How often are flights from Chicago to Boston delayed?

Historically, on average around 23% 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 149 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 is the cheapest airline that flies from Chicago to Boston Logan Intl?

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

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

According to our data, JetBlue have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

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

As of February 2026, there are 46 flights per day flying from Chicago to Boston. The most common time of day flights depart is 7:00AM, with 45% of flights taking off at noon.

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. Sunday has historically seen more delays on average compared to the rest of the week.

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

As of February 2026, 326 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Fri, with 18% 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 38% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 6 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

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 6 as of February 2026.

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.

$66 Cheap Flights from Chicago to Boston in 2026

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.

12:10 pm - 8:05 pm

MDW

BOS

6h 55m

1 stop

7:05 am - 9:00 am

BOS

MDW

2h 55mnonstop

$130Southwest

Sat, Mar 7 - Sun, Mar 8

6:00 am - 9:25 am

ORD

BOS

2h 25mnonstop

7:00 am - 9:00 am

BOS

ORD

3h 00mnonstop

$131United Airlines

Fri, Apr 17 - Sun, Apr 19

9:30 pm - 12:59 am

ORD

BOS

2h 29mnonstop

7:00 am - 9:00 am

BOS

ORD

3h 00mnonstop

$132United Airlines

Mon, Mar 30 - Fri, Apr 3

1:55 pm - 5:10 pm

MDW

BOS

2h 15mnonstop

6:10 am - 7:55 am

BOS

MDW

2h 45mnonstop

$132Southwest

Thu, Apr 9 - Sun, Apr 12

7:40 am - 11:05 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$133JetBlue

Fri, Feb 6 - Sun, Feb 8

7:40 am - 11:05 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$134JetBlue

Fri, Feb 6 - Sun, Feb 8

4:30 pm - 7:44 pm

ORD

BOS

2h 14mnonstop

7:00 am - 9:05 am

BOS

ORD

3h 05mnonstop

$136American Airlines

Fri, Feb 6 - Sun, Feb 8

7:00 am - 10:23 am

ORD

BOS

2h 23mnonstop

7:00 am - 9:05 am

BOS

ORD

3h 05mnonstop

$138American Airlines

Fri, Feb 6 - Sun, Feb 8

6:40 pm - 1:09 am

MDW

BOS

5h 29m

1 stop

5:29 am - 8:54 am

BOS

MDW

4h 25m

1 stop

$139Delta

Wed, Mar 4 - Thu, Mar 5

7:17 am - 3:28 pm

ORD

BOS

7h 11m

1 stop

5:45 am - 5:15 pm

BOS

ORD

12h 30m

1 stop

$140Spirit Airlines

Tue, Apr 7 - Tue, Apr 14

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets

United Airlines

Apr 17

ORD6:00 amChicago O'Hare Intl

2h 25m

BOS9:25 amBoston Logan Intl

Apr 19

BOS7:00 amBoston Logan Intl

3h 00m

ORD9:00 amChicago O'Hare Intl

$131

United Airlines

Mar 30

ORD9:30 pmChicago O'Hare Intl

2h 29m

BOS12:59 amBoston Logan Intl

Apr 3

BOS7:00 amBoston Logan Intl

3h 00m

ORD9:00 amChicago O'Hare Intl

$132

United Airlines

Apr 3

ORD6:23 pmChicago O'Hare Intl

2h 36m

BOS9:59 pmBoston Logan Intl

Apr 6

BOS7:00 amBoston Logan Intl

3h 00m

ORD9:00 amChicago O'Hare Intl

$137

JetBlue flights from Chicago to Boston

Our best JetBlue deals on Chicago to Boston flight tickets

JetBlue

Feb 6

ORD7:40 amChicago O'Hare Intl

2h 25m

BOS11:05 amBoston Logan Intl

Feb 8

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$133

JetBlue

Feb 6

ORD7:40 amChicago O'Hare Intl

2h 25m

BOS11:05 amBoston Logan Intl

Feb 8

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$134

JetBlue

Feb 5

ORD7:40 amChicago O'Hare Intl

2h 25m

BOS11:05 amBoston Logan Intl

Feb 10

BOS3:35 pmBoston Logan Intl

3h 08m

ORD5:43 pmChicago O'Hare Intl

$135

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 3/7

12:10 pm-8:05 pm

1 stop6h 55m

Boston Logan Intl

Sun 3/8

7:05 am-9:00 am

Nonstop2h 55m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/17

6:00 am-9:25 am

Nonstop2h 25m

Boston Logan Intl

Sun 4/19

7:00 am-9:00 am

Nonstop3h 00m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/30

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Fri 4/3

7:00 am-9:00 am

Nonstop3h 00m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/9

1:55 pm-5:10 pm

Nonstop2h 15m

Boston Logan Intl

Sun 4/12

6:10 am-7:55 am

Nonstop2h 45m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/8

3:35 pm-5:43 pm

Nonstop3h 08m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

7:40 am-11:05 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/8

3:35 pm-5:43 pm

Nonstop3h 08m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

4:30 pm-7:44 pm

Nonstop2h 14m

Boston Logan Intl

Sun 2/8

7:00 am-9:05 am

Nonstop3h 05m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

7:00 am-10:23 am

Nonstop2h 23m

Boston Logan Intl

Sun 2/8

7:00 am-9:05 am

Nonstop3h 05m

$138

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 3/4

