Find Cheap Flights from Jamaica to Chicago Midway

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

Airports
Origin
Montego Bay
$413
only
$413
Kingston
$663
only
$663
Destination
Chicago
$413
only
$413
Sat, Apr 14
MBJ
MDW
9h 07m
Sun, Apr 22
MDW
MBJ
17h 01m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DTW
Excellent 10.0

Pls see above

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

Sat, Apr 14
MBJ
MDW
9h 07m
Sat, Apr 21
MDW
MBJ
7h 00m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

ATL
DTW
Excellent 10.0

Pls see above

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

Fri, Apr 20
MBJ
MDW
10h 53m
Fri, Apr 27
MDW
MBJ
10h 22m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

ATL
DTW
Excellent 10.0

Pls see above

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

Tue, Apr 17
MBJ
MDW
7h 53m
Tue, Apr 24
MDW
MBJ
13h 40m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

Sat, Apr 14
MBJ
MDW
10h 53m
Tue, Apr 24
MDW
MBJ
9h 00m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

Tue, Apr 17
MBJ
MDW
7h 53m
Sun, Apr 22
MDW
MBJ
7h 05m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

Mon, Apr 16
MBJ
MDW
22h 00m
Mon, Apr 23
MDW
MBJ
6h 35m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

Mon, Apr 16
MBJ
MDW
22h 00m
Sun, Apr 22
MDW
MBJ
7h 05m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

Sun, Apr 15
MBJ
MDW
9h 04m
Mon, Apr 23
MDW
MBJ
7h 59m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

Sun, Apr 15
MBJ
MDW
9h 07m
Tue, Apr 24
MDW
MBJ
9h 00m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

Sun, Apr 15
MBJ
MDW
9h 07m
Sun, Apr 22
MDW
MBJ
13h 40m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DTW
Excellent 10.0

Pls see above

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

Sat, Feb 17
MBJ
MDW
7h 43m
Mon, Mar 19
MDW
MBJ
7h 24m
Trip: 30 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

ATL
DTW
Excellent 10.0

Pls see above

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

Sun, Mar 18
MBJ
MDW
9h 19m
Mon, Mar 19
MDW
MBJ
17h 31m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

Tue, Jul 3
KIN
MDW
13h 55m
Sun, Jul 8
MDW
KIN
7h 36m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

Tue, Mar 27
KIN
MDW
8h 19m
Mon, Apr 2
MDW
KIN
12h 53m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

ATL
DTW
Excellent 10.0

Pls see above

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

Sat, Feb 17
KIN
MDW
7h 18m
Mon, Mar 19
MDW
KIN
6h 17m
Trip: 30 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

Fri, Mar 16
MBJ
MDW
9h 19m
Mon, Mar 19
MDW
MBJ
17h 31m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

Sat, Mar 17
MBJ
MDW
7h 29m
Mon, Mar 19
MDW
MBJ
6h 25m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

Wed, Mar 28
KIN
MDW
8h 19m
Wed, Apr 4
MDW
KIN
12h 16m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

Fri, Apr 6
MBJ
MDW
9h 07m
Fri, Apr 13
MDW
MBJ
17h 01m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

Jamaica to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Jamaica
Flight Price $413
Airlines Delta
*
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