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Cheap flights from Redmond to Chicago from $160

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 4/13. 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
0 bags

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Cheap round-trip flights

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Alaska Airlines Logo
5:52 am - 2:38 pmRDM-ORD
6h 46m1 stop
Alaska Airlines Logo
3:35 pm - 9:15 pmORD-RDM
7h 40m1 stop
$296Alaska Airlines
Find Deal
Tue, Jan 13 - Tue, Jan 20
Alaska Airlines Logo
5:52 am - 5:10 pmRDM-ORD
9h 18m1 stop
Alaska Airlines Logo
3:35 pm - 9:15 pmORD-RDM
7h 40m1 stop
$298Alaska Airlines
Find Deal
Wed, Jan 14 - Tue, Jan 20
Alaska Airlines Logo
8:45 am - 5:10 pmRDM-ORD
6h 25m1 stop
Alaska Airlines Logo
6:06 pm - 9:15 pmORD-RDM
29h 09m1 stop
$300Alaska Airlines
Find Deal
Wed, Feb 4 - Mon, Feb 9
Delta Logo
5:45 am - 1:38 pmRDM-ORD
5h 53m1 stop
Delta Logo
2:20 pm - 10:46 amORD-RDM
22h 26m1 stop
$301Delta
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Tue, Jan 13 - Mon, Jan 19
Delta Logo
11:30 am - 9:52 pmRDM-ORD
8h 22m2 stops
Delta Logo
7:20 am - 11:50 amORD-RDM
6h 30m1 stop
$304Delta
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Tue, Jan 13 - Sat, Jan 24
Alaska Airlines Logo
1:10 pm - 11:37 pmRDM-ORD
8h 27m1 stop
Alaska Airlines Logo
8:00 am - 12:54 pmORD-RDM
6h 54m1 stop
$305Alaska Airlines
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Thu, Jan 15 - Wed, Jan 21
United Airlines Logo
7:50 pm - 6:02 amRDM-ORD
8h 12m1 stop
United Airlines Logo
7:10 am - 12:57 pmORD-RDM
7h 47m1 stop
$309United Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Hawaiian Airlines Logo
9:00 am - 5:53 pmRDM-ORD
6h 53m1 stop
Hawaiian Airlines Logo
7:00 am - 11:33 amORD-RDM
6h 33m1 stop
$318Hawaiian Airlines
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Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
8:45 am - 5:10 pmRDM-ORD
6h 25m1 stop
Multiple Airlines Logo
2:20 pm - 11:52 pmORD-RDM
11h 32m2 stops
$544Multiple Airlines
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Sun, Jan 18 - Mon, Jan 19
Multiple Airlines Logo
8:45 am - 5:10 pmRDM-ORD
6h 25m1 stop
Multiple Airlines Logo
12:59 pm - 11:15 pmORD-RDM
36h 16m2 stops
$602Multiple Airlines
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Sun, Jan 18 - Wed, Jan 21

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
Jan 13
RDM5:52 amBend/Redmond
6h 46m
1 stop
ORD2:38 pmChicago O'Hare Intl
Jan 20
ORD3:35 pmChicago O'Hare Intl
7h 40m
1 stop
RDM9:15 pmBend/Redmond
$296
Find similar
Alaska Airlines
Jan 14
RDM5:52 amBend/Redmond
9h 18m
1 stop
ORD5:10 pmChicago O'Hare Intl
Jan 20
ORD3:35 pmChicago O'Hare Intl
7h 40m
1 stop
RDM9:15 pmBend/Redmond
$298
Find similar
Alaska Airlines
Feb 4
RDM8:45 amBend/Redmond
6h 25m
1 stop
ORD5:10 pmChicago O'Hare Intl
Feb 9
ORD6:06 pmChicago O'Hare Intl
29h 09m
1 stop
RDM9:15 pmBend/Redmond
$300
Find similar

Delta flights from Redmond to Chicago

Our best Delta deals on Redmond to Chicago flight tickets
Delta
Jan 13
RDM5:45 amBend/Redmond
5h 53m
1 stop
ORD1:38 pmChicago O'Hare Intl
Jan 19
ORD2:20 pmChicago O'Hare Intl
22h 26m
1 stop
RDM10:46 amBend/Redmond
$301
Find similar
Delta
Jan 13
RDM11:30 amBend/Redmond
8h 22m
2 stops
ORD9:52 pmChicago O'Hare Intl
Jan 24
ORD7:20 amChicago O'Hare Intl
6h 30m
1 stop
RDM11:50 amBend/Redmond
$304
Find similar
Delta
Jan 13
RDM11:30 amBend/Redmond
8h 22m
2 stops
ORD9:52 pmChicago O'Hare Intl
Jan 19
ORD2:20 pmChicago O'Hare Intl
22h 26m
1 stop
RDM10:46 amBend/Redmond
$306
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 November 3, 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

Tue 1/13

5:52 am-2:38 pm

1 stop6h 46m

Chicago O'Hare Intl

Tue 1/20

3:35 pm-9:15 pm

1 stop7h 40m

$296

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 1/14

5:52 am-5:10 pm

1 stop9h 18m

Chicago O'Hare Intl

Tue 1/20

3:35 pm-9:15 pm

1 stop7h 40m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 2/4

8:45 am-5:10 pm

1 stop6h 25m

Chicago O'Hare Intl

Mon 2/9

6:06 pm-9:15 pm

1 stop29h 09m

$300

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 1/13

5:45 am-1:38 pm

1 stop5h 53m

Chicago O'Hare Intl

Mon 1/19

2:20 pm-10:46 am

1 stop22h 26m

$301

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 1/13

11:30 am-9:52 pm

2 stops8h 22m

Chicago O'Hare Intl

Sat 1/24

7:20 am-11:50 am

1 stop6h 30m

$304

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 1/15

1:10 pm-11:37 pm

1 stop8h 27m

Chicago O'Hare Intl

Wed 1/21

8:00 am-12:54 pm

1 stop6h 54m

$305

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 12/5

7:50 pm-6:02 am

1 stop8h 12m

Chicago O'Hare Intl

Tue 12/9

7:10 am-12:57 pm

1 stop7h 47m

$309

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 4/16

9:00 am-5:53 pm

1 stop6h 53m

Chicago O'Hare Intl

Mon 4/20

7:00 am-11:33 am

1 stop6h 33m

$318

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sun 1/18

8:45 am-5:10 pm

1 stop6h 25m

Chicago O'Hare Intl

Mon 1/19

2:20 pm-11:52 pm

2 stops11h 32m

$544

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sun 1/18

8:45 am-5:10 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 1/21

12:59 pm-11:15 pm

2 stops36h 16m

$602

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 January is, on average, the cheapest month to fly to Chicago from Redmond, with most prices found around $280. If you’re not able to fly to Chicago in January, then May is your next best option. Flight prices from Redmond to Chicago during May average around $337.

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 9% 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

Direct flights

None
There are no direct flights from Redmond to Chicago. There are no popular flight routes from Redmond to Chicago.
Search flight deals

  • 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 49m, 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
11,235 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
8,997 reviews
Search United Airlines flights
DeltaPriceFrom $288Free CancellationRating
7.9
8,001 reviews
Search Delta 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