Find Cheap Flights from White Plains Westchester County to Chicago Midway (HPN - MDW)

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Looking for a cheap flight? 25% of our users found flights on this route for $216 or less.

FAQs for Booking White Plains Westchester County to Chicago Midway Flights

How long does a flight from White Plains Westchester County to Chicago Midway take?
An average nonstop flight takes 3h 42m, covering a distance of 729 miles.
Which airlines provide the cheapest flights from White Plains Westchester County to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($164)
Do I need a passport to fly between White Plains Westchester County and Chicago Midway?
No.
What’s the cheapest day of the week to fly White Plains Westchester County to Chicago Midway?
For White Plains Westchester County to Chicago Midway, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway back to White Plains Westchester County, the best deals are generally found on Saturday, with Thursday being the most expensive.

Book cheap flights from White Plains Westchester County to Chicago Midway (round-trip)

Airports
Origin
White Plains
$164
only
$164
Destination
Chicago
$164
only
$164
Tue, Jan 9
HPN
MDW
4h 29m
Thu, Jan 11
MDW
HPN
5h 45m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

Tue, Mar 20
HPN
MDW
3h 42m
Wed, Mar 28
MDW
HPN
5h 36m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

ATL
MEX
Excellent 8.6

Sandwich for dinner

Mon, Feb 26
HPN
MDW
7h 25m
Thu, Mar 1
MDW
HPN
6h 14m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

ATL
MEX
Excellent 8.6

Sandwich for dinner

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

Thu, Apr 12
HPN
MDW
3h 42m
Tue, Apr 17
MDW
HPN
5h 46m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

Mon, May 28
HPN
MDW
6h 01m
Fri, Jun 8
MDW
HPN
5h 06m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

Thu, Dec 21
HPN
MDW
4h 20m
Fri, Dec 29
MDW
HPN
3h 59m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

LGA
YUL
Excellent 8.0

it was easy to navigate .

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

YYZ
YQB
Okay 5.0

They had to change tires before we lelt in Toronto. And we spent more than one hour on the tarmac.

Mon, Dec 25
HPN
MDW
4h 16m
Thu, Dec 28
MDW
HPN
3h 59m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
YUL
Excellent 8.0

it was easy to navigate .

MCO
YYZ
Excellent 8.3

On time as scheduled.

N/A

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

*
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