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Find Cheap Flights from Newburgh Stewart to Chicago (SWF - CHI)

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Newburgh Stewart to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Newburgh Stewart
Flight Price $158
Distance 702 miles
Airlines American Airlines, Delta

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $221 or less.

FAQs for Booking Newburgh Stewart to Chicago Flights

How long does a flight from Newburgh Stewart to Chicago take?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 4h 13m.
Which airlines provide the cheapest flights from Newburgh Stewart to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($158) and Delta ($168)
Do I need a passport to fly between Newburgh Stewart and Chicago?
No.
What’s the cheapest day of the week to fly Newburgh Stewart to Chicago?
For Newburgh Stewart to Chicago, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Newburgh Stewart, the best deals are generally found on Saturday, with Friday being the most expensive.

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

Airports
Origin
Newburgh
$158
only
$158
Destination
Chicago
$158
only
$158
$168
only
$168
Sat, Oct 27
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 24m
Sat, Nov 3
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 01m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JAX
CLT
Good 6.0

Bumpy

AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

BCN
JFK
Good 7.6

Even on a big ole B777 you better upgrade to bigger seats

MSP
MIA
Mediocre 3.3

Let's see - I was in first class. The flight itself was fine - and only one hour + late!

Food - Served the "breakfast" (when it was called a protein plate) I had coming (into MSP). for "lunch" on the way back (called it a meat plate for lunch. One slice turkey, one slice jamon, one egg, cinnamon roll and fruit. Just because they don't want to serve bread - they call it a protein plate? I'm not on a protein diet. Food was pretty sick for the amount I paid for the fight. Stewardess said it was against Republic's rules to give a customer a can of tonic water (so I could add to the small amount of vodka) - she also told me that it was against Delta's, American's and United's rules to give a can - strange? First Class seat did not recline. First Class was freezing per every flight on this segment (the stewardesses sit in the back and don't want to be uncomfortable - if they make the front warm - the back is too hot for them (not joking on this one). So many things to list - that I will finish on the AA site.

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

Mon, Nov 12
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 47m
Fri, Nov 23
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 33m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
PBI
LGA
Excellent 10.0

Boarding was on time; flight departures on time and arrived earlier than expected! Pilot told us exactly what was the status and gave us updates; cabin was well air conditioned; flight attendants were friendly; bags came out very quick! Very nice flight

JFK
MXP
Excellent 8.0

The flight was very smooth and the landing also was very good. The selection of movie are plenty.

LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

JFK
CUN
Okay 5.6

Flight was delayed.

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

Sat, Nov 3
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 24m
Wed, Nov 7
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 03m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MSY
CLT
Excellent 9.0

organized boarding, quick and professional, flight crew was awesome, very comfortable flight, much appreciated no

No entertainment options on 2+ hour flight. Would have been nice to have.

BCN
JFK
Good 7.6

Even on a big ole B777 you better upgrade to bigger seats

AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

ORD
MCO
Excellent 8.0

Great crew, on-time arrival, quick boarding

Crowded seats in the back of the plane, Low quality and bland snack options

LGA
ILM
Okay 5.6

Being delayed

Tue, Dec 18
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
5h 40m
Mon, Dec 24
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 41m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

MSP
MIA
Mediocre 3.3

Let's see - I was in first class. The flight itself was fine - and only one hour + late!

Food - Served the "breakfast" (when it was called a protein plate) I had coming (into MSP). for "lunch" on the way back (called it a meat plate for lunch. One slice turkey, one slice jamon, one egg, cinnamon roll and fruit. Just because they don't want to serve bread - they call it a protein plate? I'm not on a protein diet. Food was pretty sick for the amount I paid for the fight. Stewardess said it was against Republic's rules to give a customer a can of tonic water (so I could add to the small amount of vodka) - she also told me that it was against Delta's, American's and United's rules to give a can - strange? First Class seat did not recline. First Class was freezing per every flight on this segment (the stewardesses sit in the back and don't want to be uncomfortable - if they make the front warm - the back is too hot for them (not joking on this one). So many things to list - that I will finish on the AA site.

