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Cheap flights from Chicago to Redmond from $218

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 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Redmond

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
7:20 am - 4:26 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
11h 06m1 stop San Diego
Alaska Airlines Logo
5:12 pm - 1:25 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
18h 13m1 stop San Diego
$435Alaska Airlines
Sat, Oct 3 - Sat, Oct 10
Alaska Airlines Logo
7:00 am - 12:38 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 38m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:00 am - 6:20 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 20m1 stop Seattle/Tacoma Intl
$435Alaska Airlines
Wed, Oct 28 - Sat, Oct 31
Delta Logo
12:50 pm - 6:44 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 54m1 stop Seattle/Tacoma Intl
Delta Logo
12:30 pm - 9:55 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 25m1 stop Salt Lake City
$435Delta
Tue, Sep 15 - Tue, Sep 22
United Airlines Logo
2:32 pm - 9:11 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 39m1 stop Denver Intl
United Airlines Logo
1:52 pm - 10:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 07m1 stop San Francisco
$435United Airlines
Tue, Sep 15 - Tue, Sep 22
United Airlines Logo
12:51 pm - 5:53 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 02m1 stop San Francisco
United Airlines Logo
7:20 am - 5:05 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 45m1 stop Los Angeles
$435United Airlines
Sat, Sep 19 - Sat, Sep 26
American Airlines Logo
6:17 pm - 11:56 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 39m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:24 am - 4:09 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 45m1 stop Phoenix Sky Harbor Intl
$435American Airlines
Wed, Oct 21 - Sat, Oct 24
Alaska Airlines Logo
7:20 am - 12:53 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 33m1 stop San Diego
Alaska Airlines Logo
1:37 pm - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 22m1 stop Seattle/Tacoma Intl
$435Alaska Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
2:32 pm - 9:11 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 39m1 stop Denver Intl
United Airlines Logo
6:00 am - 2:50 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 50m1 stop San Francisco
$435United Airlines
Sat, Sep 12 - Tue, Sep 15
Delta Logo
8:29 am - 6:50 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
12h 21m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
Delta Logo
6:10 am - 4:53 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 43m1 stop Seattle/Tacoma Intl
$440Delta
Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
6:59 am - 2:14 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 15m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
2:46 pm - 11:43 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 57m1 stop Phoenix Sky Harbor Intl
$481American Airlines
Mon, Sep 28 - Sat, Oct 3

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Delta flights from Chicago to Redmond

Our best Delta deals on Chicago to Redmond flight tickets
Delta
Sep 12
ORD2:05 pmChicago O'Hare Intl
10h 48m
2 stops
RDM10:53 pmBend/Redmond
Sep 15
RDM1:44 pmBend/Redmond
8h 13m
1 stop
ORD11:57 pmChicago O'Hare Intl
$440
Delta
Sep 12
ORD2:05 pmChicago O'Hare Intl
10h 48m
2 stops
RDM10:53 pmBend/Redmond
Sep 15
RDM7:24 pmBend/Redmond
10h 32m
2 stops
ORD7:56 amChicago O'Hare Intl
$445
Delta
Sep 12
MDW9:29 amChicago Midway
11h 15m
2 stops
RDM6:44 pmBend/Redmond
Sep 15
RDM7:24 pmBend/Redmond
11h 43m
2 stops
MDW9:07 amChicago Midway
$477

Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets
Alaska Airlines
Oct 28
ORD7:00 amChicago O'Hare Intl
7h 38m
1 stop
RDM12:38 pmBend/Redmond
Oct 31
RDM8:00 amBend/Redmond
8h 20m
1 stop
ORD6:20 pmChicago O'Hare Intl
$435
Alaska Airlines
Oct 3
ORD7:20 amChicago O'Hare Intl
12h 22m
2 stops
RDM5:42 pmBend/Redmond
Oct 10
RDM6:06 pmBend/Redmond
9h 34m
1 stop
ORD5:40 amChicago O'Hare Intl
$464
Alaska Airlines
Sep 2
ORD9:00 amChicago O'Hare Intl
9h 44m
1 stop
RDM4:44 pmBend/Redmond
Sep 5
RDM10:09 amBend/Redmond
11h 50m
1 stop
ORD11:59 pmChicago O'Hare Intl
$473

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 August 10, 2026.
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

Cheapest round-trip

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 10/3

7:20 am-4:26 pm

1 stop11h 06m

Bend/Redmond

Sat 10/10

5:12 pm-1:25 pm

1 stop18h 13m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Wed 10/28

7:00 am-12:38 pm

1 stop7h 38m

Bend/Redmond

Sat 10/31

8:00 am-6:20 pm

1 stop8h 20m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Tue 9/15

12:50 pm-6:44 pm

1 stop7h 54m

Bend/Redmond

Tue 9/22

12:30 pm-9:55 pm

1 stop7h 25m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Tue 9/15

2:32 pm-9:11 pm

1 stop8h 39m

Bend/Redmond

Tue 9/22

1:52 pm-10:59 pm

1 stop7h 07m

$435
Quickest round-trip

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 9/19

12:51 pm-5:53 pm

1 stop7h 02m

Bend/Redmond

Sat 9/26

7:20 am-5:05 pm

1 stop7h 45m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Wed 10/21

6:17 pm-11:56 pm

1 stop7h 39m

Bend/Redmond

Sat 10/24

5:24 am-4:09 pm

1 stop8h 45m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 9/19

7:20 am-12:53 pm

1 stop7h 33m

Bend/Redmond

Sat 9/26

1:37 pm-11:59 pm

1 stop8h 22m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 9/12

2:32 pm-9:11 pm

1 stop8h 39m

Bend/Redmond

Tue 9/15

6:00 am-2:50 pm

1 stop6h 50m

$435

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Wed 10/21

8:29 am-6:50 pm

2 stops12h 21m

Bend/Redmond

Sat 10/24

6:10 am-4:53 pm

1 stop8h 43m

$440

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Mon 9/28

6:59 am-2:14 pm

1 stop9h 15m

Bend/Redmond

Sat 10/3

2:46 pm-11:43 pm

1 stop6h 57m

$481

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

Prices are currently typical for flights on this route.

Typical prices usually range from $415 to $538.
The lowest price recently found on this route was $435.

What is the cheapest month to fly to Redmond?

The month of November is another great option to travel to Redmond, with average flight prices from Chicago averaging around $398.

Can stopping save me money on Chicago to Redmond flights?

You could potentially save up to 18% 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

Fastest flight time

6h 41m

Direct flights

None
The fastest flight from Chicago to Redmond takes 6h 41m
There are no direct flights from Chicago to Redmond. There are no popular flight routes from Chicago to Redmond.
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Frequently asked questions about flying from Chicago to Redmond

  • 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 41m.

  • 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
United AirlinesPriceFrom $278Free CancellationRating
7.4
10,097 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,897 reviews
Search American Airlines flights
DeltaPriceFrom $329Free CancellationRating
7.8
8,497 reviews
Search Delta flights
Alaska AirlinesPriceFrom $412Free CancellationRating
7.9
12,790 reviews
Search Alaska Airlines flights

Traveling to a place near Redmond?

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