Find Cheap Flights from Central America to Chicago Midway

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Thu 1/18
Thu 1/25
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Book cheap flights from Central America to Chicago Midway (round-trip)

Airports
Origin
Guatemala City
$369
only
$369
San Jose
$462
only
$462
Destination
Chicago
$369
only
$369
Tue, Feb 13
GUA
MDW
14h 35m
Wed, Feb 21
MDW
GUA
11h 05m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
SEA
Excellent 10.0

Staff was very friendly and helpful.

MEX
LAX
Good 6.0

Nothing

My shoes were stolen

MEX
TYO
Okay 4.6

"Free" booze.

Some of the worst service I have seen. Odd hours to wake and feed passengers, and restrictions on bathroom usage.

CUN
MEX
Excellent 9.0

Regardless of the problems I had. the ticket agent was nice and tried to find the best situation to please me and my family so we can all board into the same plane

GDL
ORD
Excellent 9.0

The crew is always respectful and patient at AeroMexico

Thu, Jan 25
GUA
MDW
8h 24m
Mon, Jan 29
MDW
GUA
11h 19m
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
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.

SAN
LAX
Excellent 10.0

on time

YUL
DTW
Mediocre 2.0

Not applied

Not applied

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, Feb 22
GUA
MDW
21h 25m
Fri, Mar 9
MDW
GUA
18h 48m
Trip: 16 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 438 reviews
Overall
7.1
Boarding
7.2
Comfort
6.7
Crew
7.6
Entertainment
5.1
Food
5.5
GDL
MDW
Good 7.5

Punctuality, friendly flight crew

Boarding was an unorganized free-for-all

MTY
MEX
Mediocre 2.0

Ticket agents we're respectful

Never received email boarding pass. No kiosks. Charged for boarding pass even though they could see my reservation/confirmation# Website States checked bags15kgs/carry on 7kgs. At check-in stated only 10 klgs total so we had to pay again due to overage. Only water free on flight. I fly every week for work.

SEA
GDL
Mediocre 2.0

Everything

MEX
JFK
Okay 4.3

Delay in boarding not well organized

SMF
GDL
Okay 5.3

Puntuales y eficientes

Pocas cortesías en alimentos y bebidas

Fri, Feb 16
GUA
MDW
14h 35m
Fri, Feb 23
MDW
GUA
11h 00m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
SEA
Excellent 10.0

Staff was very friendly and helpful.

JFK
MEX
Good 6.0

Our flight was delayed and upon asking the supervisor for more information she was extremely rude and rolled her eyes.

CUN
MEX
Excellent 9.0

Regardless of the problems I had. the ticket agent was nice and tried to find the best situation to please me and my family so we can all board into the same plane

MEX
TYO
Okay 4.6

"Free" booze.

Some of the worst service I have seen. Odd hours to wake and feed passengers, and restrictions on bathroom usage.

GDL
LAX
Mediocre 3.0

The flight schedule is unstable. We were in the lounge and didn’t hear any notice of the flight. Almost missed it.

Fri, Mar 9
GUA
MDW
22h 17m
Tue, Mar 13
MDW
GUA
11h 50m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
CUN
MEX
Excellent 9.6

MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

GDL
SJC
Excellent 9.6

The service and food

Some crew had attitude

JFK
MEX
Good 6.0

Our flight was delayed and upon asking the supervisor for more information she was extremely rude and rolled her eyes.

Sat, Jan 27
GUA
MDW
6h 59m
Wed, Jan 31
MDW
GUA
8h 30m
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
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.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

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

SAN
LAX
Excellent 10.0

on time

Wed, Jan 31
GUA
MDW
14h 35m
Thu, Feb 8
MDW
GUA
12h 05m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
SJC
Excellent 9.6

The service and food

Some crew had attitude

MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

MEX
LAX
Good 6.0

Nothing

My shoes were stolen

CUN
MEX
Excellent 9.6

GDL
LAX
Mediocre 3.0

The flight schedule is unstable. We were in the lounge and didn’t hear any notice of the flight. Almost missed it.

Tue, Jan 30
GUA
MDW
9h 12m
Sun, Feb 4
MDW
GUA
14h 35m
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
DEN
SLC
Excellent 10.0

Delta is great

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.

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.

SAN
LAX
Excellent 10.0

on time

Thu, Feb 1
GUA
MDW
14h 35m
Thu, Feb 8
MDW
GUA
12h 05m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

GDL
SJC
Excellent 9.6

The service and food

Some crew had attitude

GDL
ORD
Excellent 9.0

The crew is always respectful and patient at AeroMexico

CUN
MEX
Excellent 9.6

CUN
MEX
Excellent 9.0

Regardless of the problems I had. the ticket agent was nice and tried to find the best situation to please me and my family so we can all board into the same plane

Thu, Feb 8
GUA
MDW
14h 35m
Thu, Feb 15
MDW
GUA
10h 58m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
LAX
Good 6.0

Nothing

My shoes were stolen

CUN
MEX
Excellent 9.6

MEX
SEA
Excellent 10.0

Staff was very friendly and helpful.

MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

GDL
ORD
Excellent 9.0

The crew is always respectful and patient at AeroMexico

Thu, Feb 8
SJO
MDW
9h 24m
Mon, Feb 12
MDW
SJO
8h 56m
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
DEN
SLC
Excellent 10.0

Delta is great

HKG
SEA
Good 6.0

The flight was on time and the arrival was early

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

SAN
LAX
Excellent 10.0

on time

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

Fri, Feb 16
GUA
MDW
14h 35m
Fri, Feb 23
MDW
GUA
11h 00m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

JFK
MEX
Good 6.0

Our flight was delayed and upon asking the supervisor for more information she was extremely rude and rolled her eyes.

MEX
GDL
Mediocre 2.0

I was flying to MEX from LAX and i had to get through customs which took a long time, but got to the Aeromexico ticket counter to get my boarding pass and they told me that they start boarding 45min before departure time and I got tot he counter at with 35 min to departure and they told me that I missed my flight and had to buy another flight which was two hours later. I don't understand why they couldn't let me through or hold for me. It ruin my ground transportation reservation which I had to reschedule. The whole thing was frustrating and cost me more money that what i thought i was saving.

MEX
SEA
Excellent 10.0

Staff was very friendly and helpful.

MEX
LAX
Good 6.0

Nothing

My shoes were stolen

Tue, May 1
SJO
MDW
14h 48m
Thu, May 10
MDW
SJO
13h 10m
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

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.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

LAX
SJC
Excellent 10.0

It’s was the best flight in my life

MEX
ATL
Excellent 10.0

Delta siempre excelente servicio al cliente.

Sat, Feb 17
GUA
MDW
13h 56m
Mon, Feb 26
MDW
GUA
11h 00m
Trip: 10 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
SJC
Excellent 9.6

The service and food

Some crew had attitude

CUN
MEX
Excellent 9.0

Regardless of the problems I had. the ticket agent was nice and tried to find the best situation to please me and my family so we can all board into the same plane

GDL
ORD
Excellent 9.0

The crew is always respectful and patient at AeroMexico

MEX
LAX
Good 6.0

Nothing

My shoes were stolen

MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

Thu, May 17
SJO
MDW
9h 17m
Thu, May 24
MDW
SJO
8h 40m
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
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

DEN
SLC
Excellent 10.0

Delta is great

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.

Tue, Mar 6
GUA
MDW
22h 17m
Tue, Mar 20
MDW
GUA
18h 25m
Trip: 14 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
LAX
Good 6.0

Nothing

My shoes were stolen

GDL
LAX
Mediocre 3.0

The flight schedule is unstable. We were in the lounge and didn’t hear any notice of the flight. Almost missed it.

MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

JFK
MEX
Good 6.0

Our flight was delayed and upon asking the supervisor for more information she was extremely rude and rolled her eyes.

MEX
IAH
Good 7.3

The plane was comfortable and the crew was great.

The boarding was ridiculous. They never posted what gate the flight went out of. If it wasn't for Kayak we would not have known when to go. The flight was delayed but they never did update that information. It did not leave on time like the board said. They just all of a sudden said they were boarding the flight.

Fri, Apr 20
GUA
MDW
8h 16m
Fri, Apr 27
MDW
GUA
13h 53m
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
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

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.

YUL
DTW
Mediocre 2.0

Not applied

Not applied

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
GUA
MDW
16h 03m
Tue, Mar 13
MDW
GUA
18h 25m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
MEX
LAX
Good 6.0

Nothing

My shoes were stolen

MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

CUN
MEX
Excellent 9.6

MEX
SEA
Excellent 10.0

Staff was very friendly and helpful.

MEX
GDL
Mediocre 2.0

I was flying to MEX from LAX and i had to get through customs which took a long time, but got to the Aeromexico ticket counter to get my boarding pass and they told me that they start boarding 45min before departure time and I got tot he counter at with 35 min to departure and they told me that I missed my flight and had to buy another flight which was two hours later. I don't understand why they couldn't let me through or hold for me. It ruin my ground transportation reservation which I had to reschedule. The whole thing was frustrating and cost me more money that what i thought i was saving.

Thu, Apr 26
GUA
MDW
8h 32m
Tue, May 1
MDW
GUA
11h 16m
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

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

SAN
LAX
Excellent 10.0

on time

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.

Wed, Mar 28
GUA
MDW
21h 17m
Wed, Apr 4
MDW
GUA
17h 45m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 5164 reviews
Overall
7.3
Boarding
7.3
Comfort
7.3
Crew
7.7
Entertainment
7.1
Food
6.9
GDL
LAX
Mediocre 3.0

The flight schedule is unstable. We were in the lounge and didn’t hear any notice of the flight. Almost missed it.

JFK
MEX
Good 6.0

Our flight was delayed and upon asking the supervisor for more information she was extremely rude and rolled her eyes.

MEX
TYO
Okay 4.6

"Free" booze.

Some of the worst service I have seen. Odd hours to wake and feed passengers, and restrictions on bathroom usage.

MEX
LAX
Good 6.0

Nothing

My shoes were stolen

MEX
ORD
Excellent 8.0

good price -

late leaving - not the worst

Central America to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Central America
Flight Price $369
Airlines Aeromexico, Delta, Volaris
*
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