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

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Good to know

Average price:
£233
(avg. price over the last 2 weeks)
Good deal:
£132
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, 56 days before departure.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 12% 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 231 (non-stop) flights between Chicago Midway and New York per week, averaging 34 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 Southwest (£63) and Delta (£110)
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 (33 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 Saturday is the most expensive. Flying from New York back to Chicago Midway, the best deals are generally found on Thursday, with Tuesday being the most expensive.

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

Airports
Origin
Chicago
£63
only
£63
Destination
New York
£63
only
£63
£110
only
£110
Wed, 10 Jan
MDW
LGA
2h 00m
Wed, 7 Mar
LGA
MDW
2h 30m
Trip: 57 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

MDW
LGA
Good 7.0

Boarding

No entertainment

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.

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.

Sat, 6 Jan
MDW
JFK
4h 22m
Sat, 27 Jan
JFK
MDW
5h 08m
£110
Trip: 22 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
MEX
OK 4.0

Arriving to the destination

ATL
BNA
Mediocre 2.0

They lost my bag.

ATL
MGM
OK 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

SJC
SEA
OK 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

Thu, 18 Jan
MDW
LGA
2h 05m
Mon, 22 Jan
LGA
MDW
2h 30m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
ELP
HOU
Excellent 10.0

Arrival

Too long

MDW
LGA
Good 6.0

Smooth flight.

Sitting on the runway too long.

MDW
BWI
Excellent 10.0

Boarding and exiting went fine. Other than a rude passenger, the flight attendants were very courteous, even to her.

MDW
LGA
Excellent 10.0

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

MDW
LGA
Excellent 10.0

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

Fri, 2 Feb
MDW
LGA
2h 00m
Wed, 7 Mar
LGA
MDW
2h 30m
Trip: 34 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
MDW
LGA
Excellent 10.0

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

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.

MDW
LGA
Good 6.0

Smooth flight.

Sitting on the runway too long.

MDW
BWI
Excellent 10.0

Boarding and exiting went fine. Other than a rude passenger, the flight attendants were very courteous, even to her.

ELP
HOU
Excellent 10.0

Arrival

Too long

Thu, 8 Feb
MDW
LGA
2h 05m
Mon, 12 Feb
LGA
MDW
2h 45m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
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.

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.

MDW
LGA
Excellent 10.0

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

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, 20 Feb
MDW
LGA
2h 00m
Thu, 1 Mar
LGA
MDW
2h 45m
Trip: 10 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
MDW
BWI
Excellent 10.0

Boarding and exiting went fine. Other than a rude passenger, the flight attendants were very courteous, even to her.

MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

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?

MDW
LGA
Excellent 10.0

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

Mon, 12 Feb
MDW
LGA
2h 00m
Wed, 21 Feb
LGA
MDW
2h 45m
Trip: 10 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
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.

MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

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.

BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

Tue, 9 Jan
MDW
JFK
5h 50m
Wed, 17 Jan
JFK
MDW
6h 45m
£110
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

LAX
MEX
Excellent 10.0

Comfortable seats

ATL
BNA
Mediocre 2.0

They lost my bag.

SJC
SEA
OK 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

Sat, 3 Feb
MDW
LGA
2h 00m
Tue, 6 Feb
LGA
MDW
2h 45m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
MDW
BWI
Excellent 10.0

Boarding and exiting went fine. Other than a rude passenger, the flight attendants were very courteous, even to her.

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
Good 7.0

Boarding

No entertainment

MDW
LGA
Good 6.0

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

BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

Wed, 10 Jan
MDW
JFK
7h 24m
Wed, 7 Mar
JFK
MDW
7h 58m
£110
Trip: 57 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
BNA
Mediocre 2.0

They lost my bag.

SEA
SFO
Excellent 10.0

Being on time.

