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 18 and 24 direct flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 31m. The most common departure time is 08:00 and most flights take off in the morning. Each week, there are 157 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday. Visit our flight page for the latest deals!>/a>

Question 3

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 £62 for a one-way ticket and £125 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 4

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 (62 flights per week), United Airlines (56 flights per week), and Delta (27 flights per week). Visit our flight page for the latest deals!>/a>

Question 5

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

Accepted Answer

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

Question 6

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 06:00 and will be landing in Boston at 09:20.

Question 7

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 21:32 and lands at 00:59.

Question 8

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, Finnair, Iberia, and British Airways.

Question 9

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 10

Which airline alliances offer flights from Chicago to Boston?

Accepted Answer

oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Boston, with oneworld being the most commonly used for this route.

Question 11

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 12

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 September, where tickets cost £135 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is £201 and £190 respectively.

Question 13

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 14

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 15

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 16

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 17

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

Accepted Answer

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 18

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 (£92) and Southwest (£105).

Question 19

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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Low season	February
High season	October
Cheapest flight	£46

ORD - BOS

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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, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Friday 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 September, where tickets cost £135 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is £201 and £190 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 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 (£92) and Southwest (£105).

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 (62 flights per week), United Airlines (56 flights per week), and Delta (27 flights per week).

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

There is only one cabin class option available for the route, which is 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 06:00 and will be landing in Boston at 09:20.

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 21:32 and lands at 00:59.

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 £62 for a one-way ticket and £125 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, Finnair, Iberia, and British Airways.

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.

Which airline alliances offer flights from Chicago to Boston?

oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Boston, with oneworld being the most commonly used for this 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

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Cabin class types available on flights to Boston

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Choose which airport to fly into in Chicago

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