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Chicago Midway to Massachusetts Flight Information

Flights Arrive in Massachusetts
Flights Depart from Chicago Midway
Flight Price $160
Airlines Delta, Major Airline

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

Airports
Origin
Chicago
$160
only
$160
Destination
Boston
$160
only
$160
Tue, Feb 26
MDW
Chicago Midway
BOS
Boston Logan International
5h 18m
Sun, Mar 3
BOS
Boston Logan International
MDW
Chicago Midway
4h 18m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
SNA
DTW
Mediocre 2.0

Pros: Flight was overbooked!!!! How dare you overbook your planes? If you do that, get new plane!!! People loosing time and money.. 9 people couldn’t get seat on the play they paid for... tomorrows flight is same sting... this is last time fling delta... and we are silver medallions... who fly a lot!!!

Cons: Flight was overbooked!!!! How dare you overbook your planes? If you do that, get new plane!!! People loosing time and money.. 9 people couldn’t get seat on the play they paid for... tomorrows flight is same sting... this is last time fling delta... and we are silver medallions... who fly a lot!!!

ATL
CDG
Okay 5.3

Cons: Don't call it "food." the meals were terrible. Also stop creating so much single use plastic.

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

DTW
NRT
Excellent 9.3

Pros: Crew was very friendly for the most part. There seems to be a chance in the way they interact with customers. It's noticeable. The food still is not bad, not great. Drink selection was pretty extensive and impressive. Free wifi for messaging apps is great.

Cons: Electrical plug is right at your knee level. Bread is rock hard an inedible. Plane felt very dry compared to other Delta planes. Would be good to know when the Wifi will be off (as it is off as we "approach the North Pole"). I wish we didn't have to repack bags that are over 52lb.

ATL
HSV
Excellent 10.0

Cons: Quick 30 minute flight

Sat, Jun 22
MDW
Chicago Midway
BOS
Boston Logan International
2h 15m
Sat, Jun 29
BOS
Boston Logan International
MDW
Chicago Midway
2h 40m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 27
MDW
Chicago Midway
BOS
Boston Logan International
5h 18m
Tue, Mar 5
BOS
Boston Logan International
MDW
Chicago Midway
4h 53m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LGA
CLT
Excellent 10.0

Pros: Crew was great

Cons: I actually can not complain

ATL
DFW
Excellent 8.0

Pros: The movies

Cons: NA

NAS
ATL
Excellent 10.0

Pros: seats and entertainment was great

MSP
AMS
Okay 5.0

Pros: Crew are not friendly and I didn't have proper food. I have not asked to choose meal. I thought I can tell in flight that I want veg meal.

Cons: Since rools are changing in international travel. You should inform the new tools to the customer.

ATL
CDG
Okay 5.3

Cons: Don't call it "food." the meals were terrible. Also stop creating so much single use plastic.

Mon, Mar 4
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Thu, Mar 7
BOS
Boston Logan International
MDW
Chicago Midway
4h 33m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PDX
SLC
Good 6.6

Cons: Being on time

PHF
ATL
Excellent 10.0

Cons: Great early morning flight.

SNA
DTW
Mediocre 2.0

Pros: Flight was overbooked!!!! How dare you overbook your planes? If you do that, get new plane!!! People loosing time and money.. 9 people couldn’t get seat on the play they paid for... tomorrows flight is same sting... this is last time fling delta... and we are silver medallions... who fly a lot!!!

Cons: Flight was overbooked!!!! How dare you overbook your planes? If you do that, get new plane!!! People loosing time and money.. 9 people couldn’t get seat on the play they paid for... tomorrows flight is same sting... this is last time fling delta... and we are silver medallions... who fly a lot!!!

