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Cheap flights from Chicago Midway Airport to Redmond from $190

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Redmond departing on 9/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Redmond

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:51 pm - 11:49 pm
MDW
-
RDM
11h 58m
2 stops
Delta Logo
7:36 pm - 9:17 am
RDM
-
MDW
11h 41m
2 stops
$380Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
1:51 pm - 11:49 pm
MDW
-
RDM
11h 58m
2 stops
Delta Logo
7:36 pm - 8:39 am
RDM
-
MDW
11h 03m
2 stops
$385Delta
Tue, Aug 18 - Tue, Aug 25
Delta Logo
1:14 pm - 11:47 pm
MDW
-
RDM
12h 33m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$389Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
1:47 pm - 11:08 pm
MDW
-
RDM
11h 21m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$399Delta
Mon, Sep 14 - Mon, Sep 21
Delta Logo
1:00 pm - 10:46 pm
MDW
-
RDM
11h 46m
2 stops
Delta Logo
5:55 am - 6:37 pm
RDM
-
MDW
10h 42m
2 stops
$474Delta
Fri, Nov 6 - Mon, Nov 9
Delta Logo
1:49 pm - 10:36 pm
MDW
-
RDM
10h 47m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$492Delta
Sat, Jul 4 - Thu, Jul 9
Delta Logo
1:14 pm - 11:47 pm
MDW
-
RDM
12h 33m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$505Delta
Fri, Sep 25 - Sun, Sep 27
Delta Logo
1:27 pm - 10:58 pm
MDW
-
RDM
11h 31m
2 stops
Delta Logo
7:36 pm - 8:39 am
RDM
-
MDW
11h 03m
2 stops
$519Delta
Thu, Aug 6 - Tue, Aug 11
Delta Logo
1:27 pm - 10:58 pm
MDW
-
RDM
11h 31m
2 stops
Delta Logo
7:36 pm - 8:39 am
RDM
-
MDW
11h 03m
2 stops
$551Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
1:00 pm - 11:47 pm
MDW
-
RDM
12h 47m
2 stops
Delta Logo
7:24 pm - 8:50 am
RDM
-
MDW
11h 26m
2 stops
$580Delta
Thu, Sep 24 - Sun, Sep 27

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Delta flights from Chicago Midway Airport to Redmond

Our best Delta deals on Chicago Midway Airport to Redmond flight tickets
Delta
Aug 18
MDW1:51 pmChicago Midway
11h 58m
2 stops
RDM11:49 pmBend/Redmond
Aug 25
RDM7:36 pmBend/Redmond
11h 41m
2 stops
MDW9:17 amChicago Midway
$380
Delta
Aug 18
MDW1:51 pmChicago Midway
11h 58m
2 stops
RDM11:49 pmBend/Redmond
Aug 25
RDM7:36 pmBend/Redmond
11h 03m
2 stops
MDW8:39 amChicago Midway
$385
Delta
Sep 23
MDW1:00 pmChicago Midway
12h 47m
2 stops
RDM11:47 pmBend/Redmond
Sep 28
RDM7:24 pmBend/Redmond
11h 26m
2 stops
MDW8:50 amChicago Midway
$389

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated June 11, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Redmond that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 8/18

1:51 pm-11:49 pm

2 stops11h 58m

Bend/Redmond

Tue 8/25

7:36 pm-9:17 am

2 stops11h 41m

$380

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 8/18

1:51 pm-11:49 pm

2 stops11h 58m

Bend/Redmond

Tue 8/25

7:36 pm-8:39 am

2 stops11h 03m

$385

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 9/23

1:14 pm-11:47 pm

2 stops12h 33m

Bend/Redmond

Mon 9/28

7:24 pm-8:50 am

2 stops11h 26m

$389

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Mon 9/14

1:47 pm-11:08 pm

2 stops11h 21m

Bend/Redmond

Mon 9/21

7:24 pm-8:50 am

2 stops11h 26m

$399

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 11/6

1:00 pm-10:46 pm

2 stops11h 46m

Bend/Redmond

Mon 11/9

5:55 am-6:37 pm

2 stops10h 42m

$474
Quickest round-trip

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 7/4

1:49 pm-10:36 pm

2 stops10h 47m

Bend/Redmond

Thu 7/9

7:25 pm-8:37 am

2 stops11h 12m

$492

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 9/25

1:14 pm-11:47 pm

2 stops12h 33m

Bend/Redmond

Sun 9/27

7:24 pm-8:50 am

2 stops11h 26m

$505

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 8/6

1:27 pm-10:58 pm

2 stops11h 31m

Bend/Redmond

Tue 8/11

7:36 pm-8:39 am

2 stops11h 03m

$519

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 8/6

1:27 pm-10:58 pm

2 stops11h 31m

Bend/Redmond

Mon 8/10

7:36 pm-8:39 am

2 stops11h 03m

$551

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 9/24

1:00 pm-11:47 pm

2 stops12h 47m

Bend/Redmond

Sun 9/27

7:24 pm-8:50 am

2 stops11h 26m

$580

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Redmond from

How to get the cheapest flight ticket from Chicago Midway Airport to Redmond

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Bend/Redmond?

Delta is the most popular carrier operating from Chicago Midway to Bend/Redmond

When to book flights from Chicago Midway Airport to Redmond

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Redmond according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Redmond (MDW to RDM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Redmond

Fastest flight time

10h 47m

Direct flights

None
The fastest flight from Chicago Midway Airport to Redmond takes 10h 47m
There are no direct flights from Chicago Midway Airport to Redmond. There are no popular flight routes from Chicago Midway Airport to Redmond.
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Frequently asked questions about flying from Chicago Midway Airport to Redmond

  • How far is Chicago Midway to Bend/Redmond by plane?

    The distance between Chicago Midway and Bend/Redmond is about 1684.2 mi. 10h 47m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago Midway Airport to Bend/Redmond Airport?

    Prices for flights from Chicago Midway Airport to Bend/Redmond Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Bend/Redmond Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Bend/Redmond Airport.

  • What documentation or ID do you need to fly to Bend/Redmond Airport?

    The travel and health documents you'll need for your trip to Bend/Redmond Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Bend/Redmond Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Redmond?

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

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Redmond?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Redmond. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Redmond with flexible booking policies on momondo?

Flights from Chicago to Redmond with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Redmond?

momondo provides multiple filters to help you find the best flight to Redmond from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Redmond right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Redmond flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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