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Cheap flights from Chicago to Redmond from $114

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 12/5. 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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0 bags

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Cheap round-trip flights

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Alaska Airlines Logo
8:00 am - 9:15 pmORD-RDM
15h 15m1 stop
Alaska Airlines Logo
5:52 am - 2:38 pmRDM-ORD
6h 46m1 stop
$202Alaska Airlines
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Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
7:45 am - 12:12 amORD-RDM
18h 27m1 stop
Alaska Airlines Logo
9:00 am - 11:59 pmRDM-ORD
12h 59m1 stop
$212Alaska Airlines
Find Deal
Thu, Feb 26 - Sun, Mar 1
Alaska Airlines Logo
5:51 pm - 12:50 pmORD-RDM
20h 59m1 stop
Alaska Airlines Logo
3:51 pm - 6:21 amRDM-ORD
12h 30m1 stop
$214Alaska Airlines
Find Deal
Fri, Dec 5 - Sun, Dec 7
Alaska Airlines Logo
9:00 am - 9:15 pmORD-RDM
14h 15m2 stops
Alaska Airlines Logo
5:52 am - 2:38 pmRDM-ORD
6h 46m1 stop
$219Alaska Airlines
Find Deal
Wed, Jan 14 - Sun, Jan 18
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
Delta Logo
7:00 am - 5:18 pmRDM-ORD
8h 18m1 stop
$253Delta
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Fri, Nov 14 - Tue, Nov 18
Delta Logo
9:20 am - 6:40 pmMDW-RDM
11h 20m2 stops
Delta Logo
11:30 am - 8:50 amRDM-MDW
19h 20m2 stops
$254Delta
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Tue, Mar 3 - Wed, Mar 4
Delta Logo
2:12 pm - 6:54 pmORD-RDM
6h 42m1 stop
Delta Logo
7:34 pm - 8:41 amRDM-ORD
11h 07m2 stops
$258Delta
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Fri, Nov 14 - Tue, Nov 18
United Airlines Logo
7:10 am - 12:57 pmORD-RDM
7h 47m1 stop
United Airlines Logo
7:51 pm - 6:02 amRDM-ORD
8h 11m1 stop
$319United Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
United Airlines Logo
3:55 pm - 9:07 pmORD-RDM
7h 12m1 stop
United Airlines Logo
1:17 pm - 10:50 pmRDM-ORD
7h 33m1 stop
$367United Airlines
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Sat, Nov 8 - Tue, Nov 11
United Airlines Logo
6:15 am - 12:19 pmORD-RDM
8h 04m1 stop
United Airlines Logo
3:51 pm - 12:58 amRDM-ORD
7h 07m1 stop
$399United Airlines
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Wed, Apr 1 - Thu, Apr 2

Delta flights from Chicago to Redmond

Our best Delta deals on Chicago to Redmond flight tickets
Delta
Nov 14
ORD6:13 pmChicago O'Hare Intl
6h 40m
1 stop
RDM10:53 pmBend/Redmond
Nov 18
RDM7:00 amBend/Redmond
8h 18m
1 stop
ORD5:18 pmChicago O'Hare Intl
$253
Find similar
Delta
Mar 3
MDW9:20 amChicago Midway
11h 20m
2 stops
RDM6:40 pmBend/Redmond
Mar 4
RDM11:30 amBend/Redmond
19h 20m
2 stops
MDW8:50 amChicago Midway
$254
Find similar
Delta
Nov 14
ORD2:12 pmChicago O'Hare Intl
6h 42m
1 stop
RDM6:54 pmBend/Redmond
Nov 18
RDM7:34 pmBend/Redmond
11h 07m
2 stops
ORD8:41 amChicago O'Hare Intl
$258
Find similar

United Airlines flights from Chicago to Redmond

Our best United Airlines deals on Chicago to Redmond flight tickets
United Airlines
Nov 13
ORD7:10 amChicago O'Hare Intl
7h 47m
1 stop
RDM12:57 pmBend/Redmond
Nov 17
RDM7:51 pmBend/Redmond
8h 11m
1 stop
ORD6:02 amChicago O'Hare Intl
$319
Find similar
United Airlines
Nov 8
ORD3:55 pmChicago O'Hare Intl
7h 12m
1 stop
RDM9:07 pmBend/Redmond
Nov 11
RDM1:17 pmBend/Redmond
7h 33m
1 stop
ORD10:50 pmChicago O'Hare Intl
$367
Find similar
United Airlines
Apr 1
ORD6:15 amChicago O'Hare Intl
8h 04m
1 stop
RDM12:19 pmBend/Redmond
Apr 2
RDM3:51 pmBend/Redmond
7h 07m
1 stop
ORD12:58 amChicago O'Hare Intl
$399
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 October 22, 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

8:00 am-9:15 pm

1 stop15h 15m

Bend/Redmond

Sun 1/18

5:52 am-2:38 pm

1 stop6h 46m

$202

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 2/26

7:45 am-12:12 am

1 stop18h 27m

Bend/Redmond

Sun 3/1

9:00 am-11:59 pm

1 stop12h 59m

$212

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 12/5

5:51 pm-12:50 pm

1 stop20h 59m

Bend/Redmond

Sun 12/7

3:51 pm-6:21 am

1 stop12h 30m

$214

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 1/14

9:00 am-9:15 pm

2 stops14h 15m

Bend/Redmond

Sun 1/18

5:52 am-2:38 pm

1 stop6h 46m

$219

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 11/14

6:13 pm-10:53 pm

1 stop6h 40m

Bend/Redmond

Tue 11/18

7:00 am-5:18 pm

1 stop8h 18m

$253

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 3/3

9:20 am-6:40 pm

2 stops11h 20m

Bend/Redmond

Wed 3/4

11:30 am-8:50 am

2 stops19h 20m

$254

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 11/14

2:12 pm-6:54 pm

1 stop6h 42m

Bend/Redmond

Tue 11/18

7:34 pm-8:41 am

2 stops11h 07m

$258

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 11/13

7:10 am-12:57 pm

1 stop7h 47m

Bend/Redmond

Mon 11/17

7:51 pm-6:02 am

1 stop8h 11m

$319

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 11/8

3:55 pm-9:07 pm

1 stop7h 12m

Bend/Redmond

Tue 11/11

1:17 pm-10:50 pm

1 stop7h 33m

$367

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 4/1

6:15 am-12:19 pm

1 stop8h 04m

Bend/Redmond

Thu 4/2

3:51 pm-12:58 am

1 stop7h 07m

$399

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 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 37% on your flight if you consider stops on a Chicago to Redmond flight.

How have Chicago to Redmond flight prices changed over time?

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

Direct flights

None
There are no direct flights from Chicago to Redmond. There are no popular flight routes from Chicago to Redmond.
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  • 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 16m.

  • 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
Hawaiian AirlinesPriceFrom $246Free CancellationRating
7.8
2,787 reviews
Search Hawaiian Airlines flights
American AirlinesPriceFrom $250Free CancellationRating
7.2
11,029 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $278Free CancellationRating
8.0
11,147 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
8,988 reviews
Search United Airlines flights
DeltaPriceFrom $278Free CancellationRating
7.9
7,981 reviews
Search Delta 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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