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Cheap flights from Redmond to Chicago from $114

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 4/22. 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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Find the cheapest flights from Redmond to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
1:13 pm - 9:29 pm
RDM
-
ORD
6h 16m
1 stop
United Airlines Logo
2:45 pm - 8:50 pm
ORD
-
RDM
8h 05m
1 stop
$237United Airlines
Tue, Mar 10 - Wed, Mar 11
Delta Logo
12:33 pm - 9:18 pm
RDM
-
ORD
6h 45m
1 stop
Delta Logo
2:09 pm - 11:57 pm
ORD
-
RDM
11h 48m
2 stops
$242Delta
Wed, Apr 29 - Sat, May 2
Delta Logo
6:20 am - 6:00 pm
RDM
-
ORD
9h 40m
2 stops
Delta Logo
1:19 pm - 10:55 pm
ORD
-
RDM
11h 36m
2 stops
$247Delta
Tue, Mar 10 - Wed, Mar 11
Delta Logo
11:24 am - 9:34 pm
RDM
-
ORD
8h 10m
2 stops
Delta Logo
1:19 pm - 10:55 pm
ORD
-
RDM
11h 36m
2 stops
$257Delta
Tue, Mar 10 - Wed, Mar 11
Delta Logo
6:05 am - 4:39 pm
RDM
-
ORD
8h 34m
1 stop
Delta Logo
7:20 am - 11:53 am
ORD
-
RDM
6h 33m
1 stop
$262Delta
Wed, Apr 15 - Sun, Apr 19
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
Delta Logo
7:20 am - 11:53 am
ORD
-
RDM
6h 33m
1 stop
$267Delta
Wed, Apr 15 - Sun, Apr 19
Delta Logo
12:35 pm - 9:34 pm
RDM
-
ORD
6h 59m
1 stop
Delta Logo
6:00 pm - 11:57 pm
ORD
-
RDM
7h 57m
1 stop
$272Delta
Wed, Apr 8 - Mon, Apr 13
Delta Logo
12:35 pm - 9:34 pm
RDM
-
ORD
6h 59m
1 stop
Delta Logo
1:36 pm - 11:57 pm
ORD
-
RDM
12h 21m
2 stops
$277Delta
Wed, Apr 8 - Mon, Apr 13
Alaska Airlines Logo
1:52 pm - 11:59 pm
RDM
-
ORD
8h 07m
1 stop
Alaska Airlines Logo
6:00 am - 12:58 pm
ORD
-
RDM
8h 58m
1 stop
$278Alaska Airlines
Wed, May 6 - Sun, May 10
United Airlines Logo
1:54 pm - 12:59 am
RDM
-
ORD
9h 05m
1 stop
United Airlines Logo
6:17 am - 12:11 pm
ORD
-
RDM
7h 54m
1 stop
$282United Airlines
Fri, Mar 6 - Sun, Mar 8

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
May 6
RDM1:52 pmBend/Redmond
8h 07m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 10
ORD6:00 amChicago O'Hare Intl
8h 58m
1 stop
RDM12:58 pmBend/Redmond
$278
Alaska Airlines
Mar 10
RDM9:02 amBend/Redmond
12h 57m
2 stops
ORD11:59 pmChicago O'Hare Intl
Mar 11
ORD3:54 pmChicago O'Hare Intl
7h 38m
1 stop
RDM9:32 pmBend/Redmond
$285
Alaska Airlines
Mar 9
RDM12:46 pmBend/Redmond
22h 25m
1 stop
ORD1:11 pmChicago O'Hare Intl
Mar 13
ORD3:54 pmChicago O'Hare Intl
7h 38m
1 stop
RDM9:32 pmBend/Redmond
$303

Delta flights from Redmond to Chicago

Our best Delta deals on Redmond to Chicago flight tickets
Delta
Apr 29
RDM12:33 pmBend/Redmond
6h 45m
1 stop
ORD9:18 pmChicago O'Hare Intl
May 2
ORD2:09 pmChicago O'Hare Intl
11h 48m
2 stops
RDM11:57 pmBend/Redmond
$242
Delta
Mar 10
RDM6:20 amBend/Redmond
9h 40m
2 stops
ORD6:00 pmChicago O'Hare Intl
Mar 11
ORD1:19 pmChicago O'Hare Intl
11h 36m
2 stops
RDM10:55 pmBend/Redmond
$247
Delta
Mar 10
RDM11:24 amBend/Redmond
8h 10m
2 stops
ORD9:34 pmChicago O'Hare Intl
Mar 11
ORD1:19 pmChicago O'Hare Intl
11h 36m
2 stops
RDM10:55 pmBend/Redmond
$257

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 February 10, 2026.
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 3/10

1:13 pm-9:29 pm

1 stop6h 16m

Chicago O'Hare Intl

Wed 3/11

2:45 pm-8:50 pm

1 stop8h 05m

$237

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/29

12:33 pm-9:18 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 5/2

2:09 pm-11:57 pm

2 stops11h 48m

$242

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 3/10

6:20 am-6:00 pm

2 stops9h 40m

Chicago O'Hare Intl

Wed 3/11

1:19 pm-10:55 pm

2 stops11h 36m

$247

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 3/10

11:24 am-9:34 pm

2 stops8h 10m

Chicago O'Hare Intl

Wed 3/11

1:19 pm-10:55 pm

2 stops11h 36m

$257

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/15

6:05 am-4:39 pm

1 stop8h 34m

Chicago O'Hare Intl

Sun 4/19

7:20 am-11:53 am

1 stop6h 33m

$262

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/15

11:35 am-9:18 pm

2 stops7h 43m

Chicago O'Hare Intl

Sun 4/19

7:20 am-11:53 am

1 stop6h 33m

$267

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/8

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Mon 4/13

6:00 pm-11:57 pm

1 stop7h 57m

$272

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 4/8

12:35 pm-9:34 pm

1 stop6h 59m

Chicago O'Hare Intl

Mon 4/13

1:36 pm-11:57 pm

2 stops12h 21m

$277

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/6

1:52 pm-11:59 pm

1 stop8h 07m

Chicago O'Hare Intl

Sun 5/10

6:00 am-12:58 pm

1 stop8h 58m

$278

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 3/6

1:54 pm-12:59 am

1 stop9h 05m

Chicago O'Hare Intl

Sun 3/8

6:17 am-12:11 pm

1 stop7h 54m

$282

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 cheapest month to fly to Chicago?

The month of December is, on average, the cheapest month to fly to Chicago from Redmond, with most prices found around $324. If you’re not able to fly to Chicago in December, then November is your next best option. Flight prices from Redmond to Chicago during November average around $330.

Can stopping save me money on Redmond to Chicago flights?

You could potentially save up to 28% 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

Fastest flight time

6h 16m

Direct flights

None
The fastest flight from Redmond to Chicago takes 6h 16m
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 6h 16m, 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
11,874 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,273 reviews
Search United Airlines flights
DeltaPriceFrom $288Free CancellationRating
7.9
8,180 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
Munster
Crown Point
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