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

20 flights are operational daily from Boston to Chicago as of October 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 cheapest airline that flies from Boston Logan Intl to Chicago?

JetBlue, United Airlines, and Delta 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 142 per week as of October 2025. The most frequent departure day is Thu, with 46% of weekly flights leaving on this day.

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 28m 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 October 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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16:05 - 18:02BOS-ORD

2h 57mdirect

07:10 - 10:36ORD-BOS

2h 26mdirect

£90Delta

Find Deal

Thu, 4 Dec - Sun, 7 Dec

09:40 - 11:40BOS-ORD

3h 00mdirect

18:17 - 21:45ORD-BOS

2h 28mdirect

£93United Airlines

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Thu, 13 Nov - Fri, 5 Dec

19:52 - 21:47BOS-ORD

2h 55mdirect

10:35 - 13:59ORD-BOS

2h 24mdirect

£94Delta

Find Deal

Sun, 14 Dec - Fri, 19 Dec

10:40 - 12:40BOS-ORD

3h 00mdirect

16:00 - 19:20ORD-BOS

2h 20mdirect

£96United Airlines

Find Deal

Thu, 13 Nov - Wed, 19 Nov

15:55 - 17:55BOS-ORD

3h 00mdirect

11:20 - 14:44ORD-BOS

2h 24mdirect

£99JetBlue

Find Deal

Mon, 10 Nov - Thu, 13 Nov

16:15 - 18:19BOS-ORD

3h 04mdirect

18:11 - 21:44ORD-BOS

2h 33mdirect

£99United Airlines

Find Deal

Wed, 24 Dec - Wed, 31 Dec

15:35 - 17:44BOS-ORD

3h 09mdirect

10:45 - 14:09ORD-BOS

2h 24mdirect

£100JetBlue

Find Deal

Thu, 15 Jan - Tue, 20 Jan

11:28 - 22:24BOS-ORD

11h 56m1 stop

06:00 - 12:02ORD-BOS

5h 02m1 stop

£109Frontier

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Thu, 4 Dec - Sun, 7 Dec

05:00 - 12:15BOS-ORD

8h 15m1 stop

13:45 - 22:15ORD-BOS

7h 30m1 stop

£127Southwest

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Mon, 10 Nov - Wed, 12 Nov

05:00 - 12:15BOS-ORD

8h 15m1 stop

13:45 - 23:15ORD-BOS

8h 30m1 stop

£131Southwest

Find Deal

Mon, 10 Nov - Fri, 14 Nov

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

JetBlue

10 Nov

BOS15:55Boston Logan Intl

3h 00m

ORD17:55Chicago O'Hare Intl

13 Nov

ORD11:20Chicago O'Hare Intl

2h 24m

BOS14:44Boston Logan Intl

£99

Find similar

JetBlue

15 Jan

BOS15:35Boston Logan Intl

3h 09m

ORD17:44Chicago O'Hare Intl

20 Jan

ORD10:45Chicago O'Hare Intl

2h 24m

BOS14:09Boston Logan Intl

£100

Find similar

JetBlue

13 Nov

BOS08:30Boston Logan Intl

3h 05m

ORD10:35Chicago O'Hare Intl

17 Nov

ORD18:55Chicago O'Hare Intl

2h 32m

BOS22:27Boston Logan Intl

£101

Find similar

Southwest flights from Boston to Chicago

Our best Southwest deals on Boston to Chicago flight tickets

Southwest

13 Nov

BOS05:00Boston Logan Intl

8h 15m

1 stop

ORD12:15Chicago O'Hare Intl

14 Nov

ORD13:45Chicago O'Hare Intl

8h 30m

1 stop

BOS23:15Boston Logan Intl

£115

Find similar

Southwest

10 Nov

BOS05:00Boston Logan Intl

8h 15m

1 stop

ORD12:15Chicago O'Hare Intl

12 Nov

ORD13:45Chicago O'Hare Intl

7h 30m

1 stop

BOS22:15Boston Logan Intl

£127

Find similar

Southwest

10 Nov

BOS05:00Boston Logan Intl

8h 15m

1 stop

ORD12:15Chicago O'Hare Intl

14 Nov

ORD13:45Chicago O'Hare Intl

8h 30m

1 stop

BOS23:15Boston Logan Intl

£131

Find similar

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

£90

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 13/11

09:40-11:40

Nonstop3h 00m

Chicago O'Hare Intl

Fri 5/12

18:17-21:45

Nonstop2h 28m

£93

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 14/12

19:52-21:47

Nonstop2h 55m

Chicago O'Hare Intl

Fri 19/12

10:35-13:59

Nonstop2h 24m

£94

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 13/11

10:40-12:40

Nonstop3h 00m

Chicago O'Hare Intl

Wed 19/11

16:00-19:20

Nonstop2h 20m

£96

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

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 24/12

16:15-18:19

Nonstop3h 04m

Chicago O'Hare Intl

Wed 31/12

18:11-21:44

Nonstop2h 33m

£99

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

£100

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

11:28-22:24

1 stop11h 56m

Chicago O'Hare Intl

Sun 7/12

06:00-12:02

1 stop5h 02m

£109

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/11

05:00-12:15

1 stop8h 15m

Chicago O'Hare Intl

Wed 12/11

13:45-22:15

1 stop7h 30m

£127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/11

05:00-12:15

1 stop8h 15m

Chicago O'Hare Intl

Fri 14/11

13:45-23:15

1 stop8h 30m

£131

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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 £142, 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 £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 £165. 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 £646.

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 £225 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £385.

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 £190 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 £171 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 October 2025, prices for Boston to Chicago flights are approximately 20% 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 50m
Direct flights	Every day
Airports in Chicago	1 airport

The fastest flight from Boston to Chicago takes 2h 50m

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 28m 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 52m 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 October 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 25.93% of all bookings. The subsequent popular models are Boeing 737-900 at 12.17%, Boeing 737 MAX 8 at 11.41%, and Airbus A220-300 at 9.80%.

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 11,034 reviews		Search American Airlines flights

American Airlines Flights From Boston to Chicago
American Airlines operates around 11 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 £74 round-trip. American Airlines has been scored 7.2/10 in 11,034 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 £49

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 17/11. 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

Filter for what you want

Filter for what you want

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JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets

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Our best Southwest deals on Boston to Chicago flight tickets

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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 £165. 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 £646.

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 £225 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £385.

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 October 2025, prices for Boston to Chicago flights are approximately 20% cheaper when compared to flights at the same time last year.

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

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

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

20 flights are operational daily from Boston to Chicago as of October 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 142 per week as of October 2025. The most frequent departure day is Thu, with 46% 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?

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