Which layover airport offers the lowest fares from Chicago to Redmond?

Flights via Denver (DEN) offer the lowest average round-trip price of $281.

Which layover airport has the shortest travel time from Chicago to Redmond?

Flights connecting via Salt Lake City (SLC) have the shortest average one-way travel time: 6h 39m.

What airlines fly to Redmond?

Alaska Airlines, Delta and United Airlines are the top three most popular airlines that fly to Redmond from Chicago according to our data. Alaska Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Redmond. Keep in mind that there are 4 different airlines that fly to Redmond on a routine basis, so you have a few additional options to choose from.

Which layover airport has the shortest connection time from Chicago to Redmond?

Portland (PDX) has the shortest average layover time for this route: 1h 06m.

Which airport is the most popular layover for flights between Chicago and Redmond?

Seattle (SEA) was the most common stop: 56% of momondo users choosing 1-stop flights on this route connected there.

What is the cheapest airline that flies from Chicago to Bend/Redmond?

American Airlines, Delta, and United Airlines are the most popular carriers operating from Chicago to Bend/Redmond

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?

There are 4 operators available for flights from Chicago to Bend/Redmond Airport as of September 2026.

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.

$228 Cheap Flights from Chicago to Redmond in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Redmond

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:20 pm - 9:37 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

7h 17m1 stop Denver Intl

1:10 pm - 9:34 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

6h 24m1 stop Denver Intl

$455United Airlines

Tue, Dec 8 - Tue, Dec 15

10:39 am - 6:23 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

9h 44m1 stop San Francisco

5:00 am - 1:14 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

6h 14m1 stop Denver Intl

$455United Airlines

Sat, Oct 24 - Sat, Oct 31

4:00 pm - 10:02 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

8h 02m1 stop Salt Lake City

6:10 am - 8:30 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

12h 20m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$460Delta

Sat, Oct 24 - Sat, Oct 31

3:30 pm - 11:06 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

9h 36m2 stops Minneapolis St Paul Seattle/Tacoma Intl

6:10 am - 8:30 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

12h 20m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

$466Delta

Sat, Oct 24 - Sat, Oct 31

6:00 am - 5:01 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

13h 01m2 stops Seattle/Tacoma Intl San Francisco

5:31 pm - 2:21 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

18h 50m1 stop Seattle/Tacoma Intl

$484Alaska Airlines

Tue, Dec 8 - Tue, Dec 15

3:30 pm - 11:40 amORD Chicago O'Hare Intl-RDM Bend/Redmond

22h 10m1 stop Las Vegas Harry Reid Intl

12:20 pm - 12:59 amRDM Bend/Redmond-ORD Chicago O'Hare Intl

10h 39m2 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl

$484Multiple Airlines

Thu, Oct 8 - Mon, Oct 12

6:57 pm - 11:53 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

6h 56m1 stop Seattle/Tacoma Intl

5:15 am - 1:13 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

5h 58m1 stop Portland

$487Alaska Airlines

Sat, Jan 30 - Tue, Feb 2

5:10 pm - 11:56 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

8h 46m1 stop Phoenix Sky Harbor Intl

3:00 pm - 11:30 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

6h 30m1 stop Phoenix Sky Harbor Intl

$493American Airlines

Wed, Oct 21 - Tue, Oct 27

3:30 pm - 11:40 amORD Chicago O'Hare Intl-RDM Bend/Redmond

22h 10m1 stop Las Vegas Harry Reid Intl

12:20 pm - 5:16 amRDM Bend/Redmond-ORD Chicago O'Hare Intl

14h 56m1 stop Las Vegas Harry Reid Intl

$517Multiple Airlines

Thu, Oct 8 - Mon, Oct 12

5:00 am - 1:09 pmORD Chicago O'Hare Intl-RDM Bend/Redmond

10h 09m1 stop Phoenix Sky Harbor Intl

5:20 am - 2:50 pmRDM Bend/Redmond-ORD Chicago O'Hare Intl

7h 30m1 stop Phoenix Sky Harbor Intl

$547American Airlines

Thu, Jan 21 - Mon, Jan 25

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Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets

