Cheap flights from White Plains to Chicago from $141

The month of August is, on average, the cheapest month to fly to Chicago from White Plains, with most prices found around $463. If you’re not able to fly to Chicago in August, then February is your next best option. Flight prices from White Plains to Chicago during February average around $471.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $348. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from White Plains to Chicago for around $427.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from White Plains to Chicago during this time can be as low as $353. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $389.

Fly from White Plains Westchester County to Chicago O'Hare Intl for the best White Plains Westchester County - Chicago flight prices

You are more likely to see cheaper flights to Chicago from White Plains when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $512 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from White Plains for as low as $474 on momondo.

There are 3 cabin classes available to choose from on White Plains to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 19% on your flight if you consider stops on a White Plains to Chicago flight.

As of November 2026, prices for White Plains to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

As of November 2026, 8 flights take off from White Plains and land in Chicago each day. The most common flight departure time for this route is 12:00PM, with 66% of daily flights taking off in the afternoon.

61 flights are operational weekly from White Plains to Chicago as of November 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.