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

Airports
Origin
New York
$77
only
$77
$89
only
$89
Islip
$77
only
$77
Newark
$157
only
$157
Destination
Chicago
$77
only
$77
Thu, Mar 1
LGA
ORD
2h 41m
Sun, Mar 4
ORD
LGA
2h 08m
Trip: 4 days
4.8OkayShow reviews
Overall 4.8 Okay
Based on 452 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
ORD
Mediocre 2.0

Delayed by too much. Bad airlines

LGA
ORD
Good 7.5

everyone was very nice, got through quickly

I have a standard roller bag.. no issues going.. on the way back they wouldn't let me carry on. saw bags bigger than mine being carried on.

LGA
ORD
Mediocre 2.6

Staff was incredibly rude during boarding and upon check-in. They refused to answer questions and generally made it difficult to actually make my flight.

LGA
ORD
Good 7.0

Large seats great space

High bag fees no snacks without charge or beverages.

LGA
ORD
Excellent 10.0

The flight was delayed but the flight attendants handed out free cookies and drinks. The captain kept us updated. Service was great!

Delayed flight

Sat, May 5
ISP
ORD
2h 40m
Tue, May 8
ORD
ISP
2h 02m
Trip: 4 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33877 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MIA
CLE
Excellent 10.0

Funny flight crew who were very attentive and we made it back nearly 30 min early!

Nothing

MCO
SJU
Good 7.0

Low prices, departures and arrivals with very specific schedules On Time.

There's no food or drinking options, if you have any carry-on you'll have to pay $45.

MIA
ATL
Mediocre 3.6

The boarding went quickly and was well organized

That the price to take a small carryon was just as expensive as taking a large suitcase, ended up having to pay and extra $80 r/t for a small bag and I just that's standard for them. There were no barf bags in any seats, believe me everyone around us was looking as the person next to me was getting sick on the landing because it was crazy rough. When we finally were able to get an attendant over she was as rude as could be, I'm sure this sick person next to me was sorry she "inconvenienced" the crew member, if they just put bags in the seats pockets like every other airline this wouldn't have been an issue. The seats were very uncomfortable with no padding and not able to tilt. The tray tables were nonfunctional, too small and did not extend to get anywhere close enough to reach you. The plane ride itself felt like we were on a old school bus on a gravel road. I had a round trip ticket with frontier and both trips were equally as bad. I will never travel with them again, Most of us weren't even sure if we were going to survive take off with out the plan breaking or something.

PHX
DEN
Okay 4.0

Crew was friendly

Late departure

DEN
ONT
Okay 4.0

The flight itself was fine

I used to love frontier but now everything from baggage policies to checking in feel like a huge hassle

Fri, Mar 2
LGA
ORD
2h 48m
Sun, Mar 4
ORD
LGA
2h 10m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Mar 3
JFK
ORD
2h 58m
Mon, Mar 5
ORD
JFK
2h 08m
Trip: 3 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 25 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
JFK
ORD
Excellent 8.0

Food. Too little food and drink

JFK
ORD
Okay 4.3

What I enjoyed about this flight is that I eventually made it to Chicago.

Flight was delayed several times - blamed on Chicago ATC. The food offered was not suitable for First Class - there was chicken and vegetarian option. The FA was rather slow in serving and clearing trays. She was not interested in going around and asking for refills - when I inquired about it at dessert time, she didn't come back for 15 minutes and I had to ring the call button - she informed me they didn't have my drink of choice, so it was OK for her not to come back and tell me that. Service was terrible in First Class. American should seriously do something about that.

DEN
ORD
Good 6.4

I'm not sure where the problem was - whether with AA or Royal Jordanian, but my luggage did not make it to Amman with me. In fact, there was a whole group of passengers traveling on American from different US cities, switching to RJ in Chicago, whose luggage did not come on the flight to Amman. My advice: be sure to pack enough for a couple of days in your carryon - and don't accept an offer to check your carryon to its final destination!

JFK
ORD
Excellent 10.0

It was five star all the way.

JFK
ORD
Mediocre 2.6

nothing

This was the worst flight ever. AA is the worst airlines ever.

Fri, Mar 2
JFK
ORD
3h 00m
Sat, Mar 3
ORD
JFK
2h 20m
Trip: 2 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 16 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.

JFK
ORD
Okay 4.6

Very uncomfortable, seats did not recline and seats way too close together.

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.

