Find Cheap Flights from Massachusetts to Chicago

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

Airports
Origin
Boston
$99
only
$99
Destination
Chicago
$99
only
$99
$184
only
$184
Wed, Apr 18
BOS
ORD
2h 46m
Wed, May 2
ORD
BOS
2h 27m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Mediocre 2.0

Cheap fare

Idiots cancelled the flight.

BOS
ORD
Mediocre 3.3

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

One front desk attendant tried to be helpful

I was unable to board because my boarding pass wasn’t showing up while checking in online beforehand. Trying to explain this was useless. And I was told it was too late. Although in reality there was plenty of time. I spent the rest of my time talking to a different person whos solution was for me to take a bus to NYC from Boston and catch a flight 8 hours later; at least she tried. If they had just printed a boarding pass initially, I would have already been through security with time to spare. I just flew with United instead. I will never fly with Spirit again if I can avoid it. It’s the absolute worst. Satan must be on their board of directors.

BOS
ORD
Mediocre 3.3

Plane was delayed twice because of crew scheduling errors. Also two checked bags cost me over $100!! Terrible airline!

BOS
ORD
Mediocre 2.0

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.

Fri, Jun 1
BOS
ORD
3h 00m
Tue, Jun 5
ORD
BOS
2h 16m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 12
BOS
ORD
2h 49m
Tue, Jun 19
ORD
BOS
2h 17m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 31 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Excellent 9.0

Captain was very funny and thoughtful. Crew were great.

Plane boarded and left about 30 min late and when we arrived gate wasn't available. Things out of their control but of course have an affect on the experience. Also the plane was very oldz

BOS
ORD
Good 7.0

JetBlue booked me on next flight out: AA flight only an hour and a half after the one I missed

Had to check my fragile instrument even though there was room in a closet.

BOS
ORD
Excellent 10.0

Quick security check. Flight was on time,

BOS
ORD
Good 6.3

Solid crew, comfortable flight, free tv and Wi-Fi

A few factors led to a 6 hour delay. Not necessarily Jet Blue's fault but it was certainly a frustrating day of travel

BOS
ORD
Good 7.0

The on flight tv was down so I couldn't listen to music like I nearly always do on my flights.

I didn't like waiting on the tarmac after we landed for what seemed like 25 minutes or so

Wed, Jul 4
BOS
ORD
2h 42m
Fri, Jul 6
ORD
BOS
2h 19m
Trip: 3 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 159 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
BOS
ORD
Okay 4.6

Long delay.

BOS
ORD
Good 6.6

Despite a slight delay in take off the flight landed on time; crew was friendly and efficient

Couldn't get a seat assignment until I arrived at the gate; boarding was slow and a little disorganized; seats are small

BOS
ORD
Excellent 9.0

Relaxed flight- no issues with boarding. Very close gate transfer

BOS
ORD
Excellent 8.6

Didn’t have any food, so there should be an NA option. It was a smooth trip from start to finish with very helpful ground and in flight staffs.

BOS
ORD
Mediocre 3.0

My flight was cancelled for bad weather. It was the ONLY FLIGHT going to or from Chicago cancelled. Typical United. Never flying United again.

Mon, Mar 19
BOS
ORD
2h 58m
Thu, Mar 22
ORD
BOS
2h 14m
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 69 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
BOS
ORD
Okay 4.0

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

BOS
ORD
Mediocre 2.0

The stewardess was nice enough to give me water with my gingerale

We didn't take off until 3 hours after scheduled, and we're forced to watch ads on the overhead monitors for most of the flight. I was not impressed. Poor communication from the pilot.

BOS
ORD
Good 6.0

personal entertainment systems and charging plugs

only pretzels and no headphones offered for the entertainment systems.

BOS
ORD
Good 6.6

Seat 20f It was very uncomfortable and freezing My legs were sore after the journey. Besides until 30 seconds before actual boarding time the members didn't inform about the delay. Everybody had formed lines and we see people getting out only then.

BOS
ORD
Good 6.0

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

Thu, Mar 1
BOS
MDW
4h 25m
Fri, Mar 2
MDW
BOS
5h 26m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

JFK
CDG
Excellent 10.0

The food and the service

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

SLC
YYZ
Excellent 9.6

Z

Wed, Apr 18
BOS
ORD
2h 46m
Wed, May 2
ORD
BOS
2h 27m
Trip: 15 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Mediocre 3.6

Delayed two hours without any notice, and changes $50+ for a carry on.

BOS
ORD
Okay 4.6

Delayed flight and cancelled flight home

BOS
ORD
Okay 4.6

Arrived early

Plane was dirty

BOS
ORD
Good 7.3

Very friendly crew

Did not like being told to pay for bags, seats, etc. in addition to the ticket. Especially thought that paying to choose a seat was ridiculous. Refused to do that and got seats anyway. Pretty cheesy way for the airline to make money

BOS
ORD
Good 7.3

on time

low comfort seats

Thu, May 3
BOS
ORD
2h 46m
Tue, May 8
ORD
BOS
2h 27m
Trip: 6 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Good 6.0

Reasonable fares friendly staff

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
Good 7.3

Very friendly crew

Did not like being told to pay for bags, seats, etc. in addition to the ticket. Especially thought that paying to choose a seat was ridiculous. Refused to do that and got seats anyway. Pretty cheesy way for the airline to make money

BOS
ORD
Mediocre 3.3

Plane was delayed twice because of crew scheduling errors. Also two checked bags cost me over $100!! Terrible airline!

BOS
ORD
Mediocre 2.0

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.

