Question 1

How long does a flight from Chicago to Boston take?

Accepted Answer

The average direct flight takes 2h 15m, covering a distance of 864 miles. Visit our flight page for the latest deals!>/a>

Question 2

How many flights are there between Chicago O'Hare Intl Airport and Boston per day?

Accepted Answer

Each day, there are between 10 and 18 direct flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 26m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 105 flights. The most frequent day of departure is Monday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday. Visit our flight page for the latest deals!>/a>

Question 3

How many flights are there between Chicago O'Hare Intl Airport and Boston per day?

Accepted Answer

Each day, there are between 10 and 18 direct flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 26m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 105 flights. The most frequent day of departure is Monday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday. Visit our flight page for the latest deals!>/a>

Question 4

What is the cheapest flight from Chicago O'Hare Intl Airport to Boston?

Accepted Answer

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £48 for a one-way ticket and £95 for a return. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Boston-Logan-Intl-BOS'>Visit our flight page for the latest deals!>/a>

Question 5

Which airlines fly most frequently between Chicago and Boston?

Accepted Answer

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (42 flights per week), United Airlines (39 flights per week), and Delta (17 flights per week). Visit our flight page for the latest deals!>/a>

Question 6

Which airlines fly most frequently between Chicago and Boston?

Accepted Answer

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (42 flights per week), United Airlines (39 flights per week), and Delta (17 flights per week). Visit our flight page for the latest deals!>/a>

Question 7

What’s the cheapest day of the week to fly from Chicago to Boston?

Accepted Answer

For Chicago to Boston, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Saturday being the most expensive. Visit our flight page for the latest deals!>/a>

Question 8

What’s the cheapest day of the week to fly from Chicago to Boston?

Accepted Answer

For Chicago to Boston, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Saturday being the most expensive. Visit our flight page for the latest deals!>/a>

Question 9

What’s the earliest departure time from Chicago to Boston?

Accepted Answer

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 00:15 and will be landing in Boston at 03:39.

Question 10

What’s the latest departure time from Chicago to Boston?

Accepted Answer

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Boston jets off at 21:12 and lands at 00:45.

Question 11

Which airlines offer Wi-Fi service onboard planes from Chicago to Boston?

Accepted Answer

All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, JetBlue, Delta, British Airways, Iberia, Finnair, and Lufthansa.

Question 12

Which aircraft models fly most regularly from Chicago to Boston?

Accepted Answer

The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Boston flight route.

Question 13

On which days can I fly direct from Chicago to Boston?

Accepted Answer

There are direct flights from Chicago to Boston on a daily basis.

Question 14

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston?

Accepted Answer

The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is January, where tickets cost £144 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is £203 and £200 respectively.

Question 15

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston?

Accepted Answer

The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is January, where tickets cost £144 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is £203 and £200 respectively.

Question 16

How does KAYAK find such low prices on flights from Chicago to Boston?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Boston. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Boston-Logan-Intl-BOS'>Visit our flight page for the latest deals!>/a>

Question 17

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Boston?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago is likely to change within 7 days, so travellers know whether to wait or book now. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Boston-Logan-Intl-BOS'>Visit our flight page for the latest deals!>/a>

Question 18

What is the Hacker Fare option on flights from Chicago to Boston?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Boston with an airline and back to Chicago with another airline. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Boston-Logan-Intl-BOS'>Visit our flight page for the latest deals!>/a>

Question 19

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Boston?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Chicago-O-Hare-Intl-ORD/Boston-Logan-Intl-BOS'>Visit our flight page for the latest deals!>/a>

Question 20

How often are flights from Chicago to Boston delayed?

Accepted Answer

Weekly flights between Chicago and Boston historically see delays in approximately 22% of cases, with the average delay over the past year being 152 minutes.

Question 21

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

Accepted Answer

Based on our data, JetBlue have experienced the fewest delays on this route in the past 12 months, with only about 18% of their flights encountering any delays.

