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Massachusetts to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Massachusetts
Flight Price $139
Airlines Spirit Airlines, United Airlines, American Airlines, Delta, Southwest, JetBlue

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

Airports
Origin
Worcester
$160
only
$160
Boston
$139
only
$139
Destination
Chicago
$139
only
$139
$183
only
$183
Tue, Sep 10
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 49m
Tue, Sep 17
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 30m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Never fails to be horrible. Had to wait on plane for 30 min to be fielded. -after landing in Chicago had to sit on plane for 30 min because there was no gate.

BOS
ORD
Okay 4.6

Pros: The only good thing was the cheap airfare, but with all the other charges you end up paying the same amount for a better airline.

Cons: Steep prices for carry ons ($100 RT), no free bevs even water!

BOS
ORD
Mediocre 2.0

Pros: It went where I needed to go

Cons: There is almost nothing that would make me use this airline again. My flight wasn't even cheap, so that definitely didn't make up for the fact that I paid $50 both ways for my carry on bag, and one $30 seat fee so that I could request a window seat on a cross-country red eye. Water is not free on the plane, and still there were no seat back pockets, so the water bottle I bought (and didn't want in my bag w/ important documents) rolled around on the floor all night. I'm a small woman, and there was barely space for me to fit in the seat. Uncomfortable, expensive.

BOS
ORD
Good 6.0

Pros: PRICE

Cons: BOSTON AIRPORT PROBLEM , LOUSY BOARDING AREA. ROOM FOR 150 PEOPLE BUT 300 WAITING. NOT SPIRITS FAULT.

BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Everything

Tue, Jun 4
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 46m
Tue, Jun 11
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 36m
Trip: 8 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 183 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOS
ORD
Mediocre 2.0

Pros: The flight was bumpy but otherwise pleasant

Cons: There was a rude passenger that yelled at me as I was exciting the flight suggesting that I cut her off as we were getting off the plane thinking that I took her bag. It was outrageous and completely ruined the flight for me. I realize this has nothing to do with the flight but it just made me feel so crumby and attached that I felt the need to share it. Also the leg room was a joke. We barely had any room to move. I probably won't fly coach on united again due to the bad taste it left in my mouth. Unfortunate because it's hub is in chicago.

BOS
ORD
Excellent 9.3

Pros: The flight attendants were very nice.

Cons: The seating was a little tight but overall it was a really good flight.

BOS
ORD
Okay 5.3

Cons: Our plane was constantly moved around prior to boarding and it was 2 hours late.

BOS
ORD
Excellent 8.0

Pros: The crew from the ticket agents all the way up were great. The app for iPhone is great.

Cons: I paid for 30 minutes of WiFi to download the United app on my iPad. I wanted to watch the movies/tv shows that were available to passengers. The WiFi was spotty and slow so I wasn’t able to load the app. Needless to say I was disappointed. I also was disappointed with the seating. I am an average size person and I felt very cramped in my seat. My shoulders and neck are killing me after a 2 hour flight. I know that I chose the economy seating but I don’t remember the seats being quite so narrow or the leg room being non existent.

BOS
ORD
Okay 4.0

Cons: Had to gate check bag both ways. Flight extremely delayed on way home causing me to miss connection; minimal communication from gate crew. A complimentary drink included a Dixie cup full of soda.

Wed, Aug 14
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 48m
Thu, Aug 22
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 19m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 84 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
SNA
Good 6.3

Cons: Flight was delayed twice, and the flight was very bumpy and the pilot really had a bad landing.

PHX
ORD
Okay 4.8

Pros: The seats were comfortable

Cons: There’s zero legroom.

ANC
DFW
Mediocre 3.0

Pros: Nothing

Cons: Everything comfort communication

BOS
ORD
Good 6.0

Pros: personal entertainment systems and charging plugs

Cons: only pretzels and no headphones offered for the entertainment systems.

