How often are flights from Chicago to Boston delayed?

Historically, on average around 23% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 149 minutes.

What is the most punctual flight time for Chicago to Boston flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon have, in the past, seen delays more frequently in comparison.

How many flights depart from Chicago to Boston on average per day?

As of February 2026, 44 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 07:00, with 45% of daily flights taking off at midday.

What is the cheapest airline that flies from Chicago to Boston Logan Intl?

JetBlue, Delta, and United Airlines are the most popular carriers operating from Chicago to Boston Logan Intl

Which airline has the best punctuality record on Chicago to Boston flights?

According to our data, JetBlue have had the fewest delays on this route over the last 12 months, with about 19% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Boston on average per week?

310 flights are operational weekly from Chicago to Boston as of February 2026. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?

Prices for flights from Chicago to Boston Logan Intl Airport were last updated today.

How old do you have to be to fly from Chicago to Boston Logan Intl Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.

What documentation or ID do you need to fly to Boston Logan Intl Airport?

The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

£46 Cheap Flights from Chicago to Boston in 2026

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10:00 - 13:20

ORD

BOS

2h 20mdirect

07:00 - 09:10

BOS

ORD

3h 10mdirect

£99JetBlue

Tue, 17 Feb - Thu, 19 Feb

21:26 - 00:59

ORD

BOS

2h 33mdirect

06:00 - 07:58

BOS

ORD

2h 58mdirect

£101United Airlines

Fri, 5 Jun - Sun, 7 Jun

16:20 - 19:42

ORD

BOS

2h 22mdirect

06:00 - 07:59

BOS

ORD

2h 59mdirect

£102United Airlines

Wed, 25 Mar - Sun, 29 Mar

07:30 - 10:50

ORD

BOS

2h 20mdirect

07:16 - 09:22

BOS

ORD

3h 06mdirect

£102United Airlines

Wed, 4 Mar - Sat, 7 Mar

18:20 - 21:48

ORD

BOS

2h 28mdirect

06:00 - 08:00

BOS

ORD

3h 00mdirect

£104United Airlines

Fri, 27 Feb - Tue, 3 Mar

06:04 - 14:16

ORD

BOS

7h 12m

1 stop

07:00 - 09:10

BOS

ORD

3h 10mdirect

£105JetBlue

Mon, 2 Mar - Mon, 9 Mar

12:44 - 19:58

ORD

BOS

6h 14m

1 stop

07:00 - 09:10

BOS

ORD

3h 10mdirect

£105JetBlue

Thu, 26 Feb - Mon, 2 Mar

19:35 - 23:02

ORD

BOS

2h 27mdirect

07:15 - 09:25

BOS

ORD

3h 10mdirect

£108Delta

Mon, 30 Mar - Thu, 2 Apr

10:00 - 13:20

ORD

BOS

2h 20mdirect

18:06 - 23:00

BOS

ORD

5h 54m

1 stop

£110JetBlue

Fri, 27 Feb - Sun, 8 Mar

06:00 - 09:25

ORD

BOS

2h 25mdirect

09:20 - 11:20

BOS

ORD

3h 00mdirect

£111United Airlines

Fri, 17 Apr - Wed, 22 Apr

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets

United Airlines

17 Feb

ORD07:30Chicago O'Hare Intl

2h 20m

BOS10:50Boston Logan Intl

18 Feb

BOS09:45Boston Logan Intl

3h 05m

ORD11:50Chicago O'Hare Intl

£99

United Airlines

5 Jun

ORD21:26Chicago O'Hare Intl

2h 33m

BOS00:59Boston Logan Intl

7 Jun

BOS06:00Boston Logan Intl

2h 58m

ORD07:58Chicago O'Hare Intl

£101

United Airlines

25 Mar

ORD16:20Chicago O'Hare Intl

2h 22m

BOS19:42Boston Logan Intl

29 Mar

BOS06:00Boston Logan Intl

2h 59m

ORD07:59Chicago O'Hare Intl

£102

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets

Delta

27 Mar

ORD07:00Chicago O'Hare Intl

2h 25m

BOS10:25Boston Logan Intl

7 Apr

BOS16:25Boston Logan Intl

3h 06m

ORD18:31Chicago O'Hare Intl

£105

Delta

6 Mar

ORD10:11Chicago O'Hare Intl

2h 24m

BOS13:35Boston Logan Intl

8 Mar

BOS07:25Boston Logan Intl

3h 10m

ORD09:35Chicago O'Hare Intl

£108

Delta

8 Jul

ORD07:00Chicago O'Hare Intl

2h 28m

BOS10:28Boston Logan Intl

11 Jul

BOS07:00Boston Logan Intl

2h 58m

ORD08:58Chicago O'Hare Intl

£115

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 17/2

10:00-13:20

Nonstop2h 20m

Boston Logan Intl

Thu 19/2

07:00-09:10

Nonstop3h 10m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/6

21:26-00:59

Nonstop2h 33m

Boston Logan Intl

Sun 7/6

06:00-07:58

Nonstop2h 58m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 25/3

16:20-19:42

Nonstop2h 22m

Boston Logan Intl

Sun 29/3

06:00-07:59

Nonstop2h 59m

£102

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/3

07:30-10:50

Nonstop2h 20m

Boston Logan Intl

Sat 7/3

07:16-09:22

Nonstop3h 06m

£102

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 27/2

18:20-21:48

Nonstop2h 28m

Boston Logan Intl

Tue 3/3

06:00-08:00

Nonstop3h 00m

£104

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 2/3

06:04-14:16

1 stop7h 12m

Boston Logan Intl

Mon 9/3

07:00-09:10

Nonstop3h 10m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 26/2

12:44-19:58

1 stop6h 14m

Boston Logan Intl

Mon 2/3

07:00-09:10

Nonstop3h 10m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 30/3

19:35-23:02

Nonstop2h 27m

Boston Logan Intl

Thu 2/4

07:15-09:25

Nonstop3h 10m

£108

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 27/2

10:00-13:20

Nonstop2h 20m

Boston Logan Intl

Sun 8/3

18:06-23:00

1 stop5h 54m

£110

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 17/4

06:00-09:25

Nonstop2h 25m

Boston Logan Intl

Wed 22/4

09:20-11:20

Nonstop3h 00m

£111

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How to get the cheapest flight ticket from Chicago to Boston

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Boston?

