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$125+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
RDM — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$236
(Alaska Airlines)

One-way from

$125
(Hawaiian Airlines)

Popular in

February

Cheapest in

May

Average price

$420
From Bend/Redmond to Chicago (CHI)
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One-way flight from Bend/Redmond to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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 June 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/611:58 amRDM - ORD
1 stop8h 32mAlaska Airlines
Wed 8/133:09 pmORD - RDM
1 stop10h 50mAlaska Airlines
Deal found 6/9$236
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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 9/173:41 pmRDM - ORD
1 stop6h 18mHawaiian Airlines
Mon 9/226:20 amORD - RDM
1 stop8h 17mHawaiian Airlines
Deal found 6/10$254
This Delta deal was found by Cheapflights users on 6/10. 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 9/176:20 amRDM - ORD
2 stops13h 33mDelta
Mon 9/226:00 pmORD - RDM
1 stop6h 44mDelta
Deal found 6/10$274
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 10/46:20 amRDM - MDW
2 stops9h 47mDelta
Sat 10/112:00 pmMDW - RDM
2 stops10h 44mDelta
Deal found 6/11$289
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/111:35 pmRDM - ORD
1 stop9h 13mAmerican Airlines
Sun 7/135:00 amORD - RDM
1 stop10h 01mAmerican Airlines
Deal found 6/10$319
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:00 amRDM - ORD
1 stop6h 12mUnited Airlines
Fri 9/263:51 pmORD - RDM
2 stops22h 54mUnited Airlines
Deal found 6/11$496
This United deal was found by Cheapflights users on 6/11. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/117:30 pmRDM - ORD
1 stop14h 02mMultiple Airlines
Thu 6/125:55 pmORD - RDM
1 stop8h 04mMultiple Airlines
Deal found 6/11$1,669

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 June 12, 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

Wed 8/6

11:58 am-10:30 pm

1 stop8h 32m

Chicago O'Hare Intl

Wed 8/13

3:09 pm-11:59 pm

1 stop10h 50m

$236

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 9/17

3:41 pm-11:59 pm

1 stop6h 18m

Chicago O'Hare Intl

Mon 9/22

6:20 am-12:37 pm

1 stop8h 17m

$254

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 9/17

6:20 am-9:53 pm

2 stops13h 33m

Chicago O'Hare Intl

Mon 9/22

6:00 pm-10:44 pm

1 stop6h 44m

$274

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 10/4

6:20 am-6:07 pm

2 stops9h 47m

Chicago Midway

Sat 10/11

2:00 pm-10:44 pm

2 stops10h 44m

$289

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 7/11

1:35 pm-12:48 am

1 stop9h 13m

Chicago O'Hare Intl

Sun 7/13

5:00 am-1:01 pm

1 stop10h 01m

$319

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Fri 9/26

5:00 am-1:12 pm

1 stop6h 12m

Chicago O'Hare Intl

Fri 9/26

3:51 pm-12:45 pm

2 stops22h 54m

$496

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 9/4

1:31 pm-11:59 pm

1 stop8h 28m

$125

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Wed 7/16

1:35 pm-10:33 pm

1 stop6h 58m

$130

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Thu 9/4

12:30 pm-11:59 pm

2 stops9h 29m

$131

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 7/12

7:30 pm-8:25 am

2 stops10h 55m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 12 results
1
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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 June 12, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Redmond to Chicago, such as Alaska Airlines, Delta and Hawaiian Airlines. 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

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $236. Additional round-trip tickets that might be worth considering are offered by Hawaiian Airlines and Delta, with the lowest prices starting at $254 and $274, respectively. Alaska Airlines is priced at 51% 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 $125. Users have also found prices from $130 and $131 on American Airlines 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 Redmond?

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

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Alternative routes for Redmond to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$263Average$412FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$268Average$533FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$306Average$542FlexibilityNo cancel feeOn-time69%

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