$183+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Jul 17 — Jul 241
Round-trip
1 adult, Economy
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Find cheap flights from Redmond to Chicago with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Redmond to ChicagoExplore the most affordable flight options available from Redmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 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 June 17, 2026.
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 7/31:25 pm
RDM
- ORD
1 stop8h 14m
Delta
Wed 7/81:00 pm
ORD
- RDM
1 stop7h 43m
Delta
Deal found 6/16![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/14. 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 7/312:24 pm
RDM
- ORD
1 stop7h 33m
Delta
Sat 7/117:45 am
ORD
- RDM
1 stop5h 50m
Delta
Deal found 6/14![Delta logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Wed 7/157:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Tue 7/218:20 pm
ORD
- RDM
1 stop14h 44m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/14. 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 8/46:15 am
RDM
- ORD
2 stops13h 15m
Delta
Wed 8/125:56 pm
ORD
- RDM
1 stop7h 02m
Delta
Deal found 6/14![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 9/111:44 pm
RDM
- ORD
1 stop8h 13m
Delta
Tue 9/1512:50 pm
ORD
- RDM
1 stop7h 54m
Delta
Deal found 6/16![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 6/14. 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 8/46:15 am
RDM
- ORD
2 stops13h 15m
Delta
Tue 8/117:48 am
ORD
- RDM
2 stops12h 57m
Delta
Deal found 6/14![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 6/16. 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 9/166:20 am
RDM
- MDW
2 stops10h 13m
Delta
Sat 9/199:49 am
MDW
- RDM
2 stops10h 55m
Delta
Deal found 6/16![Delta logo]()
$380
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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 9/107:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Mon 9/147:00 pm
ORD
- RDM
1 stop6h 58m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 9/117:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Tue 9/151:47 pm
MDW
- RDM
2 stops11h 21m
Delta
Deal found 6/16![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 6/16. 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 8/207:36 pm
RDM
- ORD
2 stops10h 54m
Delta
Sun 8/237:44 pm
ORD
- RDM
1 stop6h 05m
Delta
Deal found 6/16![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 6/14. 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 7/156:13 am
RDM
- ORD
1 stop8h 30m
Delta
Sat 7/186:55 am
ORD
- RDM
1 stop7h 50m
Delta
Deal found 6/14![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 6/16. 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 9/107:24 pm
RDM
- ORD
2 stops11h 06m
Delta
Mon 9/147:01 am
ORD
- RDM
2 stops13h 43m
Delta
Deal found 6/16![Delta logo]()
$399
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 June 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 June 17, 2026.
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/161:03 pm
RDM
- ORD
1 stop6h 57m
United Airlines
Sat 9/191:00 pm
ORD
- RDM
1 stop7h 15m
United Airlines
Deal found 6/12![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/12. 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 9/161:33 pm
RDM
- ORD
1 stop8h 14m
Delta
Sat 9/192:05 pm
ORD
- RDM
2 stops10h 30m
Delta
Deal found 6/12![Delta logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Mon 9/147:00 pm
ORD
- RDM
1 stop6h 58m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 6/13. 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.
Wed 8/126:15 am
RDM
- ORD
2 stops13h 15m
Delta
Mon 8/177:44 pm
ORD
- RDM
1 stop6h 05m
Delta
Deal found 6/13![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 6/17. 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 10/65:55 am
RDM
- ORD
2 stops8h 38m
Delta
Sun 10/117:00 am
ORD
- RDM
1 stop6h 58m
Delta
Deal found 6/17![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 6/15. 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.
Thu 8/2012:30 pm
RDM
- ORD
1 stop7h 00m
Delta
Sun 8/237:44 pm
ORD
- RDM
1 stop6h 05m
Delta
Deal found 6/15![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 6/17. 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.
Thu 9/101:44 pm
RDM
- ORD
1 stop8h 13m
Delta
Mon 9/147:40 pm
ORD
- RDM
1 stop6h 07m
Delta
Deal found 6/17![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 9/117:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Tue 9/151:47 pm
MDW
- RDM
2 stops11h 21m
Delta
Deal found 6/17![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 6/14. 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.
