Find Cheap Flights from Chicago Midway to New York (MDW - NYC)

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Good to know

Average price: £163
Good deal: £126
(avg. price over the last 2 weeks)
or less (return)

When to Book Flights from Chicago Midway to New York

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

The cheapest flight from Chicago Midway to New York was found, on average, 57 days before departure.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 30% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago Midway to New York Flights

How long does a flight from Chicago Midway to New York take?
An average non-stop flight takes 2h 00m, covering a distance of 718 miles.
How many flights are there between Chicago Midway and New York?
There are 192 (non-stop) flights between Chicago Midway and New York per week, averaging 30 per day.
Which airlines provide the cheapest flights from Chicago Midway to New York?
In the past 3 days, the cheapest return tickets were found on Delta (£106) and Southwest (£119)
Do I need a passport to fly between Chicago Midway and New York?
No.
Which airlines fly most frequently between Chicago Midway and New York?
Southwest (27 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Chicago Midway to New York?
For Chicago Midway to New York, Wednesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from New York back to Chicago Midway, the best deals are generally found on Monday, with Friday being the most expensive.

Book cheap flights from Chicago Midway to New York (return)

Airports
Origin
Chicago
£106
only
£106
Destination
New York
£119
only
£119
£106
only
£106
Newark
£125
only
£125
Wed, 25 Apr
MDW
JFK
6h 02m
Tue, 1 May
JFK
MDW
6h 53m
£106
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOI
SLC
Good 7.6

The crew

The delay

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

Sat, 3 Mar
MDW
LGA
2h 00m
Tue, 6 Mar
LGA
MDW
2h 30m
£119
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 24 reviews
Boarding
8.8
Comfort
8.5
Crew
9.1
Entertainment
8.0
Food
7.9
MDW
LGA
Good 6.0

Wifi was on but signal was too weak....no wifi

MDW
LGA
Good 6.0

Smooth flight.

Sitting on the runway too long.

MDW
LGA
OK 4.6

Southwest still offers free bags and the available wifi is convenient. The crew onboard was pleasant and professional.

LGA is just the worst! We were delayed and it's impossible to get in and out of the airport. Cabins are dated and feel spartan. Not having assigned seats is archaic and stressful. People don't actually follow the rules, and it makes the flight feel more like flying on a bus. The staff at midway was strangely rude and dismissive when asked about upgrading my boarding position.

MDW
LGA
Excellent 10.0

The Crew on Flight 4012 was the absolute best!!!

MDW
LGA
Excellent 9.6

No coat closet

Tue, 1 May
MDW
JFK
6h 21m
Sat, 5 May
JFK
MDW
4h 02m
£106
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

Mon, 5 Mar
MDW
JFK
5h 55m
Mon, 12 Mar
JFK
MDW
7h 02m
£116
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

Mon, 26 Feb
MDW
LGA
2h 00m
Wed, 28 Feb
LGA
MDW
2h 30m
£137
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 24 reviews
Boarding
8.8
Comfort
8.5
Crew
9.1
Entertainment
8.0
Food
7.9
PHX
SMF
Good 6.6

Flight was on time. Boarding was excellent I am handicapsnd was accommodated very well. Phx was not as good as Sacrsmento the

MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

MDW
LGA
Excellent 8.0

Flight departed on time and arrived early. Also, was only about half full.

Didn't like the flight was scheduled for 5:55am - that's way too early for me.

SAN
MCI
Good 7.0

Typically efficient operation. The airport staff and flight crew were the usual friendly and accommodating folks I have come to expect. The snacks have gotten worse over the years, but it’s the same across most domestic airlines. I feel fortunate that Southwest still allows you to check luggage w/o additional charge.

I vacillate about open seating.

MDW
LGA
Excellent 10.0

They are always on time, always efficient, always friendly.

Tue, 20 Mar
MDW
EWR
7h 20m
Wed, 21 Mar
EWR
MDW
4h 15m
£125
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
CUN
LAX
OK 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

CLE
ATL
OK 4.6

Short trip

Very hot ride

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

Tue, 3 Apr
MDW
EWR
5h 49m
Tue, 10 Apr
EWR
MDW
3h 46m
£125
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOI
SLC
Good 7.6

The crew

The delay

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

Wed, 28 Feb
MDW
LGA
2h 00m
Sat, 3 Mar
LGA
MDW
2h 30m
£151
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 24 reviews
Boarding
8.8
Comfort
8.5
Crew
9.1
Entertainment
8.0
Food
7.9
MDW
LGA
Good 6.0

Wifi was on but signal was too weak....no wifi

MDW
LGA
Excellent 10.0

They are always on time, always efficient, always friendly.

SAN
MCI
Good 7.0

Typically efficient operation. The airport staff and flight crew were the usual friendly and accommodating folks I have come to expect. The snacks have gotten worse over the years, but it’s the same across most domestic airlines. I feel fortunate that Southwest still allows you to check luggage w/o additional charge.

I vacillate about open seating.

MDW
LGA
Excellent 8.0

Flight departed on time and arrived early. Also, was only about half full.

Didn't like the flight was scheduled for 5:55am - that's way too early for me.

PHX
SMF
Good 6.6

Flight was on time. Boarding was excellent I am handicapsnd was accommodated very well. Phx was not as good as Sacrsmento the

Wed, 4 Apr
MDW
EWR
5h 02m
Tue, 10 Apr
EWR
MDW
6h 57m
£125
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
CUN
LAX
OK 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

CLE
ATL
OK 4.6

Short trip

Very hot ride

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

Thu, 1 Mar
MDW
LGA
2h 00m
Sat, 3 Mar
LGA
MDW
2h 40m
£151
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 24 reviews
Boarding
8.8
Comfort
8.5
Crew
9.1
Entertainment
8.0
Food
7.9
MDW
LGA
Excellent 8.0

Flight departed on time and arrived early. Also, was only about half full.

