Trips

Find Cheap Flights from Massachusetts to Chicago Midway

Search hundreds of travel sites at once for deals on flights to Chicago Midway

Sun 8/19
Sun 8/26
Any month
Compare vs. KAYAK |

Massachusetts to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Massachusetts
Flight Price $164
Airlines Delta, Major Airline

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

Airports
Origin
Boston
$164
only
$164
Destination
Chicago
$164
only
$164
Sat, Aug 25
BOS
Boston Logan International
MDW
Chicago Midway
8h 17m
Tue, Aug 28
MDW
Chicago Midway
BOS
Boston Logan International
5h 37m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
DSM
Excellent 10.0

Quick and easy.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

Mon, Sep 10
BOS
Boston Logan International
MDW
Chicago Midway
2h 35m
Fri, Sep 14
MDW
Chicago Midway
BOS
Boston Logan International
2h 20m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Aug 28
BOS
Boston Logan International
MDW
Chicago Midway
4h 24m
Wed, Sep 5
MDW
Chicago Midway
BOS
Boston Logan International
6h 44m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

ATL
LGA
Excellent 10.0

On time

LGA
YUL
Excellent 10.0

On time

Wed, Aug 29
BOS
Boston Logan International
MDW
Chicago Midway
4h 20m
Wed, Sep 5
MDW
Chicago Midway
BOS
Boston Logan International
6h 44m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

DTW
DSM
Excellent 10.0

Quick and easy.

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

Thu, Aug 30
BOS
Boston Logan International
MDW
Chicago Midway
4h 15m
Mon, Sep 10
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
YUL
Excellent 10.0

On time

ITH
DTW
Excellent 10.0

Quick and easy

LAX
TUS
Okay 5.6

The bag service

The flight delays

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

Sun, Sep 2
BOS
Boston Logan International
MDW
Chicago Midway
6h 41m
Tue, Sep 4
MDW
Chicago Midway
BOS
Boston Logan International
6h 44m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
TUS
Okay 5.6

The bag service

The flight delays

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

ITH
DTW
Excellent 10.0

Quick and easy

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

Wed, Sep 5
BOS
Boston Logan International
MDW
Chicago Midway
5h 32m
Sat, Sep 8
MDW
Chicago Midway
BOS
Boston Logan International
7h 54m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
YUL
Excellent 10.0

On time

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

Thu, Sep 6
BOS
Boston Logan International
MDW
Chicago Midway
4h 04m
Tue, Sep 11
MDW
Chicago Midway
BOS
Boston Logan International
5h 34m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
TUS
Okay 5.6

The bag service

The flight delays

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

ATL
LGA
Excellent 10.0

On time

Sat, Sep 8
BOS
Boston Logan International
MDW
Chicago Midway
4h 05m
Mon, Sep 10
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ITH
DTW
Excellent 10.0

Quick and easy

DTW
DSM
Excellent 10.0

Quick and easy.

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

LAX
TUS
Okay 5.6

The bag service

The flight delays

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

Sat, Sep 8
BOS
Boston Logan International
MDW
Chicago Midway
4h 05m
Mon, Sep 10
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ITH
DTW
Excellent 10.0

Quick and easy

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
YUL
Excellent 10.0

On time

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

Tue, Sep 11
BOS
Boston Logan International
MDW
Chicago Midway
5h 34m
Tue, Sep 18
MDW
Chicago Midway
BOS
Boston Logan International
3h 52m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
TUS
Okay 5.6

The bag service

The flight delays

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

DTW
DSM
Excellent 10.0

Quick and easy.

Sat, Sep 15
BOS
Boston Logan International
MDW
Chicago Midway
7h 33m
Tue, Sep 18
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

DTW
DSM
Excellent 10.0

Quick and easy.

ATL
LGA
Excellent 10.0

On time

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

Tue, Sep 18
BOS
Boston Logan International
MDW
Chicago Midway
6h 21m
Sat, Sep 22
MDW
Chicago Midway
BOS
Boston Logan International
5h 28m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

ATL
LGA
Excellent 10.0

On time

LGA
YUL
Excellent 10.0

On time

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

Wed, Sep 19
BOS
Boston Logan International
MDW
Chicago Midway
5h 37m
Mon, Sep 24
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
YUL
Excellent 10.0

On time

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

LAX
TUS
Okay 5.6

The bag service

The flight delays

ITH
DTW
Excellent 10.0

Quick and easy

Thu, Sep 20
BOS
Boston Logan International
MDW
Chicago Midway
4h 04m
Wed, Sep 26
MDW
Chicago Midway
BOS
Boston Logan International
6h 44m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

LGA
YUL
Excellent 10.0

On time

ITH
DTW
Excellent 10.0

Quick and easy

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

Sat, Sep 22
BOS
Boston Logan International
MDW
Chicago Midway
6h 59m
Mon, Sep 24
MDW
Chicago Midway
BOS
Boston Logan International
4h 38m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
YUL
Excellent 10.0

On time

DTW
DSM
Excellent 10.0

Quick and easy.

LAX
TUS
Okay 5.6

The bag service

The flight delays

ATL
LGA
Excellent 10.0

On time

Tue, Sep 25
BOS
Boston Logan International
MDW
Chicago Midway
4h 26m
Tue, Oct 2
MDW
Chicago Midway
BOS
Boston Logan International
4h 57m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

ITH
DTW
Excellent 10.0

Quick and easy

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

Wed, Sep 26
BOS
Boston Logan International
MDW
Chicago Midway
6h 21m
Sat, Sep 29
MDW
Chicago Midway
BOS
Boston Logan International
7h 53m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ITH
DTW
Excellent 10.0

Quick and easy

ATL
LGA
Excellent 10.0

On time

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

DTW
DSM
Excellent 10.0

Quick and easy.

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

Thu, Sep 27
BOS
Boston Logan International
MDW
Chicago Midway
6h 21m
Mon, Oct 1
MDW
Chicago Midway
BOS
Boston Logan International
3h 53m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LGA
Excellent 10.0

On time

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

ITH
DTW
Excellent 10.0

Quick and easy

Sat, Sep 29
BOS
Boston Logan International
MDW
Chicago Midway
4h 05m
Tue, Oct 2
MDW
Chicago Midway
BOS
Boston Logan International
7h 22m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,616 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LGA
Excellent 10.0

On time

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

Forgot password?

Enter the email associated with your account in the field below and we'll email you a link to reset your password.

Cancel