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

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Thu 12/14
Thu 12/21
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Good to Know

Low Season:
January
Best time to beat the crowds
4%
expected price decrease
High Season:
April
Most popular time to fly
15%
expected price increase
Average Price:
$580
(avg. price over the last 2 weeks)
Good Deal:
$580
or less (round trip)

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

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

Top tips for Finding a Cheap Flight

The cheapest flight from Boston Logan International to Chicago O'Hare International was found 69 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 8% cheaper 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 Boston Logan International to Chicago O'Hare International Flights

How long does a flight from Boston Logan International to Chicago O'Hare International take?
An average nonstop flight takes 2h 46m, covering a distance of 864 miles.
How many flights are there between Boston Logan International and Chicago O'Hare International?
There are 726 (nonstop) flights between Boston Logan International and Chicago O'Hare International per week, averaging 110 per day.
Which airlines provide the cheapest flights from Boston Logan International to Chicago O'Hare International?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($105), British Airways ($115) and Multiple Airlines ($119).
Do I need a passport to fly between Boston Logan International and Chicago O'Hare International?
No.
Which airlines fly most frequently between Boston Logan International and Chicago O'Hare International?
United (18 times daily), American Airlines (16 times daily), Alaska Airlines (15 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Boston Logan International to Chicago O'Hare International?
For Boston Logan International to Chicago O'Hare International, Saturday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago O'Hare International back to Boston Logan International, the best deals are generally found on Wednesday, with Thursday being the most expensive.

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

Airports
Origin
Boston
$105
only
$105
Destination
Chicago
$105
only
$105
Sat, Jan 20
BOS
ORD
2h 58m
Wed, Jan 24
ORD
BOS
2h 14m
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 64 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
BOS
ORD
Good 6.0

personal entertainment systems and charging plugs

only pretzels and no headphones offered for the entertainment systems.

BOS
ORD
Mediocre 3.6

Delayed 3 hrs and then sat on runway upon arrival at ohare. I was forced to check my rollerboard even though I've fit it perfectly in the overhead compartment just yesterday on my previous flight (also American airline).

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
Excellent 8.0

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

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.

Tue, Jan 2
BOS
ORD
3h 03m
Fri, Jan 5
ORD
BOS
2h 12m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 13970 reviews
Overall
7.5
Boarding
7.6
Comfort
7.2
Crew
8.0
Entertainment
7.0
Food
6.9
FRA
LHR
Mediocre 2.0

Absolute nightmare dealing with British cancelled flight and then having them rebook me with American, their "partner" company. Spent three hours this morning dealing with these two unprofessional companies and their lack of communication between each other.

EWR
LHR
Good 6.0

My seat was comfortable, with good head and neck support.

BA doesn't allow guitars as carry ins, unlike most every other overseas carrier. That's a major negative for me, and I've spread the word to other musicians who will avoid the company. Terrible policy.

FCO
LHR
Excellent 8.5

Great crew

Being charged more than $3 for a cup of tea!

DEN
LHR
Excellent 8.3

Seats were comfortable and staff was very attentive as well as respectful of us when I was sleeping

There was condensation leaking from the ceiling of the cabin. A crew member said this was normal, would have been nice to know this ahead of time to reassure me that for a first-time overseas flier that this is normal.

MXP
LHR
Excellent 8.0

Flight was not to crowded

Seat are smaller than usual

Thu, Dec 28
BOS
ORD
3h 11m
Wed, Jan 3
ORD
BOS
2h 12m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jan 11
BOS
ORD
3h 03m
Tue, Jan 23
ORD
BOS
2h 11m
Trip: 13 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
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
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
Mediocre 2.0

Late flight delayed

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
Excellent 10.0

Overhead space limited

Fri, Jan 26
BOS
ORD
2h 51m
Sun, Jan 28
ORD
BOS
2h 14m
Trip: 3 days
6.6GoodShow reviews
Overall 6.6 Good
Based on 154 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
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.

BOS
ORD
Excellent 10.0

Competent, organized, pleasant and efficient staff, on time

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
Mediocre 2.0

Refund was prompt

Flight was canceled

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.

