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Cheap flights from Redmond to Chicago from $179

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 5/30. 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.
Delta Logo
6:10 am - 4:47 pm
RDM
-
ORD
8h 37m
1 stop
Delta Logo
2:09 pm - 10:58 pm
ORD
-
RDM
10h 49m
2 stops
$368Delta
Wed, Jun 3 - Wed, Jun 17
Delta Logo
1:15 pm - 11:38 pm
RDM
-
ORD
8h 23m
1 stop
Delta Logo
5:59 pm - 10:58 pm
ORD
-
RDM
6h 59m
1 stop
$369Delta
Tue, Jul 28 - Wed, Aug 5
Alaska Airlines Logo
5:31 pm - 6:20 am
RDM
-
ORD
10h 49m
1 stop
Alaska Airlines Logo
7:49 pm - 9:14 am
ORD
-
RDM
15h 25m
1 stop
$373Alaska Airlines
Fri, May 29 - Tue, Jun 2
Delta Logo
1:15 pm - 11:38 pm
RDM
-
ORD
8h 23m
1 stop
Delta Logo
3:48 pm - 11:49 pm
ORD
-
RDM
10h 01m
2 stops
$374Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
7:20 pm - 8:45 am
RDM
-
ORD
11h 25m
2 stops
Delta Logo
12:47 pm - 6:38 pm
ORD
-
RDM
7h 51m
1 stop
$378Delta
Fri, May 29 - Tue, Jun 2
Alaska Airlines Logo
8:31 am - 6:53 pm
RDM
-
ORD
8h 22m
1 stop
Alaska Airlines Logo
6:00 am - 12:38 pm
ORD
-
RDM
8h 38m
1 stop
$379Alaska Airlines
Tue, Oct 6 - Sun, Oct 11
Delta Logo
5:05 am - 6:33 pm
RDM
-
MDW
11h 28m
2 stops
Delta Logo
1:49 pm - 10:36 pm
MDW
-
RDM
10h 47m
2 stops
$379Delta
Sat, Jun 6 - Sat, Jun 13
Delta Logo
6:26 am - 7:30 pm
RDM
-
ORD
11h 04m
2 stops
Delta Logo
3:48 pm - 11:49 pm
ORD
-
RDM
10h 01m
2 stops
$380Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
6:10 am - 9:50 pm
RDM
-
ORD
13h 40m
2 stops
Delta Logo
7:12 am - 12:35 pm
ORD
-
RDM
7h 23m
1 stop
$383Delta
Thu, May 28 - Tue, Jun 2
Delta Logo
6:20 am - 5:57 pm
RDM
-
ORD
9h 37m
2 stops
Delta Logo
7:00 am - 11:58 am
ORD
-
RDM
6h 58m
1 stop
$384Delta
Tue, Oct 6 - Sun, Oct 11

Delta flights from Redmond to Chicago

Our best Delta deals on Redmond to Chicago flight tickets
Delta
Jun 3
RDM6:10 amBend/Redmond
8h 37m
1 stop
ORD4:47 pmChicago O'Hare Intl
Jun 17
ORD2:09 pmChicago O'Hare Intl
10h 49m
2 stops
RDM10:58 pmBend/Redmond
$368
Delta
Jul 28
RDM1:15 pmBend/Redmond
8h 23m
1 stop
ORD11:38 pmChicago O'Hare Intl
Aug 5
ORD5:59 pmChicago O'Hare Intl
6h 59m
1 stop
RDM10:58 pmBend/Redmond
$369
Delta
Jul 28
RDM1:15 pmBend/Redmond
8h 23m
1 stop
ORD11:38 pmChicago O'Hare Intl
Aug 4
ORD3:48 pmChicago O'Hare Intl
10h 01m
2 stops
RDM11:49 pmBend/Redmond
$374

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
May 29
RDM5:31 pmBend/Redmond
10h 49m
1 stop
ORD6:20 amChicago O'Hare Intl
Jun 2
ORD7:49 pmChicago O'Hare Intl
15h 25m
1 stop
RDM9:14 amBend/Redmond
$373
Alaska Airlines
Oct 6
RDM8:31 amBend/Redmond
8h 22m
1 stop
ORD6:53 pmChicago O'Hare Intl
Oct 11
ORD6:00 amChicago O'Hare Intl
8h 38m
1 stop
RDM12:38 pmBend/Redmond
$379
Alaska Airlines
Jun 12
RDM12:34 pmBend/Redmond
14h 26m
1 stop
ORD5:00 amChicago O'Hare Intl
Jun 20
ORD8:05 pmChicago O'Hare Intl
14h 59m
1 stop
RDM9:04 amBend/Redmond
$389

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 May 12, 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

Cheapest round-trip

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 6/3

6:10 am-4:47 pm

1 stop8h 37m

Chicago O'Hare Intl

Wed 6/17

2:09 pm-10:58 pm

2 stops10h 49m

$368
Quickest round-trip

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 7/28

1:15 pm-11:38 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 8/5

5:59 pm-10:58 pm

1 stop6h 59m

$369

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 5/29

5:31 pm-6:20 am

1 stop10h 49m

Chicago O'Hare Intl

Tue 6/2

7:49 pm-9:14 am

1 stop15h 25m

$373

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 7/28

1:15 pm-11:38 pm

1 stop8h 23m

Chicago O'Hare Intl

Tue 8/4

3:48 pm-11:49 pm

2 stops10h 01m

$374

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 5/29

7:20 pm-8:45 am

2 stops11h 25m

Chicago O'Hare Intl

Tue 6/2

12:47 pm-6:38 pm

1 stop7h 51m

$378

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 10/6

8:31 am-6:53 pm

1 stop8h 22m

Chicago O'Hare Intl

Sun 10/11

6:00 am-12:38 pm

1 stop8h 38m

$379

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 6/6

5:05 am-6:33 pm

2 stops11h 28m

Chicago Midway

Sat 6/13

1:49 pm-10:36 pm

2 stops10h 47m

$379

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 7/28

6:26 am-7:30 pm

2 stops11h 04m

Chicago O'Hare Intl

Tue 8/4

3:48 pm-11:49 pm

2 stops10h 01m

$380

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 5/28

6:10 am-9:50 pm

2 stops13h 40m

Chicago O'Hare Intl

Tue 6/2

7:12 am-12:35 pm

1 stop7h 23m

$383

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 10/6

6:20 am-5:57 pm

2 stops9h 37m

Chicago O'Hare Intl

Sun 10/11

7:00 am-11:58 am

1 stop6h 58m

$384

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 $125. If you’re not able to fly to Chicago in May, then February is your next best option. Flight prices from Redmond to Chicago during February average around $230.

Can stopping save me money on Redmond to Chicago flights?

You could potentially save up to 42% 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 32m

Direct flights

None
The fastest flight from Redmond to Chicago takes 6h 32m
There are no direct flights from Redmond to Chicago. There are no popular flight routes from Redmond to Chicago.
Search flight deals

Frequently asked questions about flying from Redmond to Chicago

  • 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 32m, 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 $288Free CancellationRating
7.9
12,352 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $308Free CancellationRating
7.4
9,701 reviews
Search United Airlines flights
DeltaPriceFrom $318Free CancellationRating
7.9
8,445 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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