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Massachusetts to Chicago Midway Flight Information

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

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

Airports
Origin
Boston
$160
only
$160
Destination
Chicago
$160
only
$160
Wed, Feb 27
BOS
Boston Logan International
MDW
Chicago Midway
4h 45m
Tue, Mar 5
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 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

ATL
SXM
Excellent 10.0

Cons: Crazy rough, fast landing but not boring!!!

ORD
ATL
Okay 4.0

Cons: My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole

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

PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

Mon, Mar 11
BOS
Boston Logan International
MDW
Chicago Midway
17h 08m
Thu, Mar 14
MDW
Chicago Midway
BOS
Boston Logan International
14h 49m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Feb 28
BOS
Boston Logan International
MDW
Chicago Midway
5h 48m
Tue, Mar 5
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
EZE
Okay 4.0

Cons: My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole

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.

SEA
GEG
Excellent 10.0

Pros: Early departure

Cons: Absolutely nothing

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

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

Fri, Mar 1
BOS
Boston Logan International
MDW
Chicago Midway
4h 35m
Mon, Mar 11
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
MCO
ATL
Excellent 9.3

Pros: No carry on fee, comfortable seat and pitch

Cons: Displays for zone boarding status would be helpful

FWA
MSP
Good 7.6

Pros: Great crew.

Cons: Seats could be better. But the delays in deicing the plane could have been handled better.

LGA
MSP
Excellent 10.0

Pros: The crew was nice

Cons: The food

PHX
LAX
Good 6.4

Pros: Crew was good.

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

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

Sat, Mar 2
BOS
Boston Logan International
MDW
Chicago Midway
6h 37m
Fri, Mar 8
MDW
Chicago Midway
BOS
Boston Logan International
5h 57m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
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
DCA
Excellent 8.0

Cons: Seats could’ve been assigned ahead of time

SJU
JFK
Okay 5.3

Cons: No room to move very cramped

JFK
RDU
Okay 5.6

Pros: Boarding process was smooth.

Cons: In flight service was disappointing.

LGA
MSP
Excellent 10.0

Pros: The crew was nice

Cons: The food

Sun, Mar 3
BOS
Boston Logan International
MDW
Chicago Midway
4h 18m
Fri, Mar 8
MDW
Chicago Midway
BOS
Boston Logan International
5h 57m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
YYZ
ATL
Mediocre 2.0

Pros: The crew

Cons: Timing

AMS
LAX
Excellent 10.0

Pros: Very friendly cabin crew; excellent service with a smile. Food was good considering, and Magnum ice cream bar a delightful treat. Cabin crew paid good attention to benefits of hydration and served water continuously. Seats and leg room were comfortable considering economy and no extra cost.

Cons: Plane was not as clean as it should be--plastic utensil on floor, seat rails not vacuumed--however, still rate overall comfort as excellent.

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

ATL
SXM
Excellent 10.0

Cons: Crazy rough, fast landing but not boring!!!

YUL
ATL
Excellent 9.2

Pros: Crew was amazing.

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

Mon, Mar 4
BOS
Boston Logan International
MDW
Chicago Midway
4h 53m
Mon, Mar 11
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 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
DCA
Excellent 8.0

Cons: Seats could’ve been assigned ahead of time

PHX
LAX
Good 6.4

Pros: Crew was good.

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

ATL
HSV
Excellent 10.0

Cons: Quick 30 minute flight

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

Tue, Mar 5
BOS
Boston Logan International
MDW
Chicago Midway
4h 53m
Tue, Mar 12
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

PHF
ATL
Excellent 10.0

Cons: Great early morning 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
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

PDX
SLC
Good 6.6

Cons: Being on time

Wed, Mar 6
BOS
Boston Logan International
MDW
Chicago Midway
6h 40m
Mon, Mar 25
MDW
Chicago Midway
BOS
Boston Logan International
6h 11m
Trip: 19 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

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.

ATL
SXM
Excellent 10.0

Cons: Crazy rough, fast landing but not boring!!!

DEN
SLC
Good 6.0

Pros: Good airframe.

Cons: 3+ hours delayed; didn't arrive until 3AM.

YUL
ATL
Excellent 9.2

Pros: Crew was amazing.

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

Thu, Mar 7
BOS
Boston Logan International
MDW
Chicago Midway
4h 33m
Tue, Mar 12
MDW
Chicago Midway
BOS
Boston Logan International
4h 26m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
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

DEN
SLC
Good 6.0

Pros: Good airframe.

Cons: 3+ hours delayed; didn't arrive until 3AM.

ATL
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

JFK
RDU
Okay 5.6

Pros: Boarding process was smooth.

Cons: In flight service was disappointing.

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

Mon, Mar 11
BOS
Boston Logan International
MDW
Chicago Midway
5h 35m
Wed, Mar 13
MDW
Chicago Midway
BOS
Boston Logan International
8h 22m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
MIA
Excellent 9.5

Cons: Flight was 20 minutes delayed

CLT
ATL
Excellent 10.0

Pros: Food good

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.

