How often are flights from Boston to Chicago delayed?

Historically, on average around 12% of flights between Boston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 167 minutes.

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

226 flights are operational weekly from Boston to Chicago O'Hare Intl Airport as of October 2025. The most popular departure day for this route is Wed, with 24% of flights per week taking off on this day.

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

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

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

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

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

As of October 2025, there are 32 flights per day flying from Boston to Chicago O'Hare Intl Airport. The most common time of day flights depart is 16:00, with 48% of flights taking off in the afternoon.

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

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

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

According to our data, Air Canada have had the fewest delays on this route over the last 12 months, with no flights being classified as delayed.

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

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

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

There are 2 operators available for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport as of October 2025.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The travel and health documents you'll need for your trip to Chicago O'Hare 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 Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

₹ 5,119 Cheap Flights from Boston to Chicago O'Hare Intl Airport in 2025/26

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16:05 - 18:02BOS-ORD

2h 57mdirect

07:10 - 10:36ORD-BOS

2h 26mdirect

₹ 10,414Delta

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Thu, 4 Dec - Sun, 7 Dec

16:05 - 18:02BOS-ORD

2h 57mdirect

07:10 - 10:36ORD-BOS

2h 26mdirect

₹ 10,502Delta

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Thu, 4 Dec - Sun, 7 Dec

10:40 - 12:40BOS-ORD

3h 00mdirect

07:30 - 10:49ORD-BOS

2h 19mdirect

₹ 10,767United Airlines

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Mon, 17 Nov - Thu, 19 Feb

12:50 - 14:47BOS-ORD

2h 57mdirect

10:35 - 13:59ORD-BOS

2h 24mdirect

₹ 10,943Delta

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Thu, 11 Dec - Thu, 18 Dec

18:23 - 20:23BOS-ORD

3h 00mdirect

09:20 - 12:44ORD-BOS

2h 24mdirect

₹ 11,208United Airlines

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Sat, 8 Nov - Tue, 11 Nov

07:30 - 09:33BOS-ORD

3h 03mdirect

07:10 - 10:36ORD-BOS

2h 26mdirect

₹ 11,385Delta

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Thu, 4 Dec - Sun, 7 Dec

15:55 - 17:55BOS-ORD

3h 00mdirect

11:20 - 14:44ORD-BOS

2h 24mdirect

₹ 11,473JetBlue

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Mon, 10 Nov - Thu, 13 Nov

15:35 - 17:44BOS-ORD

3h 09mdirect

10:45 - 14:09ORD-BOS

2h 24mdirect

₹ 11,649JetBlue

Find Deal

Thu, 15 Jan - Tue, 20 Jan

05:00 - 12:15BOS-ORD

8h 15m1 stop

13:45 - 21:45ORD-BOS

7h 00m1 stop

₹ 14,473Southwest

Find Deal

Fri, 16 Jan - Mon, 26 Jan

05:00 - 12:15BOS-ORD

8h 15m1 stop

13:45 - 23:15ORD-BOS

8h 30m1 stop

₹ 15,179Southwest

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Mon, 10 Nov - Mon, 10 Nov

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

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

United Airlines

17 Nov

BOS10:40Boston Logan Intl

3h 00m

ORD12:40Chicago O'Hare Intl

19 Feb

ORD07:30Chicago O'Hare Intl

2h 19m

BOS10:49Boston Logan Intl

₹ 10,767

Find similar

United Airlines

8 Nov

BOS18:23Boston Logan Intl

3h 00m

ORD20:23Chicago O'Hare Intl

11 Nov

ORD09:20Chicago O'Hare Intl

2h 24m

BOS12:44Boston Logan Intl

₹ 11,208

Find similar

United Airlines

5 Dec

BOS06:00Boston Logan Intl

3h 00m

ORD08:00Chicago O'Hare Intl

7 Dec

ORD07:30Chicago O'Hare Intl

2h 19m

BOS10:49Boston Logan Intl

₹ 11,561

Find similar

Delta flights from Boston to Chicago O'Hare Intl Airport

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

Delta

4 Dec

BOS16:05Boston Logan Intl

2h 57m

ORD18:02Chicago O'Hare Intl

7 Dec

ORD07:10Chicago O'Hare Intl

2h 26m

BOS10:36Boston Logan Intl

₹ 10,414

Find similar

Delta

4 Dec

BOS16:05Boston Logan Intl

2h 57m

ORD18:02Chicago O'Hare Intl

7 Dec

ORD07:10Chicago O'Hare Intl

2h 26m

BOS10:36Boston Logan Intl

₹ 10,502

Find similar

Delta

11 Dec

BOS16:05Boston Logan Intl

2h 57m

ORD18:02Chicago O'Hare Intl

18 Dec

ORD07:10Chicago O'Hare Intl

2h 26m

BOS10:36Boston Logan Intl

₹ 10,943

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

16:05-18:02

Nonstop2h 57m

Chicago O'Hare Intl

Sun 7/12

07:10-10:36

Nonstop2h 26m

₹ 10,414

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

16:05-18:02

Nonstop2h 57m

Chicago O'Hare Intl

Sun 7/12

07:10-10:36

Nonstop2h 26m

₹ 10,502

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 17/11

10:40-12:40

Nonstop3h 00m

Chicago O'Hare Intl

Thu 19/2

07:30-10:49

Nonstop2h 19m

₹ 10,767

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/12

12:50-14:47

Nonstop2h 57m

Chicago O'Hare Intl

Thu 18/12

10:35-13:59

Nonstop2h 24m

₹ 10,943

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/11

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Tue 11/11

09:20-12:44

Nonstop2h 24m

₹ 11,208

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

07:30-09:33

Nonstop3h 03m

Chicago O'Hare Intl

Sun 7/12

07:10-10:36

Nonstop2h 26m

₹ 11,385

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/11

15:55-17:55

Nonstop3h 00m

Chicago O'Hare Intl

Thu 13/11

11:20-14:44

Nonstop2h 24m

₹ 11,473

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 15/1

15:35-17:44

Nonstop3h 09m

Chicago O'Hare Intl

Tue 20/1

10:45-14:09

Nonstop2h 24m

₹ 11,649

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 16/1

05:00-12:15

1 stop8h 15m

Chicago O'Hare Intl

Mon 26/1

13:45-21:45

1 stop7h 00m

₹ 14,473

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/11

05:00-12:15

1 stop8h 15m

Chicago O'Hare Intl

Mon 10/11

13:45-23:15

1 stop8h 30m

₹ 15,179

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

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 Chicago O'Hare Intl Airport?

The cheapest month to fly to Chicago O'Hare Intl Airport from Boston is in September. Flight prices, which tend to average around ₹ 18,268, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago O'Hare Intl Airport in September, then you should wait until January to fly from Boston, when ticket prices are also cheap, with an average price of ₹ 18,710.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as ₹ 13,852. 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 Tuesday because tickets tend to average around ₹ 30,736. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago O'Hare Intl Airport.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Boston to Chicago O'Hare Intl Airport when you can find flight prices for as low as ₹ 21,882. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are ₹ 29,218 on average. Flights to Chicago O'Hare Intl Airport from Boston in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around ₹ 22,056 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Boston for as low as ₹ 19,857 on momondo.

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

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

Can stopping save me money on Boston to Chicago O'Hare Intl Airport flights?

You could potentially save up to 40% on your flight if you consider stops on a Boston to Chicago O'Hare Intl Airport flight.

How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?

As of October 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 26% cheaper when compared to flights at the same time last year.

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

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

Estimated return price

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

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

Best price found	₹ 20,913
Fastest flight time	2h 49m
Direct flights	Every day

The best flight deal from Boston to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is ₹ 20,913

The fastest flight from Boston to Chicago O'Hare Intl Airport takes 2h 49m

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

Search flight deals

How far is Boston Logan Intl to Chicago O'Hare Intl by plane?
Boston Logan Intl and Chicago O'Hare Intl are 1385.7 km apart from one another. A reasonable flight in good conditions will take 2h 52m.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
There are 2 operators available for flights from Boston Logan Intl Airport to Chicago O'Hare Intl Airport as of October 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare 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 Chicago O'Hare 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 Boston to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Boston and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737-800, making up 26.65% of the total bookings. Other popular models include Boeing 737-900 with 12.44%, Boeing 737 MAX 8 with 11.03%, and Airbus A220-300 with 9.99%.
What is the most popular airline from Boston to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Chicago O'Hare Intl Airport is American Airlines (70% of total bookings). The next most popular airline is Delta (30%).

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

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom ₹ 7,809	Free Cancellation	Rating 7.9 7,992 reviews		Search Delta flights
American Airlines	PriceFrom ₹ 18,275	Free Cancellation	Rating 7.2 11,032 reviews		Search American Airlines flights

Delta Flights From Boston to Chicago O'Hare Intl Airport
Delta is one of the most popular airlines flying from Boston to Chicago O'Hare Intl Airport, operating 5 flights/week on average for this route. A good Delta flight deal for Boston to Chicago O'Hare Intl Airport starts from ₹ 7,809 round-trip, up to an average price of ₹ 21,882. Our users have rated Delta at 7.9/10.
American Airlines Flights From Boston to Chicago O'Hare Intl Airport
American Airlines (7.2/10 from 11,032 reviews) operates around 12 flights from Boston to Chicago O'Hare Intl Airport in any given week. The average American Airlines airfare for this route is around ₹ 29,218, with deals from around ₹ 18,275 rare but found on momondo. Referenced prices are for round-trip Boston to Chicago O'Hare Intl Airport flight searches in the last 72 hours.

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Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Boston.

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

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

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

Once you have performed a search for Boston to Chicago 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 Boston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago O'Hare Intl Airport 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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Fri 28/11

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Cheap flights from Boston to Chicago from ₹ 5,648

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 6/11. 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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Big names, great deals

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

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

Delta flights from Boston to Chicago O'Hare Intl Airport

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

momondo Fare Finder

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

See travel insights to Chicago from

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

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

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

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

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

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

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

Can stopping save me money on Boston to Chicago O'Hare Intl Airport flights?

You could potentially save up to 40% on your flight if you consider stops on a Boston to Chicago O'Hare Intl Airport flight.

How have Boston to Chicago O'Hare Intl Airport flight prices changed over time?

As of October 2025, prices for Boston to Chicago O'Hare Intl Airport flights are approximately 26% cheaper when compared to flights at the same time last year.

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

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

How often are flights from Boston to Chicago delayed?

Historically, on average around 12% of flights between Boston and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 167 minutes.

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

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

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

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

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

According to our data, Air Canada have had the fewest delays on this route over the last 12 months, with no flights being classified as delayed.

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

As of October 2025, there are 32 flights per day flying from Boston to Chicago O'Hare Intl Airport. The most common time of day flights depart is 16:00, with 48% of flights taking off in the afternoon.

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

226 flights are operational weekly from Boston to Chicago O'Hare Intl Airport as of October 2025. The most popular departure day for this route is Wed, with 24% of flights per week taking off on this day.

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

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

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

Best price found

Fastest flight time

Direct flights

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

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

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

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

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

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

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

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

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

Delta Flights From Boston to Chicago O'Hare Intl Airport

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

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago O'Hare Intl Airport 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 Chicago

Popular Cities in the United States

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