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

Flights connecting via Seattle (SEA) have the shortest average one-way travel time: 2h 13m.

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 47% of people opting to fly with this airline when traveling to Redmond. Keep in mind that there are 5 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?

Seattle (SEA) has the shortest average layover time for this route: 0h 54m.

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

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

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

Flights via Seattle (SEA) offer the lowest average round-trip price of $466.

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

Portland (PDX) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

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 5 operators available for flights from Chicago to Bend/Redmond Airport as of July 2025.

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.

$139 Cheap Flights from Chicago to Redmond in 2025

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Find the cheapest flights from Chicago to Redmond

Round-trip

One-way

Last minute

Cheap round-trip flights

6:00 am - 12:52 pmORD-RDM

8h 52m1 stop

3:40 pm - 11:59 pmRDM-ORD

6h 19m1 stop

$278Hawaiian Airlines

Find Deal

Tue, Oct 7 - Sat, Oct 11

7:00 am - 11:44 amORD-RDM

6h 44m1 stop

4:00 pm - 5:01 amRDM-ORD

11h 01m1 stop

$279Alaska Airlines

Find Deal

Sat, Oct 25 - Wed, Oct 29

2:20 pm - 6:46 pmORD-RDM

6h 26m1 stop

7:00 am - 9:43 pmRDM-ORD

12h 43m2 stops

$284Delta

Find Deal

Tue, Oct 7 - Sat, Oct 11

6:20 am - 11:19 amORD-RDM

6h 59m1 stop

1:31 pm - 10:07 pmRDM-ORD

6h 36m1 stop

$288Hawaiian Airlines

Find Deal

Mon, Sep 15 - Wed, Sep 17

12:48 pm - 11:46 pmMDW-RDM

12h 58m2 stops

7:00 am - 5:43 pmRDM-MDW

8h 43m2 stops

$289Delta

Find Deal

Tue, Oct 7 - Sat, Oct 11

6:20 am - 12:37 pmORD-RDM

8h 17m1 stop

1:31 pm - 10:07 pmRDM-ORD

6h 36m1 stop

$289Hawaiian Airlines

Find Deal

Fri, Sep 19 - Tue, Sep 23

5:00 pm - 11:51 pmORD-RDM

8h 51m2 stops

12:35 pm - 9:57 pmRDM-ORD

7h 22m1 stop

$294Delta

Find Deal

Mon, Sep 15 - Wed, Sep 17

6:00 am - 11:42 amORD-RDM

7h 42m1 stop

12:27 pm - 11:43 pmRDM-ORD

9h 16m1 stop

$329American Airlines

Find Deal

Thu, Aug 21 - Tue, Aug 26

6:00 am - 11:42 amORD-RDM

7h 42m1 stop

12:27 pm - 11:43 pmRDM-ORD

9h 16m1 stop

$353American Airlines

Find Deal

Wed, Aug 13 - Wed, Aug 20

3:54 pm - 10:45 pmORD-RDM

8h 51m1 stop

7:32 pm - 5:18 amRDM-ORD

7h 46m1 stop

$576United Airlines

Find Deal

Fri, Aug 8 - Wed, Aug 13

United Airlines flights from Chicago to Redmond

Our best United Airlines deals on Chicago to Redmond flight tickets

United Airlines

Aug 2

ORD4:20 pmChicago O'Hare Intl

6h 39m

1 stop

RDM8:59 pmBend/Redmond

Aug 5

RDM1:13 pmBend/Redmond

7h 26m

1 stop

ORD10:39 pmChicago O'Hare Intl

$560

Find similar

United Airlines

Aug 8

ORD3:54 pmChicago O'Hare Intl

8h 51m

1 stop

RDM10:45 pmBend/Redmond

Aug 13

RDM7:32 pmBend/Redmond

7h 46m

1 stop

ORD5:18 amChicago O'Hare Intl

$576

Find similar

United Airlines

Aug 7

ORD6:30 amChicago O'Hare Intl

7h 41m

1 stop

RDM12:11 pmBend/Redmond

Aug 12

RDM5:00 amBend/Redmond

6h 20m

1 stop

ORD1:20 pmChicago O'Hare Intl

$623

Find similar

Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets

Alaska Airlines

Oct 25

ORD7:00 amChicago O'Hare Intl

6h 44m

1 stop

RDM11:44 amBend/Redmond

Oct 29

RDM4:00 pmBend/Redmond

11h 01m

1 stop

ORD5:01 amChicago O'Hare Intl

$279

Find similar

Alaska Airlines

Oct 25

ORD8:00 amChicago O'Hare Intl

6h 52m

1 stop

RDM12:52 pmBend/Redmond

Oct 29

RDM12:43 pmBend/Redmond

9h 16m

2 stops

ORD11:59 pmChicago O'Hare Intl

$297

Find similar

Alaska Airlines

Oct 19

ORD8:20 amChicago O'Hare Intl

16h 06m

1 stop

RDM10:26 pmBend/Redmond

Oct 25

RDM5:28 amBend/Redmond

16h 31m

2 stops

ORD11:59 pmChicago O'Hare Intl

$307

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 10/7

6:00 am-12:52 pm

1 stop8h 52m

Bend/Redmond

Sat 10/11

3:40 pm-11:59 pm

1 stop6h 19m

$278

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Sat 10/25

7:00 am-11:44 am

1 stop6h 44m

Bend/Redmond

Wed 10/29

4:00 pm-5:01 am

1 stop11h 01m

$279

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Tue 10/7

2:20 pm-6:46 pm

1 stop6h 26m

Bend/Redmond

Sat 10/11

7:00 am-9:43 pm

2 stops12h 43m

$284

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 9/15

6:20 am-11:19 am

1 stop6h 59m

Bend/Redmond

Wed 9/17

1:31 pm-10:07 pm

1 stop6h 36m

$288

ChicagoRedmond

MDW - RDM

MDWRDM

Chicago Midway

Tue 10/7

12:48 pm-11:46 pm

2 stops12h 58m

Bend/Redmond

Sat 10/11

7:00 am-5:43 pm

2 stops8h 43m

$289

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 9/19

6:20 am-12:37 pm

1 stop8h 17m

Bend/Redmond

Tue 9/23

1:31 pm-10:07 pm

1 stop6h 36m

$289

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Mon 9/15

5:00 pm-11:51 pm

2 stops8h 51m

Bend/Redmond

Wed 9/17

12:35 pm-9:57 pm

1 stop7h 22m

$294

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Thu 8/21

6:00 am-11:42 am

1 stop7h 42m

Bend/Redmond

