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

As of December 2025, 219 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Tue, with 25% of weekly flights taking off on this day.

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

As of December 2025, there are 31 flights per day flying from Chicago to Boston. The most common time of day flights depart is 10:00AM, with 43% of flights taking off at noon.

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.

What is the most punctual flight time for Chicago to Boston flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon have, in the past, seen delays more frequently in comparison.

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

According to our data, Spirit Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

How often are flights from Chicago to Boston delayed?

Historically, on average around 21% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 147 minutes.

What day of the week experiences the fewest flight delays on this route?

Saturday is statistically the day of the week which experiences the fewest number of 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 Chicago to Boston Logan Intl?

Delta, United Airlines, and Southwest 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 December 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

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Boston

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:45 am - 11:10 amORD-BOS

2h 25mnonstop

3:35 pm - 5:43 pmBOS-ORD

3h 08mnonstop

$118JetBlue

Find Deal

Sat, Jan 17 - Sun, Jan 18

7:45 am - 11:10 amORD-BOS

2h 25mnonstop

3:35 pm - 5:43 pmBOS-ORD

3h 08mnonstop

$119JetBlue

Find Deal

Sun, Jan 18 - Tue, Jan 20

6:50 am - 2:20 pmMDW-BOS

6h 30m1 stop

5:30 am - 7:20 amBOS-MDW

2h 50mnonstop

$119Southwest

Find Deal

Tue, Jan 6 - Tue, Jan 13

2:00 pm - 5:10 pmMDW-BOS

2h 10mnonstop

5:30 am - 7:20 amBOS-MDW

2h 50mnonstop

$120Southwest

Find Deal

Thu, Jan 8 - Fri, Jan 9

7:45 am - 11:10 amORD-BOS

2h 25mnonstop

3:35 pm - 5:43 pmBOS-ORD

3h 08mnonstop

$120JetBlue

Find Deal

Thu, Jan 15 - Thu, Jan 22

7:05 am - 10:40 amORD-BOS

2h 35mnonstop

7:55 pm - 10:01 pmBOS-ORD

3h 06mnonstop

$121Delta

Find Deal

Fri, Jan 9 - Mon, Jan 12

11:00 am - 2:20 pmORD-BOS

2h 20mnonstop

9:30 am - 11:34 amBOS-ORD

3h 04mnonstop

$122United Airlines

Find Deal

Mon, Dec 15 - Sat, Jan 17

5:35 pm - 8:50 pmMDW-BOS

2h 15mnonstop

5:20 am - 7:10 amBOS-MDW

2h 50mnonstop

$123Southwest

Find Deal

Wed, Jan 14 - Mon, Jan 19

1:55 pm - 5:15 pmORD-BOS

2h 20mnonstop

9:40 am - 11:40 amBOS-ORD

3h 00mnonstop

$127United Airlines

Find Deal

Fri, Dec 12 - Sun, Dec 14

10:45 am - 4:23 pmORD-BOS

4h 38m1 stop

4:10 pm - 6:19 pmBOS-ORD

3h 09mnonstop

$128Delta

Find Deal

Tue, Jan 20 - Wed, Jan 28

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets

JetBlue

Jan 17

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Jan 18

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$118

Find similar

JetBlue

Jan 18

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Jan 20

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$119

Find similar

JetBlue

Jan 15

ORD7:45 amChicago O'Hare Intl

2h 25m

BOS11:10 amBoston Logan Intl

Jan 22

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$120

Find similar

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets

Southwest

Jan 6

MDW6:50 amChicago Midway

6h 30m

1 stop

BOS2:20 pmBoston Logan Intl

Jan 13

BOS5:30 amBoston Logan Intl

2h 50m

MDW7:20 amChicago Midway

$119

Find similar

Southwest

Jan 8

MDW2:00 pmChicago Midway

2h 10m

BOS5:10 pmBoston Logan Intl

Jan 9

BOS5:30 amBoston Logan Intl

2h 50m

MDW7:20 amChicago Midway

$120

Find similar

Southwest

Jan 17

MDW6:40 amChicago Midway

4h 40m

1 stop

BOS12:20 pmBoston Logan Intl

Jan 20

BOS5:30 amBoston Logan Intl

2h 50m

MDW7:20 amChicago Midway

$121

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 1/18

3:35 pm-5:43 pm

Nonstop3h 08m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$119

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 1/6

6:50 am-2:20 pm

1 stop6h 30m

Boston Logan Intl

Tue 1/13

5:30 am-7:20 am

Nonstop2h 50m

$119

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/8

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Fri 1/9

5:30 am-7:20 am

Nonstop2h 50m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Thu 1/22

3:35 pm-5:43 pm

Nonstop3h 08m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/9

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Mon 1/12

7:55 pm-10:01 pm

Nonstop3h 06m

$121

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 12/15

11:00 am-2:20 pm

Nonstop2h 20m

Boston Logan Intl

Sat 1/17

9:30 am-11:34 am

Nonstop3h 04m

$122

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 1/14

