Find Cheap Flights from Chicago O'Hare International to Boston Logan International (ORD - BOS)

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Thu 2/22
Thu 3/1
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Good to Know

Low Season:
January
Best time to beat the crowds
3%
expected price decrease
High Season:
April
Most popular time to fly
12%
expected price increase
Average Price:
$212
(avg. price over the last 2 weeks)
Good Deal:
$152
or less (round trip)

When to Book Flights from Chicago O'Hare International to Boston Logan International

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $152 or less.
The cheapest flight from Chicago O'Hare International to Boston Logan International was found 80 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be March, April and May. The cheapest month to fly is January.
Morning departure is around 13% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago O'Hare International to Boston Logan International Flights

How long does a flight from Chicago O'Hare International to Boston Logan International take?
An average nonstop flight takes 2h 13m, covering a distance of 864 miles.
How many flights are there between Chicago O'Hare International and Boston Logan International?
There are 658 (nonstop) flights between Chicago O'Hare International and Boston Logan International per week, averaging 99 per day.
Which airlines provide the cheapest flights from Chicago O'Hare International to Boston Logan International?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($99), Multiple Airlines ($115) and JetBlue ($119).
Do I need a passport to fly between Chicago O'Hare International and Boston Logan International?
No.
Which airlines fly most frequently between Chicago O'Hare International and Boston Logan International?
United (16 times daily), American Airlines (12 times daily), ANA (12 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago O'Hare International to Boston Logan International?
For Chicago O'Hare International to Boston Logan International, Thursday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Boston Logan International back to Chicago O'Hare International, the best deals are generally found on Monday, with Wednesday being the most expensive.

Book cheap flights from Chicago O'Hare International to Boston Logan International (round-trip)

Airports
Origin
Chicago
$99
only
$99
Destination
Boston
$99
only
$99
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 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

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

ORD
BOS
Okay 4.0

The counter staff are rude and incompetent.

ORD
BOS
Excellent 10.0

All

Nothing

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

Wed, Apr 4
ORD
BOS
2h 17m
Mon, Apr 30
BOS
ORD
2h 46m
Trip: 27 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 27
ORD
BOS
2h 17m
Mon, Mar 5
BOS
ORD
3h 00m
Trip: 7 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 27 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
ORD
BOS
Excellent 10.0

You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom

ORD
BOS
Good 6.0

Turbulence was terrible, understand that is not JetBlue issue - wanted to note.

BOS
CLE
Good 7.6

Crew was excellent!! Pilot and flight attendants really helped to keep things going despite the many problems.

We had to switch planes because of a fuel leak. Then the second plane had computer problems. We left 4 hours after we were supposed to.

ORD
BOS
Excellent 8.0

Both ways my flight was significantly delayed. Although Jet Blue sent me notices, none of those came before I was on my way to the airport.

ORD
BOS
Okay 4.0

flight was delayed 2 hours :(

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
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 9.2

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 6.3

A 3-hour weather delay was discouraging because it happened incrementally over 7 or 8 different announcements--each time getting later. One or two would have been reasonable. The seats are tiny and there isn't really enough leg room even for me at just 5'5" tall.

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.

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
Mediocre 3.6

Wouldn't let me bring my bag even though there was plenty of space.

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

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
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 2.0

PURE HELL

ORD
BOS
Excellent 10.0

All

Nothing

Tue, May 1
ORD
BOS
2h 27m
Tue, May 8
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

PURE HELL

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

The worst experience traveling by far

It felt like they had a personal vendetta

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 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, Apr 10
ORD
BOS
2h 17m
Wed, Apr 25
BOS
ORD
2h 46m
Trip: 16 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 2.6

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

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
Excellent 10.0

All

Nothing

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

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

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
Fri, May 4
ORD
BOS
2h 27m
Sun, May 6
BOS
ORD
2h 46m
Trip: 3 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
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

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
Mediocre 2.6

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

Thu, Apr 12
ORD
BOS
2h 27m
Sun, Apr 22
BOS
ORD
3h 00m
Trip: 11 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

The worst experience traveling by far

It felt like they had a personal vendetta

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

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

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

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!

Wed, Apr 18
ORD
BOS
2h 27m
Sun, Apr 22
BOS
ORD
3h 00m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 8
ORD
BOS
2h 27m
Sat, May 12
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
Okay 4.0

The counter staff are rude and incompetent.

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
Mediocre 2.6

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

ORD
BOS
Mediocre 2.0

The worst experience traveling by far

It felt like they had a personal vendetta

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

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
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

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
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

PURE HELL

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 2.0

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.

Thu, Mar 1
ORD
BOS
2h 15m
Thu, Mar 8
BOS
ORD
2h 58m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
ORD
BOS
2h 27m
Tue, May 15
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
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 2.6

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

ORD
BOS
Excellent 10.0

All

Nothing

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

Fri, Mar 2
ORD
BOS
2h 15m
Mon, Mar 5
BOS
ORD
3h 03m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Show more results

Chicago O'Hare International to Boston Logan International Flight Information

Avg. Flight Duration 2h 36m
Flights Arrive in Boston Logan International
Flights Depart from Chicago O'Hare International
Flight Price $99
Distance 864 miles
Airlines Spirit Airlines, JetBlue, Major Airline, United
*
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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.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.