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

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Sat 1/20
Sat 1/27
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Good to Know

Low Season:
January
Best time to beat the crowds
2%
expected price decrease
High Season:
June
Most popular time to fly
12%
expected price increase
Average Price:
$381
(avg. price over the last 2 weeks)
Good Deal:
$190
or less (round trip)

When to Book Flights from New York to Chicago Midway

Average price per month
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 $190 or less.
The cheapest flight from New York to Chicago Midway was found 46 days before departure, on average.
Book at least 5 weeks before departure in order to get a below-average price.
High season is considered to be May, June and July. The cheapest month to fly is January.
Morning departure is around 5% 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 to Chicago Midway Flights

How long does a flight from New York to Chicago Midway take?
An average nonstop flight takes 4h 02m, covering a distance of 718 miles.
How many flights are there between New York and Chicago Midway?
There are 92 (nonstop) flights between New York and Chicago Midway per week, averaging 13 per day.
Which airlines provide the cheapest flights from New York to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($146)
Do I need a passport to fly between New York and Chicago Midway?
No.
Which airlines fly most frequently between New York and Chicago Midway?
Southwest (13 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly New York to Chicago Midway?
For New York to Chicago Midway, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago Midway back to New York, the best deals are generally found on Saturday, with Sunday being the most expensive.

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

Airports
Origin
New York
$146
only
$146
Destination
Chicago
$146
only
$146
Sat, Jan 20
JFK
MDW
6h 44m
Sat, Feb 3
MDW
JFK
5h 03m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CVG
SFO
Okay 5.6

Boarding was fine. And service was good.

TV controls didn’t work. So I couldn’t watch anything for the 4+ hour flight.

ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

Mon, Jan 22
JFK
MDW
6h 45m
Thu, Jan 25
MDW
JFK
5h 50m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

PDX
JFK
Excellent 8.3

Food

Leg room

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

Tue, Jan 23
JFK
MDW
6h 45m
Thu, Jan 25
MDW
JFK
7h 24m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

PDX
JFK
Excellent 8.3

Food

Leg room

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

Fri, Jan 26
JFK
MDW
7h 08m
Sat, Jan 27
MDW
JFK
4h 22m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

CVG
SFO
Okay 5.6

Boarding was fine. And service was good.

TV controls didn’t work. So I couldn’t watch anything for the 4+ hour flight.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

Sun, Jan 28
JFK
MDW
7h 50m
Mon, Jan 29
MDW
JFK
7h 23m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

PDX
JFK
Excellent 8.3

Food

Leg room

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

Wed, Jan 31
JFK
MDW
6h 45m
Mon, Feb 5
MDW
JFK
5h 50m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

CVG
SFO
Okay 5.6

Boarding was fine. And service was good.

TV controls didn’t work. So I couldn’t watch anything for the 4+ hour flight.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

Sat, Feb 3
JFK
MDW
6h 44m
Mon, Feb 5
MDW
JFK
5h 50m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

PDX
JFK
Excellent 8.3

Food

Leg room

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

Tue, Feb 6
JFK
MDW
6h 45m
Tue, Feb 13
MDW
JFK
5h 50m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

Sat, Feb 10
JFK
MDW
6h 44m
Sat, Feb 17
MDW
JFK
4h 11m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

Thu, Feb 22
JFK
MDW
7h 04m
Wed, Feb 28
MDW
JFK
5h 48m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

Fri, Feb 23
JFK
MDW
7h 04m
Tue, Feb 27
MDW
JFK
5h 48m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

Wed, Feb 28
JFK
MDW
7h 04m
Wed, Mar 7
MDW
JFK
3h 39m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

Sat, Apr 14
JFK
MDW
4h 02m
Wed, Apr 18
MDW
JFK
7h 09m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

ATL
HOU
Excellent 10.0

Nice flight and good staff and service

Sat, Feb 10
JFK
MDW
6h 13m
Tue, Feb 13
MDW
JFK
4h 24m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

PDX
JFK
Excellent 8.3

Food

Leg room

Tue, Feb 13
JFK
MDW
4h 24m
Sat, Feb 17
MDW
JFK
4h 11m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

ATL
MEX
Excellent 8.3

Tudo conforme esperado em um voo da Delta.

Nada a reclamar.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

Wed, Feb 14
JFK
MDW
4h 24m
Wed, Feb 21
MDW
JFK
5h 48m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CVG
SFO
Okay 5.6

Boarding was fine. And service was good.

TV controls didn’t work. So I couldn’t watch anything for the 4+ hour flight.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

PDX
JFK
Excellent 8.3

Food

Leg room

BOS
AUS
Good 6.0

Delayed so I was not home until middle of the night.

Thu, Feb 22
JFK
MDW
7h 04m
Mon, Feb 26
MDW
JFK
5h 53m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HOU
Excellent 10.0

Nice flight and good staff and service

PDX
JFK
Excellent 8.3

Food

Leg room

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

Sat, Feb 24
JFK
MDW
6h 44m
Tue, Feb 27
MDW
JFK
4h 13m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

PDX
JFK
Excellent 8.3

Food

Leg room

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

Thu, Mar 8
JFK
MDW
4h 09m
Tue, Mar 13
MDW
JFK
3h 39m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
ATL
Okay 5.0

As poltronas estavam OK.

No voo MEX-GRU o Sistema de Entretenimento nao funcionou por quase 3hs. A refeicao foi muito fraca, tamto no jantar quanto no café da manhã. Onde ja se viu comer feijão preto com onelete no cafe da manhã??? Deveriam pensar no tipo de passageiro q estao atendendo.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

ATL
HOU
Excellent 10.0

Nice flight and good staff and service

CUN
ATL
Mediocre 3.6

The crew on board were helpful

Delta staff at airport were unprofessional. They had us spend over an hour traveling to a different TSA line because they closed the line we were in. The other line was a 10 minute drive away. Also our bags did not reach philadelphia when we landed at 3 am.

CUN
ATL
Excellent 9.6

The weather was bad in Atlanta. We were rerouted to Minneapolis and made a connection to Philadelphia. No problems.

Thu, Mar 8
JFK
MDW
4h 09m
Tue, Mar 13
MDW
JFK
3h 39m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15315 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BNA
BOS
Mediocre 2.0

Delta staff taking care of rude/beligerant guests first vedore guests patiently/kindly waiting in line ... children watched that behavior and the jerks recieved special treatment. Flight staff ripped up guests boarding pass in face. Staff allowed ys to board plane and put our bags under plane and then crew timed out before take off. Never will use Delta again.

LGA
FLL
Excellent 8.0

When the passenger in front reclines their seat it was in my face The legroom wasn’t terrible but I had a hard time even reading since it was so close

LIM
ATL
Excellent 8.0

The crew, food, plane, everything was excellent

TLH
ATL
Mediocre 2.0

Ice in the morning in Atlanta and Delta cancels my 6pm flight to Atlanta leaving me no flight home that night.

ATL
HOU
Excellent 10.0

Nice flight and good staff and service

Show more results

New York to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from New York
Flight Price $146
Distance 718 miles
Airlines Delta
*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.