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

The number of flights available between Boston and Chicago is 476 per week as of September 2025. The most frequent departure day is Sun, with 17% of weekly flights leaving on this day.

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

68 flights are operational daily from Boston to Chicago as of September 2025. The most popular departure time for this route is 07:00, with 44% of flights per day taking off at midday.

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

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 37m 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.

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 September 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.

£43 Cheap Flights from Boston to Chicago in 2025/26

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Round-trip

One-way

Last minute

Direct

Cheap return flights

07:00 - 08:56BOS-ORD

2h 56mdirect

09:51 - 13:20ORD-BOS

2h 29mdirect

£93JetBlue

Find Deal

Sat, 27 Sep - Wed, 1 Oct

06:00 - 07:56BOS-ORD

2h 56mdirect

06:15 - 09:30ORD-BOS

2h 15mdirect

£95United Airlines

Find Deal

Thu, 16 Oct - Sun, 9 Nov

16:40 - 18:55BOS-ORD

3h 15mdirect

19:50 - 23:25ORD-BOS

2h 35mdirect

£97JetBlue

Find Deal

Fri, 26 Sep - Fri, 3 Oct

18:15 - 20:09BOS-ORD

2h 54mdirect

06:30 - 09:56ORD-BOS

2h 26mdirect

£98United Airlines

Find Deal

Sat, 18 Oct - Sun, 19 Oct

08:00 - 09:55BOS-ORD

2h 55mdirect

06:30 - 09:57ORD-BOS

2h 27mdirect

£99United Airlines

Find Deal

Sat, 4 Oct - Sun, 5 Oct

19:50 - 21:46BOS-ORD

2h 56mdirect

10:31 - 13:58ORD-BOS

2h 27mdirect

£108Delta

Find Deal

Fri, 5 Dec - Sun, 7 Dec

06:55 - 16:25BOS-ORD

10h 30m2 stops

13:30 - 22:15ORD-BOS

7h 45m1 stop

£109Southwest

Find Deal

Thu, 30 Oct - Sat, 1 Nov

05:05 - 11:50BOS-ORD

7h 45m1 stop

14:50 - 08:25ORD-BOS

16h 35m2 stops

£113Southwest

Find Deal

Sat, 18 Oct - Mon, 20 Oct

16:05 - 18:13BOS-ORD

3h 08mdirect

07:10 - 10:37ORD-BOS

2h 27mdirect

£130Delta

Find Deal

Mon, 24 Nov - Thu, 4 Dec

14:53 - 21:58BOS-ORD

8h 05m1 stop

11:57 - 23:57ORD-BOS

11h 00m1 stop

£141Spirit Airlines

Find Deal

Fri, 3 Oct - Sat, 4 Oct

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

JetBlue

27 Sept

BOS07:00Boston Logan Intl

2h 56m

ORD08:56Chicago O'Hare Intl

1 Oct

ORD09:51Chicago O'Hare Intl

2h 29m

BOS13:20Boston Logan Intl

£93

Find similar

JetBlue

26 Sept

BOS16:40Boston Logan Intl

3h 15m

ORD18:55Chicago O'Hare Intl

1 Oct

ORD19:50Chicago O'Hare Intl

2h 35m

BOS23:25Boston Logan Intl

£97

Find similar

JetBlue

15 Oct

BOS07:09Boston Logan Intl

3h 13m

ORD09:22Chicago O'Hare Intl

22 Oct

ORD10:08Chicago O'Hare Intl

2h 29m

BOS13:37Boston Logan Intl

£99

Find similar

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets

Delta

5 Dec

BOS19:50Boston Logan Intl

2h 56m

ORD21:46Chicago O'Hare Intl

7 Dec

ORD10:31Chicago O'Hare Intl

2h 27m

BOS13:58Boston Logan Intl

£108

Find similar

Delta

24 Nov

BOS16:05Boston Logan Intl

3h 08m

ORD18:13Chicago O'Hare Intl

4 Dec

ORD07:10Chicago O'Hare Intl

2h 27m

BOS10:37Boston Logan Intl

£130

Find similar

Delta

23 Nov

BOS07:30Boston Logan Intl

3h 05m

ORD09:35Chicago O'Hare Intl

28 Nov

ORD07:10Chicago O'Hare Intl

2h 26m

BOS10:36Boston Logan Intl

£145

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 27/9

07:00-08:56

Nonstop2h 56m

Chicago O'Hare Intl

Wed 1/10

09:51-13:20

Nonstop2h 29m

£93

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 16/10

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Sun 9/11

06:15-09:30

Nonstop2h 15m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 26/9

16:40-18:55

Nonstop3h 15m

Chicago O'Hare Intl

Fri 3/10

19:50-23:25

Nonstop2h 35m

£97

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 18/10

18:15-20:09

Nonstop2h 54m

Chicago O'Hare Intl

Sun 19/10

06:30-09:56

Nonstop2h 26m

£98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/10

08:00-09:55

Nonstop2h 55m

Chicago O'Hare Intl

Sun 5/10

06:30-09:57

Nonstop2h 27m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/12

19:50-21:46

Nonstop2h 56m

Chicago O'Hare Intl

Sun 7/12

10:31-13:58

Nonstop2h 27m

£108

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 30/10

06:55-16:25

2 stops10h 30m

Chicago O'Hare Intl

Sat 1/11

13:30-22:15

1 stop7h 45m

£109

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 18/10

05:05-11:50

1 stop7h 45m

Chicago O'Hare Intl

Mon 20/10

14:50-08:25

2 stops16h 35m

£113