IAD
CLT
Excellent 10.0

The flight was on time

Tiny bathrooms

MSY
CLT
Excellent 9.0

organized boarding, quick and professional, flight crew was awesome, very comfortable flight, much appreciated no

No entertainment options on 2+ hour flight. Would have been nice to have.

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

Fri, Nov 9
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
4h 13m
Mon, Nov 12
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 03m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

PBI
LGA
Excellent 10.0

Boarding was on time; flight departures on time and arrived earlier than expected! Pilot told us exactly what was the status and gave us updates; cabin was well air conditioned; flight attendants were friendly; bags came out very quick! Very nice flight

LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

LGA
PBI
Excellent 10.0

There were many delays and cancellations due to bad thunderstorms at LGA. Despite a few hours delayed (because the airport was closed due to the storm), the flight was still schedule to leave! I was very happy about that. They did issue waivers for those who could not make the later time. Once delta got the ok to fly.. The flight left the gate very fast and we arrived and exited the plane super fast too. The process was so efficient and quick, I did not feel the waiting period. The flight attendance were so happy and positive, they made he flight very enjoyable. Great job delta!

JFK
MXP
Excellent 8.0

The flight was very smooth and the landing also was very good. The selection of movie are plenty.

Sat, Oct 27
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 24m
Sat, Nov 3
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 01m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MSY
CLT
Excellent 9.0

organized boarding, quick and professional, flight crew was awesome, very comfortable flight, much appreciated no

No entertainment options on 2+ hour flight. Would have been nice to have.

ORD
MCO
Excellent 8.0

Great crew, on-time arrival, quick boarding

Crowded seats in the back of the plane, Low quality and bland snack options

LAX
SFO
Mediocre 2.0

Nothing. Just the pilot

Everything. Bad communication. 1 h delay. Then 3 hs in the plane. We ran out of gas. 2 more hours taxiing Never seen something similar. I really hope my mileage refund.

BCN
JFK
Good 7.6

Even on a big ole B777 you better upgrade to bigger seats

JAX
CLT
Good 6.0

Bumpy

Wed, Oct 24
SWF
Newburgh Stewart
MDW
Chicago Midway
5h 04m
Sat, Oct 27
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 49m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
TUS
Okay 5.6

The bag service

The flight delays

LGA
PBI
Excellent 10.0

There were many delays and cancellations due to bad thunderstorms at LGA. Despite a few hours delayed (because the airport was closed due to the storm), the flight was still schedule to leave! I was very happy about that. They did issue waivers for those who could not make the later time. Once delta got the ok to fly.. The flight left the gate very fast and we arrived and exited the plane super fast too. The process was so efficient and quick, I did not feel the waiting period. The flight attendance were so happy and positive, they made he flight very enjoyable. Great job delta!

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

Sat, Sep 15
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 23m
Sun, Sep 16
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 06m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

IAD
CLT
Excellent 10.0

The flight was on time

Tiny bathrooms

LAX
SFO
Mediocre 2.0

Nothing. Just the pilot

Everything. Bad communication. 1 h delay. Then 3 hs in the plane. We ran out of gas. 2 more hours taxiing Never seen something similar. I really hope my mileage refund.

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

ORD
MCO
Excellent 8.0

Great crew, on-time arrival, quick boarding

Crowded seats in the back of the plane, Low quality and bland snack options

Mon, Aug 20
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 12m
Sat, Sep 1
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 12m
Trip: 13 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

MSP
MIA
Mediocre 3.3

Let's see - I was in first class. The flight itself was fine - and only one hour + late!

