Flights from Westchester to Chicago

Flights tailored to your budget

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Cheap Westchester - Chicago flight offers

Find cheap flight tickets and last-minute flight deals from Westchester to Chicago

American Airlines
Fri, 10/09 (HPN) Westchester County -> (CHI) Chicago
Direct
American Airlines
Sat, 10/10 (CHI) Chicago -> (HPN) Westchester County
Direct
Price found 7 days ago
from $136
American Airlines
Fri, 10/09 (HPN) Westchester County -> (CHI) Chicago
Direct
American Airlines
Sat, 10/10 (CHI) Chicago -> (HPN) Westchester County
Direct
Price found 7 days ago
from $136

Info about flights from Westchester to Chicago

Some useful info about flights from Westchester to Chicago to help you plan your next trip

Best price last 15 days $136
Average flight duration 2h 55m
Cheapest month October
Average number of flights per week 2
First flight time 05:56
Last flight time 19:59
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Top airlines on the route Westchester - Chicago

Airlines providing flights to Chicago from Westchester

American Airlines
American Airlines
DELTA
DELTA

How much is a flight from Westchester to Chicago?

There’s no fixed price — fares between Westchester County and Chicago can vary a lot by day or time.

$136 is the lowest fare found in the past 15 days.

Flying during the week can be more affordable, as weekend flights tend to be pricier. Also consider demand and availability: the last remaining seats often come at higher fares!

Flying between Westchester County and Chicago? Consider these airports

Depending on your destination and where you’re starting from, it might make sense to look beyond the main hubs.

  • Airports in Westchester County: Westchester County has only one airport in service, Westchester County.
  • Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.

Check if your destination airport has a rail link — it can make getting around easier. Jetcost lets you view options from all Westchester County airports in a single search.

Flights from Westchester County to Chicago

Adjust your flight filters for Westchester – Chicago

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to United States? These cities are popular too: Atlanta, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.
Frequently Asked Questions

Frequently asked questions about flights from Westchester to Chicago.

How much does an airline ticket from Westchester to Chicago cost?

The lowest price recorded in the last 15 days for a flight from Westchester to Chicago is $136.

How far is Westchester County from Chicago?

Westchester County is about 725 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Westchester County?

Westchester County has one airport: Westchester County.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Westchester County to Chicago?

The best time to book a flight from Westchester County to Chicago is 1 month in advance, while the worst time is 2 weeks in advance.

What is the cheapest month to fly from Westchester County to Chicago?

The cheapest month to fly from Westchester County to Chicago is October.

What is the most expensive month to fly from Westchester County to Chicago?

The most expensive month to fly from Westchester County to Chicago is May.

What is the best day of the week to fly from Westchester County to Chicago?

For flights from Westchester County to Chicago Sunday is on average the cheapest day to fly, while Sunday is the most expensive day to fly.