LAX
MEX
Mediocre 2.0

Pros: Nothing

Cons: Everything. Awful plane, seats and service

EYW
ATL
Mediocre 3.6

Pros: Sat in the Key West airport for five hours because of delays. Somehow the other airlines managed to get their people on and off the island. Although they say they can’t land in a 25 mph crosswind we were watching the weather. It mostly stayed below 20 mph for hours before departure

Tue, Mar 5
MDW
Chicago Midway
BOS
Boston Logan International
7h 15m
Mon, Mar 11
BOS
Boston Logan International
MDW
Chicago Midway
6h 40m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
JAX
ATL
Excellent 9.6

Pros: Smooth

Cons: Boarding

LGA
CLT
Excellent 10.0

Pros: Crew was great

Cons: I actually can not complain

LAX
MEX
Mediocre 2.0

Pros: Nothing

Cons: Everything. Awful plane, seats and service

MEX
SLC
Excellent 9.3

Pros: Yes

EWR
ATL
Excellent 10.0

Pros: Amazing crew & comfortable seats.

Fri, Mar 8
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Sun, Mar 17
BOS
Boston Logan International
MDW
Chicago Midway
4h 18m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PHF
ATL
Excellent 10.0

Cons: Great early morning flight.

LGA
MSP
Excellent 10.0

Pros: The crew was nice

Cons: The food

AUS
ATL
Excellent 10.0

Pros: Getting offered a stipend to change flights - getting my preferred rental car

Cons: A direct flight

JFK
BTV
Good 6.0

Cons: More room.

YUL
ATL
Excellent 9.2

Pros: Crew was amazing.

Cons: Delayed departure due to late crew arrival. Not a huge deal.

Wed, Jun 26
MDW
Chicago Midway
BOS
Boston Logan International
2h 15m
Sat, Jun 29
BOS
Boston Logan International
MDW
Chicago Midway
2h 40m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 11
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Tue, Mar 19
BOS
Boston Logan International
MDW
Chicago Midway
4h 33m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
AMS
Excellent 8.3

Pros: Crew was awesome. Always available if needed

Cons: Food was just ok. Could have a little more movie selection

MSY
ATL
Excellent 8.0

Cons: Leg room was lacking.

MEX
SLC
Excellent 9.3

Pros: Yes

PIT
MSP
Good 7.6

Cons: Even the comfort seats are crammed together too close. One can barely move. Dreadful

CLT
ATL
Excellent 10.0

Pros: Food good

Wed, Mar 13
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Wed, Mar 20
BOS
Boston Logan International
MDW
Chicago Midway
6h 19m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
HSV
Excellent 10.0

Cons: Quick 30 minute flight

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

MEX
SLC
Excellent 9.3

Pros: Yes

CLT
ATL
Excellent 10.0

Pros: Food good

SAV
ATL
Good 6.0

Pros: boarding was on time

Tue, Mar 19
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Tue, Mar 26
BOS
Boston Logan International
MDW
Chicago Midway
6h 19m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
SEA
Good 6.0

Cons: Flight was delayed more than 4 hours. I switched flights to try to beat the 4 hour delay but was still delayed 4 hours. After verifying with delta t am members that my bags had been rechecked they had not

ATL
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

SEA
GEG
Excellent 10.0

Pros: Early departure

Cons: Absolutely nothing

PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

SLC
MCI
Mediocre 2.0

Cons: Never made it because of my originating flight

Wed, Mar 20
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Mon, Mar 25
BOS
Boston Logan International
MDW
Chicago Midway
5h 35m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
YUL
LGA
Excellent 10.0

Pros: Zee was our flight attendant and she was absolutely wonderful. Personable, attentive, and she made sure each and every person on the plane was comfortable and happy, going so far as to move solo passengers to empty rows so they could have more space. I wish she could be on every flight I take.

SLC
MCI
Mediocre 2.0

Cons: Never made it because of my originating flight

PHF
ATL
Excellent 10.0

Cons: Great early morning flight.

PDX
SLC
Good 6.6

Cons: Being on time

PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

Mon, Apr 1
MDW
Chicago Midway
BOS
Boston Logan International
6h 12m
Thu, Apr 4
BOS
Boston Logan International
MDW
Chicago Midway
4h 05m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
SFO
SLC
Good 6.0

Cons: Flight was delayed, for unkown reasons.