BUF
DTW
OK 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

ATL
MGM
OK 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

LAX
MEX
Excellent 10.0

Comfortable seats

Fri, 5 Jan
MDW
LGA
2h 05m
Tue, 9 Jan
LGA
MDW
2h 30m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
MDW
LGA
Good 6.0

Smooth flight.

Sitting on the runway too long.

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?

MDW
LGA
Excellent 10.0

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

MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

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.

Thu, 11 Jan
MDW
JFK
5h 50m
Fri, 19 Jan
JFK
MDW
7h 08m
£110
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

ATL
BNA
Mediocre 2.0

They lost my bag.

SEA
SFO
Excellent 10.0

Being on time.

ATL
MGM
OK 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

Sat, 13 Jan
MDW
JFK
4h 22m
Sat, 20 Jan
JFK
MDW
6h 44m
£110
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

LAX
MEX
Excellent 10.0

Comfortable seats

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

SJC
SEA
OK 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

Sat, 13 Jan
MDW
LGA
2h 00m
Fri, 19 Jan
LGA
MDW
2h 30m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
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.

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
Good 6.0

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

MDW
LGA
Excellent 10.0

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

BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

Sat, 13 Jan
MDW
JFK
4h 22m
Sat, 20 Jan
JFK
MDW
6h 44m
£110
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

PHX
LAX
OK 5.6

Everything except food. I asked them for halal food when I bought tickets. But they didn't serve me halal food. Very very disappointed.

Food and food.

ATL
BNA
Mediocre 2.0

They lost my bag.

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

BOS
AUS
Excellent 10.0

i liked the aircraft and the fact that you could watch movies on your phone!

you couldn't hear the staff when they started boarding the plane

Sat, 3 Mar
MDW
LGA
2h 00m
Tue, 6 Mar
LGA
MDW
2h 30m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
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
Good 6.0

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

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?

MDW
LGA
Excellent 10.0

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

MDW
BWI
Excellent 10.0

Boarding and exiting went fine. Other than a rude passenger, the flight attendants were very courteous, even to her.

Wed, 17 Jan
MDW
JFK
5h 50m
Thu, 25 Jan
JFK
MDW
6h 45m
£110
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
MGM
OK 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

SJC
SEA
OK 5.3

Crew was friendly and helpful

Our flight was delayed by almost 2 hours and caused me to miss my connecting flight. Next available flight was a 6 hour layover that I was not expecting.

BUF
DTW
OK 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

Thu, 18 Jan
MDW
JFK
5h 50m
Fri, 26 Jan
JFK
MDW
6h 45m
£110
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
IND
ATL
Excellent 8.3

Ind-atl flight was absolutely amazing i couldn’t find really anything wrong with the flight besides spacing for seats

Spacing with seats

ATL
BNA
Mediocre 2.0

They lost my bag.

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

ATL
MGM
OK 5.0

Very uncomfortable and cold. Wasn’t space didn’t serve anything no WiFi or tv like other flight

Sat, 10 Feb
MDW
LGA
2h 00m
Sun, 11 Feb
LGA
MDW
2h 30m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 21 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

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?

BUR
PHX
Excellent 9.3

This flight was delayed for me by 30min, there was a lot of turbulence and didn't serve anything for the flight. Other than that, I was flying with Southwest to different cities all week and everything went well.

N/A

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.

Fri, 19 Jan
MDW
JFK
5h 50m
Sat, 27 Jan
JFK
MDW
6h 55m
£110
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14085 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.4
BUF
DTW
OK 4.0

No help with baggage when boarding the plane, they hurry you up for nothing, because we had to wait 20 mi utes to take off.

DTW
MEX
OK 4.0

Arriving to the destination

SYR
DTW
Excellent 8.0

Nice crew

Normal too squished conditions.

LAX
SYD
Excellent 10.0

adjustable head rest is great - being given a pillow is great - the plane was not too cold to sleep either (as they often are)

PHX
LAX
OK 5.6

Everything except food. I asked them for halal food when I bought tickets. But they didn't serve me halal food. Very very disappointed.

Food and food.

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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.