Book Alaska Airlines Flights to Chicago O'Hare International from C$421 Round-trip

The best Alaska Airlines flight deals to Chicago O'Hare International

Looking for a last-minute deal or the best direct flight? Find the biggest savings on one-way and round-trip flights to Chicago O'Hare International with Alaska Airlines right here.

Chicago.C$421 per passenger.Departing Sun, May 25, returning Wed, May 28.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Calgary on Sun, May 25, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Wed, May 28, arriving in Calgary.Price includes taxes and charges.From C$421, select.

Chicago.C$475 per passenger.Departing Fri, Jun 6, returning Tue, Jun 10.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Fri, Jun 6, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Tue, Jun 10, arriving in Vancouver International.Price includes taxes and charges.From C$475, select.

Chicago.C$497 per passenger.Departing Fri, May 30, returning Wed, Jun 4.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Fri, May 30, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Wed, Jun 4, arriving in Vancouver International.Price includes taxes and charges.From C$497, select.

Chicago.C$564 per passenger.Departing Tue, Jul 8, returning Tue, Jul 15.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Tue, Jul 8, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Tue, Jul 15, arriving in Vancouver International.Price includes taxes and charges.From C$564, select.

Chicago.C$571 per passenger.Departing Fri, Oct 24, returning Fri, Oct 31.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Calgary on Fri, Oct 24, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Fri, Oct 31, arriving in Calgary.Price includes taxes and charges.From C$571, select.

Chicago.C$594 per passenger.Departing Wed, Aug 6, returning Tue, Aug 19.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Wed, Aug 6, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Tue, Aug 19, arriving in Vancouver International.Price includes taxes and charges.From C$594, select.

Chicago.C$606 per passenger.Departing Fri, Jun 27, returning Tue, Jul 1.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Fri, Jun 27, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Tue, Jul 1, arriving in Vancouver International.Price includes taxes and charges.From C$606, select.

Chicago.C$608 per passenger.Departing Fri, Nov 14, returning Sun, Nov 16.Round-trip flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departing from Vancouver International on Fri, Nov 14, arriving in Chicago O'Hare International.Inbound indirect flight with Alaska Airlines, departing from Chicago O'Hare International on Sun, Nov 16, arriving in Vancouver International.Price includes taxes and charges.From C$608, select.

Find the cheapest time to fly to Chicago O'Hare International with Alaska Airlines

Flexible on travel dates? Here's when plane tickets are cheapest.

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Alternative routes to Chicago

Compare routes to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier.

Flying to Chicago O'Hare International with Alaska Airlines

The things to know before you go.

Cheapest flight found	C$421
Cheapest month to fly	September
Nearby cities to visit	Chicago

How to find cheap flights to Chicago O'Hare International with Alaska Airlines

Looking for cheap plane tickets to Chicago O'Hare International? Here are a few tips on how to find the best price.

Simply hit "search"

We've compared every online travel agent and flight provider to find the cheapest Alaska Airlines plane tickets to anywhere in the world, including Chicago O'Hare International.

Fly from Calgary

At the moment, the best route to Chicago O'Hare International with Alaska Airlines is from Calgary.

Flex your dates for the best rates

If you’re flexible on your departure dates, hit Whole month as you search. You'll see the cheapest month, and even day, to fly to Chicago O'Hare International with Alaska Airlines.

Set up a Price Alert

Got your eye on a specific flight to Chicago O'Hare International but not quite ready to book? No worries. We'll let you know when the price of the flight goes up or down so you can book when the time is just right. You're even able to watch specific Alaska Airlines flights.

Book your Alaska Airlines flight to Chicago O'Hare International Airport with extra peace of mind

Find flexible Alaska Airlines flights to Chicago O'Hare International Airport

Alaska Airlines might offer amendable tickets to Chicago O'Hare International Airport, which means you won't lose out if your booking has to be changed or canceled.

Add travel cost protection

Make sure you have the right travel insurance before flying to Chicago O'Hare International Airport. That way you can cover the costs of any unexpected events, such as delays or lost luggage.

Reduce your carbon footprint

To check whether there are any lower-emissions flights available on your route, simply check the “only show flights with lower CO₂ emissions” box when you search for a flight with us.

Flying to Chicago O'Hare International with Alaska Airlines: FAQs

How long is the flight to Chicago O'Hare International with Alaska Airlines?

The average Alaska Airlines flight time from Canada to Chicago O'Hare International is 2 hours and 22 minutes.

Does Alaska Airlines fly into any other airports in or near Chicago?

No – if you want to travel with Alaska Airlines, Chicago O'Hare International is currently the only airport serving Chicago.

Which other airlines can I fly to Chicago O'Hare International with?

At the moment, United, Air Canada, Qatar Airways, American Airlines and Republic Airways all fly to Chicago O'Hare International too.

What’s the cheapest month to fly to Chicago O'Hare International with Alaska Airlines?

Although it's difficult to get an accurate idea of when Alaska Airlines flights to Chicago O'Hare International are cheapest, the cheapest plane tickets are currently for departures in May.