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Cheap flights from Redmond to Chicago 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 Redmond to Chicago departing on 10/1. 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

Hawaiian Airlines Logo
3:41 pm - 12:03 amRDM-ORD
6h 22m1 stop
Hawaiian Airlines Logo
7:00 am - 11:35 amORD-RDM
6h 35m1 stop
$278Hawaiian Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Alaska Airlines Logo
5:58 pm - 7:03 amRDM-ORD
11h 05m1 stop
Alaska Airlines Logo
1:01 pm - 6:51 pmORD-RDM
7h 50m1 stop
$279Alaska Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Delta Logo
7:00 am - 5:20 pmRDM-ORD
8h 20m1 stop
Delta Logo
3:58 pm - 10:56 pmORD-RDM
8h 58m2 stops
$284Delta
Find Deal
Sat, Sep 13 - Sat, Sep 20
Hawaiian Airlines Logo
3:41 pm - 12:03 amRDM-ORD
6h 22m1 stop
Hawaiian Airlines Logo
7:00 am - 11:35 amORD-RDM
6h 35m1 stop
$288Hawaiian Airlines
Find Deal
Wed, Sep 17 - Sun, Sep 21
Alaska Airlines Logo
12:30 pm - 11:59 pmRDM-ORD
9h 29m1 stop
Alaska Airlines Logo
6:20 am - 11:19 amORD-RDM
6h 59m1 stop
$289Alaska Airlines
Find Deal
Sat, Aug 23 - Mon, Sep 1
Hawaiian Airlines Logo
5:25 am - 1:11 pmRDM-ORD
5h 46m1 stop
Hawaiian Airlines Logo
3:20 pm - 9:06 pmORD-RDM
7h 46m1 stop
$293Hawaiian Airlines
Find Deal
Thu, Sep 4 - Thu, Sep 4
Delta Logo
7:00 am - 9:57 pmRDM-ORD
12h 57m2 stops
Delta Logo
6:10 pm - 10:56 pmORD-RDM
6h 46m1 stop
$294Delta
Find Deal
Wed, Sep 17 - Mon, Sep 22
Alaska Airlines Logo
12:43 pm - 5:01 amRDM-ORD
14h 18m1 stop
Alaska Airlines Logo
7:00 am - 12:03 pmORD-RDM
7h 03m1 stop
$298Alaska Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
7:30 pm - 8:28 amRDM-ORD
10h 58m2 stops
Delta Logo
7:55 am - 6:50 pmORD-RDM
12h 55m2 stops
$299Delta
Find Deal
Fri, Sep 12 - Tue, Sep 16
United Airlines Logo
2:00 pm - 11:14 pmRDM-ORD
7h 14m1 stop
United Airlines Logo
4:20 pm - 10:57 pmORD-RDM
8h 37m1 stop
$483United Airlines
Find Deal
Thu, Dec 18 - Mon, Dec 22

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
Sep 2
RDM5:58 pmBend/Redmond
11h 05m
1 stop
ORD7:03 amChicago O'Hare Intl
Sep 9
ORD1:01 pmChicago O'Hare Intl
7h 50m
1 stop
RDM6:51 pmBend/Redmond
$279
Find similar
Alaska Airlines
Aug 23
RDM12:30 pmBend/Redmond
9h 29m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 1
ORD6:20 amChicago O'Hare Intl
6h 59m
1 stop
RDM11:19 amBend/Redmond
$289
Find similar
Alaska Airlines
Oct 30
RDM12:43 pmBend/Redmond
14h 18m
1 stop
ORD5:01 amChicago O'Hare Intl
Nov 2
ORD7:00 amChicago O'Hare Intl
7h 03m
1 stop
RDM12:03 pmBend/Redmond
$298
Find similar

Hawaiian Airlines flights from Redmond to Chicago

Our best Hawaiian Airlines deals on Redmond to Chicago flight tickets
Hawaiian Airlines
Sep 13
RDM3:41 pmBend/Redmond
6h 22m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 20
ORD7:00 amChicago O'Hare Intl
6h 35m
1 stop
RDM11:35 amBend/Redmond
$278
Find similar
Hawaiian Airlines
Sep 17
RDM3:41 pmBend/Redmond
6h 22m
1 stop
ORD12:03 amChicago O'Hare Intl
Sep 21
ORD7:00 amChicago O'Hare Intl
6h 35m
1 stop
RDM11:35 amBend/Redmond
$288
Find similar
Hawaiian Airlines
Sep 4
RDM5:25 amBend/Redmond
5h 46m
1 stop
ORD1:11 pmChicago O'Hare Intl
Sep 4
ORD3:20 pmChicago O'Hare Intl
7h 46m
1 stop
RDM9:06 pmBend/Redmond
$293
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Redmond to Chicago 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 2, 2025.
Use the filters below to find and compare flights from Redmond to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 9/13

