How long does a flight from Chicago to Boston take?

The average direct flight takes 2h 28m , covering a distance of 864 miles.

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

Each day, there are between 25 and 26 direct flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 33m. The most common departure time is 15:00 and most flights take off in the morning. Each week, there are 181 flights. The most frequent day of departure is Monday, when 14% of all weekly flights depart. The fewest flights depart on a Saturday.

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

In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £84 for a one-way ticket and £166 for a return.

Which airlines fly most frequently between Chicago and Boston?

American Airlines connects Chicago to Boston with 70 flights per week. United Airlines also offers 70 flights per week, while Delta follows with 27 flights per week.

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

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

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 09:29.

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 21:24 and lands at 00:54.

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: JetBlue, American Airlines, Delta, British Airways, Iberia, and Finnair.

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.

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 £156 (return) on average. On the other hand, the most expensive months are September and October, where the average cost of round-trip tickets is £253 and £237 respectively.

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.

How often are flights from Chicago to Boston delayed?

Weekly flights between Chicago and Boston historically see delays in approximately 26% of cases , with the average delay over the past year being 159 minutes.

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

Based on our data, Delta have experienced the fewest delays on this route in the past 12 months, with only about 22% of their flights encountering any delays.

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 Sunday has typically experienced more delays than other days.

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.

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.

Which airlines provide the cheapest flights from Chicago to Boston?

In the past 5 days, the cheapest return tickets from Chicago to Boston were found on Delta (£166) and JetBlue (£170).

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 , which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

How much is a return flight from Chicago O'Hare Intl Airport to Boston?

Flight prices are below average for this route right now. Flights to Boston from Chicago O'Hare Intl Airport usually cost between £176 and £300 in October. The lowest price found in the past 5 days was £166 on Delta (29 Oct–2 Nov).

£84 CHEAP FLIGHTS from Chicago to Boston (ORD - BOS)

Save 28% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Cheapest return fare

£166

Typical prices: £145-£280

Delta

Thu 29/10Mon 2/11

ORD - BOS • 1 stop

Cheapest direct flights

£170

Typical prices: £122-£230

United Airlines

Tue 9/2Thu 11/2

ORD - BOS • Direct

Advice from real travellers

AI-powered summary based on content written by travel experts. AI can make mistakes.

JetBlue adds Even More Space seats; Delta offers free Wi-Fi for SkyMiles members.

At ORD, security lines can top 30 minutes; arrive early for smoother departure.

Expert advice

Direct flights

Every day

You can fly direct with American Airlines, Delta, and others. Average duration is 2h 33m

Direct flights

Avoid delays

Delta

Most punctual • 78% on-time

Morning flights

Best time • Fewest delays

Insights

When to book

3 weeks

in advance

Our data shows that travellers who book at least 3 weeks in advance save around 23% compared to booking last minute.

Insights

When to travel

January

Cheapest • 24% price drop

July

Most popular

Good to know

Start a new search

KAYAK searches hundreds of sites at once to find you the best travel deals.

We hope you love your trip to Boston!

Flight Deals

Cheap Flights from Chicago to Boston (ORD-BOS)

Discover the best prices for you by selecting your travel dates on KAYAK.

Return

One-way

Last minute

Direct

Recent return flight deals from Chicago to Boston

Thu, 29 Oct - Mon, 2 Nov

06:30 - 14:54ORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 24m1 stop Atlanta Hartsfield-Jackson

18:25 - 23:57BOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 32m1 stop Atlanta Hartsfield-Jackson

£166Delta

Thu, 29 Oct - Mon, 2 Nov

06:30 - 14:54ORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 24m1 stop Atlanta Hartsfield-Jackson

18:25 - 23:57BOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 32m1 stop Atlanta Hartsfield-Jackson

£167Delta

Thu, 29 Oct - Mon, 2 Nov

08:29 - 16:15ORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 46m1 stop Detroit Metropolitan Wayne County

18:25 - 23:57BOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 32m1 stop Atlanta Hartsfield-Jackson

£169Delta

Fri, 23 Oct - Mon, 26 Oct

06:10 - 14:29ORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop New York John F Kennedy Intl

