How often are flights from Chicago to Boston delayed?

Historically, on average around 22% 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 152 minutes.

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

According to our data, JetBlue have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

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

Generally, flights departing in the morning tend to experience fewer delays. Flights 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 which experiences the fewest number of delays on this flight route. Thursday has historically seen more delays on average compared to the rest of the week.

What airlines fly to Boston?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

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

Delta and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Boston Logan Intl

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

Prices for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport are updated daily.

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?

As of December 2025, there are 7 operators available to choose from for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Boston Logan Intl Airport.

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

The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$62 Cheap Flights from Chicago O'Hare Intl Airport to Boston in 2025/26

Q: How many flights depart from Chicago O'Hare Intl Airport to Boston on average per day?

23 flights are operational daily from Chicago O'Hare Intl Airport to Boston as of December 2025. The most popular departure time for this route is 11:00AM, with 49% of flights per day taking off at noon.

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7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$120JetBlue

Thu, Jan 29 - Thu, Feb 5

6:05 am - 2:38 pm

ORD

BOS

7h 33m1 stop

5:23 pm - 8:18 am

BOS

ORD

15h 55m1 stop

$124Spirit Airlines

Wed, Jan 28 - Wed, Jan 28

5:57 pm - 1:13 am

ORD

BOS

6h 16m1 stop

5:23 pm - 8:18 am

BOS

ORD

15h 55m1 stop

$125Multiple Airlines

Wed, Jan 14 - Wed, Jan 21

9:23 am - 4:19 pm

ORD

BOS

29h 56m1 stop

12:10 pm - 7:41 pm

BOS

ORD

8h 31m1 stop

$126Multiple Airlines

Tue, Jan 13 - Thu, Jan 15

7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$127JetBlue

Sat, Jan 17 - Tue, Jan 20

7:05 am - 10:40 am

ORD

BOS

2h 35mnonstop

7:30 am - 9:41 am

BOS

ORD

3h 11mnonstop

$128Delta

Sat, Jan 17 - Sun, Jan 18

5:25 pm - 8:45 pm

ORD

BOS

2h 20mnonstop

7:00 am - 9:05 am

BOS

ORD

3h 05mnonstop

$129American Airlines

Sat, Jan 17 - Sun, Jan 18

7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$130JetBlue

Tue, Jan 20 - Fri, Jan 23

9:23 am - 4:19 pm

ORD

BOS

29h 56m1 stop

5:34 am - 10:36 pm

BOS

ORD

18h 02m1 stop

$131Multiple Airlines

Tue, Jan 20 - Thu, Jan 29

7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$132JetBlue

Tue, Jan 20 - Fri, Jan 23

Spirit Airlines flights from Chicago O'Hare Intl Airport to Boston

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Boston flight tickets

Spirit Airlines

Jan 28

ORD6:05 amChicago O'Hare Intl

7h 33m

1 stop

BOS2:38 pmBoston Logan Intl

Jan 28

BOS5:23 pmBoston Logan Intl

15h 55m

1 stop

ORD8:18 amChicago O'Hare Intl

$124

Find similar

Spirit Airlines

Jan 20

ORD9:23 amChicago O'Hare Intl

29h 56m

1 stop

BOS4:19 pmBoston Logan Intl

Jan 23

BOS3:43 pmBoston Logan Intl

27h 09m

1 stop

ORD5:52 pmChicago O'Hare Intl

$140

Find similar

Spirit Airlines

Jan 17

ORD12:44 pmChicago O'Hare Intl

9h 35m

1 stop

BOS11:19 pmBoston Logan Intl

Jan 18

BOS7:00 amBoston Logan Intl

13h 41m

1 stop

ORD7:41 pmChicago O'Hare Intl

$154

Find similar

JetBlue flights from Chicago O'Hare Intl Airport to Boston

Our best JetBlue deals on Chicago O'Hare Intl Airport to Boston flight tickets

JetBlue

Jan 29

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Feb 5

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$120

Find similar

JetBlue

Jan 17

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Jan 20

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$125

Find similar

JetBlue

Jan 17

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Jan 20

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$127

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/29

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Thu 2/5

3:35 pm-5:43 pm

Nonstop3h 08m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/28

6:05 am-2:38 pm

1 stop7h 33m

Boston Logan Intl

Wed 1/28

5:23 pm-8:18 am

1 stop15h 55m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/14

5:57 pm-1:13 am

1 stop6h 16m

Boston Logan Intl

Wed 1/21

5:23 pm-8:18 am

1 stop15h 55m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/13

9:23 am-4:19 pm

1 stop29h 56m

Boston Logan Intl

Thu 1/15

12:10 pm-7:41 pm

1 stop8h 31m

$126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

5:25 pm-8:45 pm

Nonstop2h 20m

Boston Logan Intl

Sun 1/18

7:00 am-9:05 am

Nonstop3h 05m

$129

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Fri 1/23

3:35 pm-5:43 pm

Nonstop3h 08m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

9:23 am-4:19 pm

1 stop29h 56m

Boston Logan Intl

Thu 1/29

5:34 am-10:36 pm

1 stop18h 02m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Fri 1/23

3:35 pm-5:43 pm

Nonstop3h 08m

$132

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $192. If you aren’t able to travel during the month of January, then book flights to Boston from Chicago O'Hare Intl Airport during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $192.

