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

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White Plains Westchester County to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from White Plains Westchester County
Flight Price $172
Distance 729 miles
Airlines Delta

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?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 3h 47m.
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 ($172)
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 Wednesday is the most expensive. Flying from Chicago Midway back to White Plains Westchester County, the best deals are generally found on Tuesday, with Thursday being the most expensive.

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

Airports
Origin
White Plains
$172
only
$172
Destination
Chicago
$172
only
$172
Tue, Oct 30
HPN
White Plains Westchester County
MDW
Chicago Midway
3h 47m
Tue, Nov 6
MDW
Chicago Midway
HPN
White Plains Westchester County
3h 40m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

Fri, Dec 7
HPN
White Plains Westchester County
MDW
Chicago Midway
3h 59m
Sun, Dec 9
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 01m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

Tue, Dec 11
HPN
White Plains Westchester County
MDW
Chicago Midway
3h 59m
Wed, Dec 12
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 01m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Fri, Jan 4
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 10m
Sun, Jan 6
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 01m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

Sat, Oct 27
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 58m
Tue, Oct 30
MDW
Chicago Midway
HPN
White Plains Westchester County
4h 56m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

Sat, Nov 3
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 58m
Tue, Nov 6
MDW
Chicago Midway
HPN
White Plains Westchester County
3h 40m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SJD
LAX
Excellent 8.3

Crews were nice

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

Wed, Nov 7
HPN
White Plains Westchester County
MDW
Chicago Midway
4h 04m
Sat, Nov 10
MDW
Chicago Midway
HPN
White Plains Westchester County
4h 13m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

Fri, Nov 9
HPN
White Plains Westchester County
MDW
Chicago Midway
6h 14m
Tue, Nov 13
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 29m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

SJD
LAX
Excellent 8.3

Crews were nice

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

Thu, Nov 15
HPN
White Plains Westchester County
MDW
Chicago Midway
4h 04m
Thu, Nov 22
MDW
Chicago Midway
HPN
White Plains Westchester County
3h 30m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SJD
LAX
Excellent 8.3

Crews were nice

Thu, Jan 17
HPN
White Plains Westchester County
MDW
Chicago Midway
5h 46m
Mon, Jan 21
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 35m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

Fri, Jan 18
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 28m
Mon, Jan 21
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 01m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Sat, Jan 19
HPN
White Plains Westchester County
MDW
Chicago Midway
5h 46m
Mon, Jan 21
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 35m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

Fri, Feb 1
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 28m
Sun, Feb 3
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 35m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

SJD
LAX
Excellent 8.3

Crews were nice

Wed, Oct 10
HPN
White Plains Westchester County
MDW
Chicago Midway
6h 31m
Thu, Oct 18
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 28m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

SJD
LAX
Excellent 8.3

Crews were nice

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

DTW
CLT
Excellent 8.0

Didn’t get our beverage and snack till we were almost ready to land at Charlotte

Sat, Oct 20
HPN
White Plains Westchester County
MDW
Chicago Midway
7h 58m
Wed, Oct 24
MDW
Chicago Midway
HPN
White Plains Westchester County
7h 29m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

Sat, Oct 27
HPN
White Plains Westchester County
MDW
Chicago Midway
5h 58m
Mon, Oct 29
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 28m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

MSP
EWR
Okay 4.3

Seats more comfortable, plan wasn’t too full

No charging port for cellphone.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

Sat, Oct 27
HPN
White Plains Westchester County
MDW
Chicago Midway
5h 58m
Mon, Oct 29
MDW
Chicago Midway
HPN
White Plains Westchester County
5h 28m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

SJD
LAX
Excellent 8.3

Crews were nice

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

Thu, Dec 20
HPN
White Plains Westchester County
MDW
Chicago Midway
3h 59m
Sat, Jan 12
MDW
Chicago Midway
HPN
White Plains Westchester County
4h 26m
Trip: 24 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
OGG
Okay 4.3

Why use old planes for such a long flight? Toilet overflowed, poor quality tv, and only peanuts?

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
MXP
Good 7.6

There were actual meals served on the flight. They were pretty good. Free movies available.

There was one cranky flight attendant. The seats don’t recline quite enough to be able to sleep.

Mon, Nov 19
HPN
White Plains Westchester County
MDW
Chicago Midway
4h 04m
Mon, Nov 26
MDW
Chicago Midway
HPN
White Plains Westchester County
3h 40m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
CLT
LGA
Mediocre 3.3

We were deplained twice from two different plains going to LGA. We are now booked on a third plain going to JFK. Hope we can get home. I have a surgical appointment tomorrow.

We bought First Class tickets. But we were downgraded How do you think we should feel ? We have been in Charlotte since 9:30 AM It is now 6:45 PM Should we use the train to go home?

SLC
AMS
Excellent 9.6

You guys did an all around great job and my flight experience was the best I’ve ever had. The quality of the service was exceptional.

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

SJD
LAX
Excellent 8.3

Crews were nice

AMS
DTW
Excellent 8.0

Didn’t like the fact that online check in didn’t work on the Delta app.di

Wed, Oct 10
HPN
White Plains Westchester County
MDW
Chicago Midway
5h 40m
Sun, Oct 14
MDW
Chicago Midway
HPN
White Plains Westchester County
4h 59m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,314 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SJD
LAX
Excellent 8.3

Crews were nice

DEN
JFK
Good 7.6

The flight attendants were all helpful and pleasant. The seats were comfortable. We were provided with plenty of liquids.

The landing was pretty tough and we took off almost a half hour late.

ATL
LAX
Good 6.3

Seatback tv.

Stewardess berated a man for leaving his backpack on the floor in front of him rather than politely addressing the issue. She told him you know better than that and don’t ever do that again. It was totally uncalled for.

SEA
MSP
Okay 4.6

Hostess were professional and warm

Seats was too tight, no leg room and no room for stretching

JFK
LAS
Excellent 8.0

The wait

The screen didn’t change in time

*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.

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