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Cheap flights from Chicago to Redmond from $140

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 to Redmond departing on 2/14. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
3:35 pm - 9:15 pm
ORD
-
RDM
7h 40m1 stop
Alaska Airlines Logo
3:57 pm - 1:10 pm
RDM
-
ORD
19h 13m1 stop
$271Alaska Airlines
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
6:06 pm - 12:30 pm
ORD
-
RDM
20h 24m2 stops
Alaska Airlines Logo
5:09 am - 1:10 pm
RDM
-
ORD
6h 01m1 stop
$279Alaska Airlines
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
3:44 pm - 11:59 am
ORD
-
RDM
22h 15m1 stop
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
$291Alaska Airlines
Tue, Jan 27 - Sun, Feb 1
Delta Logo
1:20 pm - 10:45 pm
ORD
-
RDM
11h 25m2 stops
Delta Logo
6:35 am - 9:34 pm
RDM
-
ORD
12h 59m2 stops
$296Delta
Fri, Mar 6 - Tue, Mar 10
Alaska Airlines Logo
6:06 pm - 12:30 pm
ORD
-
RDM
20h 24m2 stops
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
$299Alaska Airlines
Mon, Jan 26 - Sun, Feb 1
Alaska Airlines Logo
6:06 pm - 12:54 pm
ORD
-
RDM
20h 48m1 stop
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
$304Alaska Airlines
Mon, Jan 26 - Sun, Feb 1
Alaska Airlines Logo
6:06 pm - 11:52 pm
ORD
-
RDM
7h 46m1 stop
Alaska Airlines Logo
3:57 pm - 5:10 pm
RDM
-
ORD
23h 13m2 stops
$306Alaska Airlines
Wed, Jan 14 - Wed, Jan 21
Alaska Airlines Logo
3:35 pm - 10:46 pm
ORD
-
RDM
9h 11m2 stops
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
$319Alaska Airlines
Tue, Jan 27 - Sun, Feb 1
Alaska Airlines Logo
3:54 pm - 9:32 pm
ORD
-
RDM
7h 38m1 stop
Alaska Airlines Logo
9:02 am - 12:01 pm
RDM
-
ORD
24h 59m1 stop
$321Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
Delta Logo
1:28 pm - 10:45 pm
MDW
-
RDM
11h 17m2 stops
Delta Logo
6:35 am - 5:55 pm
RDM
-
MDW
9h 20m2 stops
$389Delta
Fri, Mar 6 - Tue, Mar 10

Delta flights from Chicago to Redmond

Our best Delta deals on Chicago to Redmond flight tickets
Delta
Mar 25
ORD7:20 amChicago O'Hare Intl
6h 35m
1 stop
RDM11:55 amBend/Redmond
Apr 1
RDM6:35 amBend/Redmond
11h 24m
2 stops
ORD7:59 pmChicago O'Hare Intl
$341
Find similar
Delta
Jun 14
ORD7:20 amChicago O'Hare Intl
6h 42m
1 stop
RDM12:02 pmBend/Redmond
Jun 19
RDM5:20 pmBend/Redmond
12h 06m
2 stops
ORD7:26 amChicago O'Hare Intl
$354
Find similar
Delta
Jun 14
ORD7:20 amChicago O'Hare Intl
6h 42m
1 stop
RDM12:02 pmBend/Redmond
Jun 19
RDM12:30 pmBend/Redmond
9h 17m
1 stop
ORD11:47 pmChicago O'Hare Intl
$374
Find similar

Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets
Alaska Airlines
Jan 14
ORD3:35 pmChicago O'Hare Intl
7h 40m
1 stop
RDM9:15 pmBend/Redmond
Jan 18
RDM5:52 amBend/Redmond
6h 46m
1 stop
ORD2:38 pmChicago O'Hare Intl
$271
Find similar
Alaska Airlines
Jan 14
ORD6:06 pmChicago O'Hare Intl
20h 24m
2 stops
RDM12:30 pmBend/Redmond
Jan 18
RDM5:09 amBend/Redmond
6h 01m
1 stop
ORD1:10 pmChicago O'Hare Intl
$279
Find similar
Alaska Airlines
Jan 27
ORD3:44 pmChicago O'Hare Intl
22h 15m
1 stop
RDM11:59 amBend/Redmond
Feb 1
RDM8:45 amBend/Redmond
13h 05m
1 stop
ORD11:50 pmChicago O'Hare Intl
$291
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 December 18, 2025.
Use the filters below to find and compare flights from Chicago to Redmond that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 1/14

3:35 pm-9:15 pm

1 stop7h 40m

Bend/Redmond

Sun 1/18

3:57 pm-1:10 pm

1 stop19h 13m

$271

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 1/14

6:06 pm-12:30 pm

2 stops20h 24m

Bend/Redmond

Sun 1/18

5:09 am-1:10 pm

1 stop6h 01m

$279

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 1/27

3:44 pm-11:59 am

1 stop22h 15m

Bend/Redmond

Sun 2/1

8:45 am-11:50 pm

1 stop13h 05m

$291

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 3/6

1:20 pm-10:45 pm

2 stops11h 25m

Bend/Redmond

Tue 3/10

6:35 am-9:34 pm

2 stops12h 59m

$296

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 1/26

6:06 pm-12:30 pm

2 stops20h 24m

Bend/Redmond

Sun 2/1

8:45 am-11:50 pm

1 stop13h 05m

$299

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 1/26

6:06 pm-12:54 pm

1 stop20h 48m

Bend/Redmond

Sun 2/1

8:45 am-11:50 pm

1 stop13h 05m

$304

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 1/14

6:06 pm-11:52 pm

1 stop7h 46m

Bend/Redmond

Wed 1/21

3:57 pm-5:10 pm

2 stops23h 13m

$306

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 1/27

3:35 pm-10:46 pm

2 stops9h 11m

Bend/Redmond

Sun 2/1

8:45 am-11:50 pm

1 stop13h 05m

$319

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 2/14

3:54 pm-9:32 pm

1 stop7h 38m

Bend/Redmond

Wed 2/18

9:02 am-12:01 pm

1 stop24h 59m

$321

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Fri 3/6

1:28 pm-10:45 pm

2 stops11h 17m

Bend/Redmond

Tue 3/10

6:35 am-5:55 pm

2 stops9h 20m

$389

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Redmond from

How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Redmond?

What is the cheapest month to fly to Redmond?

The month of June is another great option to travel to Redmond, with average flight prices from Chicago averaging around $316.

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 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.

Can stopping save me money on Chicago to Redmond flights?

You could potentially save up to 45% on your flight if you consider stops on a Chicago to Redmond flight.

How have Chicago to Redmond flight prices changed over time?

As of December 2025, prices for Chicago to Redmond flights are approximately 10% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Redmond

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

Cheap Chicago to Redmond (CHI to RDM) flight deals and tips

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

Fastest flight time

6h 10m

Direct flights

None
The fastest flight from Chicago to Redmond takes 6h 10m
There are no direct flights from Chicago to Redmond. There are no popular flight routes from Chicago to Redmond.
Search flight deals

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

    Bend/Redmond is 1688.2 mi away from Chicago. In terms of flight time, this usually takes a little over 6h 10m.

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

    Prices for flights from Chicago to Bend/Redmond Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Bend/Redmond Airport?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Bend/Redmond Airport.

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

    The required travel and health documents for your Bend/Redmond Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Bend/Redmond Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Chicago to Redmond?

Best airlines flying from Chicago to Redmond

Compare and see reviews for airlines that fly from Chicago to Redmond with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $139Free CancellationRating
7.9
8,008 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $246Free CancellationRating
7.8
2,820 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $278Free CancellationRating
8.0
11,479 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $345Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights

Traveling to a place near Redmond?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Redmond from Chicago.

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

Yes. momondo enables you to select and highlight flights to Redmond from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Redmond.

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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