Find Cheap Flights from Illinois to Boston Logan International

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Wed 2/28
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Book cheap flights from Illinois to Boston Logan International (round-trip)

Airports
Origin
Chicago
$99
only
$99
Destination
Boston
$99
only
$99
Wed, Apr 18
ORD
BOS
2h 27m
Wed, Apr 25
BOS
ORD
2h 46m
Trip: 8 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Mediocre 2.0

PURE HELL

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Excellent 10.0

All

Nothing

ORD
BOS
Okay 4.0

The counter staff are rude and incompetent.

Wed, Apr 11
ORD
BOS
2h 13m
Wed, May 2
BOS
ORD
2h 46m
Trip: 22 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 7
ORD
BOS
2h 12m
Tue, Apr 10
BOS
ORD
2h 46m
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 172 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
BOS
Okay 4.0

Bumpy but spectacular ride through a thunderstorm on descent.

Flight assistants were not particularly helpful with our baby. Same complaint about baggage, but on this longer flight, why make us pay extra for food and entertainment too?!

ORD
BOS
Excellent 9.2

Boarding went well and all agents and crew encountered were very nice

in flight entertainment through personal devices didn't work very well. Needed to use United wi-fi, and watch on United app. Great idea, but wi-fi kept cutting out.

ORD
BOS
Good 7.6

It was ok

Too much confusion on seating...people were moved because of double seating then I was asked to move I seat back. I only agreed so the parent could sit with his two children

ORD
BOS
Good 7.2

The flight was as comfortable as can be. I really appreciated the great cup of coffee brewed. This was the 2nd and final segment of an overnight itinerary. What else can be said?

ORD
BOS
Okay 4.3

Flight was short.

I was not informed about the delay until after I checked my bag, otherwise I might have chosen another flight. I was informed that though I could possibly change flights, my bag might not. I have the UA app, and did not receive timely notification. Free WIFI would have been nice as a compensation. A 4 hour delay means I miss my bus and extends my travel time significantly, one more night away from home. You did offer $50 of mt next UA flight for the next year, but I don't fly that often. Considering the reason for the delay was they were waiting for a plane was frustrating.

Tue, Jun 5
ORD
BOS
2h 16m
Tue, Jul 3
BOS
ORD
2h 53m
Trip: 29 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 26
ORD
BOS
2h 27m
Mon, Apr 30
BOS
ORD
2h 46m
Trip: 5 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Mediocre 2.0

PURE HELL

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Mediocre 2.0

People were nice- not their fault they are screwing your clients over-

Okay, it took me nine hours to get out of Boston on spirit . Return flight, I had no trouble , but I was so scared of getting bad news again, I started shaking at check in, then crying, not my usual travel behavio. I did not and do not want to use your two free vouchers- but had zero choice in choosing to do that - if I refused to volunteer , I would not be helped by spirit to fly to Chicago at all that day. Some choice. So, basically I paid spirit 200$ to poke a stick in my eye, and because I "volunteered ", spirit has generously agreed to poke a stick in my eye, two more times!! for free!!!!- (door for flight already closed when I volunteered- seriously , volunteered??) I was refused a seat on a flight when I was a confirmed ticket holder- there was no volunteering, call it what you will. Fool me once, shame on you . Fool me twice , shame on me. Just booked Rt to Santo Domingo - with jet blue. Thanks for nothing , Spirit.

ORD
BOS
Mediocre 2.0

Would not let me use my ticket because I missed incoming flight

Worst customer experience had to book new flight cost another hundred dollars flight was then delayed for 3 hours a total nightmare

Fri, Apr 27
ORD
BOS
2h 27m
Sat, May 5
BOS
ORD
2h 46m
Trip: 9 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

they charged $52 for 1 baggage then $55 if overweight. That is a rip off. Never again.

ORD
BOS
Excellent 10.0

All

Nothing

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Mediocre 2.0

People were nice- not their fault they are screwing your clients over-

Okay, it took me nine hours to get out of Boston on spirit . Return flight, I had no trouble , but I was so scared of getting bad news again, I started shaking at check in, then crying, not my usual travel behavio. I did not and do not want to use your two free vouchers- but had zero choice in choosing to do that - if I refused to volunteer , I would not be helped by spirit to fly to Chicago at all that day. Some choice. So, basically I paid spirit 200$ to poke a stick in my eye, and because I "volunteered ", spirit has generously agreed to poke a stick in my eye, two more times!! for free!!!!- (door for flight already closed when I volunteered- seriously , volunteered??) I was refused a seat on a flight when I was a confirmed ticket holder- there was no volunteering, call it what you will. Fool me once, shame on you . Fool me twice , shame on me. Just booked Rt to Santo Domingo - with jet blue. Thanks for nothing , Spirit.