ATL
CDG
Okay 5.3

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

PDX
SLC
Good 6.6

Cons: Being on time

Wed, Mar 13
BOS
Boston Logan International
MDW
Chicago Midway
4h 53m
Mon, Mar 25
MDW
Chicago Midway
BOS
Boston Logan International
6h 11m
Trip: 13 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
PWM
Excellent 8.4

Cons: Plane was way too hot and stuffy, wasn't until about 20 min into flight before started to cool down.

LGA
RDU
Good 6.4

Cons: Please reduce your delays - again we took off with more than an hour delay and by definition you are responsible of that disagreement, you are the company I am paying for the service....

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

PIT
MSP
Good 7.6

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

Sun, Mar 17
BOS
Boston Logan International
MDW
Chicago Midway
4h 18m
Wed, Mar 20
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LHR
MSP
Excellent 9.3

Pros: The crew were kind and courteous. The seat was comfortable.

ATL
MSP
Excellent 10.0

Pros: My flight was missed due to immigration taking almost 3 hours to get through the line. Delta went out of their way to make sure that I was able to get to my destination on a later flight as comfortable as possible.

Cons: Maybe not traveling through Atlanta if there is immigration clearance involved. I was really slow.

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

PIT
MSP
Good 7.6

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

ORD
ATL
Okay 4.0

Cons: My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole

Mon, Jun 17
BOS
Boston Logan International
MDW
Chicago Midway
13h 29m
Fri, Jun 28
MDW
Chicago Midway
BOS
Boston Logan International
16h 29m
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 18
BOS
Boston Logan International
MDW
Chicago Midway
6h 19m
Wed, Mar 20
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
EWR
ATL
Excellent 10.0

Pros: Amazing crew & comfortable seats.

JFK
RDU
Okay 5.6

Pros: Boarding process was smooth.

Cons: In flight service was disappointing.

SLC
JAC
Excellent 8.0

Pros: It was a quick service

Cons: Better food

RDU
CLE
Mediocre 2.0

Pros: Very bad crew. Seats very uncomfortable

Cons: Crew could have been better

ATL
HSV
Excellent 10.0

Cons: Quick 30 minute flight

Tue, Mar 19
BOS
Boston Logan International
MDW
Chicago Midway
4h 33m
Tue, Mar 26
MDW
Chicago Midway
BOS
Boston Logan International
5h 20m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
MSP
Excellent 10.0

Pros: My flight was missed due to immigration taking almost 3 hours to get through the line. Delta went out of their way to make sure that I was able to get to my destination on a later flight as comfortable as possible.

Cons: Maybe not traveling through Atlanta if there is immigration clearance involved. I was really slow.

PVG
ATL
Okay 4.0

Pros: Food were bad. Out of air condition

PHF
ATL
Excellent 10.0

Cons: Great early morning flight.

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
DFW
Excellent 8.0

Pros: The movies

Cons: NA

Sat, Mar 23
BOS
Boston Logan International
MDW
Chicago Midway
6h 37m
Mon, Mar 25
MDW
Chicago Midway
BOS
Boston Logan International
6h 11m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
ATL
DCA
Excellent 8.0

Cons: Seats could’ve been assigned ahead of time

LGA
CLT
Excellent 10.0

Pros: Crew was great

Cons: I actually can not complain

IAD
AMS
Excellent 9.0

Pros: Super comfortable seats. Lots of movie options.

Cons: Food was not very good

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.

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

Sun, Mar 24
BOS
Boston Logan International
MDW
Chicago Midway
4h 18m
Tue, Mar 26
MDW
Chicago Midway
BOS
Boston Logan International
6h 11m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
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
EZE
Okay 4.0

Cons: My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole

PVG
ATL
Excellent 8.6

Cons: Overall: pretty good.

FWA
MSP
Good 7.6

Pros: Great crew.

Cons: Seats could be better. But the delays in deicing the plane could have been handled better.

YUL
ATL
Excellent 9.2

Pros: Crew was amazing.

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

Mon, Mar 25
BOS
Boston Logan International
MDW
Chicago Midway
5h 35m
Wed, Mar 27
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 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.

PHX
LAX
Good 6.4

Pros: Crew was good.

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

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

MCO
ATL
Excellent 9.3

Pros: No carry on fee, comfortable seat and pitch

Cons: Displays for zone boarding status would be helpful

MEX
SLC
Excellent 9.3

Pros: Yes

Tue, Mar 26
BOS
Boston Logan International
MDW
Chicago Midway
4h 53m
Wed, Mar 27
MDW
Chicago Midway
BOS
Boston Logan International
3h 39m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
SEA
GEG
Excellent 10.0

Pros: Early departure

Cons: Absolutely nothing

PIT
MSP
Good 7.6

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

HSV
ATL
Excellent 8.0

Pros: Good boarding process. Friendly flight attendants.

Cons: Its a long, long flight so can't really complain too much. Overall, it was a good flight.

PDX
SLC
Good 6.6

Cons: Being on time

IAD
AMS
Excellent 9.0

Pros: Super comfortable seats. Lots of movie options.

Cons: Food was not very good

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