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$145+ Cheap flights from Midway (MDW) to Redmond (RDM)

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — RDM
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheap flight deals from Midway to Redmond

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Redmond (RDM). 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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$281
(Delta)

One-way from

$145
(Delta)

Popular in

March

Cheapest in

June
Provider with most accurate pricing for Chicago Midway-Bend/Redmond flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Bend/Redmond flights.
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From Chicago Midway to Bend/Redmond
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One-way flight from Chicago Midway to Bend/Redmond
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Highest demand for flights based on searches. 13% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Find flight deals from Midway to Redmond

Cheapest flights from Midway to Redmond
Explore the most affordable flight options available from Midway to Redmond. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This Delta deal was found by Cheapflights users on 1/4. 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 4/152:12 pmMDW - RDM
2 stops11h 47mDelta
Wed 4/296:05 amRDM - MDW
2 stops9h 49mDelta
Deal found 1/4$357
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/61:29 pmMDW - RDM
2 stops11h 16mDelta
Tue 3/106:20 amRDM - MDW
2 stops9h 34mDelta
Deal found 1/5$370
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:10 pmMDW - RDM
2 stops11h 48mDelta
Wed 4/156:05 amRDM - MDW
2 stops9h 49mDelta
Deal found 1/5$400
This Delta deal was found by Cheapflights users on 1/4. 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 1/201:49 pmMDW - RDM
2 stops10h 58mDelta
Sat 1/245:50 amRDM - MDW
2 stops14h 32mDelta
Deal found 1/4$412
This Delta deal was found by Cheapflights users on 1/4. 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 5/131:00 pmMDW - RDM
2 stops11h 47mDelta
Sun 5/246:20 amRDM - MDW
2 stops10h 11mDelta
Deal found 1/4$495
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/261:00 pmMDW - RDM
2 stops11h 47mDelta
Sat 8/15:20 pmRDM - MDW
2 stops13h 22mDelta
Deal found 1/5$528
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:12 pmMDW - RDM
2 stops11h 47mDelta
Sun 5/36:05 amRDM - MDW
2 stops9h 49mDelta
Deal found 1/5$556
This Delta deal was found by Cheapflights users on 1/4. 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 1/51:49 pmMDW - RDM
2 stops11h 01mDelta
Mon 1/125:45 amRDM - MDW
2 stops10h 47mDelta
Deal found 1/4$586
This Delta deal was found by Cheapflights users on 1/4. 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 3/249:35 amMDW - RDM
2 stops8h 38mDelta
Fri 3/276:19 amRDM - MDW
2 stops10h 21mDelta
Deal found 1/4$630
This Delta deal was found by Cheapflights users on 1/3. 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 7/41:00 pmMDW - RDM
2 stops11h 47mDelta
Thu 10/155:55 amRDM - MDW
2 stops13h 50mDelta
Deal found 1/3$705
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:00 pmMDW - RDM
2 stops11h 47mDelta
Mon 6/155:20 pmRDM - MDW
2 stops13h 22mDelta
Deal found 1/5$818
This Delta deal was found by Cheapflights users on 1/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/41:49 pmMDW - RDM
2 stops10h 56mDelta
Sun 3/85:15 amRDM - MDW
2 stops11h 25mDelta
Deal found 1/5$1,045

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Redmond 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 January 6, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Redmond that are best for you.

Fly from

Midway

Fly to

Redmond

Route

Depart

Return

Price

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 3/6

1:29 pm-10:45 pm

2 stops11h 16m

Bend/Redmond

Tue 3/10

6:20 am-5:54 pm

2 stops9h 34m

$370

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 1/20

1:49 pm-10:47 pm

2 stops10h 58m

Bend/Redmond

Sat 1/24

5:50 am-10:22 pm

2 stops14h 32m

$412

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Mon 1/26

1:49 pm-10:47 pm

2 stops10h 58m

Bend/Redmond

Sun 2/1

7:00 am-10:22 pm

2 stops13h 22m

$586

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 1/27

9:50 am-4:36 pm

2 stops8h 46m

Bend/Redmond

Sun 2/1

7:00 am-10:22 pm

2 stops13h 22m

$586

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 3/4

1:49 pm-10:45 pm

2 stops10h 56m

Bend/Redmond

Sun 3/8

5:15 am-6:40 pm

2 stops11h 25m

$1,045

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 3/5

1:29 pm-10:45 pm

2 stops11h 16m

Bend/Redmond

Sun 3/8

6:20 am-6:40 pm

2 stops10h 20m

$1,065

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 2/3

9:33 am-4:31 pm

2 stops8h 58m

$145

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sun 4/5

1:10 pm-10:58 pm

2 stops11h 48m

$165

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 1/13

1:49 pm-10:47 pm

2 stops10h 58m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Compare providers for flights from Midway to Redmond

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 Midway to Redmond in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Redmond flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Redmond flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Redmond flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Redmond flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-Redmond 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 Midway to Redmond

Have a flexible travel schedule? Discover the best time to fly to Redmond from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to Redmond. 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 into for flights to Redmond from Chicago Midway?

    For a flight from Chicago Midway to Redmond, you will be flying into Bend/Redmond. Bend/Redmond (RDM) is just 1.8 mi from the center of the city. Bend/Redmond is the only Redmond airport and it handles 0 inbound flights from Chicago Midway per day. 0 airlines have flights to Bend/Redmond from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Redmond?

    Departing from Chicago Midway Airport to Redmond will take you 11h 16m. There are 1683 mi between Chicago Midway Airport and Redmond.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Redmond 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 Redmond?

Book flights to Redmond if you plan to visit one of these locations
Bend
Madras

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