Cheap flights from Albany, New York to Chicago from $99

The month of January is, on average, the cheapest month to fly to Chicago from Albany, New York, with most prices found around $301. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Albany, New York to Chicago during September average around $307.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $449. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Albany, New York to Chicago for around $587.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Albany, New York to Chicago during this time can be as low as $424. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $520.

Fly from Albany Intl to Chicago O'Hare Intl for the best Albany Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Albany, New York when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $358 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Albany, New York for as low as $256 on momondo.

There are 4 cabin classes available to choose from on Albany Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Albany, New York to Chicago.

As of February 2026, prices for Albany, New York to Chicago flights are approximately 5% cheaper when compared to flights at the same time last year.

Delta, Southwest, and United Airlines are the most popular carriers operating from Albany Intl to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Albany, New York according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of February 2026, 15 flights take off from Albany, New York and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 51% of daily flights taking off at noon.

As of February 2026, 108 flights take off from Albany, New York and land in Chicago each week. The most common flight departure day for this route is Thu, with 19% of weekly flights taking off on this day.