$204+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Aug 31 — Sep 71
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 August 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 August 1, 2026.
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/121:52 pm
RDM
- ORD
1 stop7h 18m
United Airlines
Tue 9/1512:58 pm
ORD
- RDM
1 stop7h 34m
United Airlines
Deal found 7/31![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:24 pm
RDM
- ORD
2 stops10h 32m
Delta
Sat 9/197:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/29![Delta logo]()
$412
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:46 pm
RDM
- ORD
1 stop7h 44m
American Airlines
Wed 9/161:59 pm
ORD
- RDM
1 stop7h 06m
American Airlines
Deal found 7/29![American Airlines logo]()
$421
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/117:24 pm
RDM
- ORD
2 stops11h 14m
Delta
Wed 9/167:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/29![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:10 am
RDM
- ORD
1 stop8h 43m
Delta
Sun 10/257:35 am
ORD
- RDM
1 stop6h 10m
Delta
Deal found 7/29![Delta logo]()
$427
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Wed 9/168:00 am
ORD
- RDM
2 stops16h 25m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$430
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/117:24 pm
RDM
- ORD
2 stops11h 14m
Delta
Tue 9/151:55 pm
ORD
- RDM
2 stops12h 03m
Delta
Deal found 7/31![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/117:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Tue 9/152:00 pm
MDW
- RDM
2 stops11h 58m
Delta
Deal found 7/31![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 10/167:34 pm
RDM
- MDW
2 stops11h 10m
Delta
Wed 10/2112:27 pm
MDW
- RDM
2 stops8h 23m
Delta
Deal found 7/29![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:44 pm
RDM
- ORD
1 stop8h 13m
Delta
Mon 9/147:40 pm
ORD
- RDM
1 stop6h 18m
Delta
Deal found 7/29![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Mon 9/142:00 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 7/27![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:24 pm
RDM
- MDW
2 stops11h 43m
Delta
Sat 9/199:59 am
MDW
- RDM
2 stops10h 45m
Delta
Deal found 7/29![Delta logo]()
$528
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 August 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 August 1, 2026.
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/291:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Sat 9/54:45 pm
ORD
- RDM
1 stop7h 33m
Delta
Deal found 7/30![Delta logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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.
Tue 10/276:00 am
RDM
- ORD
1 stop6h 53m
Alaska Airlines
Sat 10/317:00 am
ORD
- RDM
1 stop7h 38m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:24 pm
RDM
- ORD
2 stops10h 32m
Delta
Sat 9/197:00 am
ORD
- RDM
1 stop8h 04m
Delta
Deal found 7/29![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:25 pm
RDM
- ORD
1 stop8h 09m
Delta
Wed 11/49:59 am
ORD
- RDM
2 stops10h 51m
Delta
Deal found 7/31![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 7/28. 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.
Fri 9/117:24 pm
RDM
- ORD
2 stops11h 14m
Delta
Tue 9/157:40 pm
ORD
- RDM
1 stop6h 18m
Delta
Deal found 7/28![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:10 am
RDM
- ORD
1 stop8h 43m
Delta
Sun 10/117:00 am
ORD
- RDM
1 stop7h 45m
Delta
Deal found 7/31![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/117:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Tue 9/152:00 pm
MDW
- RDM
2 stops11h 58m
Delta
Deal found 7/31![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:44 pm
RDM
- ORD
1 stop8h 13m
Delta
Mon 9/147:40 pm
ORD
- RDM
1 stop6h 18m
Delta
Deal found 7/29![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/117:24 pm
RDM
- ORD
2 stops11h 14m
Delta
Mon 9/145:44 pm
ORD
- RDM
1 stop7h 24m
Delta
Deal found 7/31![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Mon 9/142:00 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 7/27![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:24 pm
RDM
- MDW
2 stops11h 43m
Delta
Sat 9/199:59 am
MDW
- RDM
2 stops10h 45m
Delta
Deal found 7/31![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:34 pm
RDM
- MDW
2 stops11h 10m
Delta
Sun 10/1810:01 am
MDW
- RDM
2 stops10h 49m
Delta
Deal found 7/28![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:34 pm
RDM
- MDW
2 stops11h 10m
Delta
Sun 10/251:27 pm
MDW
- RDM
2 stops11h 39m
Delta
Deal found 7/27![Delta logo]()
$603
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/217:36 pm
RDM
- MDW
2 stops11h 03m
Delta
Mon 8/2412:46 pm
MDW
- RDM
2 stops13h 03m
Delta
Deal found 7/29![Delta logo]()
$694
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated August 1, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:25 pm
RDM
- MDW
2 stops11h 12m
Delta
Wed 8/512:46 pm
MDW
- RDM
2 stops13h 03m
Delta
Deal found 7/27![Delta logo]()
$817
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:10 am
RDM
- MDW
2 stops11h 23m
Delta
Tue 8/111:25 pm
MDW
- RDM
2 stops11h 33m
Delta
Deal found 7/28![Delta logo]()
$768
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/207:36 pm
RDM
- MDW
2 stops11h 03m
Delta
Mon 8/241:51 pm
MDW
- RDM
2 stops11h 07m
Delta
Deal found 7/31![Delta logo]()
$601
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/217:36 pm
RDM
- MDW
2 stops11h 03m
Delta
Mon 8/2412:46 pm
MDW
- RDM
2 stops13h 03m
Delta
Deal found 7/29![Delta logo]()
$694
This Alaska Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:25 am
RDM
- ORD
2 stops10h 24m
Alaska Airlines
Wed 8/266:54 pm
ORD
- RDM
1 stop7h 04m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$547
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:24 pm
RDM
- ORD
1 stop10h 56m
Alaska Airlines
Sun 8/306:00 am
ORD
- RDM
1 stop8h 34m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:36 pm
RDM
- ORD
2 stops10h 54m
Delta
Mon 8/317:48 am
ORD
- RDM
1 stop6h 03m
Delta
Deal found 7/29![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:03 pm
RDM
- ORD
1 stop7h 42m
United Airlines
Wed 9/212:51 pm
ORD
- RDM
1 stop7h 37m
United Airlines
Deal found 7/30![United Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/271:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Wed 9/211:22 am
ORD
- RDM
2 stops13h 36m
Delta
Deal found 7/30![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 7/30. 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.
