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Walla Walla

$277+ Cheap flights from Chicago (CHI) to Walla Walla (ALW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ALW
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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Cheap flight deals from Chicago to Walla Walla

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Walla Walla (ALW). 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 January 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$277
(Alaska Airlines)
Provider with most accurate pricing for Chicago (CHI)-Walla Walla flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Walla Walla flights.
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From Chicago (CHI) to Walla Walla
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Find flight deals from Chicago to Walla Walla

Cheapest flights from Chicago to Walla Walla
Explore the most affordable flight options available from Chicago to Walla Walla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 14, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/12. 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 2/175:29 pm
ORD
-
ALW
1 stop8h 29m
Alaska Airlines
Sat 2/215:53 am
ALW
-
ORD
1 stop6h 18m
Alaska Airlines
Deal found 1/12$277
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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.
Thu 2/265:29 pm
ORD
-
ALW
1 stop8h 29m
Alaska Airlines
Sat 2/285:53 am
ALW
-
ORD
1 stop6h 18m
Alaska Airlines
Deal found 1/12$294
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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.
Thu 5/147:45 pm
ORD
-
ALW
1 stop6h 32m
Alaska Airlines
Sat 5/163:14 pm
ALW
-
ORD
1 stop6h 45m
Alaska Airlines
Deal found 1/12$354
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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.
Fri 3/135:29 pm
ORD
-
ALW
1 stop24h 17m
Alaska Airlines
Sun 3/155:53 am
ALW
-
ORD
1 stop28h 08m
Alaska Airlines
Deal found 1/12$383
This Alaska Airlines deal was found by Cheapflights users on 1/12. 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 2/96:06 pm
ORD
-
ALW
1 stop22h 54m
Alaska Airlines
Mon 2/164:26 pm
ALW
-
ORD
1 stop22h 07m
Alaska Airlines
Deal found 1/12$388
This Travelocity deal was found by Cheapflights users on 1/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/198:00 am
ORD
-
ALW
1 stop8h 57m
Alaska Airlines
Sun 3/223:37 pm
ALW
-
ORD
1 stop6h 22m
Alaska Airlines
Deal found 1/12$391
This Travelocity deal was found by Cheapflights users on 1/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/207:24 pm
ORD
-
ALW
1 stop6h 35m
Alaska Airlines
Sun 3/223:37 pm
ALW
-
ORD
1 stop6h 22m
Alaska Airlines
Deal found 1/12$425

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Walla Walla 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 January 14, 2026.
Use the filters below to find and compare flights from Chicago to Walla Walla that are best for you.

Fly from

Chicago

Fly to

Walla Walla

Route

Depart

Return

Price

ChicagoWalla Walla

ORD - ALW

ORDALW

Chicago O'Hare Intl

Tue 2/17

5:29 pm-11:58 pm

1 stop8h 29m

Walla Walla

Sat 2/21

5:53 am-2:11 pm

1 stop6h 18m

$277

ChicagoWalla Walla

ORD - ALW

ORDALW

Chicago O'Hare Intl

Thu 2/26

5:29 pm-11:58 pm

1 stop8h 29m

Walla Walla

Sat 2/28

5:53 am-2:11 pm

1 stop6h 18m

$294

ChicagoWalla Walla

ORD - ALW

ORDALW

Chicago O'Hare Intl

Fri 3/13

3:54 pm-3:46 pm

1 stop25h 52m

Walla Walla

Sun 3/15

5:53 am-12:01 pm

1 stop28h 08m

$383

ChicagoWalla Walla

ORD - ALW

ORDALW

Chicago O'Hare Intl

Mon 2/9

6:06 pm-3:00 pm

1 stop22h 54m

Walla Walla

Mon 2/16

4:26 pm-4:33 pm

1 stop22h 07m

$388

ChicagoWalla Walla

ORD - ALW

ORDALW

Chicago O'Hare Intl

Thu 3/19

6:00 am-2:57 pm

1 stop10h 57m

Walla Walla

Sun 3/22

3:37 pm-11:59 pm

1 stop6h 22m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Compare providers for flights from Chicago to Walla Walla

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Walla Walla in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Walla Walla flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Walla Walla flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Walla Walla flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Walla Walla flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Walla Walla flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Walla Walla

Have a flexible travel schedule? Discover the best time to fly to Walla Walla from Chicago 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 Chicago to Walla Walla

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Walla Walla (average of $278). Flying from Chicago to Walla Walla in February is currently the most expensive (average of $848). 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.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Walla Walla. 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 into for flights to Walla Walla from Chicago?

    Walla Walla (ALW) is the airport you will fly into if you book a flight from Chicago to Walla Walla. You should not have trouble finding flights to Walla Walla from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Walla Walla airport from Chicago. It is only a 3.3 mi journey from Walla Walla (ALW) to Walla Walla’s city center.

  • How long is the flight from Chicago to Walla Walla?

    Departing from Chicago to Walla Walla will take you 8h 29m. Chicago and Walla Walla are separated by a distance of 1525 mi.

  • What is the cheapest airline to fly from Chicago to Walla Walla round-trip?

    Currently priced at $345, Alaska Airlines will fly you from Chicago to Walla Walla and back. In addition to Alaska Airlines, many other airlines offer competitively priced options for your trip.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Walla Walla 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 Chicago to Walla Walla?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Walla Walla (average of $278). Flying from Chicago to Walla Walla in February is currently the most expensive (average of $848). 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

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Alternative routes for Chicago to Walla Walla

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Chicago to Walla Walla

Discover the top airline that operate flights from Chicago to Walla Walla. 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 January 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$345Average$522FlexibilityNo cancel feeOn-time75%

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