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 24/11

16:05-18:13

Nonstop3h 08m

Chicago O'Hare Intl

Thu 4/12

07:10-10:37

Nonstop2h 27m

£130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/10

14:53-21:58

1 stop8h 05m

Chicago O'Hare Intl

Sat 4/10

11:57-23:57

1 stop11h 00m

£141

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

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

Other information

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Boston is in January. Flight prices, which tend to average around £144, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Chicago from Boston during September instead. Flights to Chicago in September, while not as cheap as those in January, still average around £146.

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 £137. 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 Sunday, with ticket prices averaging around £515.

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 £203 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £373.

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

Fly from Boston Logan Intl to Chicago Midway 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 £184 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 £160 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 September 2025, prices for Boston to Chicago flights are approximately 24% 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

Best price found	£87
Fastest flight time	2h 48m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Chicago	1 airport

The best one-way flight to Chicago from Boston in the past 72 hours is £87. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £152.

The fastest flight from Boston to Chicago takes 2h 48m

Direct flights go from Boston to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Southwest..

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 37m 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.
How far is Boston Logan Intl to Chicago by plane?
Chicago is 847.9 mi away from Boston Logan Intl. 2h 48m 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 September 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 26.57% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.75%, Boeing 737-900 at 11.40%, and Airbus A220-300 at 10.27%.

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 £72	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

American Airlines Flights From Boston to Chicago
American Airlines operates around 53 flights from Boston to Chicago every week. The average price of these flights found in the last 72 hours has been £155, but momondo users have found American Airlines deals from Boston to Chicago from as low as £98 round-trip. American Airlines has been scored 7.2/10 in 10,000 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 £47

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 18/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Boston to Chicago

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JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets

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Use the filters below to find and compare flights from Boston to Chicago that are best for you.

See travel insights to Chicago from

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 £137. 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 Sunday, with ticket prices averaging around £515.

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 £203 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £373.

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

Fly from Boston Logan Intl to Chicago Midway 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 September 2025, prices for Boston to Chicago flights are approximately 24% 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 many flights depart from Boston to Chicago on average per day?

68 flights are operational daily from Boston to Chicago as of September 2025. The most popular departure time for this route is 07:00, with 44% of flights per day taking off at midday.

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

The number of flights available between Boston and Chicago is 476 per week as of September 2025. The most frequent departure day is Sun, with 17% 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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Is flying the fastest 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

Airports listed have a maximum distance of 78.5 mi from Chicago