BOS
ORD
Good 7.3

on time

low comfort seats

Wed, Jun 13
BOS
ORD
2h 36m
Tue, Jun 19
ORD
BOS
2h 17m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jul 3
BOS
ORD
2h 53m
Wed, Jul 4
ORD
BOS
2h 17m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 18
BOS
ORD
2h 46m
Tue, Apr 24
ORD
BOS
2h 27m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Good 7.3

on time

low comfort seats

BOS
ORD
Good 6.0

Reasonable fares friendly staff

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
Mediocre 2.0

One front desk attendant tried to be helpful

I was unable to board because my boarding pass wasn’t showing up while checking in online beforehand. Trying to explain this was useless. And I was told it was too late. Although in reality there was plenty of time. I spent the rest of my time talking to a different person whos solution was for me to take a bus to NYC from Boston and catch a flight 8 hours later; at least she tried. If they had just printed a boarding pass initially, I would have already been through security with time to spare. I just flew with United instead. I will never fly with Spirit again if I can avoid it. It’s the absolute worst. Satan must be on their board of directors.

BOS
ORD
Okay 4.6

Arrived early

Plane was dirty

BOS
ORD
Good 7.3

Very friendly crew

Did not like being told to pay for bags, seats, etc. in addition to the ticket. Especially thought that paying to choose a seat was ridiculous. Refused to do that and got seats anyway. Pretty cheesy way for the airline to make money

Tue, Jul 17
BOS
ORD
3h 00m
Tue, Jul 24
ORD
BOS
2h 17m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 3
BOS
ORD
2h 46m
Tue, May 8
ORD
BOS
2h 27m
Trip: 6 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Okay 5.3

Crew was great.

We had a mechanical issue which delayed the flight by 30-45 minutes. That wasn't so bad but the whole strategy that Spirit employs is sketchy. We booked our flight through Kayak at a set price and then when we checked in with Spirit online there were no seats available that we didn't have to pay an upgrade fee. To me that is fals marketing or even bait and switch. Won't be flying with them again.

BOS
ORD
Good 6.0

Reasonable fares friendly staff

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 4.6

Delayed flight and cancelled flight home

BOS
ORD
Mediocre 3.3

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

One front desk attendant tried to be helpful

I was unable to board because my boarding pass wasn’t showing up while checking in online beforehand. Trying to explain this was useless. And I was told it was too late. Although in reality there was plenty of time. I spent the rest of my time talking to a different person whos solution was for me to take a bus to NYC from Boston and catch a flight 8 hours later; at least she tried. If they had just printed a boarding pass initially, I would have already been through security with time to spare. I just flew with United instead. I will never fly with Spirit again if I can avoid it. It’s the absolute worst. Satan must be on their board of directors.

Tue, Aug 28
BOS
ORD
2h 47m
Wed, Sep 5
ORD
BOS
2h 10m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 7
BOS
ORD
3h 00m
Sat, Mar 10
ORD
BOS
2h 17m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 31 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Excellent 9.6

When I sat into my comfortable seat with its amazing leg room, I asked the woman next to me if she had flown Jet Blue previously. She replied that it is now her favorite airline. At the end of the trip I agreed that it is a distinctly different and great airline. My complaint is that I have to travel from NE Wisconsin to Chicago in order to use Jet Blue. When are you coming to MKE? The way the food and drink orders were handled worked well, and the selections were amazing! Needless to say, the media offered was wonderful.

The crew did a good job, but one of the female staff seemed stressed. I hope she was able to get some relief and rest.

BOS
ORD
Excellent 10.0

Changed to 3 hour earlier flight WITHOUT extra "change fee". It was FREE !! Enjoyed in flight TV with FREE drinks and snacks. As United goes backwards in customer service and costs, JetBlue leaps forward. Good work JetBlue.

More options in snack boxes and/or food items

BOS
ORD
Excellent 8.6

leg room & movie

BOS
ORD
Good 6.6

Most of the basics were good.

The flight was substantially delayed and when we got to Chicago we had to wait a long time for a gate agent so that we could deplane because only one gate agent was working at that hour (10:20 p.m.). Also, the flight delay notifications came after I was close to the airport and at the airport--earlier notifications (if possible) would help. The tv/movie portion of the entertainment was not working at all.

BOS
ORD
Good 7.0

The on flight tv was down so I couldn't listen to music like I nearly always do on my flights.

I didn't like waiting on the tarmac after we landed for what seemed like 25 minutes or so

Tue, Apr 3
BOS
MDW
5h 42m
Thu, Apr 5
MDW
BOS
5h 29m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 18
BOS
MDW
4h 16m
Tue, Apr 24
MDW
BOS
3h 33m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

SLC
YYZ
Excellent 9.6

Z

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Wed, Aug 1
BOS
ORD
2h 50m
Tue, Aug 7
ORD
BOS
2h 17m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 23
BOS
ORD
2h 46m
Sun, May 27
ORD
BOS
2h 27m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
BOS
ORD
Mediocre 3.6

Delayed two hours without any notice, and changes $50+ for a carry on.

BOS
ORD
Good 7.3

on time

low comfort seats

BOS
ORD
Mediocre 3.3

Plane was delayed twice because of crew scheduling errors. Also two checked bags cost me over $100!! Terrible airline!

BOS
ORD
Good 6.0

Reasonable fares friendly staff

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 5.3

Crew was great.

We had a mechanical issue which delayed the flight by 30-45 minutes. That wasn't so bad but the whole strategy that Spirit employs is sketchy. We booked our flight through Kayak at a set price and then when we checked in with Spirit online there were no seats available that we didn't have to pay an upgrade fee. To me that is fals marketing or even bait and switch. Won't be flying with them again.

Tue, May 1
BOS
MDW
4h 09m
Tue, May 15
MDW
BOS
4h 05m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

Massachusetts to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Massachusetts
Flight Price $99
Airlines Spirit Airlines, JetBlue, United, American Airlines, Delta
*
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