JFK
ORD
Mediocre 2.0

Although the bag was in the overhead bin and contained only a military uniform item, a GPS, and several pieces of mail with my name and address on them, I was told there was no guarantee hey would find my bag. A sixth grader with mediocre enthusiasm could easily have reunited me with my bag. IT HAD MY NAME AND ADDRESS INSIDE. Its been 6 days and the best answer I got was "We are not responsible for items you leave on our aircraft. We don't know if anyone even found it". Really? Is this that difficult to figure out? Can a strange bag left on a plane be overlooked for six days? That scares me.

CUN
ATL
Good 7.0

Staff was friendly. Flight was smooth.

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

Tue, May 8
JFK
ORD
2h 37m
Wed, May 16
ORD
JFK
2h 14m
Trip: 9 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 54 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
ORD
Okay 4.0

This flight was very scary particularly mid air. Haven flown many times I knew this was different from usual turbulence cause my clouds or rough air. Jet blue should check

JFK
ORD
Excellent 10.0

The free wifi

The tv

JFK
ORD
Excellent 9.0

Everything on time.

The seat in hard.

JFK
ORD
Excellent 10.0

Everything Entertainment Early landing

Nothing

JFK
ORD
Excellent 8.0

Jetblue left on time from JFK

Fri, Mar 2
LGA
ORD
2h 31m
Sun, Mar 4
ORD
LGA
2h 08m
Trip: 3 days
4.8OkayShow reviews
Overall 4.8 Okay
Based on 452 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
ORD
Mediocre 2.0

Delayed by too much. Bad airlines

LGA
ORD
Okay 4.0

$55 for a carry on is unbelievable! Flight was delayed for 2.5 hours. No reasons why until I got on the plane and the poilt told us why it was late. First and last time flying with spirit

LGA
ORD
Good 6.5

Price Crew

Seats dont recline Not even a bottle of water provided

LGA
ORD
Good 7.5

everyone was very nice, got through quickly

I have a standard roller bag.. no issues going.. on the way back they wouldn't let me carry on. saw bags bigger than mine being carried on.

LGA
ORD
Excellent 10.0

Super Flight Attendants On time flight

Sat, Mar 24
EWR
ORD
2h 35m
Sat, Mar 31
ORD
EWR
2h 06m
Trip: 8 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 120 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
EWR
ORD
Excellent 8.3

We had tickets for 2150 flight, and they moved us to earlier flight on our request with no additional charge. Everyone was very professional, and flight was smooth, and we even arived earlier than scheduled. Thank you.

EWR
ORD
Okay 4.0

Are the rows getting even smaller?!

EWR
ORD
Mediocre 2.0

Nothing

3 hours late. No sympathy for missing last bus out of O'Hare.

EWR
ORD
Good 6.0

Delayed due to a late crew member. Arrived 2 hours late into O'Hare making for a very tight connection. Other than the delay, all was fine.

EWR
ORD
Mediocre 3.3

The seats are wayyyyyyy to close together. Everyone in my rows had their knees pressed up against the seat infront of them. The tv seemed like some sort of ritual torture lots of commercials and ads. Pay extra is you don't want to be indoctrinated.

Sun, Jun 3
EWR
ORD
2h 39m
Tue, Jun 12
ORD
EWR
2h 19m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 11
ISP
ORD
2h 45m
Wed, Apr 18
ORD
ISP
2h 33m
Trip: 8 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33877 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
ONT
Okay 4.0

The flight itself was fine

I used to love frontier but now everything from baggage policies to checking in feel like a huge hassle

LAS
AUS
Mediocre 2.0

Booked with kayak. Reservation came from KIwi.com? Frontier flight was canceled for maintenance. No email notification that I was automatically rebooked onto United flight by frontier. 4 hrs spent trying to get through to frontier booking agent to find out. No way to call internation number at kiwi.com. Will NOT ever book again with kayak.

ORD
DEN
Mediocre 2.0

The flight was delayed

PHX
DEN
Okay 4.0

Crew was friendly

Late departure

MCO
SJU
Good 7.0

Low prices, departures and arrivals with very specific schedules On Time.

There's no food or drinking options, if you have any carry-on you'll have to pay $45.

Sun, Apr 15
ISP
ORD
2h 45m
Sat, Apr 21
ORD
ISP
2h 33m
Trip: 7 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33877 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
ONT
Okay 4.0

The flight itself was fine

I used to love frontier but now everything from baggage policies to checking in feel like a huge hassle

PHX
DEN
Okay 4.0

Crew was friendly

Late departure

ORD
DEN
Mediocre 2.0

The flight was delayed

MCO
SJU
Good 7.0

Low prices, departures and arrivals with very specific schedules On Time.