DFW
CHA
Excellent 10.0

Pros: Right on time

Cons: Wife on board

Wed, Aug 14
ORH
Worcester
ORD
Chicago O'Hare Intl
4h 05m
Tue, Aug 20
ORD
Chicago O'Hare Intl
ORH
Worcester
6h 17m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

CLT
ATL
Good 7.6

Cons: We were late getting into ATL.

ATL
ECP
Excellent 9.0

Pros: Quick flight

Cons: I wish there was a way to access the delta movies in small planes that don’t have seat back entertainment

SYD
LAX
Excellent 8.6

Cons: I really like more legs room and comfort and crew member were very good and helpful. Regarding food I say it’s just ok.

PBI
ATL
Okay 4.6

Cons: Plane was FREEZING!!!

Tue, Jul 16
BOS
Boston Logan Intl
MDW
Chicago Midway
2h 35m
Tue, Jul 23
MDW
Chicago Midway
BOS
Boston Logan Intl
2h 10m
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
BOS
MDW
Good 6.0

Cons: Delayed flight

SAN
TPA
Excellent 8.6

Pros: Great non-stop flight!

Cons: More pretzels or maybe a bottle of peanuts

HOU
DAL
Excellent 9.0

Pros: Crew did a great job. Drinks served, full plane.

MSP
DEN
Excellent 9.3

Pros: Very helpful and friendly agents at the gate in MSP.

Cons: Took a long time to get a soft drink, and we were in the 4th row. It was almost halfway through the two hour flight.

SAN
PHX
Good 7.3

Pros: friendly crew in the airport and on plane

Cons: wifi was broken

Fri, Aug 30
ORH
Worcester
ORD
Chicago O'Hare Intl
7h 11m
Thu, Sep 5
ORD
Chicago O'Hare Intl
ORH
Worcester
8h 10m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17,387 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
LGA
MCO
Excellent 9.3

Cons: The tvs didn't work.

JFK
CUN
Okay 5.0

Pros: Issues with the plane.

JFK
SJC
Mediocre 2.0

Cons: Delayed for two hours and they offered no explanation until the last minute.

JFK
SEA
Excellent 10.0

Pros: Mint seating and service is excellent.

TPA
BDL
Good 6.0

Pros: The crew was very nice.

Cons: I was going home for a funeral, so my thoughts were just in another world and not occupied with the travel.

Tue, Jun 4
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 52m
Wed, Jun 5
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 36m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Cons: Not worth the hassle. After paying for bags and seats it costs more than a good airline. Cancelled my flight and basically offered no assistance. They blamed 'weather' because of thunderstorms. No reason not to wait out a thunderstorm. Requested a refund and still don't have my money back.

BOS
ORD
Mediocre 2.0

Pros: n/a

Cons: The flight was cancelled due to the plane being stuck in another city due to weather. I've had this happen before with other airlines, and they were able to rebook me on another airline's flight, with no price difference. With Spirit, they only were able to refund my money or move me to another date, four days later, which would have caused me to miss the event I was supposed to attend over the weekend. I thought since I was flying solo, without my kids in tow, using a cut-rate airline would have worked out. I've had no problems with JetBlue or SW in the past. But I would stay away from using Spirit.

BOS
ORD
Mediocre 2.0

Cons: My flight was cancelled less than 2 hours before the departure. I was told this at the airline counter. I took 7 o'clock AMTRAK to go Chicago and then took Blue line (45 minutes) to get to O'Hara airport. The girl at the counter did not explain why the airplane was cancelled. She offered a flight next day at the same time. My poster presentation was at 8:30AM next day. There was no alternative flight from Chicago to Boston. I just cannot believe this. I totally missed my conference presentation. BAD!

BOS
ORD
Good 6.6

Pros: Price, but know what to expect.

Cons: Spirit charges even for water.

BOS
ORD
Excellent 8.5

Pros: Boarding was fairly quick, but it was a smaller plane than many.

