Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Redmond to Chicago from $137

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 1/29. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Redmond to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
8:45 am - 5:10 pm
RDM
-
ORD
6h 25m1 stop
Alaska Airlines Logo
6:06 pm - 11:52 pm
ORD
-
RDM
7h 46m1 stop
$264Alaska Airlines
Mon, Feb 2 - Fri, Feb 6
Alaska Airlines Logo
1:10 pm - 11:37 pm
RDM
-
ORD
8h 27m1 stop
Alaska Airlines Logo
8:00 am - 11:52 pm
ORD
-
RDM
17h 52m1 stop
$271Alaska Airlines
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
Alaska Airlines Logo
8:00 am - 11:52 pm
ORD
-
RDM
17h 52m1 stop
$274Alaska Airlines
Wed, Jan 14 - Sun, Jan 18
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
Alaska Airlines Logo
2:06 pm - 11:52 pm
ORD
-
RDM
11h 46m2 stops
$280Alaska Airlines
Mon, Feb 2 - Fri, Feb 6
Alaska Airlines Logo
8:45 am - 11:50 pm
RDM
-
ORD
13h 05m1 stop
Alaska Airlines Logo
2:06 pm - 9:15 pm
ORD
-
RDM
9h 09m2 stops
$290Alaska Airlines
Wed, Jan 14 - Sun, Jan 18
Delta Logo
7:00 am - 9:52 pm
RDM
-
ORD
12h 52m2 stops
Delta Logo
7:20 am - 11:55 am
ORD
-
RDM
6h 35m1 stop
$297Delta
Fri, Jan 23 - Sat, Jan 24
Alaska Airlines Logo
1:31 pm - 10:45 pm
RDM
-
ORD
7h 14m1 stop
Alaska Airlines Logo
6:00 am - 12:37 pm
ORD
-
RDM
8h 37m1 stop
$298Alaska Airlines
Wed, May 27 - Wed, Jun 3
Delta Logo
6:20 am - 6:41 pm
RDM
-
ORD
10h 21m2 stops
Delta Logo
7:20 am - 12:02 pm
ORD
-
RDM
6h 42m1 stop
$304Delta
Wed, May 27 - Wed, Jun 3
Alaska Airlines Logo
3:57 pm - 2:38 pm
RDM
-
ORD
20h 41m2 stops
Alaska Airlines Logo
2:06 pm - 11:52 pm
ORD
-
RDM
11h 46m2 stops
$314Alaska Airlines
Mon, Feb 2 - Fri, Feb 6
Alaska Airlines Logo
1:10 pm - 11:37 pm
RDM
-
ORD
8h 27m1 stop
Alaska Airlines Logo
6:06 pm - 12:30 pm
ORD
-
RDM
20h 24m2 stops
$316Alaska Airlines
Wed, Jan 14 - Sun, Jan 18

Alaska Airlines flights from Redmond to Chicago

Our best Alaska Airlines deals on Redmond to Chicago flight tickets
Alaska Airlines
Feb 2
RDM8:45 amBend/Redmond
6h 25m
1 stop
ORD5:10 pmChicago O'Hare Intl
Feb 6
ORD6:06 pmChicago O'Hare Intl
7h 46m
1 stop
RDM11:52 pmBend/Redmond
$264
Find similar
Alaska Airlines
Jan 14
RDM1:10 pmBend/Redmond
8h 27m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 18
ORD8:00 amChicago O'Hare Intl
17h 52m
1 stop
RDM11:52 pmBend/Redmond
$271
Find similar
Alaska Airlines
Jan 14
RDM8:45 amBend/Redmond
13h 05m
1 stop
ORD11:50 pmChicago O'Hare Intl
Jan 18
ORD8:00 amChicago O'Hare Intl
17h 52m
1 stop
RDM11:52 pmBend/Redmond
$274
Find similar

Delta flights from Redmond to Chicago

Our best Delta deals on Redmond to Chicago flight tickets
Delta
Jan 23
RDM7:00 amBend/Redmond
12h 52m
2 stops
ORD9:52 pmChicago O'Hare Intl
Jan 24
ORD7:20 amChicago O'Hare Intl
6h 35m
1 stop
RDM11:55 amBend/Redmond
$297
Find similar
Delta
May 27
RDM6:20 amBend/Redmond
10h 21m
2 stops
ORD6:41 pmChicago O'Hare Intl
Jun 3
ORD7:20 amChicago O'Hare Intl
6h 42m
1 stop
RDM12:02 pmBend/Redmond
$304
Find similar
Delta
May 27
RDM12:30 pmBend/Redmond
9h 17m
1 stop
ORD11:47 pmChicago O'Hare Intl
Jun 1
ORD1:35 pmChicago O'Hare Intl
11h 12m
2 stops
RDM10:47 pmBend/Redmond
$344
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 December 23, 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

Mon 2/2

8:45 am-5:10 pm

1 stop6h 25m

Chicago O'Hare Intl

Fri 2/6

6:06 pm-11:52 pm

1 stop7h 46m

$264

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 1/14

1:10 pm-11:37 pm

1 stop8h 27m

Chicago O'Hare Intl

Sun 1/18

8:00 am-11:52 pm

1 stop17h 52m

$271

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 1/14

8:45 am-11:50 pm

1 stop13h 05m

Chicago O'Hare Intl

Sun 1/18

8:00 am-11:52 pm

1 stop17h 52m

$274

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 2/2

8:45 am-11:50 pm

1 stop13h 05m

Chicago O'Hare Intl

Fri 2/6

2:06 pm-11:52 pm

2 stops11h 46m

$280

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 1/14

8:45 am-11:50 pm

1 stop13h 05m

Chicago O'Hare Intl

Sun 1/18

2:06 pm-9:15 pm

2 stops9h 09m

$290

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 1/23

7:00 am-9:52 pm

2 stops12h 52m

Chicago O'Hare Intl

Sat 1/24

7:20 am-11:55 am

1 stop6h 35m

$297

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/27

1:31 pm-10:45 pm

1 stop7h 14m

Chicago O'Hare Intl

Wed 6/3

6:00 am-12:37 pm

1 stop8h 37m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 5/27

6:20 am-6:41 pm

2 stops10h 21m

Chicago O'Hare Intl

Wed 6/3

7:20 am-12:02 pm

1 stop6h 42m

$304

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 2/2

3:57 pm-2:38 pm

2 stops20h 41m

Chicago O'Hare Intl

Fri 2/6

2:06 pm-11:52 pm

2 stops11h 46m

$314

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 1/14

1:10 pm-11:37 pm

1 stop8h 27m

Chicago O'Hare Intl

Sun 1/18

6:06 pm-12:30 pm

2 stops20h 24m

$316

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January is, on average, the cheapest month to fly to Chicago from Redmond, with most prices found around $309. If you’re not able to fly to Chicago in January, then December is your next best option. Flight prices from Redmond to Chicago during December average around $324.

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 15% on your flight if you consider stops on a Redmond to Chicago flight.

How have Redmond to Chicago flight prices changed over time?

As of December 2025, prices for Redmond to Chicago flights are approximately 144% more expensive when compared to flights at the same time last year.

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 01m

Direct flights

None
The fastest flight from Redmond to Chicago takes 6h 01m
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 01m, 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
11,513 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $278Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
DeltaPriceFrom $288Free CancellationRating
7.9
8,014 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
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/22
Thu 1/29
By creating a price alert you accept our terms of use and privacy policy.

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