How long is the flight from Chicago to Boston?

Departing from Chicago to Boston will take you 2h 10m. Chicago and Boston are separated by a distance of 857 mi. Both multi-stop and direct flights can be found to your destination and back.

In terms of precipitation, rainfall in Boston ranges from 78.0 - 101.0 inches per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Boston when rainfall is around 78.0 mm.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -1.0 C).

What are the cheapest flights from Chicago to Boston?

The cheapest flight price from Chicago to Boston is £104. On average you can expect to pay £226. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £238.

What are the most reliable airlines from Chicago to Boston?

No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Envoy Air (94%), ITA Airways (77%) or Royal Jordanian (77%) as they are the most reliable in getting you off to your destination on time.

What airport do you fly into for flights to Boston from Chicago?

Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 44 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

Can I find deals for flights from Chicago to Boston that include hotel bookings?

Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers holiday packages that include both flights and hotel.

How can I find direct flights from Chicago to Boston?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.

Can I find deals for business class flights from Chicago to Boston?

Yes. Cheapflights offers flight deals from Chicago to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

£84+ Cheap Flights from Chicago to Boston

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in January or February, booked 57 days in advance, depart on a Friday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Boston

Enter your travel dates to find the best prices.

Cheapest

Best

Direct

Last-minute

One-way

Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 October 2026.

Thu 29/1006:30 -

1 stop7h 24m

Mon 2/1118:25 -

1 stop6h 32m

Deal found 8/10£166

Thu 5/1106:04 -

1 stop6h 40m

Thu 12/1105:30 -

1 stop5h 16m

Deal found 7/10£167

Fri 23/1006:10 -

1 stop7h 19m

Mon 26/1017:15 -

Nonstop3h 14m

Deal found 6/10£170

Thu 5/1110:20 -

1 stop5h 50m

Thu 12/1114:25 -

2 stops7h 05m

Deal found 7/10£171

Thu 12/1107:50 -

2 stops5h 40m

Mon 16/1117:45 -

1 stop6h 00m

Deal found 6/10£172

Fri 13/1119:45 -

Nonstop2h 23m

Wed 18/1120:40 -

Nonstop2h 56m

Deal found 8/10£173

Fri 13/1118:45 -

Nonstop2h 20m

Mon 16/1107:10 -

Nonstop2h 45m

Deal found 8/10£173

Wed 25/1119:00 -

Nonstop2h 25m

Fri 27/1107:05 -

Nonstop2h 45m

Deal found 8/10£174

Wed 11/1107:35 -

2 stops8h 35m

Mon 16/1113:20 -

2 stops7h 25m

Deal found 8/10£175

Wed 4/1112:50 -

1 stop5h 15m

Sat 7/1108:10 -

2 stops10h 15m

Deal found 7/10£175

Mon 26/1019:10 -

Nonstop2h 43m

Thu 29/1007:30 -

Nonstop2h 54m

Deal found 8/10£178

Mon 21/1221:49 -

Nonstop2h 29m

Thu 24/1205:45 -

Nonstop3h 06m

Deal found 7/10£179

Best flights from Chicago to Boston
Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 8 October 2026.

