SWF - CHI

Find Cheap Flights from New York Stewart to Chicago

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New York (SWF)
Chicago All airports
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New York Stewart to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from New York Stewart
Flight Price $174
Distance 698 miles
Airlines American Airlines, Delta

Good to Know

Average Price:
$454
(avg. price over the last 2 weeks)
Good Deal:
$316
or less (round trip)

When to Book Flights from New York Stewart to Chicago

Estimated round-trip price
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 $315 or less.
The cheapest flight from New York Stewart to Chicago was found 90 days before departure, on average.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 511% more expensive 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 Stewart to Chicago Flights

How long does a flight from New York Stewart to Chicago take?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 3h 58m.
Which airlines provide the cheapest flights from New York Stewart to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($174) and Delta ($193)
Do I need a passport to fly between New York Stewart and Chicago?
No.
What’s the cheapest day of the week to fly New York Stewart to Chicago?
For New York Stewart to Chicago, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago back to New York Stewart, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

Airports
Origin
New York
$174
only
$174
Destination
Chicago
$174
only
$174
$212
only
$212
Sat, Aug 24
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 28m
Wed, Sep 4
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 58m
Trip: 12 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
PHX
LHR
Excellent 8.3

Pros: Crew was very nice, and helpful.

Cons: I remember you used to get to choose from some seats even if you didn't pay extra. Since the smaller airlines started charging to choose, now the big ones are doing it as well. I checked in for two tickets at the same time, but my wife and i were still separated. Frustrating

BUF
CLT
Excellent 8.5

Cons: This leg of my trip went off without a hitch boarding and crew were very professional.

ORD
LAX
Good 7.3

Cons: One of the best flight attendant service I’ve observed in my 30+ years of flying.

DFW
RDU
Mediocre 3.3

Pros: Apologetic crew

Cons: Massively delayed with no compensation

CLT
AGS
Okay 4.0

Cons: This leg was terrible, the plane sat on the runway for over an hour! The captain did not initially say anything for 30 minutes.

Sat, Sep 7
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
3h 58m
Tue, Sep 10
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 58m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,196 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
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!!!

IAH
ATL
Mediocre 2.3

Cons: The flight had over six hours in combined delays!!!

PHL
ATL
Okay 5.2

Pros: The flight was average, but the quality of travel on Delta this year has been the worst I’ve ever seen. It’s average at best and I’m considering going back to American because I have yet to have a true Delta flight consistent with previous years, the whole reason I switched to Delta.

Cons: Everything

DTW
FLL
Good 6.3

Cons: Flight was delayed due to crew not being available.

SLC
PDX
Good 7.0

Pros: Just fine, beverage service was friendly.

Cons: The entertainment system was out the entire flight. The flight attendants were just talking to each other as we left, even when I tried to say thank you.

Sat, Oct 12
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
5h 40m
Wed, Oct 23
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 41m
Trip: 12 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
KOA
DFW
Okay 5.3

Pros: Overall the plane was in good shape with a nice infotainment screen and charging options.

Cons: Add support for Bluetooth headsets on entertainment screens. For the love of all that is good in the world make those seats more comfortable! The isles were super narrow and difficult to exit quickly while carrying my carry-on

DFW
MKE
Okay 4.0

Pros: Nothing. It was a miserable 2+ hrs.

Cons: Work harder at making flying more comfortable for travelers without breaking the bank.

ORD
LGA
Good 7.3

Cons: Delayed

MIA
DCA
Okay 5.3

Pros: Landing while raining the pilots did a great job

Cons: faster boarding, going out of the plane, the internet on plane was included but didn’t work

RNO
DFW
Good 6.3

Pros: Gate check of carry-on luggage was nice. The connecting flight from DFW to FLL was on time and the boarding process was very smoothly executed by the gate agent. Well done!!

Cons: The flight out of RNO early in the morning was chaotic. One of the kiosks was down and the line to self-check was long and moved very slowly because there was only one agent behind the self-check baggage drop. She did well keeping up but there was a long line of unhappy customers due to the long wait. No snack was offered but I did get a glass of water. Not enough overhead storage for the carry-on bags because passengers get the luggage check tag but brought the carry-on onboard anyway.

Sat, Sep 7
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 51m
Tue, Sep 10
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 38m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
BNA
MSP
Good 6.8

Cons: Check carefully! Our flights were changed and the first was only ten min difference so didn’t think anything of it but when we went to check in they said we would probably miss our connection. The problem was not the time but they changed GATES were really far apart. Was resolved but kind of a hassl

JFK
MIA
Excellent 8.3

Pros: Comfortable Seating!