6:40 pm-1:09 am

1 stop5h 29m

Boston Logan Intl

Thu 3/5

5:29 am-8:54 am

1 stop4h 25m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/7

7:17 am-3:28 pm

1 stop7h 11m

Boston Logan Intl

Tue 4/14

5:45 am-5:15 pm

1 stop12h 30m

$140

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, January 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 January, then book flights to Boston from Chicago during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $207.

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 $237. 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 $294.

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 $213. 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 $290 per ticket.

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

Fly from Chicago Midway 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 $229 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 $187 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 February 2026, prices for Chicago to Boston flights are approximately 7% more expensive 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	$78
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Boston	1 airport

The best one-way flight to Boston from Chicago in the past 72 hours is $78. The best round-trip flight deal from Chicago to Boston found on momondo in the last 72 hours is $167.

The fastest flight from Chicago to Boston takes 2h 15m

Direct flights go from Chicago to Boston every day.

There is 1 airport in Boston. From Chicago there are direct flights to 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 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 6 as of February 2026.
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 20.96% of all bookings. The subsequent popular models are Embraer 175 at 17.19%, Airbus A220-300 at 9.56%, and Boeing 737 MAX 9 at 9.28%.
What is the most popular airline from Chicago to Boston?
Based on momondo bookings for flights between Chicago and Boston, the leading airline is United Airlines, making up 32% of the total bookings. Other popular airlines include American 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 $61	Free Cancellation	Rating 7.2 2,892 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $79	Free Cancellation	Rating 6.3 8,396 reviews	Search Spirit Airlines flights
Delta	PriceFrom $91	Free Cancellation	Rating 7.9 8,132 reviews	Search Delta flights
American Airlines	PriceFrom $117	Free Cancellation	Rating 7.2 11,212 reviews	Search American Airlines flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,231 reviews	Search United Airlines flights
Southwest	PriceFrom $136	Free Cancellation	Rating 8.0 4,272 reviews	Search Southwest flights

Southwest Flights From Chicago to Boston
Southwest flight deals from Chicago to Boston start from $136 round-trip. Over the 16 Southwest flights for this route in a normal week, average airfare is usually $243 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, 8,132 ratings). Delta flies from Chicago to Boston around 15 times per week, with deals starting from $91 round-trip and rising to an average price of around $216.

Hampton Beach

Salem

Ogunquit

Old Orchard Beach

Hampton

York Beach

Kennebunkport

Plymouth

Cambridge

South Yarmouth

Narragansett

Gloucester

Falmouth

Nashua

Brockton

Laconia

Warwick

Sturbridge

Chatham

Concord

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

Wed 3/4

Wed 3/11

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 $66

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 2/25. 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

United Airlines flights from Chicago to Boston

Our best United Airlines deals on Chicago to Boston flight tickets

JetBlue flights from Chicago to Boston

Our best JetBlue 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

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 $237. 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 $294.

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 Midway 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 February 2026, prices for Chicago to Boston flights are approximately 7% more expensive 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, JetBlue, 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 23% 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 149 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. Sunday 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, JetBlue have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

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

As of February 2026, there are 46 flights per day flying from Chicago to Boston. The most common time of day flights depart is 7:00AM, with 45% of flights taking off at noon.

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

As of February 2026, 326 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Fri, with 18% 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