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

48 flights are operational daily from Boston to Chicago as of November 2025. The most popular departure time for this route is 16:00, with 47% of flights per day taking off in the afternoon.

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.

How often are flights from Boston to Chicago delayed?

Historically, on average around 13% 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 168 minutes.

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

The number of flights available between Boston and Chicago is 341 per week as of November 2025. The most frequent departure day is Thu, with 21% of weekly flights leaving 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. Thursday has historically seen more delays on average compared to the rest of the week.

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

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

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

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

Is flying the fastest way to get from Boston to Chicago?

The quickest way to travel this route is to take a flight from Boston to Chicago, doing so can potentially save up to 25h 30m of travel time. While these options may take longer, booking a train from Boston to Chicago or a bus from Boston to Chicago may suit your needs if travel time is less of a factor in your decision making.

Is flying the cheapest way to get from Boston to Chicago?

Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from £90. While they may not be the most cost-effective options currently available a train from Boston to Chicago or a bus from Boston to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

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

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

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

There is 1 operator available for flights from Boston Logan Intl Airport to Chicago as of November 2025.

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

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 Boston Logan Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

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

£44 Cheap Flights from Boston to Chicago in 2025/26

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07:00 - 09:10BOS-ORD

3h 10mdirect

10:00 - 13:23ORD-BOS

2h 23mdirect

£90JetBlue

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Tue, 17 Feb - Tue, 24 Feb

08:30 - 10:35BOS-ORD

3h 05mdirect

20:38 - 00:06ORD-BOS

2h 28mdirect

£93JetBlue

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Tue, 9 Dec - Fri, 12 Dec

08:30 - 10:35BOS-ORD

3h 05mdirect

20:15 - 23:44ORD-BOS

2h 29mdirect

£95JetBlue

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Wed, 17 Dec - Sat, 20 Dec

08:30 - 10:35BOS-ORD

3h 05mdirect

20:38 - 00:06ORD-BOS

2h 28mdirect

£97JetBlue

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Wed, 3 Dec - Fri, 5 Dec

18:23 - 20:23BOS-ORD

3h 00mdirect

21:12 - 00:45ORD-BOS

2h 33mdirect

£99United Airlines

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Mon, 15 Dec - Thu, 18 Dec

16:31 - 18:46BOS-ORD

3h 15mdirect

19:41 - 23:10ORD-BOS

2h 29mdirect

£100JetBlue

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Sun, 28 Dec - Sun, 4 Jan

07:00 - 09:10BOS-ORD

3h 10mdirect

10:00 - 13:23ORD-BOS

2h 23mdirect

£101JetBlue

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Tue, 17 Feb - Thu, 26 Feb

19:52 - 21:47BOS-ORD

2h 55mdirect

07:10 - 10:36ORD-BOS

2h 26mdirect

£103Delta

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Tue, 16 Dec - Fri, 19 Dec

15:35 - 17:44BOS-ORD

3h 09mdirect

07:45 - 11:10ORD-BOS

2h 25mdirect

£105JetBlue

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Wed, 21 Jan - Mon, 26 Jan

17:29 - 19:43BOS-ORD

3h 14mdirect

19:41 - 23:10ORD-BOS

2h 29mdirect

£106JetBlue

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Mon, 15 Dec - Thu, 18 Dec

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

JetBlue

17 Feb

BOS07:00Boston Logan Intl

3h 10m

ORD09:10Chicago O'Hare Intl

25 Feb

ORD10:00Chicago O'Hare Intl

2h 23m

BOS13:23Boston Logan Intl

£90

Find similar

JetBlue

13 Dec

BOS08:30Boston Logan Intl

3h 05m

ORD10:35Chicago O'Hare Intl

16 Dec

ORD11:25Chicago O'Hare Intl

2h 24m

BOS14:49Boston Logan Intl

£93

Find similar

JetBlue

17 Dec

BOS08:30Boston Logan Intl

3h 05m

ORD10:35Chicago O'Hare Intl

21 Dec

ORD19:41Chicago O'Hare Intl

2h 29m

BOS23:10Boston Logan Intl

£95

Find similar

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets

United Airlines

15 Dec

BOS18:23Boston Logan Intl

3h 00m

ORD20:23Chicago O'Hare Intl

18 Dec

ORD21:12Chicago O'Hare Intl

2h 33m

BOS00:45Boston Logan Intl

£99

Find similar

United Airlines

14 Dec

BOS09:40Boston Logan Intl

3h 00m

ORD11:40Chicago O'Hare Intl

26 Dec

ORD21:12Chicago O'Hare Intl

2h 33m

BOS00:45Boston Logan Intl

£101

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

£113

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Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 17/2

