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

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Good to know

Low season:
January
Best time to beat the crowds
2%
expected price decrease
High season:
June
Most popular time to fly
11%
expected price increase
Average price:
£177
(avg. price over the last 2 weeks)
Good deal:
£142
or less (return)

When to Book Flights from New York to Chicago Midway

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for £141 or less.
The cheapest flight from New York to Chicago Midway was found, on average, 46 days before departure.
Book at least 5 weeks before departure in order to get a below-average price.
High season is considered to be May, June and July. The cheapest month to fly is January.
Morning departure is around 5% 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 New York to Chicago Midway Flights

How long does a flight from New York to Chicago Midway take?
An average non-stop flight takes 4h 09m, covering a distance of 718 miles.
How many flights are there between New York and Chicago Midway?
There are 213 (non-stop) flights between New York and Chicago Midway per week, averaging 30 per day.
Which airlines provide the cheapest flights from New York to Chicago Midway?
In the past 3 days, the cheapest return tickets were found on Delta (£108)
Do I need a passport to fly between New York and Chicago Midway?
No.
Which airlines fly most frequently between New York and Chicago Midway?
Southwest (30 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from New York to Chicago Midway?
For New York to Chicago Midway, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago Midway back to New York, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

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

Airports
Origin
New York
£108
only
£108
Destination
Chicago
£108
only
£108
Sat, 20 Jan
JFK
MDW
6h 44m
Mon, 22 Jan
MDW
JFK
5h 06m
£108
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Thu, 25 Jan
JFK
MDW
4h 24m
Mon, 29 Jan
MDW
JFK
4h 24m
£108
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

Tue, 6 Feb
JFK
MDW
6h 19m
Wed, 7 Feb
MDW
JFK
5h 50m
£108
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

Thu, 1 Mar
JFK
MDW
4h 09m
Tue, 6 Mar
MDW
JFK
3h 39m
£108
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Wed, 24 Jan
JFK
MDW
4h 24m
Sun, 28 Jan
MDW
JFK
5h 50m
£109
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

Tue, 6 Feb
JFK
MDW
6h 19m
Thu, 8 Feb
MDW
JFK
7h 24m
£109
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

Tue, 16 Jan
JFK
MDW
7h 08m
Wed, 24 Jan
MDW
JFK
8h 23m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Wed, 17 Jan
JFK
MDW
6h 45m
Thu, 25 Jan
MDW
JFK
7h 24m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

Thu, 18 Jan
JFK
MDW
6h 45m
Fri, 26 Jan
MDW
JFK
6h 42m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

Fri, 19 Jan
JFK
MDW
7h 08m
Sat, 27 Jan
MDW
JFK
5h 03m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

Sat, 20 Jan
JFK
MDW
6h 44m
Sun, 28 Jan
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

Sun, 21 Jan
JFK
MDW
4h 24m
Mon, 29 Jan
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Mon, 22 Jan
JFK
MDW
7h 08m
Tue, 30 Jan
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

Tue, 23 Jan
JFK
MDW
6h 45m
Wed, 31 Jan
MDW
JFK
8h 23m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

Wed, 24 Jan
JFK
MDW
7h 08m
Thu, 1 Feb
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

Thu, 25 Jan
JFK
MDW
6h 45m
Fri, 2 Feb
MDW
JFK
7h 13m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

Fri, 26 Jan
JFK
MDW
6h 45m
Sat, 3 Feb
MDW
JFK
4h 22m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

JFK
PHX
Good 6.6

The crew was late so we were delayed two hours. I find that extremely infuriating when you are a passenger and have to show up two hours before your flight. I also would lose my job if I was two hours late for a client.

Sat, 27 Jan
JFK
MDW
5h 08m
Sat, 3 Feb
MDW
JFK
4h 22m
£111
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

YYZ
ATL
Excellent 8.0

The boarding was very organised and the crew very friendly. The snacks that they offer is great too

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Sun, 28 Jan
JFK
MDW
4h 24m
Mon, 5 Feb
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

SEA
SNA
Excellent 8.6

The wifi wasn't strong enough to download the app to watch movies on the plane.

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Wed, 31 Jan
JFK
MDW
7h 08m
Thu, 8 Feb
MDW
JFK
5h 50m
£111
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
FLL
DTW
Excellent 10.0

New plane with knight entertainment screens at all seats!

Delayed, bit crew was friendly and efficient!

JFK
MIA
OK 5.3

Some of the flight attendants were rude and not very welcoming at all.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SEA
AUS
Excellent 9.0

Boarding was not smooth. They got me and my son mixed up as we have same name.

DTW
BNA
Mediocre 2.0

Sat on the plane on the tarmac for over an hour in the cold...

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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.