Food - Served the "breakfast" (when it was called a protein plate) I had coming (into MSP). for "lunch" on the way back (called it a meat plate for lunch. One slice turkey, one slice jamon, one egg, cinnamon roll and fruit. Just because they don't want to serve bread - they call it a protein plate? I'm not on a protein diet. Food was pretty sick for the amount I paid for the fight. Stewardess said it was against Republic's rules to give a customer a can of tonic water (so I could add to the small amount of vodka) - she also told me that it was against Delta's, American's and United's rules to give a can - strange? First Class seat did not recline. First Class was freezing per every flight on this segment (the stewardesses sit in the back and don't want to be uncomfortable - if they make the front warm - the back is too hot for them (not joking on this one). So many things to list - that I will finish on the AA site.

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

BCN
JFK
Good 7.6

Even on a big ole B777 you better upgrade to bigger seats

MSY
CLT
Excellent 9.0

organized boarding, quick and professional, flight crew was awesome, very comfortable flight, much appreciated no

No entertainment options on 2+ hour flight. Would have been nice to have.

Fri, Aug 17
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 58m
Mon, Aug 20
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 22m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LAX
TUS
Okay 5.6

The bag service

The flight delays

Sat, Oct 20
SWF
Newburgh Stewart
MDW
Chicago Midway
4h 27m
Sun, Oct 21
MDW
Chicago Midway
SWF
Newburgh Stewart
3h 51m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
PBI
LGA
Excellent 10.0

Boarding was on time; flight departures on time and arrived earlier than expected! Pilot told us exactly what was the status and gave us updates; cabin was well air conditioned; flight attendants were friendly; bags came out very quick! Very nice flight

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

LAX
TUS
Okay 5.6

The bag service

The flight delays

Thu, Aug 30
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 36m
Sat, Sep 1
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 12m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
JAX
CLT
Good 6.0

Bumpy

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

IAD
CLT
Excellent 10.0

The flight was on time

Tiny bathrooms

LAX
ORD
Excellent 8.6

Pilot was informative.

LAX
SFO
Mediocre 2.0

Nothing. Just the pilot

Everything. Bad communication. 1 h delay. Then 3 hs in the plane. We ran out of gas. 2 more hours taxiing Never seen something similar. I really hope my mileage refund.

Sat, Sep 29
SWF
Newburgh Stewart
ORD
Chicago O'Hare International
6h 23m
Sun, Sep 30
ORD
Chicago O'Hare International
SWF
Newburgh Stewart
4h 06m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLT
DAB
Excellent 10.0

The flight was on time and I was upgraded to First Class!

DFW
MCO
Good 7.0

Seats were nice and enjoyed the entertainment. Late flight meant loads of open seats and everyone was very happy about that.

Delayed a half hour to board because flight attendants other flight was late getting in, but they kept us informed the entire time. Wasn’t their faults. Once we were on the plane, our flight was delayed for an hour, once again the pilots kept us informed and it wasn’t their faults. But it was kinda annoying.

IAD
CLT
Excellent 10.0

The flight was on time

Tiny bathrooms

MSP
MIA
Mediocre 3.3

Let's see - I was in first class. The flight itself was fine - and only one hour + late!

Food - Served the "breakfast" (when it was called a protein plate) I had coming (into MSP). for "lunch" on the way back (called it a meat plate for lunch. One slice turkey, one slice jamon, one egg, cinnamon roll and fruit. Just because they don't want to serve bread - they call it a protein plate? I'm not on a protein diet. Food was pretty sick for the amount I paid for the fight. Stewardess said it was against Republic's rules to give a customer a can of tonic water (so I could add to the small amount of vodka) - she also told me that it was against Delta's, American's and United's rules to give a can - strange? First Class seat did not recline. First Class was freezing per every flight on this segment (the stewardesses sit in the back and don't want to be uncomfortable - if they make the front warm - the back is too hot for them (not joking on this one). So many things to list - that I will finish on the AA site.

BCN
JFK
Good 7.6

Even on a big ole B777 you better upgrade to bigger seats

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