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Tue 24/2

10:00-13:23

Nonstop2h 23m

£90

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/12

08:30-10:35

Nonstop3h 05m

Chicago O'Hare Intl

Fri 12/12

20:38-00:06

Nonstop2h 28m

£93

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 17/12

08:30-10:35

Nonstop3h 05m

Chicago O'Hare Intl

Sat 20/12

20:15-23:44

Nonstop2h 29m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 3/12

08:30-10:35

Nonstop3h 05m

Chicago O'Hare Intl

Fri 5/12

20:38-00:06

Nonstop2h 28m

£97

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 15/12

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Thu 18/12

21:12-00:45

Nonstop2h 33m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 28/12

16:31-18:46

Nonstop3h 15m

Chicago O'Hare Intl

Sun 4/1

19:41-23:10

Nonstop2h 29m

£100

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 17/2

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Thu 26/2

10:00-13:23

Nonstop2h 23m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 16/12

19:52-21:47

Nonstop2h 55m

Chicago O'Hare Intl

Fri 19/12

07:10-10:36

Nonstop2h 26m

£103

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 21/1

15:35-17:44

Nonstop3h 09m

Chicago O'Hare Intl

Mon 26/1

07:45-11:10

Nonstop2h 25m

£105

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 15/12

17:29-19:43

Nonstop3h 14m

Chicago O'Hare Intl

Thu 18/12

19:41-23:10

Nonstop2h 29m

£106

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How to get the cheapest flight ticket from Boston to Chicago

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?

The cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £143, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £147.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as £166. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £651.

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

Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £227 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £388.

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

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

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

You are more likely to see cheaper flights to Chicago from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £192 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as £170 on momondo.

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

There are 3 cabin classes available to choose from on Boston Logan Intl to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of November 2025, prices for Boston to Chicago flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from Boston to Chicago

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

Estimated return price

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

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

Fastest flight time	2h 55m
Direct flights	Every day
Airports in Chicago	1 airport

The fastest flight from Boston to Chicago takes 2h 55m

Direct flights go from Boston to Chicago every day.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

Search flight deals

Is flying the fastest way to get from Boston to Chicago?
The quickest way to travel this route is to take a flight from Boston to Chicago, doing so can potentially save up to 25h 30m of travel time. While these options may take longer, booking a train from Boston to Chicago or a bus from Boston to Chicago may suit your needs if travel time is less of a factor in your decision making.
Is flying the cheapest way to get from Boston to Chicago?
Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from £90. While they may not be the most cost-effective options currently available a train from Boston to Chicago or a bus from Boston to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.
How far is Boston Logan Intl to Chicago by plane?
Chicago is 847.9 mi away from Boston Logan Intl. 2h 55m is a normal flight duration for this route.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?
Prices for flights from Boston Logan Intl Airport to Chicago were last updated today.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There is 1 operator available for flights from Boston Logan Intl Airport to Chicago as of November 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago?
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 Boston Logan Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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. 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?
momondo data reveals that the most frequently booked plane model on the route from Boston to Chicago is Boeing 737-800, representing 25.65% of all bookings. The subsequent popular models are Boeing 737-900 at 12.29%, Boeing 737 MAX 8 at 11.16%, and Airbus A220-300 at 9.71%.

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom £75	Free Cancellation	Rating 7.2 11,047 reviews		Search American Airlines flights

American Airlines Flights From Boston to Chicago
American Airlines operates around 45 flights from Boston to Chicago every week. The average price of these flights found in the last 72 hours has been £118, but momondo users have found American Airlines deals from Boston to Chicago from as low as £75 round-trip. American Airlines has been scored 7.2/10 in 11,047 reviews.

Why use momondo?

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

It is quick and easy to find Boston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

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

An easier way to manage your Chicago 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 Boston to Chicago from £45

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 18/1. 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 Boston to Chicago

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?

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as £166. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £651.

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

Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £227 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £388.

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

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

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

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

There are 3 cabin classes available to choose from on Boston Logan Intl to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of November 2025, prices for Boston to Chicago flights are approximately 16% cheaper when compared to flights at the same time last year.

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

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

How often are flights from Boston to Chicago delayed?

Historically, on average around 13% 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 168 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?

Saturday is statistically the day of the week that experiences the fewest 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 Boston to Chicago flights?

According to our data, FLYGTA Airlines 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 on average per day?

48 flights are operational daily from Boston to Chicago as of November 2025. The most popular departure time for this route is 16:00, with 47% of flights per day taking off in the afternoon.

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

The number of flights available between Boston and Chicago is 341 per week as of November 2025. The most frequent departure day is Thu, with 21% of weekly flights leaving on this day.

When to book flights from Boston to Chicago

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

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

Fastest flight time

Direct flights

Airports in Chicago

Is flying the fastest way to get from Boston to Chicago?

Is flying the cheapest way to get from Boston to Chicago?

How far is Boston Logan Intl to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo

American Airlines Flights From Boston to 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 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

Fly into one of these airports located in Chicago