MDW

Find Cheap Flights from New York to Chicago Midway

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Wichita (ICT)
Chicago Midway
Fri 7/19
Fri 7/26
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New York to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from New York
Flight Price $174
Airlines Delta, Southwest, Major Airline

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

Airports
Origin
New York
$177
only
$177
Syracuse
$174
only
$174
Newark
$222
only
$222
Destination
Chicago
$174
only
$174
Thu, Sep 26
SYR
Syracuse Hancock Intl
MDW
Chicago Midway
3h 31m
Tue, Oct 1
MDW
Chicago Midway
SYR
Syracuse Hancock Intl
4h 00m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,312 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SLC
SNA
Excellent 10.0

Pros: Yes, . Amazing crew Seat was comfortable.

HNL
ATL
Good 7.6

Pros: I was surprised that we received two meals and constant drinks in economy. Delta definitely has better hospitality than American.

Cons: The seats were really tight between the rows. The space between the seats on the same row were typical.

FLL
JFK
Excellent 8.0

Pros: Crew was good seat comfortable

Cons: Better snacks

NRT
ATL
Excellent 10.0

Cons: Bring back the Narita to Minneapolis.

ATL
ILM
Excellent 10.0

Pros: Amazing Crew and had a real airplane to ilm for a change!

Tue, Oct 29
LGA
New York LaGuardia
MDW
Chicago Midway
2h 35m
Tue, Nov 5
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
AUS
SJC
Good 6.0

Cons: Communication. Austin airport guaranteed that connectors would be made in San Jose even with a delayed departure as planes were being held, but the connection was indeed missed and in fact the connection left San Jose early.

IND
DEN
Excellent 10.0

Pros: The smooth plane ride. We’ve used other airlines, but Southwest is our favorite by far. I’ve never had a bad experience with them in 15 years.

Cons: Nothing.

DEN
LAX
Good 7.5

Pros: Flight was on time

Cons: One of the flight attendants was super rude

BOS
MDW
Mediocre 3.3

Pros: Crew was good

Cons: Been on time. Not been hot.

MSY
BWI
Excellent 8.0

Cons: I wasn’t able to use the WiFi in my flight. It worked last time but was not even available on this flight it seemed.

Wed, Aug 14
LGA
New York LaGuardia
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
LGA
New York LaGuardia
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Sep 26
SYR
Syracuse Hancock Intl
MDW
Chicago Midway
3h 31m
Tue, Oct 1
MDW
Chicago Midway
SYR
Syracuse Hancock Intl
4h 00m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,312 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DEN
LAX
Excellent 10.0

Pros: The service, on time, employees very nice.

ILM
ATL
Excellent 10.0

Pros: Amazing crew as always

Cons: Wifi on smaller hoppers

SEA
JFK
Excellent 8.0

Pros: The crew was great, very accommodating food selection was nice.

Cons: The cabin temperature was extremely warm

YYZ
SLC
Okay 4.4

Cons: Plane had to divert from Salt-Lake City due to a storm. My son 17 years old traveling alone once in Salt-Lake City should have been given priority for an overnight stay instead of sleeping on an airport bench! Dinner + Breakfast vouchers would also have been nice compared to the 15$ food voucher...

PIT
ATL
Excellent 9.0

Pros: Amazing crew

Tue, Oct 29
LGA
New York LaGuardia
MDW
Chicago Midway
2h 35m
Tue, Nov 5
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
PVD
MCO
Excellent 9.6

Pros: Reasonable legroom, although barely adequate for this 6-footer

Cons: Baggage handling in Oakland was very slow.

SJC
ONT
Excellent 10.0

Cons: Perfect flight, plus flight attendant gave me a free glass of wine! J was friendly and cracked up when young passenger said he deserved a free beer. Probably had a SW free beverage ticket! On time! No wait gate in Ontario! Great landing!

DAL
DTW
Good 6.6

Pros: Great crew. Nice gate signage

Cons: We were delayed.

GRR
MDW
Excellent 9.6

Cons: Had to wait for a gate for about 10 minutes after landing

SJU
MCO
Excellent 9.5

Pros: First time traveling. The boarding process was confusing at first but I quickly realized it was a great way to get the passengers to actually help rather than the staff

Cons: If you are a first time traveler a way to identify as such in the page and a explainer video of what to expect would be great as an option. I like to know wht to expect and be prepared

Tue, Oct 29
LGA
New York LaGuardia
MDW
Chicago Midway
2h 35m
Tue, Nov 5
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
SAN
SJC
Okay 4.4

Cons: Flight could have left on time. And the terminal I landed at at was a 30 minute walk from baggage claim.