17:15 - 19:29BOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 14mdirect

£170JetBlue

Fri, 13 Nov - Wed, 18 Nov

19:45 - 23:08ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mdirect

20:40 - 22:36BOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mdirect

£173Delta

Tue, 9 Feb - Thu, 11 Feb

07:15 - 10:42ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mdirect

08:30 - 13:08BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 38m1 stop Newark

£178United Airlines

Mon, 26 Oct - Thu, 29 Oct

19:10 - 22:53ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mdirect

07:30 - 09:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mdirect

£179Delta

Mon, 21 Dec - Thu, 24 Dec

21:49 - 01:18ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mdirect

05:45 - 07:51BOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mdirect

£179United Airlines

Fri, 6 Nov - Mon, 9 Nov

07:25 - 11:00ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mdirect

19:00 - 23:54BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 54m1 stop Atlanta Hartsfield-Jackson

£181Delta

Wed, 13 Jan - Mon, 18 Jan

10:30 - 13:55ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mdirect

10:35 - 15:17BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 42m1 stop Newark

£183United Airlines

Recent last minute flight deals from Chicago to Boston

Sat, 10 Oct - Thu, 5 Nov

15:15 - 23:34ORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop Atlanta Hartsfield-Jackson

07:30 - 09:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mdirect

£234Delta

Sat, 10 Oct - Thu, 5 Nov

10:35 - 19:07ORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 32m1 stop Atlanta Hartsfield-Jackson

06:00 - 10:28BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 28m1 stop New York LaGuardia

£241Delta

Wed, 14 Oct - Tue, 20 Oct

20:00 - 23:36ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mdirect

16:48 - 19:00BOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mdirect

£269American Airlines

Wed, 14 Oct - Tue, 20 Oct

20:04 - 23:59ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mdirect

06:55 - 11:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

£269JetBlue

Wed, 14 Oct - Tue, 20 Oct

20:04 - 23:59ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mdirect

06:55 - 11:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

£270JetBlue

Wed, 14 Oct - Tue, 20 Oct

20:04 - 23:59ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mdirect

06:55 - 11:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

£272JetBlue

Wed, 14 Oct - Tue, 20 Oct

20:04 - 23:59ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mdirect

06:55 - 11:24BOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

£275JetBlue

Wed, 14 Oct - Tue, 20 Oct

06:50 - 12:44ORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 54m1 stop New York LaGuardia

13:33 - 15:37BOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mdirect

£276American Airlines

Thu, 15 Oct - Mon, 19 Oct

06:00 - 11:24ORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 24m1 stop Newark

08:05 - 10:00BOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mdirect

£277United Airlines

Wed, 14 Oct - Thu, 22 Oct

10:24 - 13:54ORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mdirect

09:15 - 12:59BOS Boston Logan Intl-ORD Chicago O'Hare Intl

4h 44m1 stop Detroit Metropolitan Wayne County

£282Delta

Booking Insights

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.

Prices

Airlines

Delays

How much is a return flight from Chicago O'Hare Intl Airport to Boston? This analysis is based on the cheapest return trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Boston departing in October.
What’s the cheapest day of the week to fly from Chicago to Boston? The average price of all round-trip flights from Chicago O'Hare Intl Airport to Boston clicked on KAYAK for each day over the last 12 months.: For Chicago to Boston, Sunday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Wednesday being the most expensive.
What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston? To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.: The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is January, where tickets cost £156 (return) on average. On the other hand, the most expensive months are September and October, where the average cost of round-trip tickets is £253 and £237 respectively.
How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston? To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.: 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, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Find deals

Expert advice

Our travel experts

Harriet Baskas

Expert on JetBlue

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Stefanie Waldek

Expert on Delta and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specialising in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favourite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history.

Low season	January
High season	July
Cheapest flight	£84

Best time to beat the crowds (24% less expensive on average)

Most popular time to fly (4% more expensive on average)

Flight from Chicago to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated return price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

What is the cheapest flight from Chicago O'Hare Intl Airport to Boston?
In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £84 for a one-way ticket and £166 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: JetBlue, American Airlines, Delta, British Airways, Iberia, and Finnair.
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.

Looking for a cheap flight from Boston to Chicago? 25% of our users found flights on this route for £218 or less one-way.

Direct departures

Chicago O'Hare Intl to Boston Logan Intl

Monday