Question 1

How long does a flight from Boston to Chicago take?

Accepted Answer

Direct flights from Boston generally make it to Chicago in 2h 58m. The flying distance between the two cities is 2,237 km. Visit our flight page for the latest deals!>/a>

Question 2

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

Accepted Answer

Each day, there are between 13 and 18 direct flights that take off from Boston and land in Chicago O'Hare Intl Airport, with an average flight time of 3h 10m. The most common departure time is 12:00 and most flights take off in the morning. Each week, there are 117 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

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

Accepted Answer

Each day, there are between 13 and 18 direct flights that take off from Boston and land in Chicago O'Hare Intl Airport, with an average flight time of 3h 10m. The most common departure time is 12:00 and most flights take off in the morning. Each week, there are 117 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 4

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

Accepted Answer

In the last 3 days, the lowest price for a flight from Boston to Chicago O'Hare Intl Airport was ₹ 6,137 for a one-way ticket and ₹ 12,184 for a return. <a href='/flight-routes/Boston-Logan-Intl-BOS/Chicago-O-Hare-Intl-ORD'>Visit our flight page for the latest deals!>/a>

Question 5

Which airlines fly most frequently between Boston and Chicago?

Accepted Answer

Boston and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (46 flights per week), United Airlines (38 flights per week), and Delta (26 flights per week). Visit our flight page for the latest deals!>/a>

Question 6

Which airlines fly most frequently between Boston and Chicago?

Accepted Answer

Boston and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (46 flights per week), United Airlines (38 flights per week), and Delta (26 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 Boston to Chicago?

Accepted Answer

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

Accepted Answer

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

Question 9

Which airports will I be using when flying from Boston to Chicago?

Accepted Answer

When flying out of Boston you will be using Boston Logan Intl. You will be landing at Chicago, also known as Chicago O'Hare Intl. <a href='/flight-routes/Boston-Logan-Intl-BOS/Chicago-O-Hare-Intl-ORD'>Visit our flight page for the latest deals!>/a>

Question 10

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

Accepted Answer

Early birds can take the earliest flight from Boston at 06:00 and will be landing in Chicago O'Hare Intl Airport at 08:00.

Question 11

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

Accepted Answer

If you prefer to fly at night, the latest flight from Boston to Chicago O'Hare Intl Airport jets off at 20:40 and lands at 22:44.

Question 12

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

Accepted Answer

American Airlines, JetBlue, Delta, Alaska Airlines, and Air Canada offer inflight Wi-Fi service on the Boston to Chicago flight route.

Question 13

Which aircraft models fly most regularly from Boston to Chicago?

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

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

Accepted Answer

The cheapest month for flights from Boston to Chicago O'Hare Intl Airport is September, where tickets cost ₹ 18,682 (return) on average. On the other hand, the most expensive months are April and October, where the average cost of round-trip tickets is ₹ 25,090 and ₹ 24,097 respectively.

Question 16

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

Accepted Answer

The cheapest month for flights from Boston to Chicago O'Hare Intl Airport is September, where tickets cost ₹ 18,682 (return) on average. On the other hand, the most expensive months are April and October, where the average cost of round-trip tickets is ₹ 25,090 and ₹ 24,097 respectively.

Question 17

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

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 Boston to Chicago. <a href='/flight-routes/Boston-Logan-Intl-BOS/Chicago-O-Hare-Intl-ORD'>Visit our flight page for the latest deals!>/a>

Question 18

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

Accepted Answer

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

Question 19

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

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 Chicago with an airline and back to Boston with another airline. <a href='/flight-routes/Boston-Logan-Intl-BOS/Chicago-O-Hare-Intl-ORD'>Visit our flight page for the latest deals!>/a>

Question 20

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

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 Chicago from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. <a href='/flight-routes/Boston-Logan-Intl-BOS/Chicago-O-Hare-Intl-ORD'>Visit our flight page for the latest deals!>/a>

Question 21

How often are flights from Boston to Chicago delayed?

Accepted Answer

Weekly flights between Boston and Chicago historically see delays in approximately 13% of cases, with the average delay over the past year being 168 minutes.

Question 22

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

Accepted Answer

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 10% of their flights encountering any delays.

