Find Cheap Flights from Caribbean to Chicago Midway

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Thu 1/18
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Book cheap flights from Caribbean to Chicago Midway (round-trip)

Airports
Origin
San Juan
$362
only
$362
Destination
Chicago
$362
only
$362
Thu, Feb 8
SJU
MDW
8h 10m
Wed, Feb 14
MDW
SJU
8h 04m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Excellent 10.0

Delta is great

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

Fri, Feb 9
SJU
MDW
9h 20m
Wed, Feb 14
MDW
SJU
8h 50m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

Tue, Feb 13
SJU
MDW
9h 20m
Mon, Feb 19
MDW
SJU
6h 22m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

SAN
LAX
Excellent 10.0

on time

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

Wed, Feb 14
SJU
MDW
9h 20m
Wed, Feb 28
MDW
SJU
8h 16m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

SAN
LAX
Excellent 10.0

on time

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

Fri, Feb 16
SJU
MDW
9h 04m
Mon, Feb 19
MDW
SJU
7h 57m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

DEN
SLC
Excellent 10.0

Delta is great

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

Thu, Feb 22
SJU
MDW
9h 04m
Sun, Mar 4
MDW
SJU
7h 42m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

Thu, Mar 1
SJU
MDW
8h 10m
Mon, Mar 5
MDW
SJU
7h 59m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Excellent 10.0

It’s was the best flight in my life

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

Thu, Mar 8
SJU
MDW
9h 25m
Tue, Apr 3
MDW
SJU
7h 59m
Trip: 26 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Excellent 10.0

Delta is great

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

Mon, Mar 12
SJU
MDW
8h 03m
Wed, Mar 21
MDW
SJU
7h 59m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAN
LAX
Excellent 10.0

on time

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

Tue, Mar 13
SJU
MDW
8h 03m
Wed, Mar 21
MDW
SJU
7h 59m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

SAN
LAX
Excellent 10.0

on time

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

Wed, Mar 14
SJU
MDW
8h 03m
Wed, Mar 21
MDW
SJU
7h 59m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

Thu, Mar 15
SJU
MDW
8h 03m
Wed, Mar 21
MDW
SJU
7h 59m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

FAR
MSP
Good 7.3

Love the free movies and individual screen, and the new seats are more comfortable

That it wasn’t 1970, with full meals and more leg room

Wed, Mar 28
SJU
MDW
8h 03m
Tue, Apr 3
MDW
SJU
7h 52m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

Thu, Mar 29
SJU
MDW
9h 38m
Wed, Apr 4
MDW
SJU
7h 59m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

Wed, Apr 4
SJU
MDW
9h 38m
Tue, Apr 10
MDW
SJU
6h 22m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

Tue, Apr 17
SJU
MDW
8h 03m
Sun, Apr 22
MDW
SJU
7h 59m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

DEN
SLC
Excellent 10.0

Delta is great

Wed, Apr 18
SJU
MDW
8h 03m
Tue, Apr 24
MDW
SJU
6h 22m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Excellent 10.0

It’s was the best flight in my life

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

Thu, Apr 19
SJU
MDW
8h 03m
Wed, Apr 25
MDW
SJU
6h 22m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

AUA
ATL
Excellent 10.0

The entertainment

Had to pay for bags

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

Fri, Apr 20
SJU
MDW
9h 38m
Wed, Apr 25
MDW
SJU
7h 59m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LAX
SJC
Excellent 10.0

It’s was the best flight in my life

SEA
LAX
Good 6.0

On time flight arrival

Baggage Claim was very disorganized. They indicated bags were to be picked up at a carousel that was under construction. When we went to the service desk, they directed us to another carousel which was incorrect. There was no announcement made and there was a delay in updating the baggage claim board.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

MEX
ATL
Excellent 9.0

The crew was amazingly helpful!

SAN
LAX
Excellent 10.0

on time

Tue, Apr 24
SJU
MDW
8h 03m
Mon, Apr 30
MDW
SJU
7h 59m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15239 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DEN
SLC
Excellent 10.0

Delta is great

BOS
LHR
Excellent 10.0

Great service throughout. Friendly attendants and easy boarding/deboarding processes. Would fly international with them again in a heart beat.

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

MKE
ATL
Okay 4.0

Nothing

I never got to Cabo. It took 2 hours for Delta to de-ice the plane in Milwaukee. Because of the long delay we missed the flight to Cabo. We asked Delta to book us on another flight to get us to Cabo today, Delta reps said nothing was available. Delta gave us a discounted coupon for a hotel in Atlanta and rebooked us on a flight to Cabo tomorrow.

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

Caribbean to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Caribbean
Flight Price $362
Airlines Delta
*
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