DTW
NRT
Excellent 9.3

Pros: Crew was very friendly for the most part. There seems to be a chance in the way they interact with customers. It's noticeable. The food still is not bad, not great. Drink selection was pretty extensive and impressive. Free wifi for messaging apps is great.

Cons: Electrical plug is right at your knee level. Bread is rock hard an inedible. Plane felt very dry compared to other Delta planes. Would be good to know when the Wifi will be off (as it is off as we "approach the North Pole"). I wish we didn't have to repack bags that are over 52lb.

ATL
DFW
Excellent 8.0

Pros: The movies

Cons: NA

YUL
ATL
Excellent 9.2

Pros: Crew was amazing.

Cons: Delayed departure due to late crew arrival. Not a huge deal.

SJU
JFK
Okay 5.3

Cons: No room to move very cramped

Wed, Apr 17
MDW
Chicago Midway
BOS
Boston Logan International
5h 31m
Fri, Apr 26
BOS
Boston Logan International
MDW
Chicago Midway
4h 05m
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LGA
CLT
Excellent 10.0

Pros: Crew was great

Cons: I actually can not complain

NAS
ATL
Excellent 10.0

Pros: seats and entertainment was great

PIT
MSP
Good 7.6

Cons: Even the comfort seats are crammed together too close. One can barely move. Dreadful

PHX
LAX
Good 6.4

Pros: Crew was good.

Cons: N/A. No food was served due to turbulence which is uncontrollable.

MSY
ATL
Excellent 8.0

Cons: Leg room was lacking.

Fri, May 3
MDW
Chicago Midway
BOS
Boston Logan International
5h 33m
Sun, May 5
BOS
Boston Logan International
MDW
Chicago Midway
5h 21m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
YUL
LGA
Excellent 10.0

Pros: Zee was our flight attendant and she was absolutely wonderful. Personable, attentive, and she made sure each and every person on the plane was comfortable and happy, going so far as to move solo passengers to empty rows so they could have more space. I wish she could be on every flight I take.

LGA
MSP
Excellent 10.0

Pros: The crew was nice

Cons: The food

JFK
RDU
Okay 5.6

Pros: Boarding process was smooth.

Cons: In flight service was disappointing.

MSY
ATL
Excellent 8.0

Cons: Leg room was lacking.

CLT
ATL
Excellent 10.0

Pros: Food good

Tue, May 7
MDW
Chicago Midway
BOS
Boston Logan International
5h 59m
Thu, May 16
BOS
Boston Logan International
MDW
Chicago Midway
3h 50m
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PHL
BOS
Excellent 9.0

Pros: small and uncomfortable

Cons: respectful size seat

SFO
SLC
Good 6.0

Cons: Flight was delayed, for unkown reasons.

JFK
BTV
Good 6.0

Cons: More room.

EYW
ATL
Mediocre 3.6

Pros: Sat in the Key West airport for five hours because of delays. Somehow the other airlines managed to get their people on and off the island. Although they say they can’t land in a 25 mph crosswind we were watching the weather. It mostly stayed below 20 mph for hours before departure

CLT
ATL
Excellent 10.0

Pros: Food good

Tue, May 21
MDW
Chicago Midway
BOS
Boston Logan International
5h 33m
Tue, Jun 4
BOS
Boston Logan International
MDW
Chicago Midway
4h 06m
Trip: 15 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PHL
BOS
Excellent 9.0

Pros: small and uncomfortable

Cons: respectful size seat

ATL
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

MEX
SLC
Excellent 9.3

Pros: Yes

JFK
BTV
Good 6.0

Cons: More room.

SFO
SLC
Good 6.0

Cons: Flight was delayed, for unkown reasons.