Thu 8/67:36 pm
RDM
- MDW
2 stops11h 03m
Delta
Mon 8/101:51 pm
MDW
- RDM
2 stops11h 07m
Delta
Deal found 6/14![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 6/17. 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.
Thu 9/107:24 pm
RDM
- MDW
2 stops11h 24m
Delta
Mon 9/149:30 am
MDW
- RDM
2 stops11h 14m
Delta
Deal found 6/17![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 6/14. 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 10/76:20 am
RDM
- MDW
2 stops13h 50m
Delta
Mon 10/121:00 pm
MDW
- RDM
2 stops12h 40m
Delta
Deal found 6/14![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 6/13. 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.
Wed 8/127:36 pm
RDM
- MDW
2 stops11h 41m
Delta
Sun 8/161:27 pm
MDW
- RDM
2 stops11h 31m
Delta
Deal found 6/13![Delta logo]()
$590
Last-minute flights from Redmond to ChicagoDiscover last-minute flight deals from Redmond to Chicago. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Redmond to Chicago. Data last updated June 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/16. 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.
Fri 7/31:25 pm
RDM
- ORD
1 stop8h 14m
Delta
Wed 7/81:00 pm
ORD
- RDM
1 stop7h 43m
Delta
Deal found 6/16![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 6/14. 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 7/312:24 pm
RDM
- ORD
1 stop7h 33m
Delta
Sat 7/117:45 am
ORD
- RDM
1 stop5h 50m
Delta
Deal found 6/14![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 6/14. 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 7/37:25 pm
RDM
- MDW
2 stops11h 49m
Delta
Sat 7/111:49 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 6/14![Delta logo]()
$699
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Wed 7/157:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Tue 7/218:20 pm
ORD
- RDM
1 stop14h 44m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/17. 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.
Wed 7/151:27 pm
RDM
- ORD
1 stop8h 11m
Delta
Tue 7/212:02 pm
ORD
- RDM
2 stops10h 55m
Delta
Deal found 6/17![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 6/14. 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 7/156:13 am
RDM
- ORD
1 stop8h 30m
Delta
Sat 7/186:55 am
ORD
- RDM
1 stop7h 50m
Delta
Deal found 6/14![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 7/247:25 pm
RDM
- MDW
2 stops11h 12m
Delta
Sat 8/11:49 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 6/17![Delta logo]()
$729
This Expedia deal was found by Cheapflights users on 6/15. 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.
Sat 7/257:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Fri 7/312:20 pm
ORD
- RDM
1 stop9h 49m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 6/17. 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 7/255:05 am
RDM
- MDW
2 stops11h 02m
Delta
Sat 8/11:49 pm
MDW
- RDM
2 stops11h 08m
Delta
Deal found 6/17![Delta logo]()
$789
This Alaska Airlines deal was found by Cheapflights users on 6/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Fri 7/312:20 pm
ORD
- RDM
1 stop9h 49m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 6/14. 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 7/291:27 pm
RDM
- ORD
1 stop8h 11m
Delta
Fri 7/312:02 pm
ORD
- RDM
2 stops10h 55m
Delta
Deal found 6/14![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 6/14. 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.
Thu 7/301:27 pm
RDM
- ORD
1 stop8h 11m
Delta
Fri 7/312:02 pm
ORD
- RDM
2 stops10h 55m
Delta
Deal found 6/14![Delta logo]()
$394
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 June 17, 2026.
Search for one-way flight options from Redmond to Chicago. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Delta deal was found by Cheapflights users on 6/15. 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 6/3012:24 pm
RDM
- ORD
1 stop7h 33m
Delta
Deal found 6/15![Delta logo]()
$183
This Alaska Airlines deal was found by Cheapflights users on 6/16. 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.
