HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$132+ Cheap flights from Redmond (RDM) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Redmond to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Redmond to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Redmond (RDM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$234
(Delta)

One-way from

$132
(Hawaiian Airlines)

Popular in

February

Cheapest in

May

Average price

$516
From Bend/Redmond to Chicago (CHI)
Search Deals
One-way flight from Bend/Redmond to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Redmond to Chicago

Cheapest flights from Redmond to Chicago
Explore the most affordable flight options available from Redmond to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/17:00 amRDM - ORD
1 stop8h 18mDelta
Wed 11/56:05 pmORD - RDM
1 stop6h 30mDelta
Deal found 9/9$234
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:00 amRDM - ORD
1 stop8h 18mDelta
Wed 11/192:12 pmORD - RDM
1 stop6h 42mDelta
Deal found 9/11$254
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:30 pmRDM - ORD
2 stops10h 55mDelta
Mon 10/66:05 pmORD - RDM
1 stop6h 30mDelta
Deal found 9/10$268
This KAYAK deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/91:30 pmRDM - ORD
1 stop7h 00mAlaska Airlines
Fri 12/123:35 pmORD - RDM
1 stop7h 40mAlaska Airlines
Deal found 9/11$275
This Hawaiian Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:43 pmRDM - ORD
1 stop6h 16mHawaiian Airlines
Mon 12/86:00 amORD - RDM
1 stop8h 50mHawaiian Airlines
Deal found 9/10$282
This Hawaiian Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:31 pmRDM - ORD
1 stop8h 32mHawaiian Airlines
Mon 10/63:50 pmORD - RDM
1 stop8h 36mHawaiian Airlines
Deal found 9/10$294
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:30 pmRDM - ORD
1 stop26h 26mDelta
Mon 10/62:25 pmORD - RDM
1 stop6h 21mDelta
Deal found 9/11$301
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/135:54 pmRDM - ORD
1 stop10h 30mAlaska Airlines
Wed 10/156:00 amORD - RDM
1 stop8h 52mAlaska Airlines
Deal found 9/10$307
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:50 pmRDM - ORD
1 stop8h 05mUnited Airlines
Wed 10/156:15 amORD - RDM
1 stop7h 59mUnited Airlines
Deal found 9/10$309
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:34 pmRDM - MDW
2 stops11h 27mDelta
Fri 11/211:14 pmMDW - RDM
2 stops11h 39mDelta
Deal found 9/11$329
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:34 pmRDM - MDW
2 stops11h 27mDelta
Wed 11/191:14 pmMDW - RDM
2 stops11h 39mDelta
Deal found 9/11$349
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:55 amRDM - MDW
2 stops10h 05mDelta
Mon 12/81:14 pmMDW - RDM
2 stops11h 36mDelta
Deal found 9/10$359

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Redmond to Chicago that are best for you.