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

The cheapest day to depart from Chicago O'Hare Intl Airport to Boston is on a Wednesday when prices can be found for as low as $240. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $299.

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

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago O'Hare Intl Airport to Boston in the evening for as low as $217. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $299 per ticket.

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

Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago O'Hare Intl Airport for as low as $183 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Boston flight prices changed over time?

As of December 2025, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 12% cheaper when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to Boston

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

Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Boston (ORD to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Boston

Best Price Found	$103
Fastest flight time	2h 21m
Direct flights	Every day
Airports in Boston	1 airport

The best one-way flight to Boston from Chicago O'Hare Intl Airport in the past 72 hours is $103. The best round-trip flight deal from Chicago O'Hare Intl Airport to Boston found on momondo in the last 72 hours is $187.

The fastest flight from Chicago O'Hare Intl Airport to Boston takes 2h 21m

Direct flights go from Chicago O'Hare Intl Airport to Boston every day.

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

Search flight deals

How far is Chicago O'Hare Intl to Boston Logan Intl by plane?
A flight from Chicago O'Hare Intl to Boston Logan Intl will travel around 861.0 mi. 2h 21m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?
Prices for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?
As of December 2025, there are 7 operators available to choose from for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Boston Logan Intl Airport.
What documentation or ID do you need to fly to Boston Logan Intl Airport?
The required travel and health documents for your Boston Logan Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Boston Logan Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Boston?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Boston, the leading plane model is Boeing 737-800, making up 23.86% of the total bookings. Other popular models include Embraer 175 with 13.71%, Boeing 737-900 with 13.13%, and Airbus A220-300 with 10.65%.
What is the most popular airline from Chicago O'Hare Intl Airport to Boston?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Boston, the leading airline is American Airlines, making up 35% of the total bookings. Other popular airlines include United Airlines with 34%, Delta with 18%, and JetBlue with 11%.

Best airlines flying from Chicago O'Hare Intl Airport to Boston

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Boston with momondo

Airline	Rating	Free Cancellation	Price
JetBlue	PriceFrom $78	Free Cancellation	Rating 7.2 2,895 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $83	Free Cancellation	Rating 6.3 8,188 reviews	Search Spirit Airlines flights
Delta	PriceFrom $104	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
Frontier	PriceFrom $104	Free Cancellation	Rating 5.8 3,082 reviews	Search Frontier flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,049 reviews	Search American Airlines flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Southwest	PriceFrom $144	Free Cancellation	Rating 7.9 4,249 reviews	Search Southwest flights

Delta Flights From Chicago O'Hare Intl Airport to Boston
Across 11 Delta flights from Chicago O'Hare Intl Airport to Boston this week, the average price was $226, with the best Delta deals starting from $104 round-trip. 8,007 users have rated Delta on momondo, with an average score of 7.9/10.
United Airlines Flights From Chicago O'Hare Intl Airport to Boston
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago O'Hare Intl Airport to Boston start from as low as $117 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $261. United Airlines operates 10 flights to Boston from Chicago O'Hare Intl Airport in an average week. Users have rated it 7.4/10 across 9,092 reviews.

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Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Boston. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Boston from Chicago with this policy.

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

Once you have performed a search for Chicago to Boston flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Boston from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Boston trip

We make it super easy to schedule, organize 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 O'Hare Intl Airport to Boston from $62

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Spirit Airlines flights from Chicago O'Hare Intl Airport to Boston

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See travel insights to Boston from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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?

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

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

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

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Boston flight prices changed over time?

As of December 2025, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 12% cheaper when compared to flights at the same time last year.

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

Delta and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Boston Logan Intl

What airlines fly to Boston?

How often are flights from Chicago to Boston delayed?

Historically, on average around 22% 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 152 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 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 which experiences the fewest number of delays on this flight route. Thursday 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 least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

How many flights depart from Chicago O'Hare Intl Airport to Boston on average per day?

23 flights are operational daily from Chicago O'Hare Intl Airport to Boston as of December 2025. The most popular departure time for this route is 11:00AM, with 49% of flights per day taking off at noon.

How many flights depart from Chicago O'Hare Intl Airport to Boston on average per week?

As of December 2025, there are 161 flights per week flying from Chicago O'Hare Intl Airport to Boston. The most common day of the week flights depart is Wed, with 35% of flights taking off on this day.

When to book flights from Chicago O'Hare Intl Airport to Boston

Cheap Chicago O'Hare Intl Airport to Boston (ORD to BOS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Boston

Best Price Found

Fastest flight time

Direct flights

Airports in Boston

How far is Chicago O'Hare Intl to Boston Logan Intl by plane?

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

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Boston Logan Intl Airport?

How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Boston?

What is the most popular airline from Chicago O'Hare Intl Airport to Boston?

Best airlines flying from Chicago O'Hare Intl Airport to Boston

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Boston with momondo

Delta Flights From Chicago O'Hare Intl Airport to Boston

United Airlines Flights From Chicago O'Hare Intl Airport to Boston

Traveling 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, organize 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

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