Cons: Flight delayed Quite a bit.

BHM
ATL
Mediocre 2.5

Pros: Crew was great. Delta auto rebooking caused me to miss my next flight

Cons: Contacting me before rebooking would have saved me $400

FCO
JFK
Excellent 9.3

Pros: Amount of food!

Cons: Quality of food!

MSP
KEF
Good 6.0

Pros: Free movies

Cons: Bad food, cramped seating, slow food service

Mon, Jul 1
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 29m
Sat, Aug 10
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 32m
Trip: 41 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
MSP
CLT
Mediocre 2.0

Pros: nothing. Plane never left.

Cons: Airlines that actually fly. We ended up renting a car and driving the 3.5 hours from Charlotte to Savannah and actually beat the flight that finally left after 11 pm and landed 1 am. We should have gotten the car much sooner and driven instead of sitting at the airport for 8 hours.

PHL
MIA
Good 7.6

Pros: I was able to sleep comfortably, even in the middle seat.

Cons: Not been in a middle seat

PHL
IAH
Good 6.0

Pros: Crew was ok. The basics. No issues.

Cons: WiFi and better entertainment

CLT
HPN
Mediocre 2.6

Cons: Commuter jets- uncomfortable.

GSP
DCA
Good 6.6

Pros: Seats were not too cramped.

Cons: Wifi that actually worked.

Tue, Jul 2
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 29m
Sat, Jul 6
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 32m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ABQ
ORD
Excellent 10.0

Pros: Seating, nice personnel

Cons: Long layover in Chicago

DCA
ORD
Excellent 8.0

Pros: Was not long enough

EZE
MIA
Okay 4.0

Pros: The seats are hard and unconfortable for a long trip

ORD
CHO
Excellent 10.0

Pros: Nice personnel

Cons: Crowded

LGA
IND
Excellent 10.0

Cons: All Excellent

Fri, Nov 22
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 12m
Tue, Dec 3
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
3h 51m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,196 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
TPA
Good 7.6

Cons: B.S. all the Delta Boarding groups. Geez, have you lost all common sense! C'mon... I understand the ill/med conditions passengers. How about 1 kid, then 2 kids then 3 kids, w/ cataracts, bladder probelems, Platinum, Gold, Silver, Paper, Plus 1, Plus 2, Main Cabin 1, 2 and 3.

ATL
RDU
Excellent 8.0

Pros: Did a good job despite the weather during the flight

SLC
BOI
Good 6.3

Pros: Inflight entertainment was the best I’ve seen in coach. Free games, movies, moving map, etc.

Cons: The seating is too cramped. It has just gone past what is reasonable. Seems too tight on both the knees and elbow room.

DTW
FLL
Good 6.3

Cons: Flight was delayed due to crew not being available.

SFO
SEA
Good 6.6

Cons: Connection at Schiphol often tricky;

Sat, Jun 29
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 29m
Sun, Jun 30
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 32m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
LHR
ORD
Okay 5.6

Cons: Boarding at Heathrow is horribly inefficient.

PHX
LHR
Excellent 8.3

Pros: Crew was very nice, and helpful.

Cons: I remember you used to get to choose from some seats even if you didn't pay extra. Since the smaller airlines started charging to choose, now the big ones are doing it as well. I checked in for two tickets at the same time, but my wife and i were still separated. Frustrating

DFW
GNV
Mediocre 2.0

Cons: Flight attendent was late had it been a passenger they would have left them.

CLT
MEX
Good 7.6

Cons: Could give more time before baggage and check in. Arrived exactly one hour before flight and ohh my god........ Management however pulled some miracle....

ORD
AUS
Excellent 10.0

Pros: Really easy boarding and flight. Great in flight entertainment options.

Tue, Aug 20
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 38m
Mon, Aug 26
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 33m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SEA
YVR
Mediocre 2.0

Pros: Never made the connecting flight.

CLT
SLC
Good 6.0

Pros: Inflight entertainment was great. Movies, games, moving map. Best I’ve ever seen in main cabin for free.

Cons: The seating was too cramped. It’s extremely uncomfortable. Seems tighter both on knees and elbows.

ICN
DTW
Excellent 8.6

Pros: Boarding: c'mon...too many groups and subgroups. Radiculous!

Cons: STOP the non-sense of so many boarding goups. What happened to Common Sense boarding? Ill and needing add'l medical help, First Class, Plus Class, then General Boarding. Give me a Break with all the other subgoups for Delta, all B. S. !!