DEN
LAX
Excellent 8.0

Pros: Drinks

Cons: Delayed flight

LGA
MDW
Good 6.0

Pros: I love that my bags fly for free.

Cons: I don't like flying SWA when the flights are full because the seats seem tight. I have a SW credit card though so I love using points for flights.

LGA
MDW
Good 7.0

Cons: The Internet was the worst inflight wifi experience I have ever had. It only loaded like 6 webpages for me in 1.5 hours.

SAT
MDW
Excellent 9.6

Pros: Crew did an excellent job serving us.

Cons: had a delay on the return flight, minor setback but overall good.

Tue, Oct 29
LGA
New York LaGuardia
MDW
Chicago Midway
2h 35m
Tue, Nov 5
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 8 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
BOS
BWI
Good 6.5

Cons: The seats are small but I'm also a big dude so that might be a factor

SNA
HOU
Excellent 10.0

Pros: No problems with any leg of the trip. Stewards and stewardesses were great

Cons: Non-stop flight from SNA to BOS

LGA
MDW
Good 7.0

Cons: The Internet was the worst inflight wifi experience I have ever had. It only loaded like 6 webpages for me in 1.5 hours.

BDL
MDW
Excellent 10.0

Cons: Free!

MKE
DEN
Good 7.0

Cons: Seats are horrible

Wed, Aug 14
LGA
New York LaGuardia
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
LGA
New York LaGuardia
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Sep 19
SYR
Syracuse Hancock Intl
MDW
Chicago Midway
3h 31m
Sun, Sep 22
MDW
Chicago Midway
SYR
Syracuse Hancock Intl
3h 59m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,312 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ORF
ATL
Excellent 10.0

Cons: More leg room.

LAS
SAN
Okay 4.3

Pros: Despite boarding late, and sitting on the tarmac for half an hour since we missed our take off time, and having to move passengers around to balance the weight on the plane, we made it home alive.

Cons: We landed over half an hour late. Flight attendants needed to move passengers to balance the weight on the small plane, and asked for "volunteers." When there were none, the FA stood in the aisle and said we just weren't going to take off if nobody volunteered. They should have just MOVED people.

VCE
ATL
Excellent 9.3

Pros: The crew was so nice and funny!

Cons: The food could be better, but I understand ultimately what it is: mass produced. The pretzel bread is good. The chocolate chip cookie is great. The ice cream is great. The lemon and something cheesecake dessert was too lemony for me, but my mother would have loved it.

SEA
JFK
Excellent 8.0

Pros: The crew was great, very accommodating food selection was nice.

Cons: The cabin temperature was extremely warm

ATL
PIT
Excellent 10.0

Pros: Amazing crew

Wed, Aug 14
LGA
New York LaGuardia
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
LGA
New York LaGuardia
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 24
LGA
New York LaGuardia
MDW
Chicago Midway
6h 00m
Tue, Jul 30
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 7 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
MKE
LAS
Excellent 10.0

Pros: Seats are wide and belts long enough for my thicc body

RDU
MCO
Excellent 10.0

Pros: Very nice crew, clean and lots of free entertainment options.

Cons: Nothing

LAX
DEN
Good 7.5

Pros: Crew

Cons: Seats

BDL
MDW
Excellent 10.0

Cons: Free!

BNA
EWR
Excellent 10.0

Pros: Southwest staff Frank was entertaining and good service.

Thu, Sep 19
SYR
Syracuse Hancock Intl
MDW
Chicago Midway
3h 31m
Sun, Sep 22
MDW
Chicago Midway
SYR
Syracuse Hancock Intl
3h 59m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,312 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
CVG
MCO
Excellent 8.3

Pros: Horrible storms kept us in the air for at least an hour past our scheduled landing time. And yet we experienced virtually no turbulence. The pilots did an excellent job of keeping us updated, kept things as smooth as possible with the bad weather and we had plenty of movies and games to choose

Cons: I was charged an extra $100 because my bag was 10lbs overweight. Where is this crazy fee communicated on their website? And why does it have to be so much? I didn't have a way to weigh our bag before we left. I had no idea it was so heavy - ridiculous price.

ATL
RSW
Mediocre 2.0

Pros: Nothing

Cons: Everything

PIT
BOS
Good 7.0

Cons: Wifi didn't work

SGF
ATL
Mediocre 2.0

Pros: Nothing horrible service

Cons: Everything

SLC
BUR
Okay 5.0

Pros: The crew was really nice! They were very energetic!

