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

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare International

Sat 2/17
Sat 2/24
Any month
Compare vs. KAYAK |

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:
$248
(avg. price over the last 2 weeks)
Good Deal:
$159
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

Looking for a cheap flight? 25% of our users found flights on this route for $159 or less.
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 9% 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 608 (nonstop) flights between Boston Logan International and Chicago O'Hare International per week, averaging 91 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 Spirit Airlines ($99) 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 (16 times daily), American Airlines (12 times daily), ANA (8 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, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago O'Hare International back to Boston Logan International, the best deals are generally found on Wednesday, with Tuesday being the most expensive.

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

Airports
Origin
Boston
$99
only
$99
Destination
Chicago
$99
only
$99
Fri, Apr 20
BOS
ORD
2h 46m
Sat, Apr 28
ORD
BOS
2h 27m
Trip: 9 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

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
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 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
Okay 4.6

Arrived early

Plane was dirty

BOS
ORD
Mediocre 2.0

Cheap fare

Idiots cancelled the flight.

Thu, Feb 22
BOS
ORD
2h 53m
Sat, Mar 3
ORD
BOS
2h 14m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 21
BOS
ORD
2h 46m
Thu, Apr 26
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 4.6

Delayed flight and cancelled flight home

BOS
ORD
Good 7.3

on time

low comfort seats

BOS
ORD
Okay 4.6

Arrived early

Plane was dirty

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
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.

Mon, Apr 23
BOS
ORD
2h 46m
Sat, Apr 28
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
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 3.6

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

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 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
Okay 4.6

Delayed flight and cancelled flight home

Fri, Feb 23
BOS
ORD
2h 57m
Thu, Mar 1
ORD
BOS
2h 14m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 25
BOS
ORD
2h 46m
Mon, Apr 30
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
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
Okay 4.6

Delayed flight and cancelled flight home

BOS
ORD
Mediocre 2.0

Cheap fare

Idiots cancelled the flight.

BOS
ORD
Okay 4.6

Arrived early

Plane was dirty

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.

Sat, Feb 24
BOS
ORD
2h 57m
Fri, Mar 2
ORD
BOS
2h 14m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 26
BOS
ORD
2h 46m
Sat, Apr 28
ORD
BOS
2h 27m
Trip: 3 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
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

Delayed flight and cancelled flight home

BOS
ORD
Mediocre 3.6

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

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.

Sun, Feb 25
BOS
ORD
2h 53m
Thu, Mar 1
ORD
BOS
2h 14m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Apr 29
BOS
ORD
2h 46m
Sat, May 5
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
Mediocre 3.6

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

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
Okay 4.6

Arrived early

Plane was dirty

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 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

Mon, Feb 26
BOS
ORD
2h 54m
Thu, Mar 8
ORD
BOS
2h 14m
Trip: 11 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
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
Okay 4.6

Delayed flight and cancelled flight home

BOS
ORD
Okay 4.6

Arrived early

Plane was dirty

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 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, Feb 27
BOS
ORD
2h 50m
Thu, Mar 8
ORD
BOS
2h 14m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Mon, May 7
BOS
ORD
2h 46m
Thu, May 10
ORD
BOS
2h 27m
Trip: 4 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 3.3

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

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

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

Cheap fare

Idiots cancelled the flight.

Wed, Feb 28
BOS
ORD
2h 50m
Thu, Mar 8
ORD
BOS
2h 14m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 8
BOS
ORD
2h 46m
Tue, May 15
ORD
BOS
2h 27m
Trip: 8 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
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 2.0

Cheap fare

Idiots cancelled the flight.

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
Okay 4.6

Arrived early

Plane was dirty

Thu, Mar 1
BOS
ORD
2h 53m
Thu, Mar 8
ORD
BOS
2h 14m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 10
BOS
ORD
2h 46m
Sat, May 12
ORD
BOS
2h 27m
Trip: 3 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 4.6

Arrived early

Plane was dirty

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
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

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

Sat, Mar 3
BOS
ORD
3h 01m
Thu, Mar 8
ORD
BOS
2h 14m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, May 16
BOS
ORD
2h 46m
Thu, May 17
ORD
BOS
2h 27m
Trip: 2 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

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
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 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

on time

low comfort seats

BOS
ORD
Mediocre 3.6

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

Show more results

Boston Logan International to Chicago O'Hare International Flight Information

Avg. Flight Duration 2h 35m
Flights Arrive in Chicago O'Hare International
Flights Depart from Boston Logan International
Flight Price $99
Distance 864 miles
Airlines Spirit Airlines
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
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.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

^
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.