Chicago

$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
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Cheap flight deals from Redmond to Chicago

Cheapest flights from Redmond to Chicago
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$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$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$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$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$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$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$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$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$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$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$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$439

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
Provider with most accurate pricing for Bend/Redmond-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Bend/Redmond-Chicago (CHI) flights.
From Bend/Redmond to Chicago (CHI)
One-way flight from Bend/Redmond to Chicago (CHI)
Highest demand for flights based on searches. 21% potential increase in price ($116 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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

Price

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 37 resultsSorted by cheapest first
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3
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  • 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.
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
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
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

Crew

8.5

Boarding

8.1

Comfort

7.8

Food

7.0

Overall

7.9

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Franzi,Mar 2026

SFO - PDX

I love flying with Alaska. I think they sre the best airline.

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.
  • What airport do you fly from for flights from Redmond to Chicago?

    Bend/Redmond (RDM) is the airport you will fly out of if you book a flight from Redmond to Chicago. You should not have trouble finding flights to Chicago from Bend/Redmond; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Redmond airport to Chicago. It is only a 1.8 mi journey to Bend/Redmond (RDM) from Redmond’s city center.

  • How long is the flight from Redmond to Chicago?

    United Airlines and Delta can get you from Redmond to Chicago in just under 6h 45m. Your travel time can differ by up to 2h 19m. Redmond and Chicago are separated by a distance of 1671 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Redmond to Chicago round-trip?

    Flying on Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $262. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $288 and $308, respectively. Alaska Airlines is priced at 38% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Redmond to Chicago one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $97. Users have also found prices from $139 and $159 on Alaska Airlines and United Airlines, respectively.

  • Can I find deals for flights from Redmond to Chicago that include hotel bookings?

    Yes. In addition to deals on Redmond to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Redmond to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Redmond to Chicago.

  • Can I find deals for business class flights from Redmond to Chicago?

    Yes. Cheapflights offers flight deals from Redmond to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$262Average$406FlexibilityNo cancel feeOn-time75%
DeltaCheapest$288Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$308Average$436FlexibilityNo cancel feeOn-time69%

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