Fly from

Redmond

Fly to

Chicago

Route

Depart

Return

Price

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 11/1

7:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 11/5

6:05 pm-10:35 pm

1 stop6h 30m

$234

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 11/13

7:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 11/19

2:12 pm-6:54 pm

1 stop6h 42m

$254

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/1

7:30 pm-8:25 am

2 stops10h 55m

Chicago O'Hare Intl

Mon 10/6

6:05 pm-10:35 pm

1 stop6h 30m

$268

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 12/9

1:30 pm-10:30 pm

1 stop7h 00m

Chicago O'Hare Intl

Fri 12/12

3:35 pm-9:15 pm

1 stop7h 40m

$275

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 12/4

3:43 pm-11:59 pm

1 stop6h 16m

Chicago O'Hare Intl

Mon 12/8

6:00 am-12:50 pm

1 stop8h 50m

$282

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/1

1:31 pm-12:03 am

1 stop8h 32m

Chicago O'Hare Intl

Mon 10/6

3:50 pm-10:26 pm

1 stop8h 36m

$294

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 12/3

7:20 am-6:54 pm

1 stop9h 34m

Chicago O'Hare Intl

Mon 12/8

7:59 pm-11:52 am

1 stop17h 53m

$298

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 12/3

7:34 pm-9:55 am

2 stops12h 21m

Chicago O'Hare Intl

Mon 12/8

6:13 pm-10:50 pm

1 stop6h 37m

$304

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 11/14

7:34 pm-9:01 am

2 stops11h 27m

Chicago Midway

Fri 11/21

1:14 pm-10:53 pm

2 stops11h 39m

$329

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 11/13

7:34 pm-9:01 am

2 stops11h 27m

Chicago Midway

Wed 11/19

1:14 pm-10:53 pm

2 stops11h 39m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 33 results
1
2
3
4

Best time to book a flight from Redmond to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Redmond with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Redmond to Chicago

What is the cheapest month to book a flight from Redmond to Chicago?

Currently, August is the cheapest month in which you can book a flight from Redmond to Chicago (average of $245). Flying from Redmond to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RDM to CHI?

Find hourly flight availability from Redmond to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Redmond to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 14% on airfare.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta, and Hawaiian Airlines from Redmond to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Redmond to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Redmond to Chicago?

    Bend/Redmond (RDM) is the airport you will fly out of if you book a flight from Redmond to Chicago. You should not have trouble finding flights to Chicago from Bend/Redmond; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Redmond airport to Chicago. It is only a 1.8 mi journey to Bend/Redmond (RDM) from Redmond’s city center.

  • How long is the flight from Redmond to Chicago?

    Delta can get you from Redmond to Chicago in just under 8h 18m. Your travel time can differ by up to . Redmond and Chicago are separated by a distance of 1671 mi.

  • What are the cheapest airlines flying from Redmond to Chicago round-trip?

    Flying on Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $262. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $293 and $306, respectively. Alaska Airlines is priced at 45% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Redmond to Chicago one-way?

    For one-way options, check prices for Hawaiian Airlines. According to our data, you can fly for as low as $132. Users have also found prices from $138 and $159 on Delta and Alaska Airlines, respectively.

  • Can I find deals for flights from Redmond to Chicago that include hotel bookings?

    Yes. In addition to deals on Redmond to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Redmond to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Redmond to Chicago.

  • Can I find deals for business class flights from Redmond to Chicago?

    Yes. Cheapflights offers flight deals from Redmond to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Redmond to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Redmond to Chicago (average of $245). Flying from Redmond to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Redmond to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Portland to O'Hare Intl flights
Portland to Midway flights
Boise to O'Hare Intl flights
Portland to St. Louis flights
Boise to Midway flights
Eugene to O'Hare Intl flights
Redmond to O'Hare Intl flights
Eugene to Midway flights
Redmond to Midway flights
Portland to Moline flights
Portland to Peoria flights
Eugene to St. Louis flights
Portland to Decatur flights
Boise to St. Louis flights
Medford to O'Hare Intl flights
Boise to Peoria flights
Portland to Rockford flights
Medford to St. Louis flights
Redmond to St. Louis flights
Portland to Bloomington flights
Yakima to O'Hare Intl flights
Medford to Midway flights
Eugene to Moline flights
Boise to Moline flights
Eugene to Peoria flights
Portland to Champaign flights
Portland to Evansville flights
Redmond to Evansville flights
Redmond to Bloomington flights
Boise to Champaign flights
Medford to Bloomington flights
North Bend to O'Hare Intl flights
Boise to Bloomington flights
Boise to Paducah flights
Portland to Springfield flights
Boise to Quincy flights
Boise to Springfield flights
Eugene to Dubuque flights
Portland to Paducah flights
Portland to Marion flights
Eugene to Springfield flights
Portland to Dubuque flights

Top 3 airlines flying from Redmond to Chicago

Discover the top 3 airlines that operate flights from Redmond to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$262Average$511FlexibilityNo cancel feeOn-time75%
DeltaCheapest$293Average$395FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$306Average$460FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.