3:41 pm-12:03 am

1 stop6h 22m

Chicago O'Hare Intl

Sat 9/20

7:00 am-11:35 am

1 stop6h 35m

$278

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 9/2

5:58 pm-7:03 am

1 stop11h 05m

Chicago O'Hare Intl

Tue 9/9

1:01 pm-6:51 pm

1 stop7h 50m

$279

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 9/13

7:00 am-5:20 pm

1 stop8h 20m

Chicago O'Hare Intl

Sat 9/20

3:58 pm-10:56 pm

2 stops8h 58m

$284

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 9/17

3:41 pm-12:03 am

1 stop6h 22m

Chicago O'Hare Intl

Sun 9/21

7:00 am-11:35 am

1 stop6h 35m

$288

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 8/23

12:30 pm-11:59 pm

1 stop9h 29m

Chicago O'Hare Intl

Mon 9/1

6:20 am-11:19 am

1 stop6h 59m

$289

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 9/4

5:25 am-1:11 pm

1 stop5h 46m

Chicago O'Hare Intl

Thu 9/4

3:20 pm-9:06 pm

1 stop7h 46m

$293

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 9/17

7:00 am-9:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Mon 9/22

6:10 pm-10:56 pm

1 stop6h 46m

$294

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 10/30

12:43 pm-5:01 am

1 stop14h 18m

Chicago O'Hare Intl

Sun 11/2

7:00 am-12:03 pm

1 stop7h 03m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 9/12

7:30 pm-8:28 am

2 stops10h 58m

Chicago O'Hare Intl

Tue 9/16

7:55 am-6:50 pm

2 stops12h 55m

$299

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 12/18

2:00 pm-11:14 pm

1 stop7h 14m

Chicago O'Hare Intl

Mon 12/22

4:20 pm-10:57 pm

1 stop8h 37m

$483

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 Chicago from

How to get the cheapest flight ticket from Redmond to Chicago

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 Redmond and Chicago?

What is the cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Redmond, with most prices found around $337. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Redmond to Chicago during April average around $397.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $378. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Redmond to Chicago for around $668.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Redmond to Chicago during this time can be as low as $466. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $541.

Can stopping save me money on Redmond to Chicago flights?

You could potentially save up to 50% on your flight if you consider stops on a Redmond to Chicago flight.

How have Redmond to Chicago flight prices changed over time?

When to book flights from Redmond to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Redmond to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

Find info about flight duration, direct flights, and airports for your flight from Redmond to Chicago

Best Price Found

$139

Fastest flight time

5h 46m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Redmond in the past 72 hours is $139. The best round-trip flight deal from Redmond to Chicago found on momondo in the last 72 hours is $278.
The fastest flight from Redmond to Chicago takes 5h 46m
There are no direct flights from Redmond to Chicago. Popular non-direct routes for this connection are Bend/Redmond Airport - Chicago Midway Airport and Bend/Redmond Airport - Chicago O'Hare Intl Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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  • How far is Bend/Redmond to Chicago by plane?

    A flight from Bend/Redmond to Chicago will travel around 1688.2 mi. Flights usually cover this in 5h 46m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from Bend/Redmond Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Bend/Redmond Airport to Chicago?

  • How old do you have to be to fly from Bend/Redmond Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Bend/Redmond Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Redmond to Chicago?

Best airlines flying from Redmond to Chicago

Compare and see reviews for airlines that fly from Redmond to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $262Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
DeltaPriceFrom $263Free CancellationRating
8.0
7,985 reviews
Search Delta flights
United AirlinesPriceFrom $306Free CancellationRating
7.4
8,905 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Redmond to Chicago for you.

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

All flight searches from Redmond to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Redmond to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Redmond.

I’m not ready to book a flight from Redmond to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Redmond to Chicago 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport