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 19% of their flights experiencing any sort of delay.

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. Sunday has historically seen more delays on average compared to the rest of the week.

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 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 6 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?

United Airlines is the most popular carrier operating from Chicago O'Hare Intl 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 153 minutes.

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 January 2026, there are 6 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.

$64 Cheap Flights from Chicago O'Hare Intl Airport to Boston in 2026

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

As of January 2026, there are 264 flights per week flying from Chicago O'Hare Intl Airport to Boston. The most common day of the week flights depart is Thu, with 20% of flights taking off on this day.

Q: What is the typical price of a round-trip flight between Chicago O'Hare Intl Airport and Boston?

Prices are currently low for flights on this route. Typical prices usually range from $137 to $297. The lowest price recently found on this route was $132.

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Find the cheapest flights from Chicago O'Hare Intl Airport to Boston

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:55 am - 12:21 pm

ORD

BOS

2h 26mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$132JetBlue

Mon, Feb 2 - Mon, Feb 2

7:40 am - 11:05 am

ORD

BOS

2h 25mnonstop

6:00 am - 1:58 pm

BOS

ORD

8h 58m

1 stop

$133Multiple Airlines

Sat, Jan 31 - Tue, Feb 3

4:42 pm - 12:29 am

ORD

BOS

6h 47m

1 stop

11:31 am - 11:47 pm

BOS

ORD

13h 16m

1 stop

$134Multiple Airlines

Sat, Feb 14 - Wed, Feb 18

2:00 pm - 5:24 pm

ORD

BOS

2h 24mnonstop

4:16 pm - 6:16 pm

BOS

ORD

3h 00mnonstop

$135United Airlines

Sat, Jan 31 - Fri, Feb 6

1:25 pm - 4:43 pm

ORD

BOS

2h 18mnonstop

7:00 am - 9:05 am

BOS

ORD

3h 05mnonstop

$136American Airlines

Fri, Jan 30 - Sun, Feb 1

7:05 am - 10:40 am

ORD

BOS

2h 35mnonstop

7:30 am - 9:41 am

BOS

ORD

3h 11mnonstop

$137Delta

Thu, Feb 5 - Sun, Feb 8

7:40 am - 11:05 am

ORD

BOS

2h 25mnonstop

3:20 pm - 5:25 pm

BOS

ORD

3h 05mnonstop

$138JetBlue

Sat, Jan 31 - Sun, Feb 1

10:48 am - 11:19 pm

ORD

BOS

11h 31m

1 stop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$139Multiple Airlines

Tue, Feb 3 - Wed, Feb 4

8:45 pm - 11:59 pm

ORD

BOS

2h 14mnonstop

6:30 am - 8:41 am

BOS

ORD

3h 11mnonstop

$140American Airlines

Mon, Feb 16 - Wed, Feb 18

7:05 am - 10:37 am

ORD

BOS

2h 32mnonstop

7:15 am - 9:28 am

BOS

ORD

3h 13mnonstop

$141Delta

Mon, Feb 16 - Sun, Feb 22

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

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

United Airlines

Jan 31

ORD2:00 pmChicago O'Hare Intl

2h 24m

BOS5:24 pmBoston Logan Intl

Feb 6

BOS4:16 pmBoston Logan Intl

3h 00m

ORD6:16 pmChicago O'Hare Intl

$135

United Airlines

Feb 28

ORD9:17 amChicago O'Hare Intl

2h 29m

BOS12:46 pmBoston Logan Intl

Mar 1

BOS7:45 amBoston Logan Intl

3h 05m

ORD9:50 amChicago O'Hare Intl

$152

United Airlines

Mar 14

ORD6:15 pmChicago O'Hare Intl

2h 28m

BOS9:43 pmBoston Logan Intl

Mar 19

BOS7:16 amBoston Logan Intl

3h 06m

ORD9:22 amChicago O'Hare Intl

$163

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

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

American Airlines

Jan 30

ORD1:25 pmChicago O'Hare Intl

2h 18m

BOS4:43 pmBoston Logan Intl

Feb 1

BOS7:00 amBoston Logan Intl

3h 05m

ORD9:05 amChicago O'Hare Intl

$136

American Airlines

Jan 22

ORD1:25 pmChicago O'Hare Intl

2h 18m

BOS4:43 pmBoston Logan Intl

Jan 25

BOS7:00 amBoston Logan Intl

3h 05m

ORD9:05 amChicago O'Hare Intl

$137

American Airlines

Feb 16

ORD8:45 pmChicago O'Hare Intl

2h 14m

BOS11:59 pmBoston Logan Intl

Feb 18

BOS6:30 amBoston Logan Intl

3h 11m

ORD8:41 amChicago O'Hare Intl

$140

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

Mon 2/2

8:55 am-12:21 pm

Nonstop2h 26m

Boston Logan Intl

Mon 2/2

3:35 pm-5:43 pm

Nonstop3h 08m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

Tue 2/3

6:00 am-1:58 pm

1 stop8h 58m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/14

4:42 pm-12:29 am

1 stop6h 47m

Boston Logan Intl

Wed 2/18

11:31 am-11:47 pm

1 stop13h 16m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

2:00 pm-5:24 pm

Nonstop2h 24m

Boston Logan Intl

Fri 2/6

4:16 pm-6:16 pm

Nonstop3h 00m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/30

1:25 pm-4:43 pm

Nonstop2h 18m

Boston Logan Intl

Sun 2/1

7:00 am-9:05 am

Nonstop3h 05m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/5

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sun 2/8

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/1

3:20 pm-5:25 pm

Nonstop3h 05m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/3

10:48 am-11:19 pm

1 stop11h 31m

Boston Logan Intl

Wed 2/4

3:35 pm-5:43 pm

Nonstop3h 08m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 2/16

8:45 pm-11:59 pm

Nonstop2h 14m

Boston Logan Intl

Wed 2/18

6:30 am-8:41 am

Nonstop3h 11m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 2/16

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

Sun 2/22

7:15 am-9:28 am

Nonstop3h 13m

$141

Flights are sorted by cheapest round-trip flights first.

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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Boston?

What is the cheapest month to fly to Boston?

In general, September 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 September, then book flights to Boston from Chicago O'Hare Intl Airport during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $207.

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 $236. 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 $298.

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 $214. 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 $290 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 $229 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 $187 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 January 2026, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 26% 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	$88
Fastest flight time	2h 15m
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 $88. The best round-trip flight deal from Chicago O'Hare Intl Airport to Boston found on momondo in the last 72 hours is $171.

The fastest flight from Chicago O'Hare Intl Airport to Boston takes 2h 15m

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 15m 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 January 2026, there are 6 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 22.81% of the total bookings. Other popular models include Embraer 175 with 15.41%, Boeing 737-900 with 11.50%, and Airbus A220-300 with 10.09%.
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 35%, 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 $62	Free Cancellation	Rating 7.2 2,887 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $79	Free Cancellation	Rating 6.3 8,319 reviews	Search Spirit Airlines flights
Delta	PriceFrom $92	Free Cancellation	Rating 7.9 8,048 reviews	Search Delta flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,163 reviews	Search United Airlines flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,129 reviews	Search American Airlines flights
Southwest	PriceFrom $144	Free Cancellation	Rating 8.0 4,258 reviews	Search Southwest flights

Delta Flights From Chicago O'Hare Intl Airport to Boston
Across 7 Delta flights from Chicago O'Hare Intl Airport to Boston this week, the average price was $216, with the best Delta deals starting from $92 round-trip. 8,048 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 $255. United Airlines operates 25 flights to Boston from Chicago O'Hare Intl Airport in an average week. Users have rated it 7.4/10 across 9,163 reviews.

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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 $64

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Find the cheapest flights from Chicago O'Hare Intl Airport to Boston

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

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

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

See travel insights to Boston from

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

What is the typical price of a round-trip flight between Chicago O'Hare Intl Airport and 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 January 2026, prices for Chicago O'Hare Intl Airport to Boston flights are approximately 26% 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?

United Airlines is the most popular carrier 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 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 153 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. 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 least number of 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 O'Hare Intl Airport to Boston on average per day?

37 flights are operational daily from Chicago O'Hare Intl Airport to Boston as of January 2026. The most popular departure time for this route is 7:00AM, with 55% 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 January 2026, there are 264 flights per week flying from Chicago O'Hare Intl Airport to Boston. The most common day of the week flights depart is Thu, with 20% 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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