Tue 8/26

12:27 pm-11:43 pm

1 stop9h 16m

$329

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Wed 8/13

6:00 am-11:42 am

1 stop7h 42m

Bend/Redmond

Wed 8/20

12:27 pm-11:43 pm

1 stop9h 16m

$353

ChicagoRedmond

ORD - RDM

ORDRDM

Chicago O'Hare Intl

Fri 8/8

3:54 pm-10:45 pm

1 stop8h 51m

Bend/Redmond

Wed 8/13

7:32 pm-5:18 am

1 stop7h 46m

$576

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 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.

How far in advance should I book a flight to Redmond?

You are more likely to see cheaper flights to Redmond from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Redmond for around $467 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Redmond from Chicago for as low as $250 on momondo.

Can stopping save me money on Chicago to Redmond flights?

You could potentially save up to 19% 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	$139
Fastest flight time	6h 24m
Direct flights	None
Airports in Redmond	1 airport

The best one-way flight to Redmond from Chicago in the past 72 hours is $139. The best round-trip flight deal from Chicago to Redmond found on momondo in the last 72 hours is $278.

The fastest flight from Chicago to Redmond takes 6h 24m

There are no direct flights from Chicago to Redmond. Popular non-direct routes for this connection are Chicago O'Hare Intl Airport - Bend/Redmond Airport and Chicago Midway Airport - Bend/Redmond Airport.

There is 1 airport near Redmond: Bend/Redmond (RDM)

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 24m.
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 5 operators available for flights from Chicago to Bend/Redmond Airport as of July 2025.
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 49% of the total bookings. Other popular airlines include Delta with 22%, United Airlines with 18%, and Hawaiian Airlines with 11%.

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 Airlines	PriceFrom $246	Free Cancellation	Rating 7.8 2,605 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $250	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $278	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Delta	PriceFrom $278	Free Cancellation	Rating 8.0 7,979 reviews	Search Delta flights
United Airlines	PriceFrom $370	Free Cancellation	Rating 7.4 8,896 reviews	Search United Airlines flights

Bend

Sunriver

Sisters

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.

An easier way to manage your Redmond trip

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Cheap flights from Chicago to Redmond from $139

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 9/10. 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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Big names and deals

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Filter for what you want

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Find the cheapest flights from Chicago to Redmond

Cheap round-trip flights

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Cheap last minute flights

United Airlines flights from Chicago to Redmond

Our best United Airlines deals on Chicago to Redmond flight tickets

Alaska Airlines flights from Chicago to Redmond

Our best Alaska Airlines deals on Chicago to Redmond flight tickets

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Use the filters below to find and compare flights from Chicago to Redmond that are best for you.

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?

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.

How far in advance should I book a flight to Redmond?

Can stopping save me money on Chicago to Redmond flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Redmond flight.

How have Chicago to Redmond flight prices changed over time?

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

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

What airlines fly to Redmond?

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

Portland (PDX) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Seattle (SEA) offer the lowest average round-trip price of $466.

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

Flights connecting via Seattle (SEA) have the shortest average one-way travel time: 2h 13m.

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

Seattle (SEA) has the shortest average layover time for this route: 0h 54m.

When to book flights from Chicago to Redmond

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

Fastest flight time

Direct flights

Airports in Redmond

How far is Chicago to Bend/Redmond by plane?

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

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?

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

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

Traveling to a place near Redmond?

Why use momondo?

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

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

How can momondo help me find flights 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?

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