In general, January is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around £152. The month of September is another great option to travel to Boston, with average flight prices from Chicago averaging around £152.

What is the cheapest day to depart on your flight to Boston?

The cheapest day to depart on your flight to Boston is on a Sunday when prices can be found for as low as £127. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around £659. These prices are subject to change though, so be sure to set up a Price Alert for flights to Boston.

What is the cheapest time of day to depart on your flight to Boston?

Our most recent data shows that the best time of day to fly to Boston is in the morning. Flights from Chicago to Boston during this time can be as low as £248. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around £451 per ticket.

What is the cheapest Chicago to Boston Logan Intl flight route?

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston Logan Intl flight prices

How far in advance should I book a flight to Boston?

You are more likely to see cheaper flights to Boston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around £168 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as £138 on momondo.

What cabin class options are available on Chicago to Boston Logan Intl flights?

There are 4 cabin classes available to choose from on Chicago to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Boston flight prices changed over time?

As of February 2026, prices for Chicago to Boston flights are approximately 8% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Boston

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Boston according to our flight data. Find out which month and days have the cheapest flights.

Estimated return price

Cheap Chicago to Boston (CHI to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston

Best price found	£54
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Boston	1 airport

The best one-way flight to Boston from Chicago in the past 72 hours is £54. The best return flight deal from Chicago to Boston found on momondo in the last 72 hours is £127.

The fastest flight from Chicago to Boston takes 2h 24m

Direct flights go from Chicago to Boston every day.

There is 1 airport in Boston. From Chicago there are direct flights to Boston Logan Intl (BOS).

Search flight deals

How far is Chicago to Boston Logan Intl by plane?
Chicago and Boston Logan Intl are 847.9 mi apart from one another. Flights usually cover this in 2h 24m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?
Prices for flights from Chicago to Boston Logan Intl Airport were last updated today.
How old do you have to be to fly from Chicago to Boston Logan Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.
What documentation or ID do you need to fly to Boston Logan Intl Airport?
The travel and health documents you'll need for your trip to Boston Logan Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Boston Logan Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Boston?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Boston is Boeing 737-800, representing 20.96% of all bookings. The subsequent popular models are Embraer 175 at 17.19%, Airbus A220-300 at 9.56%, and Boeing 737 MAX 9 at 9.28%.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Boston?

Finding the right flight to Boston from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Boston quick and easy, saving you time and money.

Can I find flights from Chicago to Boston with flexible booking policies on momondo?

momondo does allow users to show only those flights to Boston from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Boston?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Boston.

I’m not ready to book a flight from Chicago to Boston right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Boston, momondo offers a useful price alert feature which will track prices for flights to Boston from Chicago and alert you when they change.

An easier way to manage your Boston trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

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Cheap flights from Chicago to Boston from £50

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 13/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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How to get the cheapest flight ticket from Chicago to Boston

What is the cheapest month to fly to Boston?

What is the cheapest day to depart on your flight to Boston?

What is the cheapest time of day to depart on your flight to Boston?

Our most recent data shows that the best time of day to fly to Boston is in the morning. Flights from Chicago to Boston during this time can be as low as £248. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around £451 per ticket.

What is the cheapest Chicago to Boston Logan Intl flight route?

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago - Boston Logan Intl flight prices

How far in advance should I book a flight to Boston?

What cabin class options are available on Chicago to Boston Logan Intl flights?

There are 4 cabin classes available to choose from on Chicago to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Boston flight prices changed over time?

As of February 2026, prices for Chicago to Boston flights are approximately 8% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Boston Logan Intl?

JetBlue, Delta, and United Airlines are the most popular carriers operating from Chicago to Boston Logan Intl

How often are flights from Chicago to Boston delayed?

Historically, on average around 23% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 149 minutes.

What is the most punctual flight time for Chicago to Boston flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to Boston flights?

According to our data, JetBlue have had the fewest delays on this route over the last 12 months, with about 19% of their flights experiencing any sort of delay.

How many flights depart from Chicago to Boston on average per day?

As of February 2026, 44 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 07:00, with 45% of daily flights taking off at midday.

How many flights depart from Chicago to Boston on average per week?

310 flights are operational weekly from Chicago to Boston as of February 2026. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.

When to book flights from Chicago to Boston

Cheap Chicago to Boston (CHI to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston

Best price found

Fastest flight time

Direct flights

Airports in Boston

How far is Chicago to Boston Logan Intl by plane?

When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?

How old do you have to be to fly from Chicago to Boston Logan Intl Airport?

What documentation or ID do you need to fly to Boston Logan Intl Airport?

What is the most popular plane model from Chicago to Boston?

Travelling to a place near Boston?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Boston?

Can I find flights from Chicago to Boston with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Boston?

I’m not ready to book a flight from Chicago to Boston right now. Can momondo alert me if prices change?

An easier way to manage your Boston trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Massachusetts

Cabin classes currently available on flights to Boston

List of cabin classes available on flights landing in Boston. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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