Cons: Given the fees for luggage in both directions, I'm not sure there would be much, if any, savings round trip compared to other airlines, and that's without any of free beverage/snack/entertainment.

Thu, Aug 29
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 48m
Wed, Sep 4
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 19m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 84 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
PVR
DFW
Mediocre 2.0

Cons: We miss our flight due to immigration paper

BOS
ORD
Good 6.0

Cons: Gogo WiFi didn’t work

BOS
PHL
Good 7.0

Pros: It was fast

Cons: They could have offered headphones, the charging outlet didn’t work

DFW
BNA
Excellent 8.5

Pros: Pleasant and attentive crew

BOS
ORD
Mediocre 2.0

Cons: Terrible. Two hour delay, power plug not working, AC not working.

Wed, Jun 5
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 52m
Sat, Jun 8
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 36m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Okay 4.0

Pros: i really enjoyed being charged $57 upon arrival for a small carryon bag that went in the bin above my seat.

Cons: i didnt like the mysterious additional $80 charge I got from "flight network" on top of my standard air fare and fees, but that may have been a KAYAK scam not a SPIRIT one. I was very clearly made aware of the airfare cost and fees, why wasnt i blatently told Id be charged an additional $80? WILL NOT BE FLYING SPIRIT AGAIN AND LIKELY NOT USING KAYAK TO BOOK EITHER

BOS
ORD
Okay 4.6

Cons: Delayed flight and cancelled flight home

BOS
ORD
Okay 4.6

Pros: The only good thing was the cheap airfare, but with all the other charges you end up paying the same amount for a better airline.

Cons: Steep prices for carry ons ($100 RT), no free bevs even water!

BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: My return flight is cancelled and I realized that exactly at the time of getting boarding pass and it cause me 12 hours delay to teach my destination as I looked for alternative flight from another airlines ....All in all it's an awful service and awful trip simply I choose Spririt airlines.Charging luggage fee is another worst thing that I realized!!

BOS
ORD
Mediocre 2.3

Pros: Nothing!

Cons: 55.00 fee for carry on luggage 50.00 fee for each checked bag I understand that it was a cheap flight, but they make up for that cost with all the fees! Plus there is no inservice drinks...everything is for purchase only. No cash, only credit used. Both my flights were delayed. The first one only and hour. The second over two hours. Crew on both were unprofessional and unkept. They were all wearing different color uniforms, I never knew if it was a flight attendant or a passenger. I would skip this airline in the future and just pay the extra with a better know airline. You will be paying extra in fees anyway, by going with this company. Oh and if you don't pay the 55.00 for your carry on at time of check in--they will charge you 100.00 at the gate. Terrible!

Sat, Oct 5
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 41m
Sun, Oct 6
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 16m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 84 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
LAX
MCO
Okay 5.6

Pros: The plane was very quiet

Cons: I don’t like the stand to put your own iPads on. Just give us the screens. Seems cheap for a 5+ hour flight. Come on american.

BOS
ORD
Excellent 8.0

Pros: Direct flight, sketchy weather but we arrived pretty close to “on time”

BOS
ORD
Excellent 10.0

Pros: Best landing I’ve experienced recently!

LAS
CLT
Mediocre 2.0

Cons: Organization on when the flight would be leaving. BETTER food vouchers. And prudence goes a long way

ORD
LAX
Excellent 9.2

Cons: Flight delayed one hour

Fri, Nov 22
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 53m
Sun, Nov 24
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 16m
Trip: 3 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 183 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Long complicated and rude

BOS
ORD
Mediocre 2.0

Pros: Between the rude and smippy flight crew, getting kicked out of my premium seat for a flight attendant with only a promise of a refund if I saw the gate agent when I landed, and the a/c quitting mid flight to turn the plane into a flying sauna, I now remember why I hate to fly United.