Wed, May 29
MDW
Chicago Midway
BOS
Boston Logan International
3h 50m
Wed, Jun 5
BOS
Boston Logan International
MDW
Chicago Midway
4h 35m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
AMS
Okay 5.0

Pros: Crew are not friendly and I didn't have proper food. I have not asked to choose meal. I thought I can tell in flight that I want veg meal.

Cons: Since rools are changing in international travel. You should inform the new tools to the customer.

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

JFK
RDU
Okay 5.6

Pros: Boarding process was smooth.

Cons: In flight service was disappointing.

PHL
BOS
Excellent 9.0

Pros: small and uncomfortable

Cons: respectful size seat

SLC
MCI
Mediocre 2.0

Cons: Never made it because of my originating flight

Thu, May 30
MDW
Chicago Midway
BOS
Boston Logan International
5h 33m
Thu, Jun 6
BOS
Boston Logan International
MDW
Chicago Midway
5h 21m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DCA
LGA
Mediocre 2.0

Pros: It was quick

Cons: Horribly shaky. Thought I was going to throw up. The male flight attendant came off as rude. Just happy I got off the plane alive because it was rough

PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

YYZ
ATL
Mediocre 2.0

Pros: The crew

Cons: Timing

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

ATL
MKE
Good 6.5

Pros: The A/C worked, that's about all

Cons: Old plane, no entertainment in head rests, had to use iPad not the same movies to choose from. Seats were so uncomfortable.

Fri, May 31
MDW
Chicago Midway
BOS
Boston Logan International
5h 33m
Tue, Jun 11
BOS
Boston Logan International
MDW
Chicago Midway
5h 20m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MSP
AMS
Excellent 9.6

Pros: Crew was helpful and food was good.

YYZ
ATL
Mediocre 2.0

Pros: The crew

Cons: Timing

SAV
ATL
Excellent 10.0

Pros: The crew really took care of us. You could tell they care.

Cons: I wish the headphone jacks allowed standard headphones. I brought a nice set and didn't have an adapter. I used the ones they included which were ok, but not great.

PBI
ATL
Excellent 8.6

Pros: I liked that we were able to use the go go entertainment from the headrest. Lots of things to choose from to watch

Cons: We could of been on time, we had a connection I. Atlanta and had 15 minutes to spare

ATL
MIA
Excellent 9.5

Cons: Flight was 20 minutes delayed

Sat, Jun 1
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Wed, Jun 12
BOS
Boston Logan International
MDW
Chicago Midway
4h 23m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,976 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DTW
NRT
Excellent 9.3

Pros: Crew was very friendly for the most part. There seems to be a chance in the way they interact with customers. It's noticeable. The food still is not bad, not great. Drink selection was pretty extensive and impressive. Free wifi for messaging apps is great.

Cons: Electrical plug is right at your knee level. Bread is rock hard an inedible. Plane felt very dry compared to other Delta planes. Would be good to know when the Wifi will be off (as it is off as we "approach the North Pole"). I wish we didn't have to repack bags that are over 52lb.

MSY
DTW
Excellent 9.3

Pros: New plane. Great movie selection. More stylish seats + bathroom. Overall very good and I think Delta has really made an effort to improve it's service. It's noticeable.

Cons: Plane felt very dry compared to others. The electrical plug outlet jams right at around your knee level. Bread was cold and rock hard (seriously, can we not come up with a good solution for this?).

AUS
ATL
Excellent 10.0

Pros: Getting offered a stipend to change flights - getting my preferred rental car

Cons: A direct flight

SAV
ATL
Excellent 10.0

Pros: The crew really took care of us. You could tell they care.

Cons: I wish the headphone jacks allowed standard headphones. I brought a nice set and didn't have an adapter. I used the ones they included which were ok, but not great.

ATL
MCI
Okay 5.6

Cons: The airline cancelled the flight alluring weather conditions, when the reality was they did not wanted the plane to park in Kansas. The weather conditions were even worse on the flight I was moved to, and that flight was not cancelled. They absolutely did not care about the passengers

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