There's no food or drinking options, if you have any carry-on you'll have to pay $45.

MIA
ATL
Mediocre 3.6

The boarding went quickly and was well organized

That the price to take a small carryon was just as expensive as taking a large suitcase, ended up having to pay and extra $80 r/t for a small bag and I just that's standard for them. There were no barf bags in any seats, believe me everyone around us was looking as the person next to me was getting sick on the landing because it was crazy rough. When we finally were able to get an attendant over she was as rude as could be, I'm sure this sick person next to me was sorry she "inconvenienced" the crew member, if they just put bags in the seats pockets like every other airline this wouldn't have been an issue. The seats were very uncomfortable with no padding and not able to tilt. The tray tables were nonfunctional, too small and did not extend to get anywhere close enough to reach you. The plane ride itself felt like we were on a old school bus on a gravel road. I had a round trip ticket with frontier and both trips were equally as bad. I will never travel with them again, Most of us weren't even sure if we were going to survive take off with out the plan breaking or something.

Wed, Feb 28
LGA
ORD
2h 41m
Sun, Mar 4
ORD
LGA
2h 08m
Trip: 5 days
4.8OkayShow reviews
Overall 4.8 Okay
Based on 452 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
ORD
Okay 4.0

Boarding process was smooth. Plane was nicer than i thought it would be for the cost. Smooth journey despite major delays.

Our flight was delayed due to weather. We were notified on our cell phones that the Flight was delayed. The Spirit workers at the airline desk were too busy watching videos on their phone to change the signboard. Flight attendants, although friendly, were disheveled in appearance.

LGA
ORD
Mediocre 2.6

Staff was incredibly rude during boarding and upon check-in. They refused to answer questions and generally made it difficult to actually make my flight.

LGA
ORD
Okay 4.6

Onboarding was very simple and fast. It took less than 20 minutes.

LGA
ORD
Excellent 10.0

Super Flight Attendants On time flight

LGA
ORD
Good 6.0

The cleanliness of aircraft and on-time boarding and departure.

They charge for every in flight services. Even water is not free. The fee for checking one bag is too expensive and not fair. They beg for every penny from passengers.

Wed, May 2
ISP
ORD
2h 40m
Sat, May 5
ORD
ISP
2h 02m
Trip: 4 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 33877 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MCO
SJU
Good 7.0

Low prices, departures and arrivals with very specific schedules On Time.

There's no food or drinking options, if you have any carry-on you'll have to pay $45.

PHX
MKE
Okay 4.0

Nothing

Everything

LAS
MSN
Okay 5.6

Quick service

Expensive bags and small amount of room on the plane

DEN
ORD
Excellent 10.0

We got there ahead of schedule

PHX
DEN
Okay 4.0

Crew was friendly

Late departure

Mon, Mar 5
JFK
ORD
3h 03m
Wed, Mar 7
ORD
JFK
2h 11m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Feb 26
LGA
ORD
3h 02m
Tue, Mar 6
ORD
LGA
2h 07m
Trip: 9 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 80 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LGA
ORD
Okay 5.3

The employees were nice. That's about it for positive words.

As we were a few minutes from our scheduled boarding, the flight was canceled. The reason we were given was the weather, but the weather was fine in Chicago and it was fine in New York. No other flights were canceled, so the weather excuse didn't hold up. They wouldn't put me on another flight that day, so I ended up leaving the next morning on the first flight out but I was still late for work. They didn't seem to be very accommodating or apologetic and I didn't even offer compensation to those who had to stay overnight to wait for the next flight out. C'mon AA. Step it up! I would think that if you cancel a flight, you should help your customers get home the same day. Do whatever you can. I don't think you did whatever you could for most of us on that flight.

LGA
ORD
Excellent 10.0

On time and arrived early!

LGA
ORD
Mediocre 3.3

First flight was cancelled and alternate flight was delayed. USB charging port didn’t work. Very disappointed.

LGA
ORD
Mediocre 2.0

Fact we got there

Poor customer handling at Laguardia and no info why we were being delayed.