BOS
ORD
Okay 4.6

Pros: Honestly, don’t care for this airline. There’s always some hiccups with boarding, ride staff, mediocre cabin, etc.

Cons: Why do they always want to check bags that are your everyday carryon items (large purse, medium backpac, etc.), but allow people to carryon their larger carry on suitcases filling up the overhead bins. Those are the people they should be making check their “carry-one.” And then be rude about it on top of that.

BOS
ORD
Mediocre 2.0

Cons: Delays, had to stay overnight in Chicago since we arrived 6 hours late

BOS
ORD
Mediocre 2.0

Cons: I missed my flight to San Diego from a connecting flight by a few minutes. Now I have to sit in the airport for over three hours waiting for my next flight.. not to mention it's my bday. Thanks United.

Sat, Sep 7
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 49m
Wed, Sep 11
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 16m
Trip: 5 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Okay 4.0

Pros: Plane was clean and new looking, seating comfortable, storage good.

Cons: Long check-in line, clerk didn't seem to understand the software. Boarding lounges crowded and shabby. Website confusing and too "cute."

BOS
ORD
Good 6.0

Pros: Reasonable fares friendly staff

Cons: Try to charge my daughter an outrageous amount to check in her luggage, ended up having to leave her luggage and have it shipped. Claim a pocket book is a carry on. No other airline does this. We save on the flight but then ends up the same or more with baggage.

BOS
ORD
Okay 5.0

Cons: Carry on fee too high. They should at least provide a cup of water without a fee.

BOS
ORD
Mediocre 2.3

Pros: Nothing!

Cons: 55.00 fee for carry on luggage 50.00 fee for each checked bag I understand that it was a cheap flight, but they make up for that cost with all the fees! Plus there is no inservice drinks...everything is for purchase only. No cash, only credit used. Both my flights were delayed. The first one only and hour. The second over two hours. Crew on both were unprofessional and unkept. They were all wearing different color uniforms, I never knew if it was a flight attendant or a passenger. I would skip this airline in the future and just pay the extra with a better know airline. You will be paying extra in fees anyway, by going with this company. Oh and if you don't pay the 55.00 for your carry on at time of check in--they will charge you 100.00 at the gate. Terrible!

BOS
ORD
Mediocre 2.0

Cons: Not worth the hassle. After paying for bags and seats it costs more than a good airline. Cancelled my flight and basically offered no assistance. They blamed 'weather' because of thunderstorms. No reason not to wait out a thunderstorm. Requested a refund and still don't have my money back.

Sat, Oct 5
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 41m
Sun, Oct 6
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 16m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 84 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
BOS
ORD
Mediocre 2.0

Cons: If I actually made my connection. Delayed flight out of Boston

BOS
ORD
Good 6.3

Cons: Terrible turbulence

BOS
ORD
Okay 4.0

Cons: Paid for extra legroom, got a seat that didn't recline :(

MIA
TLH
Mediocre 2.0

Pros: On time

Cons: Gate D60 is the gate from hell. I was told to go to a different number gate 3 times, and no direction board to reference. Worst airport ever. The staff are rude and could not understand most overhead announcements because their accents and talking super fast.

BOS
ORD
Excellent 9.3

Pros: No food, no entertainment. Flight very smooth. No legroom

Cons: No legroom. They made me check carry on

Thu, Oct 17
BOS
Boston Logan Intl
MDW
Chicago Midway
2h 45m
Sat, Oct 19
MDW
Chicago Midway
BOS
Boston Logan Intl
2h 20m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
SNA
SJC
Excellent 10.0

Pros: Empty flight

Cons: Wish they didn’t switch baggage claim turnstile last minute

CUN
LAX
Okay 5.6

Pros: Crew were polite

Cons: No internet

DAL
HOU
Mediocre 3.3

Cons: The were off on their passenger count and it took over 1 hour and multiple attempts to get it right with multiple stops and starts. Even the crew and pilots were flabbergasted. Completely unacceptable.

