Cheap Flights from Walla Walla (ALW) to Chicago (MDW)

Bundle Your Flight + Hotel & Save!

Featured airlines

Top nine airline logos for desktop

    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

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

Prices were available within the past 7 days and start at for one-way flights and $1,063 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Alaska Airlines
Flights from Walla Walla (ALW) to Chicago (MDW)
Origin airport
Walla Walla Regional
Destination airport
Midway Intl.
Roundtrip price
$1,063
Distance
1538 mi

Walla Walla to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Walla Walla to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Walla Walla to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Frequently asked questions

How much is a one-way flight from Walla Walla Regional Airport to MDW?
Arrange your next trip with Expedia and you could walk away with one-way Walla Walla flights to Chicago from $711. This was the lowest price found for this particular journey with a departure date in the next three months — an Alaska Airlines flight, departing ALW on June 23 2024 and touching down at MDW. The price was last updated on May 21 2024 and has not changed since. Ready to snap up your own bargain flights? Terrific offers are at your fingertips.
Is it cheaper to buy a plane ticket from Walla Walla Regional Airport to MDW last minute?
Booking your trip from Walla Walla Regional Airport (ALW) to MDW at the last minute could save you cash if you get lucky and find a good deal. However, tickets usually don’t drop in price as the date of departure nears. If you wait, flights could also be booked out or the best seats taken. If you don’t want to risk it, book well ahead of your departure date. Keep in mind that some of the best deals can be found up to a year in advance. If your favorite airline hasn’t released its fares yet, check back regularly as offers are updated on Expedia all the time.
What is the cheapest airline flying from Walla Walla Regional Airport to Chicago Airport in the next 90 days?
The cheapest carrier traveling from Walla Walla to Chicago found on Expedia is Alaska Airlines, with fares starting at $711. This price is based on fares found on Expedia with a departure date within the next 90 days. The flight departs ALW on June 23 2024 and arrives at Midway Intl. Airport (MDW). Pricing information was updated on May 21 2024 and has not changed since.
What airports do you fly into for Chicago from Walla Walla?
With Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to choose from, making your way from Walla Walla to Chicago is no sweat. The city’s main gateway, Midway Intl. Airport (MDW), is approximately 9 mi southwest of the downtown area. Apart from ticket prices, consider things like bus or train options from the airport and the distance to your hotel when deciding where to touch down. Get your Chicago trip off to an exciting start by visiting Wrigley Field and Millennium Park.
Can I change the date of my flight from Walla Walla Regional Airport to MDW?
Easily make changes to your Walla Walla Regional Airport (ALW) to MDW ticket through the Expedia Trips portal. But before you make any adjustments, check the rules in your itinerary to find out what the carrier will allow you to do and what fees apply for changes. Some airlines have a change fee per person, in addition to any difference in airfares. But if you booked in the last 24 hours, you may be able to cancel for free and organize new flights. You can also browse our Customer Service portal for more useful advice and to chat with our Virtual Agent.
Chicago nearby Airports
Walla Walla nearby Airports
*Available to One Key members.