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

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Good to Know

Average Price:
$258
(avg. price over the last 2 weeks)
Good Deal:
$188
or less (round trip)

When to Book Flights from Chicago Midway to New York

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

FAQs for Booking Chicago Midway to New York Flights

How long does a flight from Chicago Midway to New York take?
An average nonstop flight takes 2h 05m, covering a distance of 718 miles.
How many flights are there between Chicago Midway and New York?
There are 199 (nonstop) 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 round-trip tickets were found on Delta ($148) and Southwest ($219)
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 (28 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to New York?
For Chicago Midway to New York, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from New York back to Chicago Midway, the best deals are generally found on Tuesday, with Thursday being the most expensive.

Book cheap flights from Chicago Midway to New York (round-trip)

Airports
Origin
Chicago
$148
only
$148
Destination
New York
$219
only
$219
$148
only
$148
Newark
$174
only
$174
Tue, Apr 17
MDW
JFK
7h 28m
Tue, Apr 24
JFK
MDW
7h 14m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Mon, Apr 9
MDW
LGA
2h 05m
Tue, Apr 10
LGA
MDW
2h 30m
Trip: 2 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 10.0

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

MDW
LGA
Okay 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.

BWI
CMH
Excellent 10.0

it was a bit windy during landing, but the pilot navigated the winds wonderfully.

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.

Tue, Mar 20
MDW
JFK
5h 55m
Tue, Mar 27
JFK
MDW
7h 42m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 9.6

Z

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Tue, Mar 27
MDW
EWR
4h 40m
Wed, Mar 28
EWR
MDW
3h 51m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

FLL
DTW
Excellent 10.0

I like service

Tue, Apr 3
MDW
EWR
5h 59m
Wed, Apr 4
EWR
MDW
5h 54m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

FLL
DTW
Excellent 10.0

I like service

Wed, Apr 11
MDW
LGA
2h 05m
Mon, Apr 16
LGA
MDW
2h 25m
Trip: 6 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
Okay 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
Good 6.0

Smooth flight.

Sitting on the runway too long.

MDW
LGA
Good 7.6

They handled the huge delay with good cheer.

Super late.

MDW
LGA
Okay 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 9.6

No coat closet

Wed, Apr 4
MDW
EWR
4h 21m
Wed, Apr 11
EWR
MDW
5h 54m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

Tue, May 1
MDW
EWR
5h 24m
Sat, May 5
EWR
MDW
3h 42m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

GDL
ATL
Excellent 9.6

Expensive food

Wed, May 2
MDW
EWR
5h 24m
Sat, May 5
EWR
MDW
3h 42m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

Tue, May 15
MDW
EWR
3h 44m
Wed, May 23
EWR
MDW
4h 19m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

FLL
DTW
Excellent 10.0

I like service

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

Sat, Jun 2
MDW
EWR
5h 25m
Tue, Jun 5
EWR
MDW
5h 47m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

Tue, May 1
MDW
JFK
6h 21m
Tue, May 8
JFK
MDW
6h 53m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

Sat, Jul 14
MDW
JFK
5h 59m
Sat, Jul 21
JFK
MDW
4h 19m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Sat, Aug 11
MDW
JFK
5h 59m
Sat, Aug 18
JFK
MDW
6h 45m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 9.6

Z

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Wed, Apr 4
MDW
JFK
3h 38m
Wed, Apr 11
JFK
MDW
5h 39m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

Wed, May 2
MDW
JFK
4h 07m
Sat, May 5
JFK
MDW
4h 02m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Mon, Jul 2
MDW
EWR
7h 44m
Wed, Jul 4
EWR
MDW
6h 17m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

Thu, Jul 26
MDW
EWR
5h 22m
Tue, Jul 31
EWR
MDW
6h 20m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

GDL
ATL
Excellent 9.6

Expensive food

Sat, Aug 4
MDW
EWR
6h 47m
Tue, Aug 14
EWR
MDW
6h 20m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

Media kept freezing. They had to reboot the system several times.

BDL
CVG
Okay 4.0

Great pilot..

Jam packed too small and the lady flight attendant was to bossy and not that welcoming, she was more interested in being more of a drill sergeant than the comfort of the passengers

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

FLL
DTW
Excellent 10.0

I like service

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

Tue, Aug 14
MDW
EWR
4h 28m
Tue, Aug 21
EWR
MDW
3h 41m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16147 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

FLL
DTW
Excellent 10.0

I like service

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

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Chicago Midway to New York Flight Information

Avg. Flight Duration 2h 16m
Flights Arrive in New York
Flights Depart from Chicago Midway
Flight Price $148
Distance 718 miles
Airlines Delta, Southwest
*
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