SEA
OAK
Mediocre 2.0

Cons: Where do I start? The over headlight didn’t work so I couldn’t read. Plane over packed. Land on time in Oakland after a crummy flight and waited 45 minutes for a plane to leave our gate

SMF
SNA
Mediocre 2.0

Pros: THE COMPANY THAT FILLS THE PLANE WITH FUEL OVERFILLED THE RIGHT WING SO WE HAD TO SIT FOR 45 MINUTES WHILE THE FUEL EQUALIZED . AND THEN THE FLIGHT TOOK LONGER ... AND IM GUESSING BECAUSE WE HAD TO BURN OFF THE EXTRA FUEL IN THE TANKS SO WE FLEW UP AND DOWN THE COAST AND THEN FINALLY INLAND TO LAND

Cons: NOTHING TERRIBLE FLIGHT

Wed, Jun 12
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 52m
Wed, Jun 19
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 35m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Pros: n/a

Cons: The flight was cancelled due to the plane being stuck in another city due to weather. I've had this happen before with other airlines, and they were able to rebook me on another airline's flight, with no price difference. With Spirit, they only were able to refund my money or move me to another date, four days later, which would have caused me to miss the event I was supposed to attend over the weekend. I thought since I was flying solo, without my kids in tow, using a cut-rate airline would have worked out. I've had no problems with JetBlue or SW in the past. But I would stay away from using Spirit.

BOS
ORD
Good 6.0

Pros: On time.

Cons: The plane was a little run down in terms of cleanliness. The pilot didn't announce things. For instance we were on the tarmac for a while to get to the gate upon landing and he never announced the amount of time it would take...to the point where passengers verbally questioned the attendants, "How long does this plane take to get to the gate?"

BOS
ORD
Excellent 8.0

Pros: On time, security, organized

BOS
ORD
Mediocre 2.0

Cons: Didn't realize that bag would cost $50 and that there was not even water available for free. Most uncomfortable flight ever.

BOS
ORD
Mediocre 2.0

Cons: My flight was delayed twice to Boston and I had an appointment to keep. I called the Spirit customer service line repeatedly to ask about travel options and discuss my dilemma. Unfortunately, it seems that phone line is entirely automated. I could not find a human to answer my questions. I finally booked a flight with another airline that was set to arrive in Boston prior to my Spirit flight. I planned to take my return flight home to Chicago, but was informed through email that I had been removed from the flight. I was very upset to learn that my round trip was cancelled by Spirit since I did not take the departure leg of the trip due to all the delays and my time constraints. If I was able to speak to a customer service representative when I repeatedly called for answers, I may have learned of this policy. I was told I could repurchase my flight home for $150, which was too much for me to spend. I am very disappointed that Spirit's budget nature even extends to poor customer service and lack of real humans to provide information during stressful travel situations. Since Spirit has done nothing to make me want to use this airline again, I will be seeking other carriers for my future travel needs.

Sat, Sep 28
ORH
Worcester
ORD
Chicago O'Hare Intl
5h 31m
Mon, Sep 30
ORD
Chicago O'Hare Intl
ORH
Worcester
3h 46m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

ATL
ILM
Excellent 8.6

Cons: No wifi

PHL
ATL
Excellent 10.0

Cons: Safe and happy travel!

FCO
LAX
Excellent 9.0

Pros: Crew was friendly

Cons: Food was not good

KIN
ATL
Excellent 8.0

Pros: For me the boarding was of fast

Cons: The food

Mon, Jul 29
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 51m
Wed, Jul 31
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 17m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Excellent 10.0

Pros: Everything was good enough today. Only a brief delay. Sure beat the much longer delay experienced on our way to Boston earlier this week.