ORD
BOS
Mediocre 3.3

they put us on the plane and then took us off after about one hour and then about a hour after that they put us back on and taxied out and we sat for about hour and they brought us back to gate and told us they cancelled the flight so we all had to stand in line to get a refund and find another flight we got a southwest flight and got there around 12;30 and when we got to my son's house our clothes were so wet they keep the suite cases out in the rain

Tue, Feb 27
ORD
BOS
2h 14m
Wed, Mar 28
BOS
ORD
3h 03m
Trip: 29 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jun 26
ORD
BOS
2h 21m
Tue, Jul 10
BOS
ORD
2h 53m
Trip: 15 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 172 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORD
BOS
Excellent 9.0

Crew was excellent

N/A

ORD
BOS
Good 7.6

It was ok

Too much confusion on seating...people were moved because of double seating then I was asked to move I seat back. I only agreed so the parent could sit with his two children

ORD
BOS
Good 7.2

The flight was as comfortable as can be. I really appreciated the great cup of coffee brewed. This was the 2nd and final segment of an overnight itinerary. What else can be said?

ORD
BOS
Okay 4.3

Flight was short.

I was not informed about the delay until after I checked my bag, otherwise I might have chosen another flight. I was informed that though I could possibly change flights, my bag might not. I have the UA app, and did not receive timely notification. Free WIFI would have been nice as a compensation. A 4 hour delay means I miss my bus and extends my travel time significantly, one more night away from home. You did offer $50 of mt next UA flight for the next year, but I don't fly that often. Considering the reason for the delay was they were waiting for a plane was frustrating.

ORD
BOS
Good 7.6

Excellent crew and snacks, we were on time, actually arrived early in Boston.

The strong exhaust fumes while in the gate was really uncomfortable. It finally cleared once under way but 10 minutes of breathing it was not pleasant.

Sat, Apr 28
ORD
BOS
2h 27m
Sun, Apr 29
BOS
ORD
2h 46m
Trip: 2 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

Would not let me use my ticket because I missed incoming flight

Worst customer experience had to book new flight cost another hundred dollars flight was then delayed for 3 hours a total nightmare

ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Mediocre 2.0

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

ORD
BOS
Okay 4.0

The counter staff are rude and incompetent.

Wed, Feb 28
ORD
BOS
2h 14m
Thu, Mar 8
BOS
ORD
2h 57m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 1
ORD
BOS
2h 27m
Sat, May 5
BOS
ORD
2h 46m
Trip: 5 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

Would not let me use my ticket because I missed incoming flight

Worst customer experience had to book new flight cost another hundred dollars flight was then delayed for 3 hours a total nightmare

ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Mediocre 2.6

Flight was delayed twice because of staffing issues! Charged $114.00 for two checked bags!

ORD
BOS
Mediocre 2.0

PURE HELL

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

Thu, Mar 1
ORD
BOS
2h 10m
Thu, Mar 8
BOS
ORD
2h 57m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 3
ORD
BOS
2h 27m
Thu, May 10
BOS
ORD
2h 46m
Trip: 8 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

People were nice- not their fault they are screwing your clients over-

Okay, it took me nine hours to get out of Boston on spirit . Return flight, I had no trouble , but I was so scared of getting bad news again, I started shaking at check in, then crying, not my usual travel behavio. I did not and do not want to use your two free vouchers- but had zero choice in choosing to do that - if I refused to volunteer , I would not be helped by spirit to fly to Chicago at all that day. Some choice. So, basically I paid spirit 200$ to poke a stick in my eye, and because I "volunteered ", spirit has generously agreed to poke a stick in my eye, two more times!! for free!!!!- (door for flight already closed when I volunteered- seriously , volunteered??) I was refused a seat on a flight when I was a confirmed ticket holder- there was no volunteering, call it what you will. Fool me once, shame on you . Fool me twice , shame on me. Just booked Rt to Santo Domingo - with jet blue. Thanks for nothing , Spirit.