Sat 7/117:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$185
This Delta deal was found by Cheapflights users on 6/15. 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 9/236:20 am
RDM
- ORD
2 stops9h 59m
Delta
Deal found 6/15![Delta logo]()
$190
This Delta deal was found by Cheapflights users on 6/15. 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 9/237:24 pm
RDM
- MDW
2 stops11h 26m
Delta
Deal found 6/15![Delta logo]()
$190
This deal was found by Cheapflights users on 6/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:49 pm
RDM
- ORD
1 stop7h 11m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$195
This United Airlines deal was found by Cheapflights users on 6/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/243:51 pm
RDM
- ORD
1 stop7h 10m
United Airlines
Deal found 6/15![United Airlines logo]()
$213
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 6/251:59 pm
RDM
- ORD
1 stop8h 29m
American Airlines
Deal found 6/14![American Airlines logo]()
$215
This Gotogate deal was found by Cheapflights users on 6/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:34 pm
RDM
- ORD
1 stop14h 26m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$218
This deal was found by Cheapflights users on 6/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
RDM
- ORD
1 stop6h 46m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 6/14. 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 8/116:15 am
RDM
- ORD
2 stops10h 04m
Delta
Deal found 6/14![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 9/129:30 pm
RDM
- ORD
2 stops9h 04m
Delta
Deal found 6/16![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 9/129:30 pm
RDM
- MDW
2 stops9h 08m
Delta
Deal found 6/16![Delta logo]()
$265
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $367 (Delta) |
One-way from | $183 (Delta) |
Popular in | July |
Cheapest in | December |
Average price | $482 |
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 June 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 9/16
1:03 pm-10:00 pm
1 stop6h 57m
Chicago O'Hare Intl
Sat 9/19
1:00 pm-6:15 pm
1 stop7h 15m
$369
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 9/16
1:33 pm-11:47 pm
1 stop8h 14m
Chicago O'Hare Intl
Sat 9/19
2:05 pm-10:35 pm
2 stops10h 30m
$374
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Wed 8/12
6:15 am-9:30 pm
2 stops13h 15m
Chicago O'Hare Intl
Mon 8/17
7:44 pm-11:49 pm
1 stop6h 05m
$384
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Tue 10/6
5:55 am-4:33 pm
2 stops8h 38m
Chicago O'Hare Intl
Sun 10/11
7:00 am-11:58 am
1 stop6h 58m
$384
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Thu 9/10
7:07 am-7:21 pm
1 stop10h 14m
Chicago O'Hare Intl
Mon 9/14
7:00 pm-11:58 pm
1 stop6h 58m
$389
Quickest round-trip
RedmondChicago
RDM - ORD
RDMORD
Bend/Redmond
Thu 8/20
12:30 pm-9:30 pm
1 stop7h 00m
Chicago O'Hare Intl
Sun 8/23
7:44 pm-11:49 pm
1 stop6h 05m
$389
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-11:47 pm
1 stop6h 07m
$389
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Fri 9/11
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Tue 9/15
1:47 pm-11:08 pm
2 stops11h 21m
$389
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Thu 8/6
7:36 pm-8:39 am
2 stops11h 03m
Chicago Midway
Mon 8/10
1:51 pm-10:58 pm
2 stops11h 07m
$399
RedmondChicago
RDM - MDW
RDMMDW
Bend/Redmond
Thu 9/10
7:24 pm-8:48 am
2 stops11h 24m
Chicago Midway
Mon 9/14
9:30 am-6:44 pm
2 stops11h 14m
$399
Showing 1-10 of 25 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 June.
| 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 September is currently the most expensive (average of $352). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Redmond to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 17, 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.
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
7.8
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Related info for your journey
Find useful and relevant information for your journey from Redmond to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 17, 2026.
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Redmond and Chicago flights
Browse other Redmond and Chicago flight options. Last updated on June 17, 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 June 17, 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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$474 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$311 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$368 | FlexibilityNo cancel fee | On-timeN/A |