Cons: The flight attendants promoted signing up for the Spirit credit card during the last few minutes of the flight but didn't have any pens for us to use. But I wouldn't have signed up anyway after reading the conditions, such as expiring miles and limited award seats available on flights. That's OLD SCHOOL. I have a card through a bank where the miles never expire, there aren't any blackouts, and I can use the miles on any flight any airline at any time even if 100 other people ahead of me are using their mileage. HOW? The miles I receive convert to dollar amounts which purchase tickets.

BOS
ORD
Excellent 9.6

Pros: It was easy to board and get everything stowed and get seated. No issues with check in, or navigating to the gate.

Cons: It was very cold on flight, other passengers mentioned being cold too.

BOS
ORD
Excellent 8.0

Pros: On time, security, organized

BOS
ORD
Good 7.3

Pros: on time

Cons: low comfort seats

BOS
ORD
Mediocre 2.0

Cons: You have to check in an hour before ur flight or else ur flight gets cancelled.

Sat, Jun 8
BOS
Boston Logan Intl
MDW
Chicago Midway
7h 00m
Mon, Jun 10
MDW
Chicago Midway
BOS
Boston Logan Intl
2h 10m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17 reviews
Boarding
8.7
Comfort
8.4
Crew
9.0
Entertainment
8.0
Food
7.9
OKC
HOU
Okay 5.6

Pros: The crew was great.

Cons: It was freezing!!!! All of the passengers were complaining.

AUS
BWI
Excellent 8.3

Cons: App should not have been required to view programs.

FLL
DCA
Good 6.0

Pros: Overall it was okay

Cons: The pilot!!! The engines kept going off while we were in the air, and landing was not smooth at all. This is the first time that I was afraid on a flight, and I travel at least 5 times a year. This is also the first time this has ever happened to me on a flight with Southwest.

FLL
DCA
Excellent 10.0

Cons: Bag taking too long to arrive at carousel

MCI
SAN
Excellent 8.5

Pros: Clean, left on time

Cons: The baggage carousel monitor was wrong causing a avoidable delay for my retrieving my bag.

Fri, Nov 8
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 49m
Sun, Nov 10
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 16m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Cons: My flight was cancelled less than 2 hours before the departure. I was told this at the airline counter. I took 7 o'clock AMTRAK to go Chicago and then took Blue line (45 minutes) to get to O'Hara airport. The girl at the counter did not explain why the airplane was cancelled. She offered a flight next day at the same time. My poster presentation was at 8:30AM next day. There was no alternative flight from Chicago to Boston. I just cannot believe this. I totally missed my conference presentation. BAD!

BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Everything

BOS
ORD
Mediocre 3.3

Cons: I thought it was $25 to bring a carry on but it was $57. What a rip off. I will never fly spirt again.

BOS
ORD
Mediocre 2.0

Pros: nothing, if the air line is cheap don't means attitude

Cons: Staff don't know how to talk to someone very expensive price for bags always canceling flight time.....

BOS
ORD
Mediocre 2.0

Cons: You have to check in an hour before ur flight or else ur flight gets cancelled.

Thu, Aug 8
BOS
Boston Logan Intl
ORD
Chicago O'Hare Intl
2h 48m
Sat, Aug 17
ORD
Chicago O'Hare Intl
BOS
Boston Logan Intl
2h 29m
Trip: 10 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 84 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
SNA
Good 6.3

Cons: Flight was delayed twice, and the flight was very bumpy and the pilot really had a bad landing.

BOS
ORD
Mediocre 2.0

Cons: If I actually made my connection. Delayed flight out of Boston

GRU
DFW
Good 7.0

Pros: Used system wide upgrade to first class. Seat is spacious and comfortable. Mattress pad is a good addition.

Cons: Crew member serving 1st class was bad, average business was class crew is much nicer and more helpful

BOS
ORD
Good 6.0

Cons: Lots of time changes. 1 piece of luggage sent wrong destination.

BOS
PHL
Good 7.0

Pros: It was fast

Cons: They could have offered headphones, the charging outlet didn’t work

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