$138+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Apr 16 — Apr 231
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 March 17, 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 March 17, 2026.
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Wed 4/227:00 am
ORD
- RDM
1 stop7h 38m
United Airlines
Deal found 3/12![United Airlines logo]()
$272
This Expedia deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:23 pm
RDM
- ORD
1 stop8h 36m
Alaska Airlines
Wed 4/228:48 pm
ORD
- RDM
1 stop14h 00m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:05 am
RDM
- ORD
2 stops13h 13m
Delta
Wed 4/226:00 pm
ORD
- RDM
1 stop7h 06m
Delta
Deal found 3/12![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Sun 4/196:25 am
ORD
- RDM
1 stop7h 30m
United Airlines
Deal found 3/12![United Airlines logo]()
$295
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:44 am
RDM
- ORD
1 stop8h 31m
American Airlines
Fri 5/13:00 pm
ORD
- RDM
1 stop10h 23m
American Airlines
Deal found 3/15![American Airlines logo]()
$300
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:10 am
RDM
- ORD
1 stop9h 53m
Alaska Airlines
Fri 5/18:48 pm
ORD
- RDM
1 stop29h 10m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$311
This Alaska Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:23 pm
RDM
- ORD
1 stop8h 36m
Alaska Airlines
Fri 4/106:00 am
ORD
- RDM
1 stop8h 29m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:05 am
RDM
- ORD
2 stops9h 59m
Delta
Fri 5/16:00 pm
ORD
- RDM
1 stop7h 06m
Delta
Deal found 3/12![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:45 am
RDM
- MDW
2 stops10h 13m
Delta
Sat 5/21:24 pm
MDW
- RDM
2 stops11h 04m
Delta
Deal found 3/17![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:45 am
RDM
- MDW
2 stops10h 51m
Delta
Fri 5/11:24 pm
MDW
- RDM
2 stops11h 42m
Delta
Deal found 3/15![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
RDM
- MDW
2 stops11h 25m
Delta
Fri 4/101:10 pm
MDW
- RDM
2 stops12h 37m
Delta
Deal found 3/16![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:20 pm
RDM
- MDW
2 stops11h 22m
Delta
Sat 5/301:22 pm
MDW
- RDM
2 stops11h 02m
Delta
Deal found 3/13![Delta logo]()
$439
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 March 17, 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 March 17, 2026.
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Sun 4/196:25 am
ORD
- RDM
1 stop7h 30m
United Airlines
Deal found 3/12![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:33 pm
RDM
- ORD
1 stop6h 45m
Delta
Wed 4/227:35 am
ORD
- RDM
2 stops11h 26m
Delta
Deal found 3/15![Delta logo]()
$302
This Alaska Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/319:37 am
RDM
- ORD
1 stop6h 49m
Alaska Airlines
Sat 4/47:24 pm
ORD
- RDM
1 stop6h 34m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:20 am
RDM
- ORD
1 stop9h 02m
Delta
Wed 7/87:20 am
ORD
- RDM
1 stop6h 51m
Delta
Deal found 3/11![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:05 am
RDM
- ORD
2 stops13h 09m
Delta
Wed 5/207:12 am
ORD
- RDM
1 stop7h 18m
Delta
Deal found 3/12![Delta logo]()
$350
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:05 am
RDM
- ORD
2 stops13h 09m
Delta
Sat 5/305:00 pm
ORD
- RDM
1 stop7h 24m
Delta
Deal found 3/13![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:30 pm
RDM
- ORD
1 stop9h 17m
Delta
Tue 8/113:50 pm
ORD
- RDM
2 stops9h 42m
Delta
Deal found 3/14![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/267:20 pm
RDM
- MDW
2 stops11h 22m
Delta
Sat 5/301:22 pm
MDW
- RDM
2 stops11h 02m
Delta
Deal found 3/13![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:19 am
RDM
- MDW
2 stops9h 35m
Delta
Sat 4/42:05 pm
MDW
- RDM
2 stops11h 02m
Delta
Deal found 3/16![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:05 am
RDM
- MDW
2 stops9h 53m
Delta
Wed 4/221:24 pm
MDW
- RDM
2 stops11h 42m
Delta
Deal found 3/15![Delta logo]()
$516
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
RDM
- MDW
2 stops11h 25m
Delta
Sat 4/119:35 am
MDW
- RDM
