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

As of November 2025, 339 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Thu, with 20% of weekly flights taking off on this day.

What airlines fly to Boston?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Chicago according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

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

As of November 2025, there are 48 flights per day flying from Chicago to Boston. The most common time of day flights depart is 10:00AM, with 53% of flights taking off at noon.

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

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

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

Prices for flights from Chicago to Boston Logan Intl Airport are updated daily.

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

The number of operators available for flights from Chicago to Boston Logan Intl Airport is 7 as of November 2025.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.

What documentation or ID do you need to fly to Boston Logan Intl Airport?

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

$59 Cheap Flights from Chicago to Boston in 2025/26

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7:30 am - 10:49 amORD-BOS

2h 19mnonstop

12:50 pm - 2:50 pmBOS-ORD

3h 00mnonstop

$117United Airlines

Find Deal

Fri, Dec 5 - Mon, Dec 8

6:15 pm - 9:35 pmMDW-BOS

2h 20mnonstop

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

$117Southwest

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Fri, Dec 5 - Fri, Dec 12

7:00 am - 10:29 amORD-BOS

2h 29mnonstop

7:00 am - 9:32 amBOS-ORD

3h 32mnonstop

$118American Airlines

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Thu, Dec 4 - Sun, Dec 7

11:25 am - 2:49 pmORD-BOS

2h 24mnonstop

5:29 pm - 7:43 pmBOS-ORD

3h 14mnonstop

$120JetBlue

Find Deal

Wed, Dec 3 - Sun, Dec 7

11:25 am - 2:49 pmORD-BOS

2h 24mnonstop

4:46 pm - 8:35 pmBOS-ORD

4h 49m1 stop

$121JetBlue

Find Deal

Thu, Dec 4 - Mon, Dec 8

10:12 am - 11:53 pmORD-BOS

12h 41m1 stop

10:56 am - 9:48 pmBOS-ORD

11h 52m1 stop

$126Spirit Airlines

Find Deal

Wed, Dec 3 - Wed, Dec 10

3:26 pm - 11:56 pmORD-BOS

7h 30m1 stop

10:56 am - 9:48 pmBOS-ORD

11h 52m1 stop

$134Spirit Airlines

Find Deal

Sat, Dec 6 - Tue, Dec 9

7:25 am - 10:58 amORD-BOS

2h 33mnonstop

7:05 pm - 9:19 pmBOS-ORD

3h 14mnonstop

$138American Airlines

Find Deal

Thu, Dec 18 - Sat, Jan 3

10:49 am - 5:15 pmMDW-BOS

5h 26m1 stop

5:29 am - 8:54 amBOS-MDW

4h 25m1 stop

$147Delta

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Wed, Dec 3 - Wed, Dec 10

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

2:50 pm - 4:56 pmBOS-ORD

3h 06mnonstop

$152Delta

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Thu, Dec 18 - Tue, Dec 30

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets

United Airlines

Dec 5

ORD7:30 amChicago O'Hare Intl

2h 19m

BOS10:49 amBoston Logan Intl

Dec 8

BOS12:50 pmBoston Logan Intl

3h 00m

ORD2:50 pmChicago O'Hare Intl

$117

Find similar

United Airlines

Nov 18

ORD12:50 pmChicago O'Hare Intl

2h 20m

BOS4:10 pmBoston Logan Intl

Nov 19

BOS3:10 pmBoston Logan Intl

3h 00m

ORD5:10 pmChicago O'Hare Intl

$127

Find similar

United Airlines

Dec 19

ORD9:20 amChicago O'Hare Intl

2h 33m

BOS12:53 pmBoston Logan Intl

Jan 11

BOS6:21 pmBoston Logan Intl

3h 04m

ORD8:25 pmChicago O'Hare Intl

$144

Find similar

Frontier flights from Chicago to Boston

Our best Frontier deals on Chicago to Boston flight tickets

Frontier

Nov 24

MDW7:10 pmChicago Midway

11h 19m

1 stop

BOS7:29 amBoston Logan Intl

Dec 4

BOS11:28 amBoston Logan Intl

11h 44m

1 stop

MDW10:12 pmChicago Midway

$124

Find similar

Frontier

Dec 4

ORD11:44 amChicago O'Hare Intl

21h 38m

1 stop

BOS10:22 amBoston Logan Intl

Dec 8

BOS11:23 amBoston Logan Intl

7h 04m

1 stop

ORD5:27 pmChicago O'Hare Intl

$129

Find similar

Frontier

Dec 10

MDW2:49 pmChicago Midway

18h 33m

1 stop

BOS10:22 amBoston Logan Intl

Dec 15

BOS11:23 amBoston Logan Intl

11h 49m

1 stop

MDW10:12 pmChicago Midway

$134

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Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Mon 12/8

