Cheap flights from White Plains to Chicago from $138

The month of January is, on average, the cheapest month to fly to Chicago from White Plains, with most prices found around $52. If you’re not able to fly to Chicago in January, then November is your next best option. Flight prices from White Plains to Chicago during November average around $69.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $318. 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 $390.

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 $301. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $371.

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 $503 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 $454 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.

No. A direct flight is the cheapest option for a flight between White Plains to Chicago.

As of June 2026, prices for White Plains to Chicago flights are approximately 35% more expensive when compared to flights at the same time last year.

Delta is the most popular carrier operating from White Plains Westchester County to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from White Plains 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 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of June 2026, 8 flights take off from White Plains and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 72% of daily flights taking off in the afternoon.

58 flights are operational weekly from White Plains to Chicago as of June 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.