Wed, Jan 24
BOS
ORD
3h 03m
Sat, Jan 27
ORD
BOS
2h 15m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Mediocre 2.0

The plane had 2 wings

Staff is rude. Customer Service couldn't possibly be worst. All their food has meat in it. Staff is slow and incompetent. Never had a more dreadful experience with an airline. TAP IS THE WORST AIRLINE I HAVE EVER EXPERIENCED, and I fly 2 times a month.

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

BOS
ORD
Excellent 8.6

leg room & movie

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
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.

Thu, Mar 1
BOS
ORD
2h 53m
Tue, Mar 6
ORD
BOS
2h 13m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
BOS
ORD
2h 53m
Wed, Mar 7
ORD
BOS
2h 14m
Trip: 6 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 64 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
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
Okay 4.3

I was supposed to be there right now, but I'm still waiting in Chicago for my connecting flight to Dayton that was delayed.

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
Mediocre 2.0

I do not like that I am missed my flight and got stuck in a city without any re-embersement. I usually use United, but decided to use American Airlines this time. Sleeping in an airport tonight. Thanks.

BOS
ORD
Good 6.0

personal entertainment systems and charging plugs

only pretzels and no headphones offered for the entertainment systems.

Tue, Feb 6
BOS
ORD
3h 03m
Tue, Feb 20
ORD
BOS
2h 11m
Trip: 15 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Excellent 10.0

Overhead space limited

BOS
ORD
Mediocre 2.0

The plane had 2 wings

Staff is rude. Customer Service couldn't possibly be worst. All their food has meat in it. Staff is slow and incompetent. Never had a more dreadful experience with an airline. TAP IS THE WORST AIRLINE I HAVE EVER EXPERIENCED, and I fly 2 times a month.

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

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
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

Fri, Mar 9
BOS
ORD
11h 38m
Sun, Mar 11
ORD
BOS
10h 43m
Trip: 3 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 173 reviews
Overall
5.6
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
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
Okay 4.6

Arrived early

Plane was dirty

BOS
ORD
Mediocre 2.0

Cheap fare

Idiots cancelled the flight.

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.

Tue, Apr 24
BOS
ORD
3h 01m
Tue, May 1
ORD
BOS
2h 21m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Mediocre 2.0

The plane had 2 wings

Staff is rude. Customer Service couldn't possibly be worst. All their food has meat in it. Staff is slow and incompetent. Never had a more dreadful experience with an airline. TAP IS THE WORST AIRLINE I HAVE EVER EXPERIENCED, and I fly 2 times a month.

BOS
ORD
Mediocre 2.0

Late flight delayed

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
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 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.

Tue, May 1
BOS
ORD
2h 47m
Sat, May 5
ORD
BOS
2h 18m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Jan 26
BOS
ORD
3h 03m
Sun, Jan 28
ORD
BOS
2h 14m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
BOS
ORD
2h 46m
Mon, May 14
ORD
BOS
2h 18m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
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

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
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
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
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, Dec 19
BOS
ORD
3h 07m
Wed, Dec 20
ORD
BOS
2h 08m
Trip: 2 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 64 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
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

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

BOS
ORD
Good 6.0

personal entertainment systems and charging plugs

only pretzels and no headphones offered for the entertainment systems.

BOS
ORD
Mediocre 2.0

I do not like that I am missed my flight and got stuck in a city without any re-embersement. I usually use United, but decided to use American Airlines this time. Sleeping in an airport tonight. Thanks.

BOS
ORD
Okay 4.0

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

Fri, Mar 2
BOS
ORD
2h 56m
Wed, Mar 7
ORD
BOS
2h 15m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 24
BOS
ORD
3h 01m
Sat, Apr 28
ORD
BOS
2h 13m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Mediocre 2.0

Late flight delayed

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 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 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 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.

Sat, Dec 16
BOS
ORD
3h 04m
Tue, Dec 19
ORD
BOS
2h 15m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 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
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

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
Mediocre 2.0

Late flight delayed

Mon, Dec 18
BOS
ORD
3h 04m
Thu, Dec 21
ORD
BOS
2h 15m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 29 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
BOS
ORD
Excellent 8.6

leg room & movie

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 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
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
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

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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.