HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$139+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$270
(Trip.com)

One-way from

$139
(Hawaiian Airlines)

Popular in

February

Cheapest in

May

Average price

$457
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. 19% potential increase in price ($119 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 July 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 July 30, 2025.

This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:57 pmRDM - ORD
1 stop6h 07mHawaiian Airlines
Sat 9/206:20 amORD - RDM
1 stop8h 25mHawaiian Airlines
Deal found 7/30$270
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 9/23:57 pmRDM - ORD
1 stop19h 14mAlaska Airlines
Tue 9/98:00 amORD - RDM
1 stop6h 37mAlaska Airlines
Deal found 7/29$279
This Delta deal was found by Cheapflights users on 7/27. 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 9/247:00 amRDM - ORD
2 stops12h 57mDelta
Sat 9/277:55 amORD - RDM
1 stop5h 58mDelta
Deal found 7/27$284
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/211:55 pmRDM - ORD
1 stop6h 48mAmerican Airlines
Sun 8/248:00 amORD - RDM
1 stop6h 56mAmerican Airlines
Deal found 7/28$299
This Delta deal was found by Cheapflights users on 7/30. 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 9/137:30 pmRDM - MDW
2 stops11h 23mDelta
Sat 9/209:20 amMDW - RDM
2 stops11h 30mDelta
Deal found 7/30$329
This United Airlines deal was found by Cheapflights users on 7/27. 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 8/187:32 pmRDM - ORD
1 stop7h 46mUnited Airlines
Wed 8/206:15 amORD - RDM
1 stop7h 59mUnited Airlines
Deal found 7/27$379

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 July 30, 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 9/13

3:57 pm-12:04 am

1 stop6h 07m

Chicago O'Hare Intl

Sat 9/20

6:20 am-12:45 pm

1 stop8h 25m

$270

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Tue 9/2

3:57 pm-1:11 pm

1 stop19h 14m

Chicago O'Hare Intl

Tue 9/9

8:00 am-12:37 pm

1 stop6h 37m

$279

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 9/24

7:00 am-9:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Sat 9/27

7:55 am-11:53 am

1 stop5h 58m

$284

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 8/21

1:55 pm-10:43 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 8/24

8:00 am-12:56 pm

1 stop6h 56m

$299

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 9/13

7:30 pm-8:53 am

2 stops11h 23m

Chicago Midway

Sat 9/20

9:20 am-6:50 pm

2 stops11h 30m

$329

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Mon 8/18

7:32 pm-5:18 am

1 stop7h 46m

Chicago O'Hare Intl

Wed 8/20

6:15 am-12:14 pm

1 stop7h 59m

$379

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/1

1:31 pm-10:07 pm

1 stop6h 36m

$139

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 8/29

1:55 pm-10:43 pm

1 stop6h 48m

$150

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 9/4

7:00 am-9:00 pm

2 stops12h 00m

$155

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 10/1

5:25 am-12:03 am

2 stops16h 38m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 12 results
1
2

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 July 30, 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.

How much does it cost to fly round-trip from Redmond to Chicago?

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 July 30, 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

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Flying on Hawaiian Airlines is currently your cheapest option to Chicago, with prices starting at $270. Additional round-trip tickets that might be worth considering are offered by Alaska Airlines and Delta, with the lowest prices starting at $279 and $284, respectively. Hawaiian Airlines is priced at 43% 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 $139. Users have also found prices from $140 and $150 on United Airlines and American 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
Valparaiso
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
Boise to O'Hare Intl flights
Portland to Midway flights
Redmond to O'Hare Intl flights
Portland to St. Louis flights
Redmond to Midway flights
Boise to Midway flights
Redmond to St. Louis flights
Eugene to O'Hare Intl flights
Eugene to Midway flights
Boise to St. Louis flights
Medford to O'Hare Intl flights
Portland to Peoria flights
Portland to Rockford flights
Boise to Moline flights
Yakima to O'Hare Intl flights
Eugene to St. Louis flights
Redmond to Bloomington flights
Portland to Decatur flights
Portland to Moline flights
Medford to Midway flights
Medford to St. Louis flights
Boise to Peoria flights
Portland to Bloomington flights
Portland to Champaign flights
Portland to Evansville flights
Eugene to Peoria flights
Redmond to Evansville flights
Portland to Springfield flights
Eugene to Springfield flights
Eugene to Moline flights
Boise to Champaign flights
North Bend to O'Hare Intl flights
Boise to Paducah flights
Medford to Bloomington flights
Portland to Paducah flights
Portland to Marion flights
Eugene to Dubuque flights
Boise to Quincy flights
Boise to Springfield flights
Boise to Bloomington 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$262Average$525FlexibilityNo cancel feeOn-time75%
DeltaCheapest$263Average$391FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$306Average$498FlexibilityNo 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.