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Mon 1/19

5:20 am-7:10 am

Nonstop2h 50m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

1:55 pm-5:15 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/14

9:40 am-11:40 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

10:45 am-4:23 pm

1 stop4h 38m

Boston Logan Intl

Wed 1/28

4:10 pm-6:19 pm

Nonstop3h 09m

$128

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Delays

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 July instead. Flights to Boston in July, while not as cheap as those in September, still average around $213.

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 $239. 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 $302.

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 $219. 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 $298 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 $233 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 $181 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 December 2025, prices for Chicago to Boston flights are approximately 16% 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	$65
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 $65. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $131.

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)

Search flight deals

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 December 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 24.62% of all bookings. The subsequent popular models are Boeing 737-900 at 13.26%, Embraer 175 at 12.47%, and Airbus A220-300 at 11.22%.
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
JetBlue	PriceFrom $79	Free Cancellation	Rating 7.2 2,904 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $83	Free Cancellation	Rating 6.3 8,155 reviews	Search Spirit Airlines flights
Delta	PriceFrom $103	Free Cancellation	Rating 7.9 8,009 reviews	Search Delta flights
Frontier	PriceFrom $104	Free Cancellation	Rating 5.8 3,094 reviews	Search Frontier flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,041 reviews	Search American Airlines flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,064 reviews	Search United Airlines flights
Southwest	PriceFrom $135	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights

Southwest Flights From Chicago to Boston
Southwest flight deals from Chicago to Boston start from $135 round-trip. Over the 12 Southwest flights for this route in a normal week, average airfare is usually $249 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, 8,009 ratings). Delta flies from Chicago to Boston around 9 times per week, with deals starting from $103 round-trip and rising to an average price of around $225.

Hampton Beach

Salem

Ogunquit

Old Orchard Beach

Hampton

York Beach

Plymouth

Kennebunkport

South Yarmouth

Cambridge

Narragansett

Gloucester

Nashua

Falmouth

Laconia

Brockton

Concord

Everett

Sturbridge

Chatham

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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Thu 1/1

Thu 1/8

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

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 2/15. 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 and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets

momondo Fare Finder

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

See travel insights to Boston from

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 $239. 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 $302.

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

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

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

What airlines fly to Boston?

How often are flights from Chicago to Boston delayed?

Historically, on average around 21% of flights between Chicago and Boston have experienced a delay on any given week. The average delay length over the past 12 months has been 147 minutes.

What is the most punctual flight time for Chicago to Boston flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the early afternoon 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 which experiences the fewest number of 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 Chicago to Boston flights?

According to our data, Spirit Airlines have had the least number of delays on this route over the last 12 months; with about 13% of their flights experiencing any sort of delay.

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

As of December 2025, there are 31 flights per day flying from Chicago to Boston. The most common time of day flights depart is 10:00AM, with 43% of flights taking off at noon.

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

As of December 2025, 219 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Tue, with 25% 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