2 stops8h 38m
Delta
Deal found 3/16![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:55 am
RDM
- MDW
2 stops10h 36m
Delta
Wed 7/82:00 pm
MDW
- RDM
2 stops10h 47m
Delta
Deal found 3/13![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:20 pm
RDM
- MDW
2 stops13h 22m
Delta
Thu 6/111:00 pm
MDW
- RDM
2 stops12h 32m
Delta
Deal found 3/17![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/105:20 pm
RDM
- MDW
2 stops13h 22m
Delta
Fri 6/122:00 pm
MDW
- RDM
2 stops10h 47m
Delta
Deal found 3/16![Delta logo]()
$600
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:20 am
RDM
- MDW
2 stops10h 11m
Delta
Fri 6/122:00 pm
MDW
- RDM
2 stops10h 47m
Delta
Deal found 3/16![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/304:55 pm
RDM
- MDW
2 stops15h 01m
Delta
Fri 4/32:05 pm
MDW
- RDM
2 stops11h 42m
Delta
Deal found 3/15![Delta logo]()
$630
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated March 17, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated March 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:19 am
RDM
- MDW
2 stops9h 35m
Delta
Sat 4/42:05 pm
MDW
- RDM
2 stops11h 02m
Delta
Deal found 3/16![Delta logo]()
$487
This Alaska Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:23 pm
RDM
- ORD
1 stop8h 36m
Alaska Airlines
Fri 4/106:00 am
ORD
- RDM
1 stop8h 29m
Alaska Airlines
Deal found 3/16![Alaska Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:15 am
RDM
- MDW
2 stops11h 25m
Delta
Fri 4/101:10 pm
MDW
- RDM
2 stops12h 37m
Delta
Deal found 3/16![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Wed 4/227:00 am
ORD
- RDM
1 stop7h 38m
United Airlines
Deal found 3/12![United Airlines logo]()
$272
This Expedia deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:23 pm
RDM
- ORD
1 stop8h 36m
Alaska Airlines
Wed 4/228:48 pm
ORD
- RDM
1 stop14h 00m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:05 am
RDM
- ORD
2 stops13h 13m
Delta
Wed 4/226:00 pm
ORD
- RDM
1 stop7h 06m
Delta
Deal found 3/12![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Sun 4/196:25 am
ORD
- RDM
1 stop7h 30m
United Airlines
Deal found 3/12![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:45 am
RDM
- MDW
2 stops10h 13m
Delta
Sat 5/21:24 pm
MDW
- RDM
2 stops11h 04m
Delta
Deal found 3/17![Delta logo]()
$358
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:44 am
RDM
- ORD
1 stop8h 31m
American Airlines
Fri 5/13:00 pm
ORD
- RDM
1 stop10h 23m
American Airlines
Deal found 3/15![American Airlines logo]()
$300
This Alaska Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:10 am
RDM
- ORD
1 stop9h 53m
Alaska Airlines
Fri 5/18:48 pm
ORD
- RDM
1 stop29h 10m
Alaska Airlines
Deal found 3/12![Alaska Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:05 am
RDM
- ORD
2 stops9h 59m
Delta
Fri 5/16:00 pm
ORD
- RDM
1 stop7h 06m
Delta
Deal found 3/12![Delta logo]()
$325
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:45 am
RDM
- MDW
2 stops10h 51m
Delta
Fri 5/11:24 pm
MDW
- RDM
2 stops11h 42m
Delta
Deal found 3/15![Delta logo]()
$420
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 March 17, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:44 am
RDM
- ORD
1 stop8h 31m
American Airlines
Deal found 3/14![American Airlines logo]()
$138
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1412:33 pm
RDM
- ORD
1 stop6h 45m
Delta
Deal found 3/16![Delta logo]()
$139
This Delta deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:45 am
RDM
- MDW
2 stops10h 51m
Delta
Deal found 3/16![Delta logo]()
$144
This United Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:55 pm
RDM
- ORD
1 stop9h 04m
United Airlines
Deal found 3/16![United Airlines logo]()
$154
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:48 pm
RDM
- ORD
1 stop9h 32m
United Airlines
Deal found 3/12![United Airlines logo]()
$162
This Trip.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:59 pm
RDM
- ORD
2 stops11h 51m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$176
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:35 am
