Cheap Flights from Westchester County to Chicago Midway

Compare Westchester County to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Westchester County to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Westchester County Airport to Chicago Midway Airport? If you want to travel next month, return fares start from R 5,349. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Westchester County to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Westchester County to Chicago Midway flights are currently cheapest in September.

Westchester County to Chicago Midway: Alternative routes

Compare routes from Westchester County to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

White Plains to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 2,547
Cheapest month to flySeptember

Finding cheap flights from Westchester County to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Westchester County to Chicago Midway is R 5,349. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Westchester County to Chicago Midway. But we found flights with one or more stops from R 5,349.
As of June 2026, there are no flights flying from Westchester County to Chicago Midway.
The cheapest month to fly from Westchester County to Chicago Midway is usually July.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Westchester County Airport to Chicago Midway Airport on Tuesday, 7 July 2026.
No airlines currently offer direct flights between Westchester County Airport and Chicago Midway Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Delta offers the cheapest flight tickets to Chicago Midway.

Travelling from Westchester County Airport (HPN) to Chicago Midway Airport (MDW): what you need to know

  • Chicago is one hour behind White Plains and follows the UTC-6 timezone.

  • To ensure you get on your HPN to MDW flight, leave plenty of time to check in and find your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.

  • During popular months like July, it's best to get to the airport earlier than normal. Plan to arrive two hours before domestic departures and four hours ahead for an international flight when you travel during peak periods in general.

  • If you want to split up your journey, simply uncheck 'Direct flights only' when searching for your ticket from Westchester County Airport to Chicago Midway Airport. These are the most popular stopovers between HPN and MDW:

    • Charlotte Douglas Airport

    • Detroit Wayne County Airport

    • Washington Ronald Reagan Airport

How to find the cheapest flights from Westchester County Airport (HPN) to Chicago Midway Airport (MDW)

  • R 2,547 is currently the best price for a one-way Westchester County Airport to Chicago Midway Airport flight. Return flights start from R 5,349. These prices may change depending on demand and availability.

  • Don't leave things to the last minute. You're more likely to find cheap tickets from HPN to MDW if you book ahead. Airlines often offer some fantastic early bird deals.

  • Finding cheap flights from Westchester County Airport to Chicago Midway Airport is easy if you can be flexible with your trip dates. Use the 'Whole month' function to see the best prices throughout the month and snap up a great deal.

  • Save time looking for cheap flights from HPN to MDW by setting up a Price Alert. We'll send you an email or notification through the app when fares go down.

  • Find the right flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Westchester County Airport to Chicago Midway Airport, use the 'Sort by' tool. You can also filter results by airline, departure and arrival times, and journey duration.

Handy information about Westchester County Airport (HPN)

  • You'll find HPN at 240 Airport Road, Suite 202.

  • Of all flights departing from Westchester County Airport, 73% land on time at their destination.

  • Central White Plains to Westchester County Airport is approximately 6 kilometres. Depending on traffic, it'll take about 10 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • Expect a trip time of about 25 minutes on public transport.

  • Get your flight from Westchester County Airport to Chicago Midway Airport off to a stress-free start. Just a quick ride from HPN, stay at Sonesta White Plains Downtown and you'll be well-rested for the journey ahead.

Arriving at Chicago Midway Airport (MDW)

  • The last thing you need is a lengthy trip to your hotel if you're landing late on a Westchester County Airport to Chicago Midway Airport flight. Stay at one of these accommodation options near MDW instead:

  • Pick up a Chicago Midway Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are well-known companies to choose from here.

  • Reserving your vehicle from Chicago Midway Airport about four weeks in advance gives you the best shot at securing a great deal.

When to fly to Chicago Midway Airport (MDW)

  • July is the busiest month for flights from Westchester County Airport to Chicago Midway Airport. To skip the crowds, go to Chicago in December.

  • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your flights from Westchester County Airport to Chicago Midway Airport in this month if this is the type of weather you enjoy.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from HPN to MDW sometime then if you want to travel when it's cooler.

Explore more of the United States

  • You've seen Chicago, now it's time to discover other corners of the United States. Journey about 451 kilometres south-east to Columbus to tick off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you on the go.

  • Indianapolis is another well-known destination in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.