Question 23

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 24

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

Accepted Answer

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

Question 25

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

Accepted Answer

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

Question 26

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

Accepted Answer

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

Question 27

Which airlines provide the cheapest flights from Boston to Chicago?

Accepted Answer

In the past 3 days, the cheapest return tickets from Boston to Chicago were found on United Airlines (₹ 12,184) and Delta (₹ 12,184).

Question 28

Which airlines provide the cheapest flights from Boston to Chicago?

Accepted Answer

In the past 3 days, the cheapest return tickets from Boston to Chicago were found on United Airlines (₹ 12,184) and Delta (₹ 12,184).

Question 29

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

Accepted Answer

To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Question 30

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

Accepted Answer

To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Question 31

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

Accepted Answer

No, with an average price for the route of ₹ 12,361, prices are generally cheapest when you fly direct.

Question 32

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

Accepted Answer

No, with an average price for the route of ₹ 12,361, prices are generally cheapest when you fly direct.

Low season	January
High season	July
Cheapest flight	₹ 6,137

BOS - ORD

₹ 6,137 Find Cheap Flights from Boston to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

Everything you should know

Cheap Flights from Boston to O'Hare Intl (BOS-ORD)

Recent return flight deals from Boston to O'Hare Intl

Recent one-way flight deals from Boston to O'Hare Intl

Recent last minute flight deals from Boston to O'Hare Intl

Recent direct flight deals from Boston to O'Hare Intl

KAYAK's insights & trends for Boston to O'Hare Intl flights

Get data-powered insights and trends into flights from Boston to O'Hare Intl 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 Boston to Chicago?

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

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

The cheapest month for flights from Boston to Chicago O'Hare Intl Airport is September, where tickets cost ₹ 18,682 (return) on average. On the other hand, the most expensive months are April and October, where the average cost of round-trip tickets is ₹ 25,090 and ₹ 24,097 respectively.

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

No, with an average price for the route of ₹ 12,361, prices are generally cheapest when you fly direct.

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

To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Which airlines provide the cheapest flights from Boston to Chicago?

In the past 3 days, the cheapest return tickets from Boston to Chicago were found on United Airlines (₹ 12,184) and Delta (₹ 12,184).

Which airlines fly most frequently between Boston and Chicago?

Boston and Chicago are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (46 flights per week), United Airlines (38 flights per week), and Delta (26 flights per week).

How often are flights from Boston to Chicago delayed?

Weekly flights between Boston and Chicago historically see delays in approximately 13% of cases, with the average delay over the past year being 168 minutes.

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

Typically, flights leaving in the morning tend to face fewer delays, whereas flights in the evening 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 Boston to Chicago flights?

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 10% of their flights encountering any delays.

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

There are 2 cabin class options for the route. These are Economy and Prem 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 Boston and Chicago O'Hare Intl Airport per day?

How long does a flight from Boston to Chicago take?

Direct flights from Boston generally make it to Chicago in 2h 58m. The flying distance between the two cities is 2,237 km.

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

Early birds can take the earliest flight from Boston at 06:00 and will be landing in Chicago O'Hare Intl Airport at 08:00.

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

If you prefer to fly at night, the latest flight from Boston to Chicago O'Hare Intl Airport jets off at 20:40 and lands at 22:44.

Good to know

When to book flights from Boston to O'Hare Intl

FAQs for booking Boston to Chicago flights

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

In the last 3 days, the lowest price for a flight from Boston to Chicago O'Hare Intl Airport was ₹ 6,137 for a one-way ticket and ₹ 12,184 for a return.

Which airports will I be using when flying from Boston to Chicago?

When flying out of Boston you will be using Boston Logan Intl. You will be landing at Chicago, also known as Chicago O'Hare Intl.

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

American Airlines, JetBlue, Delta, Alaska Airlines, and Air Canada offer inflight Wi-Fi service on the Boston to Chicago flight route.

Which aircraft models fly most regularly from Boston to Chicago?

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

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

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

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

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 Boston to Chicago.

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

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston 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 Boston to Chicago?

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 Chicago with an airline and back to Boston with another airline.

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

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 Chicago from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Boston Logan Intl to Chicago O'Hare Intl?

Everything you need to know for your flight from Boston to O'Hare Intl

Information on your arrival and departure airports

Cabin class types available on flights to O'Hare Intl

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Flights from domestic origins to O'Hare Intl

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