Alaska Airlines

Jan 30

ORD6:57 pmChicago O'Hare Intl

6h 56m

1 stop

RDM11:53 pmBend/Redmond

Feb 2

RDM5:15 amBend/Redmond

5h 58m

1 stop

ORD1:13 pmChicago O'Hare Intl

$487

Alaska Airlines

Jan 30

ORD8:00 amChicago O'Hare Intl

9h 26m

2 stops

RDM3:26 pmBend/Redmond

Feb 2

RDM2:41 pmBend/Redmond

7h 18m

1 stop

ORD11:59 pmChicago O'Hare Intl

$494

Alaska Airlines

Dec 2

ORD9:00 amChicago O'Hare Intl

9h 51m

1 stop

RDM4:51 pmBend/Redmond

Dec 6

RDM5:31 pmBend/Redmond

21h 00m

1 stop

ORD4:31 pmChicago O'Hare Intl

$499

Delta flights from Chicago to Redmond

Our best Delta deals on Chicago to Redmond flight tickets

Delta

Oct 24

ORD4:00 pmChicago O'Hare Intl

8h 02m

1 stop

RDM10:02 pmBend/Redmond

Oct 31

RDM6:10 amBend/Redmond

12h 20m

2 stops

ORD8:30 pmChicago O'Hare Intl

$460

Delta

Oct 24

ORD3:30 pmChicago O'Hare Intl

9h 36m

2 stops

RDM11:06 pmBend/Redmond

Oct 31

RDM6:10 amBend/Redmond

12h 20m

2 stops

ORD8:30 pmChicago O'Hare Intl

$466

Delta

Oct 21

ORD6:35 amChicago O'Hare Intl

8h 11m

1 stop

RDM12:46 pmBend/Redmond

Oct 27

RDM6:10 amBend/Redmond

8h 43m

1 stop

ORD4:53 pmChicago O'Hare Intl

$493

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

Tue 12/8

4:20 pm-9:37 pm

1 stop7h 17m

Bend/Redmond

Tue 12/15

1:10 pm-9:34 pm

1 stop6h 24m

$455

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 10/24

10:39 am-6:23 pm

1 stop9h 44m

Bend/Redmond

Sat 10/31

5:00 am-1:14 pm

1 stop6h 14m

$455

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 10/24

4:00 pm-10:02 pm

1 stop8h 02m

Bend/Redmond

Sat 10/31

6:10 am-8:30 pm

2 stops12h 20m

$460

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 10/24

3:30 pm-11:06 pm

2 stops9h 36m

Bend/Redmond

Sat 10/31

6:10 am-8:30 pm

2 stops12h 20m

$466

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Tue 12/8

6:00 am-5:01 pm

2 stops13h 01m

Bend/Redmond

Tue 12/15

5:31 pm-2:21 pm

1 stop18h 50m

$484

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Thu 10/8

3:30 pm-11:40 am

1 stop22h 10m

Bend/Redmond

Mon 10/12

12:20 pm-12:59 am

2 stops10h 39m

$484

Quickest round-trip

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Sat 1/30

6:57 pm-11:53 pm

1 stop6h 56m

Bend/Redmond

Tue 2/2

5:15 am-1:13 pm

1 stop5h 58m

$487

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Wed 10/21

5:10 pm-11:56 pm

1 stop8h 46m

Bend/Redmond

Tue 10/27

3:00 pm-11:30 pm

1 stop6h 30m

$493

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Thu 10/8

3:30 pm-11:40 am

1 stop22h 10m

Bend/Redmond

Mon 10/12

12:20 pm-5:16 am

1 stop14h 56m

$517

ChicagoRedmond

ORD Chicago O'Hare Intl - RDM Bend/Redmond

ORDRDM

Chicago O'Hare Intl

Thu 1/21

5:00 am-1:09 pm

1 stop10h 09m

Bend/Redmond

Mon 1/25

5:20 am-2:50 pm

1 stop7h 30m

$547

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Chicago and Redmond?

Prices are currently low for flights on this route.

Typical prices usually range from $510 to $578.
The lowest price recently found on this route was $455.

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 4% 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

Best Price Found	$228
Fastest flight time	6h 09m
Direct flights	None

The best one-way flight to Redmond from Chicago in the past 72 hours is $228. The best round-trip flight deal from Chicago to Redmond found on momondo in the last 72 hours is $455.

The fastest flight from Chicago to Redmond takes 6h 09m

There are no direct flights from Chicago to Redmond. There are no popular flight routes from Chicago to Redmond.

Search flight deals

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 09m.
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?
There are 4 operators available for flights from Chicago to Bend/Redmond Airport as of September 2026.
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?
Based on momondo bookings for flights between Chicago and Redmond, the leading airline is Alaska Airlines, making up 59% of the total bookings. Other popular airlines include Delta with 22% and United Airlines with 19%.

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 Airlines	PriceFrom $278	Free Cancellation	Rating 7.4 10,233 reviews	Search United Airlines flights
American Airlines	PriceFrom $318	Free Cancellation	Rating 7.0 12,074 reviews	Search American Airlines flights
Delta	PriceFrom $336	Free Cancellation	Rating 7.8 8,594 reviews	Search Delta flights
Alaska Airlines	PriceFrom $413	Free Cancellation	Rating 7.9 12,963 reviews	Search Alaska Airlines flights

Bend

Madras

Sunriver

Prineville

Sisters

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.

An easier way to manage your Redmond trip

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Airports servicing Oregon

Eugene Airport

Klamath Falls Kingsley Field Airport

Cheap flights from Chicago to Redmond from $228

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 10/21. 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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Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets

Delta flights from Chicago to Redmond

Our best Delta deals on Chicago to Redmond flight tickets

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See travel insights to Redmond from

How to get the cheapest flight ticket from Chicago to Redmond

What is the typical price of a round-trip flight between Chicago and Redmond?

What is the cheapest month to fly to Redmond?

Can stopping save me money on Chicago to Redmond flights?

How have Chicago to Redmond flight prices changed over time?

What is the cheapest airline that flies from Chicago to Bend/Redmond?

What airlines fly to Redmond?

Which airport is the most popular layover for flights between Chicago and Redmond?

Which layover airport offers the lowest fares from Chicago to Redmond?

Which layover airport has the shortest travel time from Chicago to Redmond?

Which layover airport has the shortest connection time from Chicago to Redmond?

When to book flights from Chicago to Redmond

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

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying 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

Traveling to a place near Redmond?

Why use momondo?

An easier way to manage your Redmond trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Oregon

Fly your favorite airline to Redmond

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Redmond

List of cabin classes available on flights landing in Redmond. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Chicago

According to popular flight searches on momondo this year

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