$188 Cheap Alaska Airlines flights Anchorage (ANC) to Chicago (ORD)

Scoring cheap one-way Alaska Airlines flights from ANC to ORD from $188 on Expedia is easy — just filter by “Price (lowest to highest).” Or check out our affordable return fares from $376 for your next getaway.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines flights to Chicago are often cheaper in the off-peak months of January and February. Whether you need a one-way or a return ticket, you could land a better deal then.

For cheap Alaska Airlines fares from Ted Stevens Anchorage Intl. Airport (ANC) to O’Hare Intl. Airport (ORD), start searching one to three months before your planned departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence the cost. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by choosing to book on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

Click on the “Nonstop” filter when browsing for direct Alaska Airlines flights from ANC to ORD. You can also compare other carriers offering the same nonstop journey.

Sort your results by “Morning” and “Early Morning” to browse the earliest departures from ANC to ORD. Jetting off early means you’re 20% less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Alaska Airlines flights from Ted Stevens Anchorage Intl. Airport (ANC) to Chicago come in to O’Hare Intl. Airport (ORD). This is the main entry point to this destination.

Alaska Airlines makes flying from ANC to ORD enjoyable with an excellent in-flight experience and top-tier customer service. You may even earn points with Mileage Plan. Make sure you sign up to Expedia’s free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future travel.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Typically, you can modify or cancel your flight, although there may be additional charges if you made your booking more than 24 hours ago. Need flexible options? Make use of our “No cancel fee” or “Changes included” filter to find flights that won’t penalize you if you have to adjust your plans. To update your itinerary, visit “Trips,” select your flight and click on “Manage Booking” for more information.