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Cheap flights from Chicago Midway Airport to Redmond from $244

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 6/4. 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
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
1:22 pm - 11:44 pm
MDW
-
RDM
12h 22m
2 stops
Delta Logo
7:20 pm - 8:42 am
RDM
-
MDW
11h 22m
2 stops
$368Delta
Tue, Jun 2 - Wed, Jun 3
Delta Logo
1:22 pm - 11:44 pm
MDW
-
RDM
12h 22m
2 stops
Delta Logo
7:20 pm - 8:43 am
RDM
-
MDW
11h 23m
2 stops
$379Delta
Tue, Jun 2 - Fri, Jun 5
Delta Logo
1:22 pm - 10:54 pm
MDW
-
RDM
11h 32m
2 stops
Delta Logo
7:20 pm - 8:42 am
RDM
-
MDW
11h 22m
2 stops
$428Delta
Fri, May 8 - Tue, May 19
Delta Logo
1:22 pm - 10:52 pm
MDW
-
RDM
11h 30m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$429Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
1:22 pm - 10:52 pm
MDW
-
RDM
11h 30m
2 stops
Delta Logo
5:05 am - 6:33 pm
RDM
-
MDW
11h 28m
2 stops
$437Delta
Mon, Jun 1 - Sat, Jun 6
Delta Logo
1:49 pm - 10:58 pm
MDW
-
RDM
11h 09m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$438Delta
Fri, Jun 12 - Tue, Jun 16
Delta Logo
1:22 pm - 11:44 pm
MDW
-
RDM
12h 22m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$439Delta
Wed, Jun 3 - Mon, Jun 8
Delta Logo
1:59 pm - 11:44 pm
MDW
-
RDM
11h 45m
2 stops
Delta Logo
5:05 am - 5:56 pm
RDM
-
MDW
10h 51m
2 stops
$442Delta
Wed, May 27 - Sun, May 31
Delta Logo
1:22 pm - 11:44 pm
MDW
-
RDM
12h 22m
2 stops
Delta Logo
7:20 pm - 9:14 am
RDM
-
MDW
11h 54m
2 stops
$448Delta
Wed, Jun 3 - Sat, Jun 6
Delta Logo
1:16 pm - 11:52 pm
MDW
-
RDM
12h 36m
2 stops
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
$458Delta
Tue, Jun 16 - Tue, Jun 23

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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
Jun 2
MDW1:22 pmChicago Midway
12h 22m
2 stops
RDM11:44 pmBend/Redmond
Jun 3
RDM7:20 pmBend/Redmond
11h 22m
2 stops
MDW8:42 amChicago Midway
$368
Delta
Jun 2
MDW1:22 pmChicago Midway
12h 22m
2 stops
RDM11:44 pmBend/Redmond
Jun 5
RDM7:20 pmBend/Redmond
11h 23m
2 stops
MDW8:43 amChicago Midway
$379
Delta
May 8
MDW1:22 pmChicago Midway
11h 32m
2 stops
RDM10:54 pmBend/Redmond
May 19
RDM7:20 pmBend/Redmond
11h 22m
2 stops
MDW8:42 amChicago Midway
$428

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 April 25, 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 6/2

1:22 pm-11:44 pm

2 stops12h 22m

Bend/Redmond

Wed 6/3

7:20 pm-8:42 am

2 stops11h 22m

$368

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 6/2

1:22 pm-11:44 pm

2 stops12h 22m

Bend/Redmond

Fri 6/5

7:20 pm-8:43 am

2 stops11h 23m

$379

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 5/8

1:22 pm-10:54 pm

2 stops11h 32m

Bend/Redmond

Tue 5/19

7:20 pm-8:42 am

2 stops11h 22m

$428

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 6/3

1:22 pm-10:52 pm

2 stops11h 30m

Bend/Redmond

Mon 6/8

7:25 pm-8:37 am

2 stops11h 12m

$429

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Mon 6/1

1:22 pm-10:52 pm

2 stops11h 30m

Bend/Redmond

Sat 6/6

5:05 am-6:33 pm

2 stops11h 28m

$437
Quickest round-trip

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 6/12

1:49 pm-10:58 pm

2 stops11h 09m

Bend/Redmond

Tue 6/16

7:25 pm-8:37 am

2 stops11h 12m

$438

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 6/3

1:22 pm-11:44 pm

2 stops12h 22m

Bend/Redmond

Mon 6/8

7:25 pm-8:37 am

2 stops11h 12m

$439

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 5/27

1:59 pm-11:44 pm

2 stops11h 45m

Bend/Redmond

Sun 5/31

5:05 am-5:56 pm

2 stops10h 51m

$442

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Wed 6/3

1:22 pm-11:44 pm

2 stops12h 22m

Bend/Redmond

Sat 6/6

7:20 pm-9:14 am

2 stops11h 54m

$448

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 6/16

1:16 pm-11:52 pm

2 stops12h 36m

Bend/Redmond

Tue 6/23

7:25 pm-8:37 am

2 stops11h 12m

$458

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

11h 09m

Direct flights

None
The fastest flight from Chicago Midway Airport to Redmond takes 11h 09m
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. 11h 09m 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
Sisters
Madras
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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