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Cheap flights from Chicago Midway Airport to Redmond from $145

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 9/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Redmond

Cheap round-trip flights

Delta Logo
3:00 pm - 10:35 pmMDW-RDM
9h 35m2 stops
Delta Logo
7:00 am - 5:43 pmRDM-MDW
8h 43m2 stops
$289Delta
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
3:00 pm - 10:35 pmMDW-RDM
9h 35m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$329Delta
Find Deal
Sat, Oct 25 - Wed, Oct 29
Delta Logo
9:35 am - 6:46 pmMDW-RDM
11h 11m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$379Delta
Find Deal
Fri, Oct 24 - Sun, Oct 26
Delta Logo
1:08 pm - 10:35 pmMDW-RDM
11h 27m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$399Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
Delta Logo
1:48 pm - 10:35 pmMDW-RDM
10h 47m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$409Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
1:48 pm - 10:35 pmMDW-RDM
10h 47m2 stops
Delta Logo
7:26 pm - 8:55 amRDM-MDW
11h 29m2 stops
$481Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
Delta Logo
2:00 pm - 10:44 pmMDW-RDM
10h 44m2 stops
Delta Logo
7:25 pm - 8:50 amRDM-MDW
11h 25m2 stops
$533Delta
Find Deal
Tue, Dec 16 - Thu, Jan 15
Delta Logo
9:20 am - 6:50 pmMDW-RDM
11h 30m2 stops
Delta Logo
7:30 pm - 8:53 amRDM-MDW
11h 23m2 stops
$553Delta
Find Deal
Sat, Sep 27 - Sun, Sep 28
Delta Logo
1:00 pm - 10:44 pmMDW-RDM
11h 44m2 stops
Delta Logo
7:25 pm - 8:50 amRDM-MDW
11h 25m2 stops
$573Delta
Find Deal
Tue, Dec 16 - Thu, Jan 15
Delta Logo
1:08 pm - 10:35 pmMDW-RDM
11h 27m2 stops
Delta Logo
7:26 pm - 8:40 amRDM-MDW
11h 14m2 stops
$633Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27

Delta flights from Chicago Midway Airport to Redmond

Our best Delta deals on Chicago Midway Airport to Redmond flight tickets
Delta
Oct 25
MDW3:00 pmChicago Midway
9h 35m
2 stops
RDM10:35 pmBend/Redmond
Oct 29
RDM7:00 amBend/Redmond
8h 43m
2 stops
MDW5:43 pmChicago Midway
$289
Find similar
Delta
Oct 25
MDW3:00 pmChicago Midway
9h 35m
2 stops
RDM10:35 pmBend/Redmond
Oct 29
RDM7:26 pmBend/Redmond
11h 29m
2 stops
MDW8:55 amChicago Midway
$329
Find similar
Delta
Oct 24
MDW9:35 amChicago Midway
11h 11m
2 stops
RDM6:46 pmBend/Redmond
Oct 26
RDM7:26 pmBend/Redmond
11h 29m
2 stops
MDW8:55 amChicago Midway
$379
Find similar

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 August 18, 2025.
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

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 10/25

3:00 pm-10:35 pm

2 stops9h 35m

Bend/Redmond

Wed 10/29

7:00 am-5:43 pm

2 stops8h 43m

$289

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 10/25

3:00 pm-10:35 pm

2 stops9h 35m

Bend/Redmond

Wed 10/29

7:26 pm-8:55 am

2 stops11h 29m

$329

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 10/24

9:35 am-6:46 pm

2 stops11h 11m

Bend/Redmond

Sun 10/26

7:26 pm-8:55 am

2 stops11h 29m

$379

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 10/7

1:08 pm-10:35 pm

2 stops11h 27m

Bend/Redmond

Sat 10/11

7:26 pm-8:55 am

2 stops11h 29m

$399

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 10/30

1:48 pm-10:35 pm

2 stops10h 47m

Bend/Redmond

Sun 11/2

7:26 pm-8:55 am

2 stops11h 29m

$409

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 10/7

1:48 pm-10:35 pm

2 stops10h 47m

Bend/Redmond

Sat 10/11

7:26 pm-8:55 am

2 stops11h 29m

$481

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 12/16

2:00 pm-10:44 pm

2 stops10h 44m

Bend/Redmond

Thu 1/15

7:25 pm-8:50 am

2 stops11h 25m

$533

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Sat 9/27

9:20 am-6:50 pm

2 stops11h 30m

Bend/Redmond

Sun 9/28

7:30 pm-8:53 am

2 stops11h 23m

$553

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 12/16

1:00 pm-10:44 pm

2 stops11h 44m

Bend/Redmond

Thu 1/15

7:25 pm-8:50 am

2 stops11h 25m

$573

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Thu 10/23

1:08 pm-10:35 pm

2 stops11h 27m

Bend/Redmond

Mon 10/27

7:26 pm-8:40 am

2 stops11h 14m

$633

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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 day to depart on your flight to Redmond?

The cheapest day to depart on your flight to Redmond is on a Wednesday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Redmond on Sunday is $627.

What is the cheapest time of day to depart on your flight to Redmond?

Our most recent data shows that the best time of day to fly to Redmond is at noon. Flights from Chicago Midway Airport to Redmond during this time can be as low as $443. In the evening is when there is more demand to fly to Redmond, so prices are often more expensive at around $522 per ticket.

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

Best Price Found

$145

Fastest flight time

9h 35m

Direct flights

None

Airports in Redmond

1 airport
The best one-way flight to Redmond from Chicago Midway Airport in the past 72 hours is $145. The best round-trip flight deal from Chicago Midway Airport to Redmond found on momondo in the last 72 hours is $289.
The fastest flight from Chicago Midway Airport to Redmond takes 9h 35m
There are no direct flights from Chicago Midway Airport to Redmond. Popular non-direct route for this connection is Chicago Midway Airport - Bend/Redmond Airport.
There is 1 airport near Redmond: Bend/Redmond (RDM)
Search flight deals

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

    The distance between Chicago Midway and Bend/Redmond is about 1684.2 mi. 9h 35m 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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