LGA
ORD
Good 7.6

My flight was delayed and redirected to a nervy airport. The staff at this airport was all on board and ready to assist everyone is getting the most current information and putting us a new connecting flights

The check in at LGA was not the smoothest. Most of the kiosk weren't working and was making it hard to check in

Wed, Feb 28
JFK
ORD
2h 58m
Mon, Mar 5
ORD
JFK
2h 08m
Trip: 6 days
6.2GoodShow reviews
Overall 6.2 Good
Based on 25 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
JFK
ORD
Good 6.0

Boarding was a mess. Gate change at last minute. Then the PA wasn't working in one spot but worked in another and instead the gate agent chose to yell, not very loudly mind you, what group was next. Many missed their queue to board.

JFK
ORD
Mediocre 3.6

Arrived on time

Baggage was lost. Did not offer beverage during the flight. Did not offer headphones during the flight. Crew was rude and took it out on the passengers. Not me, but the guy sitting next to me caught a ton of attitude over nothing from one particular crew member and no greetings/farewells on boarding and arrival.

JFK
ORD
Excellent 8.0

Food. Too little food and drink

JFK
ORD
Excellent 10.0

It was five star all the way.

JFK
ORD
Excellent 8.0

The flight was on a Boeing 737 plane with IFE at every seat. I found that very helpful and watched movie and a half.

The Priority experience at JFK is not quite Priority - just 1 TSA agent checking priority customers and not all the time - if the security line is full, no one moves.

Wed, Apr 11
JFK
ORD
2h 56m
Wed, Apr 18
ORD
JFK
2h 19m
Trip: 8 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 16 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
ORD
Good 6.3

Great service as always! I was able to rest! Yay!

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

JFK
ORD
Mediocre 2.0

Although the bag was in the overhead bin and contained only a military uniform item, a GPS, and several pieces of mail with my name and address on them, I was told there was no guarantee hey would find my bag. A sixth grader with mediocre enthusiasm could easily have reunited me with my bag. IT HAD MY NAME AND ADDRESS INSIDE. Its been 6 days and the best answer I got was "We are not responsible for items you leave on our aircraft. We don't know if anyone even found it". Really? Is this that difficult to figure out? Can a strange bag left on a plane be overlooked for six days? That scares me.

JFK
ORD
Okay 4.6

Very uncomfortable, seats did not recline and seats way too close together.

JFK
ORD
Mediocre 2.0

Unnecessary flight cancellation. I had friends taking the same flight at the same time at the same airport from different airlines and they came through for their customers. I received no consolation it assistance with overnight accommodations.

Tue, Jul 10
JFK
ORD
2h 36m
Tue, Jul 17
ORD
JFK
2h 17m
Trip: 8 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 54 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
ORD
Excellent 9.3

Love the snacks and TV option

Delayed for weather ok but then we arrived but didn't deplane for almost 1.5 hours!

JFK
ORD
Okay 5.0

The captain didn’t show up for the flight so we had to wait for a new one to get to the airport. Easily, this could have been avoided. Then we land an hour late and we sit on the runway for a long time with no information.

JFK
ORD
Excellent 8.0

Jetblue left on time from JFK

JFK
ORD
Excellent 9.0

Everything on time.

The seat in hard.

JFK
ORD
Excellent 10.0

Everything Entertainment Early landing

Nothing

Tue, Feb 27
LGA
ORD
2h 41m
Sat, Mar 3
ORD
LGA
2h 14m
Trip: 5 days
4.8OkayShow reviews
Overall 4.8 Okay
Based on 452 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
LGA
ORD
Okay 4.0

$55 for a carry on is unbelievable! Flight was delayed for 2.5 hours. No reasons why until I got on the plane and the poilt told us why it was late. First and last time flying with spirit

LGA
ORD
Mediocre 2.0

Delayed by too much. Bad airlines

LGA
ORD
Excellent 10.0

Super Flight Attendants On time flight

LGA
ORD
Okay 4.0

Boarding process was smooth. Plane was nicer than i thought it would be for the cost. Smooth journey despite major delays.

Our flight was delayed due to weather. We were notified on our cell phones that the Flight was delayed. The Spirit workers at the airline desk were too busy watching videos on their phone to change the signboard. Flight attendants, although friendly, were disheveled in appearance.

LGA
ORD
Good 7.0

Large seats great space

High bag fees no snacks without charge or beverages.

Tue, May 1
JFK
ORD
2h 52m
Fri, May 4
ORD
JFK
2h 14m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews

New York to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from New York
Flight Price $77
Airlines Spirit Airlines, Frontier, American Airlines, Delta, JetBlue, United, Major Airline
*
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