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?

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 49 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, 343 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 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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Cheap round-trip flights

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7:10 pm - 10:34 pmORD-BOS

2h 24mnonstop

12:50 pm - 2:47 pmBOS-ORD

2h 57mnonstop

$117Delta

Find Deal

vie., dic. 12 - dom., dic. 14

6:15 pm - 9:35 pmMDW-BOS

2h 20mnonstop

5:15 am - 7:00 amBOS-MDW

2h 45mnonstop

$117Southwest

Find Deal

jue., dic. 11 - dom., dic. 14

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

7:30 am - 9:33 amBOS-ORD

3h 03mnonstop

$118Delta

Find Deal

jue., dic. 11 - dom., dic. 14

7:00 am - 10:25 amORD-BOS

2h 25mnonstop

1:45 pm - 3:55 pmBOS-ORD

3h 10mnonstop

$122American Airlines

Find Deal

mié., nov. 19 - mié., dic. 3

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

5:29 pm - 7:43 pmBOS-ORD

3h 14mnonstop

$123JetBlue

Find Deal

jue., dic. 4 - lun., dic. 8

6:12 am - 1:19 amMDW-BOS

18h 07m1 stop

6:00 am - 10:17 pmBOS-MDW

17h 17m1 stop

$123Frontier

Find Deal

jue., ene. 1 - jue., ene. 8

8:40 pm - 12:13 amORD-BOS

2h 33mnonstop

6:36 am - 8:47 amBOS-ORD

3h 11mnonstop

$124American Airlines

Find Deal

vie., dic. 12 - sáb., ene. 3

10:18 am - 10:51 amMDW-BOS

23h 33m1 stop

6:00 am - 5:42 pmBOS-MDW

12h 42m1 stop

$124Frontier

Find Deal

vie., ene. 9 - mar., ene. 13

11:25 am - 2:49 pmORD-BOS

2h 24mnonstop

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

$125JetBlue

Find Deal

sáb., dic. 6 - lun., dic. 8

7:30 am - 10:49 amORD-BOS

2h 19mnonstop

6:23 pm - 8:23 pmBOS-ORD

3h 00mnonstop

$127United Airlines

Find Deal

jue., dic. 4 - lun., dic. 8

Southwest flights from Chicago to Boston

Our best Southwest deals on Chicago to Boston flight tickets

Southwest

Dec 11

MDW6:15 pmChicago Midway

2h 20m

BOS9:35 pmBoston Logan Intl

Dec 14

BOS5:15 amBoston Logan Intl

2h 45m

MDW7:00 amChicago Midway

$117

Find similar

Southwest

Dec 8

MDW6:15 pmChicago Midway

2h 20m

BOS9:35 pmBoston Logan Intl

Dec 10

BOS1:35 pmBoston Logan Intl

2h 45m

MDW3:20 pmChicago Midway

$122

Find similar

Southwest

Dec 5

MDW6:15 pmChicago Midway

2h 20m

BOS9:35 pmBoston Logan Intl

Dec 8

BOS5:30 amBoston Logan Intl

2h 45m

MDW7:15 amChicago Midway

$127

Find similar

Delta flights from Chicago to Boston

Our best Delta deals on Chicago to Boston flight tickets

Delta

Dec 12

ORD7:10 pmChicago O'Hare Intl

2h 24m

BOS10:34 pmBoston Logan Intl

Dec 14

BOS12:50 pmBoston Logan Intl

2h 57m

ORD2:47 pmChicago O'Hare Intl

$117

Find similar

Delta

Dec 11

ORD7:10 amChicago O'Hare Intl

2h 26m

BOS10:36 amBoston Logan Intl

Dec 14

BOS7:30 amBoston Logan Intl

3h 03m

ORD9:33 amChicago O'Hare Intl

$118

Find similar

Delta

Dec 11

ORD10:35 amChicago O'Hare Intl

2h 24m

BOS1:59 pmBoston Logan Intl

Dec 14

BOS7:30 amBoston Logan Intl

3h 03m

ORD9:33 amChicago O'Hare Intl

$149

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 12/12

7:10 pm-10:34 pm

Nonstop2h 24m

Boston Logan Intl

dom. 12/14

12:50 pm-2:47 pm

Nonstop2h 57m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 12/11

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

dom. 12/14

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 12/11

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

dom. 12/14

7:30 am-9:33 am

Nonstop3h 03m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 11/19

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

mié. 12/3

1:45 pm-3:55 pm

Nonstop3h 10m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 12/4

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

lun. 12/8

5:29 pm-7:43 pm

Nonstop3h 14m

$123

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 1/1

6:12 am-1:19 am

1 stop18h 07m

Boston Logan Intl

jue. 1/8

6:00 am-10:17 pm

1 stop17h 17m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 12/12

8:40 pm-12:13 am

Nonstop2h 33m

Boston Logan Intl

sáb. 1/3

6:36 am-8:47 am

Nonstop3h 11m

$124

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 1/9

10:18 am-10:51 am

1 stop23h 33m

Boston Logan Intl

mar. 1/13

6:00 am-5:42 pm

1 stop12h 42m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 12/6

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

lun. 12/8

8:30 am-10:35 am

Nonstop3h 05m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 12/4

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

lun. 12/8

6:23 pm-8:23 pm

Nonstop3h 00m

$127

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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 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 $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 $234 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 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 15m 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 8,139 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 8,007 reviews	Search Delta flights
Frontier	PriceFrom $104	Free Cancellation	Rating 5.8 3,114 reviews	Search Frontier flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights
United Airlines	PriceFrom $118	Free Cancellation	Rating 7.4 9,015 reviews	Search United Airlines flights
Southwest	PriceFrom $137	Free Cancellation	Rating 8.0 4,236 reviews	Search Southwest flights

Southwest Flights From Chicago to Boston
Southwest flight deals from Chicago to Boston start from $137 round-trip. Over the 15 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, 8,007 ratings). Delta flies from Chicago to Boston around 9 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.

An easier way to manage your Boston trip

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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 12/12. 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 and deals

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Filter for what you want

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Find the cheapest flights from Chicago to Boston

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Southwest flights from Chicago to Boston

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Our best Delta deals on Chicago to Boston flight tickets

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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 49 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, 343 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