Cons: I am not blaming the airline, but the Salt Lake Airport. Everything was slow and everything was delayed! The airport staff was friendly, but airport management needs be prepared and perform better. Compared to other airport, there was not that many people flying, and still there processing issues.

Wed, Aug 14
LGA
New York LaGuardia
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
LGA
New York LaGuardia
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 24
LGA
New York LaGuardia
MDW
Chicago Midway
6h 00m
Tue, Jul 30
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 7 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
SJU
TPA
Okay 5.0

Cons: The process of rescheduling our flights to compensate for your faulty equipment.

BWI
ALB
Good 7.3

Cons: Flight delayed And wrong message of boarding when flight was delayed

IND
DEN
Excellent 10.0

Pros: The smooth plane ride. We’ve used other airlines, but Southwest is our favorite by far. I’ve never had a bad experience with them in 15 years.

Cons: Nothing.

SAT
MDW
Excellent 9.6

Pros: Crew did an excellent job serving us.

Cons: had a delay on the return flight, minor setback but overall good.

TPA
RDU
Mediocre 2.0

Pros: Never made it

Cons: Your service and your airplanes.

Sat, Sep 7
EWR
Newark
MDW
Chicago Midway
5h 21m
Sat, Sep 14
MDW
Chicago Midway
EWR
Newark
4h 36m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,299 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
YVR
MSP
Excellent 10.0

Pros: The ability to charge my cell phone via USB ports. Also the movies on long flights is really nice

Cons: Quicker way to get off plane

ATL
ROA
Mediocre 2.0

Pros: Diverted for unclear reasons. Stuck in TSY with hotel voucher to an overbooked hotel; trying to find out of pocket accommodations after long day of no food at MIDNIGHT was a real downer! I’ll let ya know if I make it home TODAY!!!

ATL
JAX
Excellent 10.0

Cons: It was all good ✈️

MIA
MSP
Good 7.0

Cons: Flight was delayed and we missed our connection. Wondering why all the shuttles were parked and unavailable when you knew there were connection s that were tight.

MSP
LAX
Okay 5.6

Cons: Plane was too hot

Wed, Aug 14
EWR
Newark
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
EWR
Newark
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 24
LGA
New York LaGuardia
MDW
Chicago Midway
6h 00m
Tue, Jul 30
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 7 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
SNA
HOU
Excellent 10.0

Pros: No problems with any leg of the trip. Stewards and stewardesses were great

Cons: Non-stop flight from SNA to BOS

SAN
SJC
Okay 4.4

Cons: Flight could have left on time. And the terminal I landed at at was a 30 minute walk from baggage claim.

TPA
RDU
Mediocre 2.0

Pros: Never made it

Cons: Your service and your airplanes.

HOU
DAL
Okay 5.5

Cons: We sat at the gate fully boarded with doors closed for 20 minutes. No idea why.

GRR
MDW
Excellent 9.6

Cons: Had to wait for a gate for about 10 minutes after landing

Sat, Sep 7
EWR
Newark
MDW
Chicago Midway
5h 21m
Sat, Sep 14
MDW
Chicago Midway
EWR
Newark
4h 36m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,299 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
DAL
Excellent 9.3

Pros: They were great & super friendly!!

ATL
MEX
Excellent 10.0

Pros: Great and faster

FLL
JFK
Excellent 8.0

Pros: Crew was good seat comfortable

Cons: Better snacks

JFK
KIN
Excellent 8.0

Cons: Add A Display Board For When Cabin Sections Are Boarding

SAV
ATL
Excellent 10.0

Pros: Don’t wait to much

Wed, Aug 14
EWR
Newark
MDW
Chicago Midway
2h 20m
Mon, Aug 19
MDW
Chicago Midway
EWR
Newark
2h 05m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jul 24
LGA
New York LaGuardia
MDW
Chicago Midway
6h 00m
Tue, Jul 30
MDW
Chicago Midway
LGA
New York LaGuardia
2h 10m
Trip: 7 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 25 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
BNA
EWR
Excellent 10.0

Pros: Excellent service by South West

BWI
MSY
Good 6.6

Cons: The WiFi on the plane was not working and that made it difficult to keep my 4 year old son sitting still

LGA
MDW
Good 6.0

Cons: Attendants not much attentive

LAS
SAN
Excellent 10.0

Pros: Seats wide enough and belts long enough for this thicc gurl

GEG
OAK
Mediocre 3.6

Cons: How about a better boarding process that doesn’t have people in the aisle walking forward while everyone is trying to board. How about not being 2-1/2 hours late to depart. How about having an open gate to park the plane when you arrive.

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