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Cheap flights from Chicago to Redmond from $207

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
2:18 pm - 9:38 pm
ORD
-
RDM
9h 20m
1 stop
Alaska Airlines Logo
7:07 am - 7:21 pm
RDM
-
ORD
10h 14m
1 stop
$389Alaska Airlines
Wed, Sep 2 - Sat, Sep 5
Delta Logo
12:54 pm - 6:45 pm
ORD
-
RDM
7h 51m
1 stop
Delta Logo
6:15 am - 8:30 pm
RDM
-
ORD
12h 15m
2 stops
$394Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
2:00 pm - 10:58 pm
ORD
-
RDM
10h 58m
2 stops
Delta Logo
6:15 am - 8:30 pm
RDM
-
ORD
12h 15m
2 stops
$399Delta
Wed, Sep 2 - Sat, Sep 5
Alaska Airlines Logo
2:21 pm - 8:23 pm
ORD
-
RDM
8h 02m
1 stop
Alaska Airlines Logo
1:32 pm - 11:59 pm
RDM
-
ORD
8h 27m
1 stop
$413Alaska Airlines
Tue, Oct 20 - Sat, Oct 24
Delta Logo
12:54 pm - 6:45 pm
ORD
-
RDM
7h 51m
1 stop
Delta Logo
5:10 am - 4:17 pm
RDM
-
ORD
9h 07m
2 stops
$418Delta
Wed, Sep 2 - Sat, Sep 5
Delta Logo
2:00 pm - 10:58 pm
ORD
-
RDM
10h 58m
2 stops
Delta Logo
6:15 am - 5:41 pm
RDM
-
ORD
9h 26m
2 stops
$423Delta
Wed, Sep 2 - Sat, Sep 5
Alaska Airlines Logo
3:09 pm - 9:12 pm
ORD
-
RDM
8h 03m
1 stop
Alaska Airlines Logo
3:50 pm - 11:41 pm
RDM
-
ORD
5h 51m
1 stop
$425Alaska Airlines
Tue, Dec 8 - Tue, Jan 5
Delta Logo
7:30 am - 11:56 am
ORD
-
RDM
6h 26m
1 stop
Delta Logo
5:55 am - 4:49 pm
RDM
-
ORD
8h 54m
2 stops
$430Delta
Tue, Dec 8 - Tue, Jan 5
Delta Logo
7:00 am - 1:04 pm
ORD
-
RDM
8h 04m
1 stop
Delta Logo
1:44 pm - 11:57 pm
RDM
-
ORD
8h 13m
1 stop
$433Delta
Wed, Sep 23 - Mon, Sep 28
Delta Logo
3:50 pm - 10:46 pm
ORD
-
RDM
8h 56m
2 stops
Delta Logo
5:55 am - 4:49 pm
RDM
-
ORD
8h 54m
2 stops
$435Delta
Tue, Dec 8 - Tue, Jan 5

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United Airlines flights from Chicago to Redmond

Our best United Airlines deals on Chicago to Redmond flight tickets
United Airlines
Aug 28
ORD8:50 amChicago O'Hare Intl
8h 05m
1 stop
RDM2:55 pmBend/Redmond
Sep 5
RDM1:03 pmBend/Redmond
6h 27m
1 stop
ORD9:30 pmChicago O'Hare Intl
$409
United Airlines
Jul 21
ORD6:10 amChicago O'Hare Intl
8h 02m
1 stop
RDM12:12 pmBend/Redmond
Jul 28
RDM3:51 pmBend/Redmond
7h 08m
1 stop
ORD12:59 amChicago O'Hare Intl
$450
United Airlines
Jun 24
ORD3:57 pmChicago O'Hare Intl
9h 02m
1 stop
RDM10:59 pmBend/Redmond
Jun 29
RDM1:49 pmBend/Redmond
7h 10m
1 stop
ORD10:59 pmChicago O'Hare Intl
$599

Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets
Alaska Airlines
Sep 2
ORD2:18 pmChicago O'Hare Intl
9h 20m
1 stop
RDM9:38 pmBend/Redmond
Sep 5
RDM7:07 amBend/Redmond
10h 14m
1 stop
ORD7:21 pmChicago O'Hare Intl
$389
Alaska Airlines
Oct 20
ORD2:21 pmChicago O'Hare Intl
8h 02m
1 stop
RDM8:23 pmBend/Redmond
Oct 24
RDM1:32 pmBend/Redmond
8h 27m
1 stop
ORD11:59 pmChicago O'Hare Intl
$413
Alaska Airlines
Dec 8
ORD3:09 pmChicago O'Hare Intl
8h 03m
1 stop
RDM9:12 pmBend/Redmond
Jan 5
RDM3:50 pmBend/Redmond
5h 51m
1 stop
ORD11:41 pmChicago O'Hare Intl
$425

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 June 24, 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 - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/2

2:18 pm-9:38 pm

1 stop9h 20m

Bend/Redmond

Sat 9/5

7:07 am-7:21 pm

1 stop10h 14m

$389

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/2

12:54 pm-6:45 pm

1 stop7h 51m

Bend/Redmond

Sat 9/5

6:15 am-8:30 pm

2 stops12h 15m

$394

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/2

2:00 pm-10:58 pm

2 stops10h 58m

Bend/Redmond

Sat 9/5

6:15 am-8:30 pm

2 stops12h 15m

$399

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 10/20

2:21 pm-8:23 pm

1 stop8h 02m

Bend/Redmond

Sat 10/24

1:32 pm-11:59 pm

1 stop8h 27m

$413

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/2

12:54 pm-6:45 pm

1 stop7h 51m

Bend/Redmond

Sat 9/5

5:10 am-4:17 pm

2 stops9h 07m

$418

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/2

2:00 pm-10:58 pm

2 stops10h 58m

Bend/Redmond

Sat 9/5

6:15 am-5:41 pm

2 stops9h 26m

$423
Quickest round-trip

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 12/8

3:09 pm-9:12 pm

1 stop8h 03m

Bend/Redmond

Tue 1/5

3:50 pm-11:41 pm

1 stop5h 51m

$425

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 12/8

7:30 am-11:56 am

1 stop6h 26m

Bend/Redmond

Tue 1/5

5:55 am-4:49 pm

2 stops8h 54m

$430

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 9/23

7:00 am-1:04 pm

1 stop8h 04m

Bend/Redmond

Mon 9/28

1:44 pm-11:57 pm

1 stop8h 13m

$433

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 12/8

3:50 pm-10:46 pm

2 stops8h 56m

Bend/Redmond

Tue 1/5

5:55 am-4:49 pm

2 stops8h 54m

$435

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 September is another great option to travel to Redmond, with average flight prices from Chicago averaging around $149.

Can stopping save me money on Chicago to Redmond flights?

You could potentially save up to 25% on your flight if you consider stops on a Chicago to Redmond flight.

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 51m

Direct flights

None
The fastest flight from Chicago to Redmond takes 6h 51m
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 51m.

  • 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
9,879 reviews
Search United Airlines flights
American AirlinesPriceFrom $318Free CancellationRating
7.1
11,748 reviews
Search American Airlines flights
DeltaPriceFrom $329Free CancellationRating
7.8
8,428 reviews
Search Delta flights
Alaska AirlinesPriceFrom $373Free CancellationRating
7.9
12,565 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
Sunriver
Madras
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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