![Alaska Airlines logo]()
$450
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 Juli 11, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated Juli 11, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Sa 9/121:37 pm
RDM
- ORD
1 stop8h 22m
Alaska Airlines
Deal found 7/8![Alaska Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 7/10. 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.
Mi 9/237:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Deal found 7/10![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Mi 9/237:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Deal found 7/7![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” 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.
Sa 9/127:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Deal found 7/8![Delta logo]()
$212
This United Airlines deal was found by Cheapflights users on 7/10. 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.
Fr 10/91:52 pm
RDM
- ORD
1 stop9h 07m
United Airlines
Deal found 7/10![United Airlines logo]()
$224
This Alaska Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Do 8/277:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Deal found 7/5![Alaska Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/10. 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.
Fr 10/97:26 pm
RDM
- ORD
2 stops10h 37m
Delta
Deal found 7/10![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 7/10. 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.
Fr 10/97:26 pm
RDM
- MDW
2 stops11h 52m
Delta
Deal found 7/10![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Do 8/277:36 pm
RDM
- ORD
2 stops13h 06m
Delta
Deal found 7/5![Delta logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” 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.
Mo 7/2712:15 pm
RDM
- ORD
1 stop15h 22m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Mi 7/151:48 pm
RDM
- ORD
1 stop9h 03m
American Airlines
Deal found 7/5![American Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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.
Sa 8/296:15 am
RDM
- ORD
2 stops12h 15m
Delta
Deal found 7/5![Delta logo]()
$256
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 Juli 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $386 (Trip.com) |
One-way from | $207 (Alaska Airlines) |
Popular in | January |
Cheapest in | December |
Average price | $471 |
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 Juli 11, 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
Mi 9/23
7:24 pm-7:57 am
2 stops10h 33m
Chicago O'Hare Intl
Sa 9/26
5:44 pm-10:53 pm
1 stop7h 09m
$418
Quickest round-trip
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Di 9/22
12:30 pm-9:52 pm
1 stop7h 22m
Chicago O'Hare Intl
So 9/27
7:00 am-1:04 pm
1 stop8h 04m
$433
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Di 10/6
6:20 am-4:59 pm
1 stop8h 39m
Chicago O'Hare Intl
So 10/11
6:55 am-12:46 pm
1 stop7h 51m
$433
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Do 9/10
6:17 pm-6:20 am
1 stop10h 03m
Chicago O'Hare Intl
Mo 9/14
7:00 pm-9:36 am
1 stop16h 36m
$439
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Do 9/10
7:24 pm-9:07 am
2 stops11h 43m
Chicago Midway
Di 9/15
1:19 pm-11:08 pm
2 stops11h 49m
$443
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Mi 9/9
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Fr 9/11
9:59 am-6:44 pm
2 stops10h 45m
$443
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Fr 9/11
1:44 pm-11:57 pm
1 stop8h 13m
Chicago O'Hare Intl
So 9/13
5:44 pm-11:08 pm
1 stop7h 24m
$453
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Do 8/27
6:15 am-6:29 pm
2 stops10h 14m
Chicago O'Hare Intl
So 8/30
5:56 pm-10:58 pm
1 stop7h 02m
$458
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Mo 9/28
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Fr 10/2
2:00 pm-11:08 pm
2 stops11h 08m
$464
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Fr 11/13
6:20 am-4:50 pm
2 stops8h 30m
Chicago Midway
Mo 11/16
1:00 pm-10:46 pm
2 stops11h 46m
$464
Showing 1-10 of 24 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 July.
| 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, February is the cheapest month in which you can book a flight from Redmond to Chicago (average of $230). Flying from Redmond to Chicago in July is currently the most expensive (average of $378). 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 Juli 11, 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
Food
7.1
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Food
7.1
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Food
7.1
Boarding
8.1
Entertainment
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Crew
8.5
Food
7.1
Boarding
8.1
Entertainment
7.0
Comfort
7.8
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
Hammond
Lansing
Merrillville
Valparaiso
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 Juli 11, 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 2,558,603 searches. Data last updated Juli 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$311 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$474 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$318 | Average$368 | FlexibilityNo cancel fee | On-timeN/A |