ORD
BOS
Excellent 10.0

All

Nothing

ORD
BOS
Okay 4.0

The counter staff are rude and incompetent.

ORD
BOS
Mediocre 2.0

Would not let me use my ticket because I missed incoming flight

Worst customer experience had to book new flight cost another hundred dollars flight was then delayed for 3 hours a total nightmare

ORD
BOS
Mediocre 2.0

they charged $52 for 1 baggage then $55 if overweight. That is a rip off. Never again.

Fri, Mar 2
ORD
BOS
2h 12m
Thu, Mar 8
BOS
ORD
2h 58m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, May 5
ORD
BOS
2h 27m
Wed, May 9
BOS
ORD
2h 46m
Trip: 5 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

ORD
BOS
Excellent 10.0

All

Nothing

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Mediocre 2.0

The worst experience traveling by far

It felt like they had a personal vendetta

ORD
BOS
Mediocre 2.0

People were nice- not their fault they are screwing your clients over-

Okay, it took me nine hours to get out of Boston on spirit . Return flight, I had no trouble , but I was so scared of getting bad news again, I started shaking at check in, then crying, not my usual travel behavio. I did not and do not want to use your two free vouchers- but had zero choice in choosing to do that - if I refused to volunteer , I would not be helped by spirit to fly to Chicago at all that day. Some choice. So, basically I paid spirit 200$ to poke a stick in my eye, and because I "volunteered ", spirit has generously agreed to poke a stick in my eye, two more times!! for free!!!!- (door for flight already closed when I volunteered- seriously , volunteered??) I was refused a seat on a flight when I was a confirmed ticket holder- there was no volunteering, call it what you will. Fool me once, shame on you . Fool me twice , shame on me. Just booked Rt to Santo Domingo - with jet blue. Thanks for nothing , Spirit.

Sun, Mar 4
ORD
BOS
2h 16m
Tue, Mar 13
BOS
ORD
3h 01m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 9
ORD
BOS
2h 27m
Mon, May 14
BOS
ORD
2h 46m
Trip: 6 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Mediocre 2.0

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

Bad airplanes no amenities and charges even for water. Do yourself a favor and spend the extra $0-$50 for a roundtrip fare because you always end up paying at least that much more the way they nickel and dime you.

ORD
BOS
Okay 4.0

The counter staff are rude and incompetent.

ORD
BOS
Mediocre 2.0

they charged $52 for 1 baggage then $55 if overweight. That is a rip off. Never again.

ORD
BOS
Mediocre 2.6

Flight was delayed twice because of staffing issues! Charged $114.00 for two checked bags!

Mon, Mar 5
ORD
BOS
2h 14m
Wed, Mar 14
BOS
ORD
2h 58m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 9
ORD
BOS
2h 27m
Mon, May 14
BOS
ORD
2h 46m
Trip: 6 days
5.0OkayShow reviews
Overall 5.0 Okay
Based on 189 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
ORD
BOS
Mediocre 2.0

I cannot believe I had to take this flight. Spirit prides itself as the cheapest flight, well that's because they charge you for everything else! $14 for a seat, $47 for a checked bag, $42 for a carry-on bag. After I refused to pay those fees, they told me I wasn't able to get a refund on my flight. I will never take Spirit again. My flight with Jetblue was a breeze and they even gave free snacks and drinks. DON'T TAKE SPIRIT!

ORD
BOS
Mediocre 3.3

they put us on the plane and then took us off after about one hour and then about a hour after that they put us back on and taxied out and we sat for about hour and they brought us back to gate and told us they cancelled the flight so we all had to stand in line to get a refund and find another flight we got a southwest flight and got there around 12;30 and when we got to my son's house our clothes were so wet they keep the suite cases out in the rain

ORD
BOS
Mediocre 2.0

PURE HELL

ORD
BOS
Excellent 10.0

Everyone was so friendly and helpful

That I couldn't take all the friendly and helpful people home with me...to make them a proper meal

ORD
BOS
Excellent 10.0

All

Nothing

Tue, Mar 6
ORD
BOS
2h 14m
Wed, Mar 14
BOS
ORD
2h 58m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews

Illinois to Boston Logan International Flight Information

Flights Arrive in Boston Logan International
Flights Depart from Illinois
Flight Price $99
Airlines Spirit Airlines, United, Major Airline
*
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