Thu 8/277:36 pm
RDM
- MDW
2 stops11h 03m
Delta
Wed 9/29:24 am
MDW
- RDM
2 stops11h 21m
Delta
Deal found 7/30![Delta logo]()
$609
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/291:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Sat 9/54:45 pm
ORD
- RDM
1 stop7h 33m
Delta
Deal found 7/30![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/316:15 am
RDM
- ORD
1 stop8h 45m
Delta
Mon 9/77:00 am
ORD
- RDM
1 stop8h 12m
Delta
Deal found 7/31![Delta logo]()
$473
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 August 1, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 9/127:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Deal found 7/29![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 7/28. 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.
Wed 9/237:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Deal found 7/28![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:15 am
RDM
- ORD
1 stop8h 45m
United Airlines
Deal found 7/30![United Airlines logo]()
$218
This Booking.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:35 pm
RDM
- ORD
1 stop8h 24m
Alaska Airlines
Deal found 7/31![Alaska Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Deal found 7/31![Delta logo]()
$229
This deal was found by Cheapflights users on 7/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:03 pm
RDM
- ORD
1 stop7h 43m
United Airlines
Deal found 7/29![United Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 9/127:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Deal found 7/29![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Deal found 7/27![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/51:52 pm
RDM
- ORD
1 stop7h 37m
Delta
Deal found 7/31![Delta logo]()
$256
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Sun 9/612:32 pm
RDM
- ORD
2 stops15h 48m
Alaska Airlines
Deal found 7/30![Alaska Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/66:15 am
RDM
- ORD
1 stop8h 45m
Delta
Deal found 7/31![Delta logo]()
$306
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $407 (United Airlines) |
One-way from | $204 (Alaska Airlines) |
Popular in | January |
Cheapest in | December |
Average price | $406 |
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 August 1, 2026.
Use the filters below to find and compare flights from Redmond to Chicago that are best for you.
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RedmondChicago
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RDMORD
Bend/Redmond
Sat 8/29
1:52 pm-11:29 pm
1 stop7h 37m
Chicago O'Hare Intl
Sat 9/5
4:45 pm-10:18 pm
1 stop7h 33m
$407
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 9/16
7:24 pm-7:56 am
2 stops10h 32m
Chicago O'Hare Intl
Sat 9/19
7:00 am-1:04 pm
1 stop8h 04m
$412
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 10/21
1:25 pm-11:34 pm
1 stop8h 09m
Chicago O'Hare Intl
Wed 11/4
9:59 am-6:50 pm
2 stops10h 51m
$412
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Fri 9/11
7:24 pm-8:38 am
2 stops11h 14m
Chicago O'Hare Intl
Tue 9/15
7:40 pm-11:58 pm
1 stop6h 18m
$426
Quickest round-trip
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 10/27
6:00 am-2:53 pm
1 stop6h 53m
Chicago O'Hare Intl
Sat 10/31
7:00 am-12:38 pm
1 stop7h 38m
$427
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 10/6
6:10 am-4:53 pm
1 stop8h 43m
Chicago O'Hare Intl
Sun 10/11
7:00 am-12:45 pm
1 stop7h 45m
$427
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Fri 9/11
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Tue 9/15
2:00 pm-11:58 pm
2 stops11h 58m
$431
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Thu 9/10
1:44 pm-11:57 pm
1 stop8h 13m
Chicago O'Hare Intl
Mon 9/14
7:40 pm-11:58 pm
1 stop6h 18m
$441
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Fri 9/11
7:24 pm-8:38 am
2 stops11h 14m
Chicago O'Hare Intl
Mon 9/14
5:44 pm-11:08 pm
1 stop7h 24m
$446
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Thu 9/10
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Mon 9/14
2:00 pm-11:08 pm
2 stops11h 08m
$451
Showing 1-10 of 26 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 August.
| 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, December is the cheapest month in which you can book a flight from Redmond to Chicago (average of $324). Flying from Redmond to Chicago in February is currently the most expensive (average of $572). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Redmond to Chicago?
Airfare is typical for this route at the moment.
Redmond to Chicago flights typically cost between $406 and $478 in September.The cheapest round-trip price found within the last 5 days was $407 on United Airlines (Sep 12-Sep 15).
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 August 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
7.0
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.0
Entertainment
7.0
Crew
8.5
Boarding
8.1
Overall
7.9
Comfort
7.8
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Related info for your journey
Find useful and relevant information for your journey from Redmond to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
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Find flights from Redmond to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Redmond and Chicago flights
Browse other Redmond and Chicago flight options. Last updated on August 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 August 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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$311 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$368 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$320 | Average$474 | FlexibilityNo cancel fee | On-time75% |