Thu 12/1106:00 -

1 stop5h 25m

Thu 19/1114:00 -

1 stop5h 22m

Deal found 8/10£167

Thu 12/1120:25 -

1 stop10h 40m

Mon 16/1117:45 -

1 stop6h 00m

Deal found 6/10£172

Fri 30/1018:00 -

Nonstop2h 30m

Mon 2/1120:25 -

Nonstop3h 04m

Deal found 8/10£173

Mon 16/1106:00 -

1 stop6h 21m

Mon 16/1119:00 -

1 stop5h 54m

Deal found 6/10£167

Wed 25/1119:00 -

Nonstop2h 25m

Fri 27/1107:05 -

Nonstop2h 45m

Deal found 7/10£174

Thu 12/1118:44 -

1 stop4h 10m

Thu 19/1109:15 -

1 stop4h 36m

Deal found 8/10£167

Fri 30/1014:50 -

2 stops5h 30m

Thu 12/1114:30 -

1 stop8h 30m

Deal found 8/10£189

Fri 6/1107:25 -

Nonstop2h 35m

Mon 9/1120:40 -

Nonstop2h 56m

Deal found 6/10£173

Thu 5/1118:45 -

Nonstop2h 20m

Tue 10/1117:55 -

Nonstop2h 45m

Deal found 6/10£195

Fri 13/1118:15 -

1 stop5h 53m

Mon 16/1109:15 -

1 stop5h 44m

Deal found 8/10£188

Thu 19/1109:40 -

1 stop6h 10m

Thu 26/1113:05 -

Nonstop2h 40m

Deal found 5/10£203

Thu 29/1005:27 -

1 stop8h 27m

Fri 30/1014:59 -

1 stop6h 39m

Deal found 8/10£188

Tue 22/1217:45 -

Nonstop2h 29m

Wed 30/1214:55 -

Nonstop3h 06m

Deal found 7/10£195

Mon 23/1115:35 -

Nonstop2h 15m

Fri 27/1107:05 -

Nonstop2h 45m

Deal found 5/10£217

Wed 25/1119:00 -

Nonstop2h 25m

Mon 30/1119:40 -

1 stop4h 35m

Deal found 6/10£218

Thu 19/1106:00 -

1 stop6h 21m

Sun 22/1120:40 -

Nonstop2h 56m

Deal found 6/10£203

Sat 24/1016:25 -

Nonstop2h 25m

Thu 29/1022:00 -

Nonstop2h 40m

Deal found 6/10£218

Sun 24/107:00 -

1 stop4h 01m

Mon 25/111:00 -

1 stop6h 12m

Deal found 6/10£210

Fri 6/1110:10 -

1 stop6h 30m

Sun 8/1107:05 -

Nonstop2h 45m

Deal found 5/10£225

Wed 4/1117:29 -

1 stop5h 30m

Sun 8/1105:50 -

1 stop6h 50m

Deal found 6/10£210

Sun 22/1107:50 -

2 stops5h 40m

Fri 27/1107:05 -

Nonstop2h 45m

Deal found 7/10£228

Find flight deals from Chicago to Boston

Round-trip from	£166
One-way from	£84
Popular in	September
Cheapest in	January
Average price	£221
Good one-way deal	£217 or less

Delta
29/10-2/11
2 total stops
13h 56m total
Chicago to Boston

Search Deals

Delta
31/10-31/12
1 total stop
4h 20m total
Chicago to Boston

Search Deals

Highest demand for flights based on searches. 11% potential increase in price (£19 potential increase over avg. return price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 6/1

12:55-19:08

1 stop5h 13m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Mon 16/11

07:00-14:21

1 stop6h 21m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Thu 17/12

18:10-23:50

1 stop4h 40m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 9/12

06:49-14:58

1 stop7h 09m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 3/11

08:36-15:23

1 stop5h 47m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Thu 17/12

06:00-12:19

1 stop5h 19m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Mon 14/12

09:59-17:51

1 stop6h 52m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Thu 17/12

09:37-15:54

1 stop5h 17m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 5/1

10:35-19:21

1 stop7h 46m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 27/10

09:29-16:15

1 stop5h 46m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

Flights are sorted by cheapest return flights first.

Deals found on 7/10

Showing 1-10 of 42 resultsSorted by cheapest first

...

Best time to book a flight from Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.

CHI-BOS

ORD-BOS

MDW-BOS

Estimated return price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Boston

CHI-BOS

ORD-BOS

MDW-BOS

What is the cheapest month to book a flight from Chicago to Boston?

Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £152). Flying from Chicago to Boston in September is currently the most expensive (average of £237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to BOS?

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 80% versus a flight at midday.

Weekly flight availability from Chicago to Boston

The most flights from CHI to BOS are scheduled on a Wednesday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost for a return flight from Chicago to Boston?

Airfare is typical for this route at the moment.

Chicago to Boston flights typically cost between £164 and £284 in October.
The cheapest return price found within the last 5 days was £166 on Delta (29 Oct–2 Nov).

How often are flights from Chicago to Boston delayed?

About 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 155 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

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

Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

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

Over the past year, Delta have had the lowest number of delays on this route, with just 22% of flights being delayed.

How far ahead should I book a flight from Chicago to Boston?

Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

What airport do you fly into for flights to Boston from Chicago?
Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 44 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.
How long is the flight from Chicago to Boston?
Departing from Chicago to Boston will take you 2h 10m. Chicago and Boston are separated by a distance of 857 mi. Both multi-stop and direct flights can be found to your destination and back.
What are the most reliable airlines from Chicago to Boston?
No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Envoy Air (94%), ITA Airways (77%) or Royal Jordanian (77%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Chicago to Boston?
The cheapest flight price from Chicago to Boston is £104. On average you can expect to pay £226. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £238.
Can I find deals for flights from Chicago to Boston that include hotel bookings?
Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers holiday packages that include both flights and hotel.
How can I find direct flights from Chicago to Boston?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.
Can I find deals for business class flights from Chicago to Boston?
Yes. Cheapflights offers flight deals from Chicago to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Boston?
Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £152). Flying from Chicago to Boston in September is currently the most expensive (average of £237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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How does Cheapflights help users find flights from Chicago to Boston?

Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.

Can Cheapflights find flights from Chicago to Boston with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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Cheap flights from Chicago to Boston from £84

This is the cheapest retur flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/1. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Chicago to Boston

Cheapest flights from Chicago to BostonExplore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 October 2026.

Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 October 2026.

Best flights from Chicago to BostonDiscover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 8 October 2026.

Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 8 October 2026.

Direct flights from Chicago to BostonExplore direct flight options from Chicago to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 8 October 2026.

Explore direct flight options from Chicago to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 8 October 2026.

Last-minute flights from Chicago to BostonDiscover last-minute flight deals from Chicago to Boston. Data last updated 8 October 2026 and is based on user searches.

Discover last-minute flight deals from Chicago to Boston. Data last updated 8 October 2026 and is based on user searches.

One-way flights from Chicago to BostonSearch for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated 8 October 2026.

Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated 8 October 2026.

Find flight deals from Chicago to Boston

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

Best time to book a flight from Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.

Cheapflights Insights

What is the cheapest month to book a flight from Chicago to Boston?

What is the cheapest time of day to fly from CHI to BOS?

Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 8 October 2026.

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 80% versus a flight at midday.

Weekly flight availability from Chicago to Boston

Explore weekly flight availability from Chicago to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 8 October 2026.

The most flights from CHI to BOS are scheduled on a Wednesday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost for a return flight from Chicago to Boston?

Airfare is typical for this route at the moment.

Chicago to Boston flights typically cost between £164 and £284 in October.The cheapest return price found within the last 5 days was £166 on Delta (29 Oct–2 Nov).

How often are flights from Chicago to Boston delayed?

About 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 155 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

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

Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

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

Over the past year, Delta have had the lowest number of delays on this route, with just 22% of flights being delayed.

How far ahead should I book a flight from Chicago to Boston?

Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Related info for your journey

What airport do you fly into for flights to Boston from Chicago?

How long is the flight from Chicago to Boston?

What are the most reliable airlines from Chicago to Boston?

What are the cheapest flights from Chicago to Boston?

Can I find deals for flights from Chicago to Boston that include hotel bookings?

How can I find direct flights from Chicago to Boston?

Can I find deals for business class flights from Chicago to Boston?

What is the cheapest month to book a flight from Chicago to Boston?

Travelling to a place near Boston?

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Alternative routes for Chicago to Boston

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Other flights to Boston

Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 8 October 2026.

Complete your trip

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Direct flights to Massachusetts

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Search flights from Chicago to Boston by cabin class

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Chicago and Boston flights

Browse other Chicago and Boston flight options. Last updated on 8 October 2026.

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How does Cheapflights help users find flights from Chicago to Boston?

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

Can Cheapflights find flights from Chicago to Boston with no change fees?

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

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Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 October 2026.

Best flights from Chicago to Boston
Discover carefully curated flight deals from Chicago to Boston that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 8 October 2026.

Direct flights from Chicago to Boston
Explore direct flight options from Chicago to Boston based on user searches, and compare prices and availability for your desired travel dates. Data last updated 8 October 2026.

Last-minute flights from Chicago to Boston
Discover last-minute flight deals from Chicago to Boston. Data last updated 8 October 2026 and is based on user searches.

One-way flights from Chicago to Boston
Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Data last updated 8 October 2026.

Chicago to Boston flights typically cost between £164 and £284 in October.
The cheapest return price found within the last 5 days was £166 on Delta (29 Oct–2 Nov).