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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 10/31. 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

Delta Logo
7:00 am - 5:18 pmRDM-ORD
8h 18m1 stop
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$234Delta
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Sat, Nov 8 - Tue, Nov 11
Delta Logo
7:00 am - 4:50 pmRDM-ORD
7h 50m2 stops
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$287Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
12:29 pm - 9:43 pmRDM-ORD
7h 14m1 stop
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$292Delta
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Fri, Nov 7 - Tue, Nov 11
Delta Logo
7:26 pm - 9:03 amRDM-ORD
11h 37m2 stops
Delta Logo
6:13 pm - 10:53 pmORD-RDM
6h 40m1 stop
$297Delta
Find Deal
Fri, Nov 7 - Tue, Nov 11
Hawaiian Airlines Logo
7:15 am - 6:59 pmRDM-ORD
9h 44m1 stop
Hawaiian Airlines Logo
3:50 pm - 10:26 pmORD-RDM
8h 36m1 stop
$298Hawaiian Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
United Airlines Logo
1:17 pm - 8:58 pmRDM-ORD
5h 41m1 stop
United Airlines Logo
6:15 am - 12:15 pmORD-RDM
8h 00m1 stop
$299United Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
Alaska Airlines Logo
12:43 pm - 5:01 amRDM-ORD
14h 18m1 stop
Alaska Airlines Logo
3:25 pm - 8:58 pmORD-RDM
7h 33m1 stop
$308Alaska Airlines
Find Deal
Sat, Nov 8 - Fri, Nov 14
Alaska Airlines Logo
9:30 am - 6:59 pmRDM-ORD
7h 29m1 stop
Alaska Airlines Logo
6:00 am - 5:04 pmORD-RDM
13h 04m1 stop
$318Alaska Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
Hawaiian Airlines Logo
3:41 pm - 12:03 amRDM-ORD
6h 22m1 stop
Hawaiian Airlines Logo
3:50 pm - 10:26 pmORD-RDM
8h 36m1 stop
$372Hawaiian Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
American Airlines Logo
5:30 am - 3:58 pmRDM-ORD
8h 28m1 stop
American Airlines Logo
3:59 pm - 11:08 pmORD-RDM
9h 09m1 stop
$545American Airlines
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Sun, Sep 28 - Thu, Oct 2

Delta flights from Redmond to Chicago

Our best Delta deals on Redmond to Chicago flight tickets
Delta
Nov 8
RDM7:00 amBend/Redmond
8h 18m
1 stop
ORD5:18 pmChicago O'Hare Intl
Nov 11
ORD6:13 pmChicago O'Hare Intl
6h 40m
1 stop
RDM10:53 pmBend/Redmond
$234
Find similar
Delta
Nov 8
RDM7:00 amBend/Redmond
7h 50m
2 stops
ORD4:50 pmChicago O'Hare Intl
Nov 11
ORD6:13 pmChicago O'Hare Intl
6h 40m
1 stop
RDM10:53 pmBend/Redmond
$287
Find similar
Delta
Nov 7
RDM12:29 pmBend/Redmond
7h 14m
1 stop
ORD9:43 pmChicago O'Hare Intl
Nov 11
ORD6:13 pmChicago O'Hare Intl
6h 40m
1 stop
RDM10:53 pmBend/Redmond
$292
Find similar

Hawaiian Airlines flights from Redmond to Chicago

Our best Hawaiian Airlines deals on Redmond to Chicago flight tickets
Hawaiian Airlines
Oct 8
RDM7:15 amBend/Redmond
9h 44m
1 stop
ORD6:59 pmChicago O'Hare Intl
Oct 14
ORD3:50 pmChicago O'Hare Intl
8h 36m
1 stop
RDM10:26 pmBend/Redmond
$298
Find similar
Hawaiian Airlines
Oct 1
RDM3:41 pmBend/Redmond
6h 22m
1 stop
ORD12:03 amChicago O'Hare Intl
Oct 6
ORD3:50 pmChicago O'Hare Intl
8h 36m
1 stop
RDM10:26 pmBend/Redmond
$372
Find similar
Hawaiian Airlines
Oct 2
RDM3:41 pmBend/Redmond
6h 22m
1 stop
ORD12:03 amChicago O'Hare Intl
Oct 6
ORD3:50 pmChicago O'Hare Intl
8h 36m
1 stop
RDM10:26 pmBend/Redmond
$431
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 September 15, 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

Sat 11/8

7:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Tue 11/11

6:13 pm-10:53 pm

1 stop6h 40m

$234

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 11/8

7:00 am-4:50 pm

2 stops7h 50m

Chicago O'Hare Intl

Tue 11/11

6:13 pm-10:53 pm

1 stop6h 40m

$287

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 11/7

12:29 pm-9:43 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 11/11

6:13 pm-10:53 pm

1 stop6h 40m

$292

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 11/7

7:26 pm-9:03 am

2 stops11h 37m

Chicago O'Hare Intl

Tue 11/11

6:13 pm-10:53 pm

1 stop6h 40m

$297

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/8

7:15 am-6:59 pm

1 stop9h 44m

Chicago O'Hare Intl

Tue 10/14

3:50 pm-10:26 pm

1 stop8h 36m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 11/8

1:17 pm-8:58 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 11/11

6:15 am-12:15 pm

1 stop8h 00m

$299

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 11/8

12:43 pm-5:01 am

1 stop14h 18m

Chicago O'Hare Intl

Fri 11/14

3:25 pm-8:58 pm

1 stop7h 33m

$308

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 10/31

9:30 am-6:59 pm

1 stop7h 29m

Chicago O'Hare Intl

Mon 11/3

6:00 am-5:04 pm

1 stop13h 04m

$318

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/1

3:41 pm-12:03 am

1 stop6h 22m

Chicago O'Hare Intl

Mon 10/6

3:50 pm-10:26 pm

1 stop8h 36m

$372

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sun 9/28

5:30 am-3:58 pm

1 stop8h 28m

Chicago O'Hare Intl

Thu 10/2

3:59 pm-11:08 pm

1 stop9h 09m

$545

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 $337. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Redmond to Chicago during April average around $397.

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 3% 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 41m, 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
10,000 reviews
Search Alaska Airlines flights
DeltaPriceFrom $293Free CancellationRating
7.9
7,954 reviews
Search Delta flights
United AirlinesPriceFrom $306Free CancellationRating
7.4
8,929 reviews
Search United 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
Benton Harbor
Saint Joseph
Lansing
Portage
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