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Cheap flights from Westchester County to Chicago Midway (HPN - MDW)

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

What is the cheapest day to fly round-trip from Westchester County to Chicago Midway?

Leaving on a Thursday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 3% on the overall cost on flights from Westchester County to Chicago Midway.

How far in advance should I book a flight from Westchester County to Chicago Midway?

To save up to 10% on this flight, we recommend booking at least 37 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Westchester County to Chicago Midway from $177 1-2 weeks out and tickets from $177 for flights departing within the next 72 hours.

When is the cheapest time to fly from Westchester County to Chicago Midway (HPN - MDW)?

Unlike in the morning, when flights are generally more expensive, you can save up to 30% on flights from Westchester County to Chicago Midway by exploring options for tickets in the noon.

Cheap flights from Westchester County to Chicago Midway in August, September 2020

The best prices found for HPN to MDW flights for August, September
26 Jul - 28 Jul
$11441pp
HPN
White Plains Westchester County
Linear Air Taxi
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Linear Air Taxi
   
2 STOPS
HPN
White Plains Westchester County
24 Jul - 26 Jul
$12356pp
HPN
White Plains Westchester County
Linear Air Taxi
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Linear Air Taxi
   
2 STOPS
HPN
White Plains Westchester County
26 Aug - 2 Sep
$12435pp
HPN
White Plains Westchester County
Linear Air Taxi
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Linear Air Taxi
   
2 STOPS
HPN
White Plains Westchester County

Westchester County to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Westchester County found for this year
25 Sep - 26 Sep
$176pp
HPN
White Plains Westchester County
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
HPN
White Plains Westchester County
25 Sep - 27 Sep
$186pp
HPN
White Plains Westchester County
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
HPN
White Plains Westchester County
22 Oct - 26 Oct
$249pp
HPN
White Plains Westchester County
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
HPN
White Plains Westchester County

Last minute flights from Westchester County to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Westchester County, departing today and this week
26 Jul - 28 Jul
$11441pp
HPN
White Plains Westchester County
Linear Air Taxi
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Linear Air Taxi
   
2 STOPS
HPN
White Plains Westchester County
24 Jul - 26 Jul
$12356pp
HPN
White Plains Westchester County
Linear Air Taxi
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Linear Air Taxi
   
2 STOPS
HPN
White Plains Westchester County

One-way flights to Chicago Midway from Westchester County

The cheapest one-way flights from Westchester County to Chicago Midway
7:30 am - 2:47 pm
Linear Air Taxi
2 Stops
8h 17m
HPN - MDW
Linear Air Taxi
$5772
KAYAK
7:02 am - 2:47 pm
Linear Air Taxi
2 Stops
8h 45m
HPN - MDW
Linear Air Taxi
7:02 am - 2:47 pm
Linear Air Taxi
2 Stops
8h 45m
HPN - MDW
Linear Air Taxi
$7182
Travelgenio

Related info for your journey

Useful info, stats and facts about Westchester County to Chicago Midway flights.

Flight FAQs

From Westchester County to Chicago Midway

Are flight prices decreasing from Bridgeport to Chicago Midway due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Bridgeport and Chicago Midway for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Westchester County to Chicago Midway for under $200 on Cheapflights?

Yes, there are multiple flights from Westchester County to Chicago Midway for under $200. The cheapest flight booked recently is on Delta for just $176, but on average you can expect to pay $7142.

Are there nonstop flights from Westchester County to Chicago Midway for under $200 on Cheapflights?

There are no nonstop flights from Westchester County to Chicago Midway, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Westchester County to Chicago Midway for under $11500?

There are currently 2+ open flights from Westchester County to Chicago Midway within the next 7 days for less than $11500.

What days are nonstop flights available from Bridgeport to Chicago Midway?

Days when nonstop flights are available for this flight are: Friday, Saturday.

Does it rain more in Bridgeport or Chicago Midway?

When traveling, it's generally smart to pack in preparation for rain or any other conditions that may arise. The rainfall in Bridgeport is roughly greater than that of Chicago Midway. You can assume this to be the case over the next 14 days.

Is Bridgeport weather warmer or cooler than Chicago Midway?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago Midway are the same as in Bridgeport.

How long is the flight from Westchester County to Chicago Midway?

Airlines like Delta, Sun Country Air, and Linear Air Taxi fly from Westchester County to Chicago Midway in about 3h 58m. The time it takes to get you to your destination can typically vary by up to 3h 54m. This flight may include one or multiple stops.

What are the cheapest airlines flying from Westchester County to Chicago Midway round-trip?

Our cheapest airline available from Westchester County to Chicago Midway is Delta. Our recent data shows that you can find tickets from as low as $176 on this airline. Additional options worth looking into are Sun Country Air and Linear Air Taxi, starting at $332 and $8354 round-trip. You may be able to fly from Westchester County to Chicago Midway for 50% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Westchester County to Chicago Midway one-way?

The cheapest airline for a one-way flight from Westchester County to Chicago Midway is Linear Air Taxi ($5772).

Alternative routes for Westchester County to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Westchester County to Chicago Midway
Average temperature for August in Chicago Midway
82.4 °F
Avg rainfall for August in Chicago Midway
3.9 ″

Airports servicing White Plains

Airports servicing Chicago

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