CA $282 Cheap Flights from Anchorage (ANC) to Chicago (ORD)

You can find one-way and return flights from ANC to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when ANC to ORD ticket fares go up or down.

If you're looking for the cheapest time to fly from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.), January is typically your best bet. You can expect average return flight prices around CA$496 during this month. January often sees lower prices because it falls after the busy holiday travel season, when demand for flights tends to decrease. Other budget-friendly months for this route include September and October.

There are 2 airlines offering direct flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.). These are:
* United operates 12 direct flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
* American Airlines operates 7 direct flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.

United is one of the cheapest airlines offering nonstop return flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.), with tickets starting from around CA$468 for flights that can be booked for departure within the next year. Southwest Airlines offers one of the cheapest connecting return flights on this route, with a layover in Denver Intl. (DEN), starting from around CA$533. These prices are for economy/coach class per adult. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Anchorage, AK (ANC) to Chicago, IL (ORD), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best airline to fly with from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. Alaska Airlines offers the most daily flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.), which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

You'll find around 3 nonstop flights per day from Ted Stevens Anchorage Intl. (ANC) to O'Hare Intl. (ORD). For even more choices, look at flights that include layovers, as there are approximately 19 connecting flights per day. Some common connection points include Seattle - Tacoma Intl. (SEA), Denver Intl. (DEN), and Minneapolis - St. Paul Intl. (MSP).

The earliest flight from Ted Stevens Anchorage Intl. (ANC) to O'Hare Intl. (ORD) typically departs around 12:05 AM local time. This service is operated by Alaska Airlines and United. This is a seasonal service, active only in December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Saturday, with around 40 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Alaska Airlines, Delta, and United. Looking at the overall week, Saturday offers notably more flight options compared to other days, making it a great day to consider for your journey.

The most popular departure times for flights from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the late evening, from 9pm to midnight. Many major carriers, including Alaska Airlines, Delta and United, offer flights during this window. Many travellers prefer this because it allows you to make the most of your day in Anchorage before your flight, and you'll arrive in Chicago ready to start your day.

A direct flight from Anchorage, AK (ANC-Ted Stevens Anchorage Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 6 hours 18 minutes, covering a distance of approximately 4,567 kilometers. If you opt for a flight with one stop, your journey will usually be longer, taking about 10 hours 30 minutes. Flights with two or more stops generally take around 14 hours 18 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.

You can fly business class or first class between ANC and ORD. You can fly business class with Delta.

First class cabins are available on Alaska Airlines, Delta, United, and American Airlines.

It's easy to earn miles on a Anchorage, AK (ANC) to Chicago, IL (ORD) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

If you're planning to travel to Chicago from Ted Stevens Anchorage Intl. (ANC), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Seattle - Tacoma Intl. (SEA), Portland Intl. (PDX), or Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Anchorage, AK (ANC) to Chicago, IL (ORD) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Anchorage, AK (ANC) to Chicago, IL (ORD) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Anchorage, AK (ANC) to Chicago, IL (ORD) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.