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

46 flights are operational daily from Boston to Chicago as of July 2025. The most popular departure time for this route is 07:00, with 40% of flights per day taking off at midday.

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

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

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

The number of flights available between Boston and Chicago is 322 per week as of July 2025. The most frequent departure day is Thu, with 24% of weekly flights leaving on this day.

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 July 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.

£29 Cheap Flights from Boston to Chicago in 2025

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Find the cheapest flights from Boston to Chicago

Round-trip

One-way

Last minute

Direct

Cheap return flights

06:10 - 08:05BOS-ORD

2h 55mdirect

21:15 - 00:45ORD-BOS

2h 30mdirect

£88United Airlines

Find Deal

Tue, 2 Sep - Thu, 4 Sep

07:45 - 09:41BOS-ORD

2h 56mdirect

07:30 - 11:01ORD-BOS

2h 31mdirect

£96United Airlines

Find Deal

Thu, 4 Sep - Sun, 7 Sep

17:36 - 19:33BOS-ORD

2h 57mdirect

20:25 - 23:53ORD-BOS

2h 28mdirect

£104American Airlines

Find Deal

Fri, 12 Sep - Fri, 19 Sep

07:30 - 12:45BOS-ORD

6h 15m1 stop

13:50 - 20:35ORD-BOS

5h 45m1 stop

£110Southwest

Find Deal

Thu, 4 Sep - Sun, 7 Sep

05:20 - 11:50BOS-ORD

7h 30m1 stop

14:55 - 20:55ORD-BOS

5h 00m1 stop

£111Southwest

Find Deal

Sat, 30 Aug - Sat, 6 Sep

07:20 - 09:15BOS-ORD

2h 55mdirect

07:00 - 10:30ORD-BOS

2h 30mdirect

£117Delta

Find Deal

Thu, 4 Sep - Sun, 7 Sep

07:00 - 09:00BOS-ORD

3h 00mdirect

18:50 - 22:27ORD-BOS

2h 37mdirect

£119Delta

Find Deal

Thu, 27 Nov - Tue, 2 Dec

14:45 - 20:49BOS-ORD

7h 04m1 stop

19:50 - 23:25ORD-BOS

2h 35mdirect

£128JetBlue

Find Deal

Fri, 12 Sep - Fri, 19 Sep

17:05 - 22:28BOS-ORD

6h 23m1 stop

09:42 - 13:10ORD-BOS

2h 28mdirect

£134JetBlue

Find Deal

Tue, 2 Sep - Thu, 4 Sep

05:00 - 06:51BOS-ORD

2h 51mdirect

15:04 - 18:31ORD-BOS

2h 27mdirect

£146American Airlines

Find Deal

Sun, 5 Oct - Fri, 10 Oct

American Airlines flights from Boston to Chicago

Our best American Airlines deals on Boston to Chicago flight tickets

American Airlines

12 Sept

BOS17:36Boston Logan Intl

2h 57m

ORD19:33Chicago O'Hare Intl

19 Sept

ORD20:25Chicago O'Hare Intl

2h 28m

BOS23:53Boston Logan Intl

£104

Find similar

American Airlines

12 Aug

BOS19:24Boston Logan Intl

2h 57m

ORD21:21Chicago O'Hare Intl

19 Aug

ORD07:00Chicago O'Hare Intl

2h 24m

BOS10:24Boston Logan Intl

£134

Find similar

American Airlines

5 Oct

BOS05:00Boston Logan Intl

2h 51m

ORD06:51Chicago O'Hare Intl

10 Oct

ORD15:04Chicago O'Hare Intl

2h 27m

BOS18:31Boston Logan Intl

£146

Find similar

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

JetBlue

12 Sept

BOS14:45Boston Logan Intl

7h 04m

1 stop

ORD20:49Chicago O'Hare Intl

19 Sept

ORD19:50Chicago O'Hare Intl

2h 35m

BOS23:25Boston Logan Intl

£128

Find similar

JetBlue

2 Sept

BOS17:05Boston Logan Intl

6h 23m

1 stop

ORD22:28Chicago O'Hare Intl

4 Sept

ORD09:42Chicago O'Hare Intl

2h 28m

BOS13:10Boston Logan Intl

£134

Find similar

JetBlue

12 Aug

BOS06:00Boston Logan Intl

2h 55m

ORD07:55Chicago O'Hare Intl

25 Aug

ORD08:40Chicago O'Hare Intl

2h 24m

BOS12:04Boston Logan Intl

£138

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/9

06:10-08:05

Nonstop2h 55m

Chicago O'Hare Intl

Thu 4/9

21:15-00:45

Nonstop2h 30m

£88

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/9

07:45-09:41

Nonstop2h 56m

Chicago O'Hare Intl

Sun 7/9

07:30-11:01

Nonstop2h 31m

£96

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/9

17:36-19:33

Nonstop2h 57m

Chicago O'Hare Intl

Fri 19/9

20:25-23:53

Nonstop2h 28m

£104

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/9

07:30-12:45

1 stop6h 15m

Chicago O'Hare Intl

Sun 7/9

13:50-20:35

1 stop5h 45m

£110

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 30/8

05:20-11:50

1 stop7h 30m

Chicago O'Hare Intl

Sat 6/9

14:55-20:55

1 stop5h 00m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/9

07:20-09:15

Nonstop2h 55m

Chicago O'Hare Intl

Sun 7/9

07:00-10:30

Nonstop2h 30m

£117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 27/11

07:00-09:00

Nonstop3h 00m

Chicago O'Hare Intl

Tue 2/12

18:50-22:27

Nonstop2h 37m

£119

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/9

14:45-20:49

1 stop7h 04m

Chicago O'Hare Intl

Fri 19/9

19:50-23:25

Nonstop2h 35m

£128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/9

17:05-22:28

1 stop6h 23m

Chicago O'Hare Intl

Thu 4/9

09:42-13:10

Nonstop2h 28m

£134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/10

05:00-06:51

Nonstop2h 51m

Chicago O'Hare Intl

Fri 10/10

15:04-18:31

Nonstop2h 27m

£146

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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

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 £134, 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 £127. 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 £528.

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 £141 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £384.

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 £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 £159 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.

How have Boston to Chicago flight prices changed over time?

As of July 2025, prices for Boston to Chicago flights are approximately 36% 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	£45
Fastest flight time	2h 48m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Boston in the past 72 hours is £45. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £88.

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

Direct flights go from Boston to Chicago every day.

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

Search flight deals

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 July 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 25.70% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 15.07%, Boeing 737-900 at 10.81%, and Airbus A220-300 at 8.96%.

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 £74	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

American Airlines Flights From Boston to Chicago
American Airlines operates around 36 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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Chicago Midway Airport

Chicago O'Hare Intl Airport

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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 30/8. 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

Trusted and free

Trusted and free

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Find the cheapest flights from Boston to Chicago

Cheap return flights

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Cheap last-minute flights

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American Airlines flights from Boston to Chicago

Our best American Airlines deals on Boston to Chicago flight tickets

JetBlue flights from Boston to Chicago

Our best JetBlue 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 £127. 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 £528.

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 £141 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £384.

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.

How have Boston to Chicago flight prices changed over time?

As of July 2025, prices for Boston to Chicago flights are approximately 36% 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, Spirit Airlines, and JetBlue are the most popular carriers operating from Boston Logan Intl to Chicago

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

46 flights are operational daily from Boston to Chicago as of July 2025. The most popular departure time for this route is 07:00, with 40% 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 322 per week as of July 2025. The most frequent departure day is Thu, with 24% 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

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