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Cheap flights from Redmond to Chicago from $200

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 10/5. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Redmond to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:44 pm - 11:57 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 13m1 stop Seattle/Tacoma Intl
Delta Logo
7:00 am - 1:04 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 04m1 stop Seattle/Tacoma Intl
$435Delta
Sat, Sep 12 - Sat, Sep 26
Delta Logo
12:30 pm - 10:00 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 30m1 stop Salt Lake City
Delta Logo
12:50 pm - 6:44 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 54m1 stop Seattle/Tacoma Intl
$435Delta
Sat, Sep 12 - Wed, Sep 23
Alaska Airlines Logo
5:27 am - 1:09 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
5h 42m1 stop Portland
Alaska Airlines Logo
5:55 pm - 12:17 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 22m1 stop Seattle/Tacoma Intl
$435Alaska Airlines
Sat, Feb 6 - Wed, Feb 10
Alaska Airlines Logo
1:37 pm - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 22m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:18 pm - 9:38 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 20m1 stop San Diego
$435Alaska Airlines
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
1:03 pm - 9:30 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 27m1 stop Denver Intl
United Airlines Logo
12:51 pm - 6:12 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 21m1 stop San Francisco
$435United Airlines
Wed, Sep 9 - Wed, Sep 23
United Airlines Logo
1:52 pm - 11:05 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 13m1 stop San Francisco
United Airlines Logo
6:00 am - 12:06 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 06m1 stop San Francisco
$435United Airlines
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
2:46 pm - 11:43 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 57m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:59 am - 2:14 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 15m1 stop Phoenix Sky Harbor Intl
$435American Airlines
Wed, Sep 16 - Sat, Sep 19
American Airlines Logo
2:28 pm - 11:35 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 07m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
6:48 am - 1:33 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 45m1 stop Phoenix Sky Harbor Intl
$435American Airlines
Wed, Dec 2 - Sat, Dec 5
Delta Logo
6:15 am - 6:04 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
9h 49m2 stops Seattle/Tacoma Intl Salt Lake City
Delta Logo
7:00 am - 1:04 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 04m1 stop Seattle/Tacoma Intl
$440Delta
Wed, Sep 16 - Sat, Sep 19
United Airlines Logo
7:00 am - 5:00 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 00m1 stop Los Angeles
United Airlines Logo
3:56 pm - 9:18 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 22m1 stop Denver Intl
$481United Airlines
Wed, Nov 4 - Mon, Nov 9

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Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
Sep 16
RDM7:07 amBend/Redmond
10h 14m
1 stop
ORD7:21 pmChicago O'Hare Intl
Sep 19
ORD2:22 pmChicago O'Hare Intl
11h 36m
2 stops
RDM11:58 pmBend/Redmond
$492
Alaska Airlines
Sep 11
RDM6:47 pmBend/Redmond
22h 34m
2 stops
ORD7:21 pmChicago O'Hare Intl
Sep 18
ORD8:17 pmChicago O'Hare Intl
18h 36m
1 stop
RDM12:53 pmBend/Redmond
$502
Alaska Airlines
Sep 11
RDM10:16 amBend/Redmond
18h 04m
1 stop
ORD6:20 amChicago O'Hare Intl
Sep 14
ORD6:00 amChicago O'Hare Intl
8h 40m
1 stop
RDM12:40 pmBend/Redmond
$503

American Airlines flights from Redmond to Chicago

Our best American Airlines deals on Redmond to Chicago flight tickets
American Airlines
Oct 7
RDM3:00 pmBend/Redmond
7h 35m
1 stop
ORD12:35 amChicago O'Hare Intl
Oct 12
ORD6:48 amChicago O'Hare Intl
8h 56m
1 stop
RDM1:44 pmBend/Redmond
$510
American Airlines
Aug 26
RDM2:30 pmBend/Redmond
7h 58m
1 stop
ORD12:28 amChicago O'Hare Intl
Aug 29
ORD1:40 pmChicago O'Hare Intl
8h 28m
1 stop
RDM8:08 pmBend/Redmond
$511
American Airlines
Oct 22
RDM3:00 pmBend/Redmond
6h 30m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 25
ORD6:48 amChicago O'Hare Intl
8h 56m
1 stop
RDM1:44 pmBend/Redmond
$543

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 11, 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 Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Sat 9/12

1:44 pm-11:57 pm

1 stop8h 13m

Chicago O'Hare Intl

Sat 9/26

7:00 am-1:04 pm

1 stop8h 04m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Sat 9/12

12:30 pm-10:00 pm

1 stop7h 30m

Chicago O'Hare Intl

Wed 9/23

12:50 pm-6:44 pm

1 stop7h 54m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Sat 2/6

5:27 am-1:09 pm

1 stop5h 42m

Chicago O'Hare Intl

Wed 2/10

5:55 pm-12:17 am

1 stop8h 22m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 9/16

1:37 pm-11:59 pm

1 stop8h 22m

Chicago O'Hare Intl

Sat 9/19

2:18 pm-9:38 pm

1 stop9h 20m

$435
Quickest round-trip

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 9/9

1:03 pm-9:30 pm

1 stop6h 27m

Chicago O'Hare Intl

Wed 9/23

12:51 pm-6:12 pm

1 stop7h 21m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 9/16

1:52 pm-11:05 pm

1 stop7h 13m

Chicago O'Hare Intl

Sat 9/19

6:00 am-12:06 pm

1 stop8h 06m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 9/16

2:46 pm-11:43 pm

1 stop6h 57m

Chicago O'Hare Intl

Sat 9/19

6:59 am-2:14 pm

1 stop9h 15m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 12/2

2:28 pm-11:35 pm

1 stop7h 07m

Chicago O'Hare Intl

Sat 12/5

6:48 am-1:33 pm

1 stop8h 45m

$435

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 9/16

6:15 am-6:04 pm

2 stops9h 49m

Chicago O'Hare Intl

Sat 9/19

7:00 am-1:04 pm

1 stop8h 04m

$440

RedmondChicago

RDM Bend/Redmond - ORD Chicago O'Hare Intl

RDMORD

Bend/Redmond

Wed 11/4

7:00 am-5:00 pm

1 stop8h 00m

Chicago O'Hare Intl

Mon 11/9

3:56 pm-9:18 pm

1 stop7h 22m

$481

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $406 to $478.
The lowest price recently found on this route was $435.

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Redmond, with most prices found around $320. If you’re not able to fly to Chicago in November, then December is your next best option. Flight prices from Redmond to Chicago during December average around $324.

Can stopping save me money on Redmond to Chicago flights?

You could potentially save up to 13% 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 08m

Direct flights

None
The fastest flight from Redmond to Chicago takes 6h 08m
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 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
United AirlinesPriceFrom $311Free CancellationRating
7.4
10,102 reviews
Search United Airlines flights
DeltaPriceFrom $318Free CancellationRating
7.8
8,506 reviews
Search Delta flights
Alaska AirlinesPriceFrom $320Free CancellationRating
7.9
12,794 reviews
Search Alaska 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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