SEA
LAX
Mediocre 2.6

Cons: It was canceled

AMS
BOS
Excellent 10.0

Pros: Food, timeliness, comfort

Cons: Not sure

Sat, Jun 29
SWF
Newburgh Stewart
ORD
Chicago O'Hare Intl
4h 29m
Sun, Jun 30
ORD
Chicago O'Hare Intl
SWF
Newburgh Stewart
4h 32m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,529 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
AGS
CLT
Good 7.5

Cons: Flight delays twice coming out of Augusta. Barely made connection otherwise flight was ok

MIA
SAL
Mediocre 3.6

Pros: The crew was nice.

Cons: EVERYTHING! We were supposed to leave at 7:30 pm and we ended up departing at 9pm

EZE
MIA
Okay 4.0

Pros: The seats are hard and unconfortable for a long trip

ORD
BNA
Mediocre 2.0

Cons: No wifi, drinks came in the last 5 minutes flight was 1.5 hours late

CLT
SYR
Mediocre 3.0

Pros: The coffee was hot?

Cons: Communication was awful. Make flight attendant had less personality than a dusty brick. Idiot behind me was leaning on my seat so I couldn’t recline. It was just probably one of the worst experiences I’ve had flying.

Sat, Jul 20
SWF
Newburgh Stewart
MDW
Chicago Midway
6h 06m
Sun, Jul 21
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 38m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
AMS
JFK
Good 7.6

Cons: Boarding wasn't by zone but all at once.

PHL
ATL
Okay 5.2

Pros: The flight was average, but the quality of travel on Delta this year has been the worst I’ve ever seen. It’s average at best and I’m considering going back to American because I have yet to have a true Delta flight consistent with previous years, the whole reason I switched to Delta.

Cons: Everything

MCO
JFK
Excellent 10.0

Pros: Delta’s crew is the best part about flying delta!

MDW
MSP
Good 7.3

Cons: More leg room and seat width. I don’t like having other passengers pressed against me.

FCO
JFK
Excellent 9.3

Pros: Amount of food!

Cons: Quality of food!

Thu, Oct 10
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 54m
Sun, Oct 13
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 44m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
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.

SEA
YVR
Mediocre 2.0

Pros: Never made the connecting flight.

DTW
FLL
Good 6.3

Cons: Flight was delayed due to crew not being available.

JFK
MIA
Excellent 8.3

Pros: Comfortable Seating!

Cons: Flight delayed Quite a bit.

MDW
MSP
Good 7.3

Cons: More leg room and seat width. I don’t like having other passengers pressed against me.

Sat, Jul 20
SWF
Newburgh Stewart
MDW
Chicago Midway
6h 06m
Wed, Jul 24
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 38m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
BHM
ATL
Mediocre 2.5

Pros: Crew was great. Delta auto rebooking caused me to miss my next flight

Cons: Contacting me before rebooking would have saved me $400

DTW
BDL
Excellent 10.0

Pros: Loved the pilot telling us a little about the flight crew and their piloting experience(Air Force) , and how he kept us abreast of flight status/timing , as well as our location at various points along the route. The crew was very very nice!

Cons: More leg room

MNL
NRT
Excellent 8.0

Pros: The crew at the checking counters were very accommodating. Knowing that I had requested a wheelchair, they changed my seat to one that was closer to the door.

Cons: The flight attendants in my could have been more visible other than just during the food service time.

MSP
KEF
Good 6.0

Pros: Free movies

Cons: Bad food, cramped seating, slow food service

MSP
SLC
Good 7.0

Cons: The entertainment system was out completely for the whole flight

Tue, Jun 25
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 43m
Fri, Jun 28
MDW
Chicago Midway
SWF
Newburgh Stewart
10h 15m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 25,213 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
SJU
Excellent 8.6

Pros: Nice service

MSP
LAX
Okay 5.6

Cons: Plane was too hot

ICN
DTW
Excellent 8.6

Pros: Boarding: c'mon...too many groups and subgroups. Radiculous!

Cons: STOP the non-sense of so many boarding goups. What happened to Common Sense boarding? Ill and needing add'l medical help, First Class, Plus Class, then General Boarding. Give me a Break with all the other subgoups for Delta, all B. S. !!

ATL
PHL
Okay 4.3

Pros: Crew was the best I have had in 2019 on Delta, the only good crew.

Cons: Everything at the Atlanta Airport. From the airport and staff itself to those working for Delta Airlines. It has been so bad, that I am thinking of flying with American Airlines again and avoiding the Atlanta Airport all together. Absolutely the worst airport in the country, Delta not much better

BDL
ATL
Excellent 8.8

Pros: Flight was smooth

Cons: More leg room

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