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Cheap flights from Redmond to Chicago from $159

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 4/28. 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
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
1:55 pm - 11:29 pm
RDM
-
ORD
7h 34m
1 stop
United Airlines Logo
12:05 pm - 5:58 pm
ORD
-
RDM
7h 53m
1 stop
$343United Airlines
Tue, Apr 28 - Fri, May 1
Alaska Airlines Logo
3:59 pm - 2:08 pm
RDM
-
ORD
20h 09m
1 stop
Alaska Airlines Logo
6:00 am - 12:58 pm
ORD
-
RDM
8h 58m
1 stop
$348Alaska Airlines
Fri, Apr 24 - Wed, Apr 29
Delta Logo
12:33 pm - 9:18 pm
RDM
-
ORD
6h 45m
1 stop
Delta Logo
11:00 am - 11:06 pm
ORD
-
RDM
14h 06m
2 stops
$353Delta
Fri, Apr 24 - Wed, Apr 29
Delta Logo
11:35 am - 9:18 pm
RDM
-
ORD
7h 43m
2 stops
Delta Logo
11:00 am - 11:06 pm
ORD
-
RDM
14h 06m
2 stops
$358Delta
Mon, Apr 27 - Wed, Apr 29
United Airlines Logo
3:51 pm - 12:59 am
RDM
-
ORD
7h 08m
1 stop
United Airlines Logo
6:00 am - 12:53 pm
ORD
-
RDM
8h 53m
1 stop
$359United Airlines
Tue, May 26 - Sat, May 30
Delta Logo
6:10 am - 4:49 pm
RDM
-
ORD
8h 39m
1 stop
Delta Logo
2:00 pm - 10:52 pm
ORD
-
RDM
10h 52m
2 stops
$364Delta
Wed, May 27 - Wed, Jun 3
Delta Logo
6:26 am - 4:45 pm
RDM
-
ORD
8h 19m
1 stop
Delta Logo
6:55 am - 12:30 pm
ORD
-
RDM
7h 35m
1 stop
$369Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
5:05 am - 6:05 pm
RDM
-
ORD
11h 00m
2 stops
Delta Logo
2:00 pm - 10:52 pm
ORD
-
RDM
10h 52m
2 stops
$370Delta
Wed, May 27 - Wed, Jun 3
United Airlines Logo
1:55 pm - 11:29 pm
RDM
-
ORD
7h 34m
1 stop
United Airlines Logo
12:05 pm - 5:58 pm
ORD
-
RDM
7h 53m
1 stop
$374United Airlines
Fri, Apr 24 - Fri, May 1
American Airlines Logo
2:50 pm - 12:32 am
RDM
-
ORD
7h 42m
1 stop
American Airlines Logo
7:04 am - 1:17 pm
ORD
-
RDM
8h 13m
1 stop
$379American Airlines
Thu, May 14 - Sun, May 17

United Airlines flights from Redmond to Chicago

Our best United Airlines deals on Redmond to Chicago flight tickets
United Airlines
Apr 28
RDM1:55 pmBend/Redmond
7h 34m
1 stop
ORD11:29 pmChicago O'Hare Intl
May 1
ORD12:05 pmChicago O'Hare Intl
7h 53m
1 stop
RDM5:58 pmBend/Redmond
$343
United Airlines
May 26
RDM3:51 pmBend/Redmond
7h 08m
1 stop
ORD12:59 amChicago O'Hare Intl
May 30
ORD6:00 amChicago O'Hare Intl
8h 53m
1 stop
RDM12:53 pmBend/Redmond
$359
United Airlines
Apr 24
RDM1:55 pmBend/Redmond
7h 34m
1 stop
ORD11:29 pmChicago O'Hare Intl
May 1
ORD12:05 pmChicago O'Hare Intl
7h 53m
1 stop
RDM5:58 pmBend/Redmond
$374

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
Apr 24
RDM3:59 pmBend/Redmond
20h 09m
1 stop
ORD2:08 pmChicago O'Hare Intl
Apr 29
ORD6:00 amChicago O'Hare Intl
8h 58m
1 stop
RDM12:58 pmBend/Redmond
$348
Alaska Airlines
Jun 17
RDM7:22 amBend/Redmond
9h 38m
1 stop
ORD7:00 pmChicago O'Hare Intl
Jun 27
ORD7:20 amChicago O'Hare Intl
6h 27m
1 stop
RDM11:47 amBend/Redmond
$426
Alaska Airlines
Apr 29
RDM5:20 amBend/Redmond
12h 32m
2 stops
ORD7:52 pmChicago O'Hare Intl
May 2
ORD6:00 amChicago O'Hare Intl
8h 58m
1 stop
RDM12:58 pmBend/Redmond
$430

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 March 28, 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
Quickest round-trip

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 4/28

1:55 pm-11:29 pm

1 stop7h 34m

Chicago O'Hare Intl

Fri 5/1

12:05 pm-5:58 pm

1 stop7h 53m

$343

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 4/24

3:59 pm-2:08 pm

1 stop20h 09m

Chicago O'Hare Intl

Wed 4/29

6:00 am-12:58 pm

1 stop8h 58m

$348

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 4/24

12:33 pm-9:18 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 4/29

11:00 am-11:06 pm

2 stops14h 06m

$353

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 4/27

11:35 am-9:18 pm

2 stops7h 43m

Chicago O'Hare Intl

Wed 4/29

11:00 am-11:06 pm

2 stops14h 06m

$358

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 5/26

3:51 pm-12:59 am

1 stop7h 08m

Chicago O'Hare Intl

Sat 5/30

6:00 am-12:53 pm

1 stop8h 53m

$359

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/27

6:10 am-4:49 pm

1 stop8h 39m

Chicago O'Hare Intl

Wed 6/3

2:00 pm-10:52 pm

2 stops10h 52m

$364

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 7/3

6:26 am-4:45 pm

1 stop8h 19m

Chicago O'Hare Intl

Wed 7/8

6:55 am-12:30 pm

1 stop7h 35m

$369

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/27

5:05 am-6:05 pm

2 stops11h 00m

Chicago O'Hare Intl

Wed 6/3

2:00 pm-10:52 pm

2 stops10h 52m

$370

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 4/24

1:55 pm-11:29 pm

1 stop7h 34m

Chicago O'Hare Intl

Fri 5/1

12:05 pm-5:58 pm

1 stop7h 53m

$374

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 5/14

2:50 pm-12:32 am

1 stop7h 42m

Chicago O'Hare Intl

Sun 5/17

7:04 am-1:17 pm

1 stop8h 13m

$379

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 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 45% 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

7h 08m

Direct flights

None
The fastest flight from Redmond to Chicago takes 7h 08m
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 7h 08m, 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
7.9
12,133 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $308Free CancellationRating
7.4
9,501 reviews
Search United Airlines flights

  • United Airlines Flights From Redmond to Chicago

    United Airlines flight deals from Redmond to Chicago start from $308 round-trip. Over the 2 United Airlines flights for this route in a normal week, average airfare is usually $436 round-trip - but some users have found much cheaper deals with momondo.

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
Schererville
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