RDM
- ORD
2 stops7h 43m
Delta
Deal found 3/12![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:35 pm
RDM
- ORD
1 stop7h 23m
Delta
Deal found 3/14![Delta logo]()
$190
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:45 am
RDM
- MDW
2 stops10h 51m
Delta
Deal found 3/14![Delta logo]()
$195
This Expedia deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/121:23 pm
RDM
- ORD
1 stop8h 36m
Alaska Airlines
Deal found 3/13![Alaska Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:10 pm
RDM
- ORD
3 stops57h 26m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/612:10 pm
RDM
- MDW
3 stops32h 09m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$233
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 March 17, 2026.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $272 (United Airlines) |
One-way from | $138 (American Airlines) |
Popular in | March |
Cheapest in | December |
Average price | $583 |
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 March 17, 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
Wed 4/15
1:55 pm-12:59 am
1 stop9h 04m
Chicago O'Hare Intl
Sun 4/19
6:25 am-11:55 am
1 stop7h 30m
$295
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 4/15
12:33 pm-9:18 pm
1 stop6h 45m
Chicago O'Hare Intl
Wed 4/22
7:35 am-5:01 pm
2 stops11h 26m
$302
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Fri 7/3
6:20 am-5:22 pm
1 stop9h 02m
Chicago O'Hare Intl
Wed 7/8
7:20 am-12:11 pm
1 stop6h 51m
$349
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 5/12
5:05 am-8:14 pm
2 stops13h 09m
Chicago O'Hare Intl
Wed 5/20
7:12 am-12:30 pm
1 stop7h 18m
$350
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 5/26
5:05 am-8:14 pm
2 stops13h 09m
Chicago O'Hare Intl
Sat 5/30
5:00 pm-10:24 pm
1 stop7h 24m
$401
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 8/5
12:30 pm-11:47 pm
1 stop9h 17m
Chicago O'Hare Intl
Tue 8/11
3:50 pm-11:32 pm
2 stops9h 42m
$434
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Tue 5/26
7:20 pm-8:42 am
2 stops11h 22m
Chicago Midway
Sat 5/30
1:22 pm-10:24 pm
2 stops11h 02m
$439
Quickest round-trip
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 3/31
9:37 am-6:26 pm
1 stop6h 49m
Chicago O'Hare Intl
Sat 4/4
7:24 pm-11:58 pm
1 stop6h 34m
$477
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Tue 3/31
6:19 am-5:54 pm
2 stops9h 35m
Chicago Midway
Sat 4/4
2:05 pm-11:07 pm
2 stops11h 02m
$487
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Wed 4/15
6:05 am-5:58 pm
2 stops9h 53m
Chicago Midway
Wed 4/22
1:24 pm-11:06 pm
2 stops11h 42m
$516
Showing 1-10 of 37 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Redmond-Chicago flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Redmond-Chicago flight deals on Cheapflights vs. Expedia <90% 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 Expedia the most. Expedia 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
No data available for this route at this time. Please check back soon.
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 March 17, 2026.
Read reviews from past customers who have flown Alaska Airlines,Delta, andHawaiian 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
Boarding
8.1
Comfort
7.8
Food
7.0
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.0
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.0
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.0
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Crew
8.5
Boarding
8.1
Comfort
7.8
Food
7.0
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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 March 17, 2026.
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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 March 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$262 | Average$406 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$288 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$308 | Average$436 | FlexibilityNo cancel fee | On-time69% |