Question 22

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

Accepted Answer

Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Thursday has typically experienced more delays than other days.

Question 23

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

Accepted Answer

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the early afternoon have historically encountered delays more often.

Question 24

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Boston?

Accepted Answer

There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 25

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Boston?

Accepted Answer

There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 26

Which airlines provide the cheapest flights from Chicago to Boston?

Accepted Answer

In the past 3 days, the cheapest return tickets from Chicago to Boston were found on JetBlue (£102) and Delta (£102).

Question 27

Which airlines provide the cheapest flights from Chicago to Boston?

Accepted Answer

In the past 3 days, the cheapest return tickets from Chicago to Boston were found on JetBlue (£102) and Delta (£102).

Question 28

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston?

Accepted Answer

To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 5 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Question 29

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston?

Accepted Answer

To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 5 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Low season	February
High season	June
Cheapest flight	£48

ORD - BOS

£48 Find Cheap Flights from Chicago to Boston

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

Everything you should know

Cheap Flights from Chicago to Boston (ORD-BOS)

Recent return flight deals from Chicago to Boston

Recent one-way flight deals from Chicago to Boston

Recent last minute flight deals from Chicago to Boston

Recent direct flight deals from Chicago to Boston

KAYAK's insights & trends for Chicago to Boston flights

Get data-powered insights and trends into flights from Chicago to Boston to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Boston?

For Chicago to Boston, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Saturday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston?

The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is January, where tickets cost £144 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is £203 and £200 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston?

To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 5 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Which airlines provide the cheapest flights from Chicago to Boston?

In the past 3 days, the cheapest return tickets from Chicago to Boston were found on JetBlue (£102) and Delta (£102).

Which airlines fly most frequently between Chicago and Boston?

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (42 flights per week), United Airlines (39 flights per week), and Delta (17 flights per week).

How often are flights from Chicago to Boston delayed?

Weekly flights between Chicago and Boston historically see delays in approximately 22% of cases, with the average delay over the past year being 152 minutes.

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

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the early afternoon have historically encountered delays more often.

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

Statistically, Saturday is the day of the week with the fewest delays on this flight route, while Thursday has typically experienced more delays than other days.

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

Based on our data, JetBlue have experienced the fewest delays on this route in the past 12 months, with only about 18% of their flights encountering any delays.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Boston?

There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How many flights are there between Chicago O'Hare Intl Airport and Boston per day?

How long does a flight from Chicago to Boston take?

The average direct flight takes 2h 15m, covering a distance of 864 miles.

What’s the earliest departure time from Chicago to Boston?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 00:15 and will be landing in Boston at 03:39.

What’s the latest departure time from Chicago to Boston?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Boston jets off at 21:12 and lands at 00:45.

Expert advice for your flight from Chicago to Boston

Good to know - Cheap tickets from Chicago to Boston

When to book flights from Chicago to Boston

FAQs for booking Chicago to Boston flights

What is the cheapest flight from Chicago O'Hare Intl Airport to Boston?

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £48 for a one-way ticket and £95 for a return.

Which airlines offer Wi-Fi service onboard planes from Chicago to Boston?

All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, JetBlue, Delta, British Airways, Iberia, Finnair, and Lufthansa.

Which aircraft models fly most regularly from Chicago to Boston?

The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Boston flight route.

On which days can I fly direct from Chicago to Boston?

There are direct flights from Chicago to Boston on a daily basis.

How does KAYAK find such low prices on flights from Chicago to Boston?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Boston.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Boston?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

What is the Hacker Fare option on flights from Chicago to Boston?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Boston with an airline and back to Chicago with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Boston?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Boston

Prefer to fly direct from Chicago to Boston?

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

Information on your arrival and departure airports

Cabin class types available on flights to Boston

Complete your trip to Boston with a hotel stay or car hire

Find direct flights to and from Chicago and Boston

Flights to other popular destinations

Flights from domestic origins to Boston

Choose which airport to fly into in Chicago

Find deals for your return flight