Find Cheap Flights from Boston Logan International to Chicago (BOS - CHI)

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Fri 2/23
Fri 3/2
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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
10%
expected price increase
Average Price:
$533
(avg. price over the last 2 weeks)
Good Deal:
$301
or less (round trip)

When to Book Flights from Boston Logan International to Chicago

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 $300 or less.
The cheapest flight from Boston Logan International to Chicago was found 84 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 6% 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 Flights

How long does a flight from Boston Logan International to Chicago take?
An average nonstop flight takes 2h 42m, covering a distance of 851 miles.
How many flights are there between Boston Logan International and Chicago?
There are 615 (nonstop) flights between Boston Logan International and Chicago per week, averaging 91 per day.
Which airlines provide the cheapest flights from Boston Logan International to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Spirit Airlines ($99), Multiple Airlines ($119) and JetBlue ($119).
Do I need a passport to fly between Boston Logan International and Chicago?
No.
Which airlines fly most frequently between Boston Logan International and Chicago?
United (15 times daily), American Airlines (11 times daily), Alaska Airlines (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?
For Boston Logan International to Chicago, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to Boston Logan International, the best deals are generally found on Thursday, with Wednesday being the most expensive.

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

Airports
Origin
Boston
$99
only
$99
Destination
Chicago
$99
only
$99
$184
only
$184
Mon, Apr 23
BOS
ORD
2h 46m
Thu, May 17
ORD
BOS
2h 27m
Trip: 25 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 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
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

Sun, Mar 4
BOS
ORD
2h 58m
Tue, Mar 6
ORD
BOS
2h 16m
Trip: 3 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
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 9.6

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

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.

Tue, Aug 21
BOS
ORD
2h 53m
Wed, Sep 5
ORD
BOS
2h 21m
Trip: 16 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
Excellent 9.0

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

BOS
ORD
Mediocre 2.0

Terrible flight!

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
Mediocre 2.0

Refund was prompt

Flight was canceled

BOS
ORD
Excellent 10.0

Relatively short TSA, arrived at gate just as Group 1 was boarding, hopped in my seat, and enjoyed a quick, easy flight with a surprisingly good lunch of paella, salad, and torte. Very tasty. Service was great. Nice route.

It was a 737-300 so a bit dated of an aircraft, but it was - at least - clean.

Thu, Mar 1
BOS
MDW
6h 35m
Fri, Mar 2
MDW
BOS
3h 30m
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
EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

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.

SLC
YYZ
Excellent 8.0

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

JFK
CDG
Excellent 10.0

The food and the service

Tue, May 8
BOS
ORD
2h 46m
Thu, May 10
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
Mediocre 2.0

Cheap fare

Idiots cancelled the flight.

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
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
Okay 4.6

Delayed flight and cancelled flight home

Fri, Mar 23
BOS
ORD
2h 58m
Tue, Mar 27
ORD
BOS
2h 12m
Trip: 5 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
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

Cheap fare

Idiots cancelled the flight.

BOS
ORD
Okay 4.6

Delayed flight and cancelled flight home

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

on time

low comfort seats

Sun, Jun 3
BOS
ORD
2h 55m
Tue, Jun 12
ORD
BOS
2h 21m
Trip: 10 days
Overall 0.0 Poor
Based on 0 reviews
Tue, May 1
BOS
ORD
2h 46m
Wed, May 2
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
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

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

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

Arrived early

Plane was dirty

BOS
ORD
Mediocre 3.3

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

Wed, Jun 6
BOS
ORD
2h 49m
Tue, Jun 12
ORD
BOS
2h 21m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
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
Mediocre 2.0

Nothing

Delays, very bad customer service

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
Excellent 10.0

Relatively short TSA, arrived at gate just as Group 1 was boarding, hopped in my seat, and enjoyed a quick, easy flight with a surprisingly good lunch of paella, salad, and torte. Very tasty. Service was great. Nice route.

It was a 737-300 so a bit dated of an aircraft, but it was - at least - clean.

BOS
ORD
Okay 4.6

Long delay.

BOS
ORD
Excellent 10.0

Competent, organized, pleasant and efficient staff, on time

Tue, Jul 3
BOS
ORD
2h 53m
Tue, Jul 10
ORD
BOS
2h 17m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 26
BOS
ORD
2h 46m
Sun, Apr 29
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 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 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
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

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
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
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 9.0

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 6.6

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.

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
Sat, May 12
BOS
ORD
2h 46m
Mon, May 14
ORD
BOS
7h 51m
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
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
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
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, Apr 3
BOS
MDW
6h 36m
Fri, Apr 6
MDW
BOS
5h 11m
Trip: 4 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.

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

SLC
YYZ
Excellent 8.0

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

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

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
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

BOS
LGA
Mediocre 2.0

We were in the plane for 3 hours before we could depart. No one offered us a drink or snack.

FLL
DTW
Excellent 10.0

I like service

DEN
JFK
Good 6.3

Comfortable seats. Good entertainment

Going to Denver was delayed and now return trip delayed We were give 3 separate reasons. Poor communication. Just telling me a flight will be delayed is not communication. Lack of a free snack was disappointing. May have to rethink flying Delta next time.

SLC
YYZ
Excellent 8.0

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

Wed, May 2
BOS
MDW
3h 59m
Tue, May 8
MDW
BOS
4h 59m
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
JFK
CDG
Excellent 10.0

The food and the service

ATL
TGU
Mediocre 2.0

The service was horribly they dilate my flight 24 hours and I lose my flight yesterday because from Washington to Atlanta the flight was late and from Atlanta to Tegucigalpa leave early

EWR
DTW
Mediocre 3.3

I've always wanted to go to all five Manhattan boroughs in one day. Thanks to Delta, that happened.

The plane broke down as we were about to take off. Delta rebooked everyone on to new flights because it was pretty obvious that plane was not going to be fixed in time. The crew did their best given the situation. The situation was absolute bs though - we had to take a cab to JFK for our new flight and do the whole security thing again and all that annoying stuff. Thanks for wasting 8 hours of my life, Delta.

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

FLL
DTW
Excellent 10.0

I like service

Show more results

Boston Logan International to Chicago Flight Information

Avg. Flight Duration 2h 36m
Flights Arrive in Chicago
Flights Depart from Boston Logan International
Flight Price $99
Distance 851 miles
Airlines Spirit Airlines, JetBlue, United, Delta
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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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.