12:50 pm-2:50 pm

Nonstop3h 00m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Fri 12/12

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Sun 12/7

7:00 am-9:32 am

Nonstop3h 32m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/3

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/7

5:29 pm-7:43 pm

Nonstop3h 14m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Mon 12/8

4:46 pm-8:35 pm

1 stop4h 49m

$121

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/3

10:12 am-11:53 pm

1 stop12h 41m

Boston Logan Intl

Wed 12/10

10:56 am-9:48 pm

1 stop11h 52m

$126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

3:26 pm-11:56 pm

1 stop7h 30m

Boston Logan Intl

Tue 12/9

10:56 am-9:48 pm

1 stop11h 52m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/18

7:25 am-10:58 am

Nonstop2h 33m

Boston Logan Intl

Sat 1/3

7:05 pm-9:19 pm

Nonstop3h 14m

$138

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/3

10:49 am-5:15 pm

1 stop5h 26m

Boston Logan Intl

Wed 12/10

5:29 am-8:54 am

1 stop4h 25m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/18

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Tue 12/30

2:50 pm-4:56 pm

Nonstop3h 06m

$152

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How to get the cheapest flight ticket from Chicago to Boston

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 Boston?

In general, September is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $207. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during January instead. Flights to Boston in January, while not as cheap as those in September, still average around $217.

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

The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $309.

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

According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago to Boston in the evening for as low as $222. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $306 per ticket.

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

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

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

You are more likely to see cheaper flights to Boston from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $235 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $188 on momondo.

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

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

How have Chicago to Boston flight prices changed over time?

As of November 2025, prices for Chicago to Boston flights are approximately 18% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Boston

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

Estimated round-trip price

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

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

Best Price Found	$93
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Boston	1 airport

The best one-way flight to Boston from Chicago in the past 72 hours is $93. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $150.

The fastest flight from Chicago to Boston takes 2h 10m

Direct flights go from Chicago to Boston every day.

There is 1 airport near Boston: Boston Logan Intl (BOS)

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How far is Chicago to Boston Logan Intl by plane?
The distance between Chicago and Boston Logan Intl is about 847.9 mi. 2h 10m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?
Prices for flights from Chicago to Boston Logan Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago to Boston Logan Intl Airport?
The number of operators available for flights from Chicago to Boston Logan Intl Airport is 7 as of November 2025.
How old do you have to be to fly from Chicago to Boston Logan Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Boston Logan Intl Airport.
What documentation or ID do you need to fly to Boston Logan Intl Airport?
The travel and health documents you'll need for your trip to Boston Logan 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 Boston Logan 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 Chicago to Boston?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Boston is Boeing 737-800, representing 25.12% of all bookings. The subsequent popular models are Boeing 737-900 at 13.01%, Airbus A220-300 at 12.12%, and Embraer 175 at 12.01%.
What is the most popular airline from Chicago to Boston?
Based on momondo bookings for flights between Chicago and Boston, the leading airline is American Airlines, making up 31% of the total bookings. Other popular airlines include United Airlines with 30%, Delta with 16%, and Southwest with 12%.

Best airlines flying from Chicago to Boston

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $68	Free Cancellation	Rating 6.3 8,122 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $76	Free Cancellation	Rating 7.2 2,907 reviews	Search JetBlue flights
Delta	PriceFrom $102	Free Cancellation	Rating 7.9 8,001 reviews	Search Delta flights
Frontier	PriceFrom $104	Free Cancellation	Rating 5.8 3,116 reviews	Search Frontier flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
United Airlines	PriceFrom $118	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights
Southwest	PriceFrom $137	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights

Southwest Flights From Chicago to Boston
Southwest flight deals from Chicago to Boston start from $137 round-trip. Over the 16 Southwest flights for this route in a normal week, average airfare is usually $250 round-trip - but some users have found much cheaper deals with momondo.
Delta Flights From Chicago to Boston
Another popular option for Chicago to Boston flights is Delta (7.9/10, 8,001 ratings). Delta flies from Chicago to Boston around 5 times per week, with deals starting from $102 round-trip and rising to an average price of around $230.

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Boston. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Boston from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Chicago to Boston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Cheap flights from Chicago to Boston from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 12/7. 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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United Airlines flights from Chicago to Boston

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How to get the cheapest flight ticket from Chicago to Boston

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 Boston?

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

The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $309.

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

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

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

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

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

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

How have Chicago to Boston flight prices changed over time?

As of November 2025, prices for Chicago to Boston flights are approximately 18% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Boston?

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

As of November 2025, there are 48 flights per day flying from Chicago to Boston. The most common time of day flights depart is 10:00AM, with 53% of flights taking off at noon.

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

As of November 2025, 339 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Thu, with 20% of weekly flights taking off on this day.

When to book flights from Chicago to Boston

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Boston

How far is Chicago to Boston Logan Intl by plane?

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

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

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

What documentation or ID do you need to fly to Boston Logan Intl Airport?

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

What is the most popular airline from Chicago to Boston?

Best airlines flying from Chicago to Boston

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

Southwest Flights From Chicago to Boston

Delta Flights From Chicago to Boston

Traveling to a place near Boston?

Why use momondo?

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

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

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

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

An easier way to manage your Boston trip

We make it super easy to schedule, organize 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

Airports servicing Massachusetts