Didn't like the flight was scheduled for 5:55am - that's way too early for me.

PHX
SMF
Good 6.6

Flight was on time. Boarding was excellent I am handicapsnd was accommodated very well. Phx was not as good as Sacrsmento the

MDW
LGA
Good 6.0

Smooth flight.

Sitting on the runway too long.

MDW
LGA
OK 4.6

Southwest still offers free bags and the available wifi is convenient. The crew onboard was pleasant and professional.

LGA is just the worst! We were delayed and it's impossible to get in and out of the airport. Cabins are dated and feel spartan. Not having assigned seats is archaic and stressful. People don't actually follow the rules, and it makes the flight feel more like flying on a bus. The staff at midway was strangely rude and dismissive when asked about upgrading my boarding position.

MDW
LGA
OK 5.0

I got where I was going. But the concourse was freezing, the plane was cold and breezy, something I had previously not encountered. I needed as did others to wear my coat . Luggage retrieval was slow despite a plane not full. Some people did not get their luggage at all. Mine came out last and they turned the conveyor belt off just as it came in barely clearing the curtain. So I at first did not see it ??? Slow January day?

Tue, 1 May
MDW
EWR
5h 24m
Sat, 5 May
EWR
MDW
3h 42m
£125
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

Sat, 5 May
MDW
EWR
5h 52m
Tue, 8 May
EWR
MDW
3h 42m
£125
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

CLE
ATL
OK 4.6

Short trip

Very hot ride

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

Sat, 2 Jun
MDW
EWR
5h 25m
Wed, 6 Jun
EWR
MDW
3h 42m
£125
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

CLE
ATL
OK 4.6

Short trip

Very hot ride

MSP
ATL
Excellent 9.6

Entertainment is so appreciated on long flights. It was quiet. Snacks done quickly. Took a long time to board, but the flight was full. We were delayed out of gate because of this. Unloading plane went fairly quick but could have been a problem for short connections. Those people should have been allowed to leave first.

Tue, 14 Aug
MDW
JFK
7h 41m
Sat, 18 Aug
JFK
MDW
4h 30m
£125
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

Tue, 15 May
MDW
JFK
4h 25m
Sat, 19 May
JFK
MDW
4h 02m
£126
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOI
SLC
Good 7.6

The crew

The delay

IAD
CUN
Mediocre 2.0

That I landed safely

1st class was horrible.

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

Thu, 1 Mar
MDW
EWR
2h 00m
Sat, 3 Mar
EWR
MDW
2h 30m
£241
Trip: 3 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 11 reviews
Boarding
8.8
Comfort
8.5
Crew
9.1
Entertainment
8.0
Food
7.9
SMF
LAX
Good 7.3

Nothing. It was the std SWA flight. On time with nice flight crew

BWI
ATL
Good 6.3

Flight attendants could care less about my loss of belongings from overhead bin when a fellow passenger stole them. Gate agent shrugged shoulders and sent me to baggage claim. Baggage claim said there was nothing they could do. Meanwhile I don’t have a jacket/glasses/gloves for a business trip which leaves no time to repurchase.

MDW
EWR
Excellent 8.3

Always on time and clean. Pleasant and courteous staff no matter how rude some customers are. A pleasure to fly

MDW
EWR
OK 4.6

Old planes with shared tvs

MDW
EWR
Mediocre 2.0

The flight was affordable. That is the only thing this had going for it.

The flight was delayed due to air traffic at Newark. I was left in an oversized wheel chair and wasn't able to eat or use the rest room. The passengers on the plane were loud and rude. Upon our arrival (over 90 minutes late), I was whisked off the jet way in a wheelchair, with my carry ons and knee scooter thrown on my lap. The sky cap managed to hit every pole between the jet way and baggage claim.

Mon, 2 Jul
MDW
EWR
7h 44m
Wed, 4 Jul
EWR
MDW
6h 17m
£135
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

CUN
LAX
OK 5.0

I loved that I was able to get home! The crew was nice.

It was very very warm in the plane. The entertainment unit was lacking.

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

BOI
SLC
Good 7.6

The crew

The delay

Sat, 21 Jul
MDW
JFK
5h 59m
Wed, 25 Jul
JFK
MDW
4h 01m
£137
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

DTW
BDL
Excellent 10.0

Flight was on time.

Did not appreciate Aeromexico/Delta changing my flight times after I booked, giving me a more than 7 hour layover.

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

Mon, 20 Aug
MDW
JFK
4h 26m
Sat, 25 Aug
JFK
MDW
6h 45m
£137
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

ATL
LAX
Good 7.6

The plane was dirty. The grounds staff was complaining as we got on about having to work late.

ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

BOI
SLC
Good 7.6

The crew

The delay

Sat, 4 Aug
MDW
JFK
5h 59m
Sat, 11 Aug
JFK
MDW
6h 45m
£145
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16210 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
VPS
Good 7.3

Boarding was quick and so was the flight. No entertainment or food on short flights, that should be a N/A

BDL
CUN
Excellent 9.6

The plane was new and very comfortable. Free entertainment and plug for charging electronics. Love this airline!

JFK
RSW
Excellent 9.3

on time, good service,

i agreed to check in my bag at the gate when they asked for volunteers thinking I would get it at the gate of my destination but after i checked it in in gate attendant informed me that i would get my bag at the baggage claim

DTW
LAX
Good 7.0

I received a message flight would be early but it was actually late...luckily it did not affect my connection

RAP
MSP
Excellent 8.6

Very quick boarding process. There was no entertainment so I couldn't rate that.

There should be a N/A option if there is no entertainment available.

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