$137 Cheap Flights from Walla Walla (ALW) to Chicago (ORD)

View $137 flight on Sat, Oct 25, 2025Opens in a new window

Popular airlines from Walla Walla, WA (ALW-Walla Walla Regional) to Chicago O'Hare Intl. Airport (ORD)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Walla Walla to Chicago (ALW-ORD)

Prices were available within the past 7 days and start at $137 for one-way flights and $271 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Sat, Aug 30 - Sat, Sep 6
ALW
Walla Walla
ORD
Chicago
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Aug 30 from Walla Walla to Chicago, returning Sat, Sep 6, priced at $271 found 1 day ago
Hawaiian Airlines
Sat, Sep 13 - Sat, Sep 20
ALW
Walla Walla
ORD
Chicago
$275 Roundtrip, found 4 days ago
$275
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Sat, Sep 13 from Walla Walla to Chicago, returning Sat, Sep 20, priced at $275 found 4 days ago
Alaska Airlines
Sat, Sep 6 - Sat, Sep 13
ALW
Walla Walla
ORD
Chicago
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Sep 6 from Walla Walla to Chicago, returning Sat, Sep 13, priced at $276 found 1 day ago
Hawaiian Airlines
Sat, Sep 13 - Tue, Sep 23
ALW
Walla Walla
ORD
Chicago
$276 Roundtrip, found 4 days ago
$276
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Sat, Sep 13 from Walla Walla to Chicago, returning Tue, Sep 23, priced at $276 found 4 days ago
Alaska Airlines
Tue, Sep 9 - Sat, Sep 13
ALW
Walla Walla
ORD
Chicago
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Sep 9 from Walla Walla to Chicago, returning Sat, Sep 13, priced at $278 found 1 day ago
Alaska Airlines
Tue, Sep 9 - Sat, Sep 13
ALW
Walla Walla
ORD
Chicago
$286 Roundtrip, found 1 day ago
$286
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Sep 9 from Walla Walla to Chicago, returning Sat, Sep 13, priced at $286 found 1 day ago
Hawaiian Airlines
Fri, Sep 19 - Sat, Sep 20
ALW
Walla Walla
ORD
Chicago
$294 Roundtrip, found 4 days ago
$294
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Fri, Sep 19 from Walla Walla to Chicago, returning Sat, Sep 20, priced at $294 found 4 days ago
Alaska Airlines
Fri, Sep 19 - Sat, Sep 27
ALW
Walla Walla
ORD
Chicago
$296 Roundtrip, found 4 days ago
$296
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Sep 19 from Walla Walla to Chicago, returning Sat, Sep 27, priced at $296 found 4 days ago
Hawaiian Airlines
Fri, Sep 19 - Tue, Sep 23
ALW
Walla Walla
ORD
Chicago
$296 Roundtrip, found 4 days ago
$296
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Fri, Sep 19 from Walla Walla to Chicago, returning Tue, Sep 23, priced at $296 found 4 days ago
American Airlines
Tue, Sep 16 - Tue, Sep 23
ALW
Walla Walla
ORD
Chicago
$776 Roundtrip, found 2 days ago
$776
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 16 from Walla Walla to Chicago, returning Tue, Sep 23, priced at $776 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $327
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $327
Flights from Walla Walla (ALW) to Chicago (ORD)
Origin airport
Walla Walla Regional
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines
Roundtrip price
$270
Distance
1525 mi

Walla Walla to Chicago Flights

The cheapest times to fly from Walla Walla to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Walla Walla to Chicago are during the month of August. You can find some of the cheapest flights from Walla Walla to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Walla Walla to Chicago

Sunday is one of the best days to book for cheap flights from Walla Walla to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Walla Walla to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Walla Walla to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $137 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Walla Walla to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Walla Walla to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from ALW to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ALW to ORD?
The cheapest flights from ALW to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ALW to ORD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ALW to ORD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD)?
You'll have to book a flight with a layover if you're traveling from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from ALW to ORD?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD)?
Choose a flight from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute bookings from ALW to ORD are usually more expensive. To secure the cheapest rates, start searching for flights ahead of time. That said, if you can play around with your travel dates, you may find a cheap ticket right before your trip.
Is it cheaper to book an ALW to ORD flight and hotel package?
You can save money by booking an ALW to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After choosing your ideal flights and accommodations, you can add extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Walla Walla Regional Airport (ALW) to O'Hare Intl. Airport (ORD)?
You can usually reschedule or cancel your ALW to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

Walla Walla nearby Airports

Pasco

Tri-Cities to Chicago
$257.99

Pendleton

Eastern Oregon Regional to Chicago
$460.88
*Available to One Key members.