Find flights
Deals
When to book
FAQs

Cheap flights from Boston to Chicago from £81

BOS — CHI
3 Oct — 10 Oct1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 89 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap flight deals from Boston to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Boston to Chicago

Thu 1/1011:17 -
1 stop12h 42m
Sat 3/1015:50 -
1 stop18h 08m
Deal found 3/9£141
Sat 17/1006:55 -
1 stop5h 29m
Tue 20/1012:38 -
1 stop7h 11m
Deal found 3/9£155
Thu 24/920:50 -
Nonstop2h 42m
Mon 28/907:35 -
Nonstop2h 33m
Deal found 3/9£161
Thu 24/917:00 -
Nonstop3h 01m
Mon 28/907:00 -
1 stop6h 27m
Deal found 3/9£161
Fri 16/1017:12 -
Nonstop3h 02m
Thu 5/1120:24 -
Nonstop2h 44m
Deal found 2/9£167
Thu 15/1008:05 -
Nonstop2h 55m
Tue 20/1006:00 -
1 stop4h 24m
Deal found 3/9£168
Sun 15/1120:40 -
Nonstop2h 56m
Tue 17/1110:35 -
Nonstop2h 24m
Deal found 3/9£172
Fri 16/1019:40 -
Nonstop2h 51m
Fri 6/1107:25 -
Nonstop2h 35m
Deal found 2/9£174
Thu 1/1014:10 -
1 stop4h 47m
Sat 3/1006:50 -
Nonstop2h 39m
Deal found 2/9£175
Sat 10/1019:40 -
Nonstop2h 51m
Sat 24/1007:25 -
Nonstop2h 35m
Deal found 3/9£175

Find flight deals from Boston to Chicago

Round-trip from

£141

One-way from

£81

Popular in

June

Cheapest in

January

Average price

£172

Good one-way deal

£94 or less
Frontier
  • Frontier
  • 1/10-3/10
  • 2 total stops
  • 30h 50m total
  • Boston to Chicago
Search Deals
American Airlines
  • American Airlines
  • 9/11-31/12
  • Nonstop
  • 3h 14m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£9 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
Search Deals
Average for round-trip flights in September 2026
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 26/11

13:35-15:30

Nonstop2h 55m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£81
Fastest return journey

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 4/10

07:30-09:24

Nonstop2h 54m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£93

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 28/10

17:15-19:29

Nonstop3h 14m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£102

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 26/10

09:12-11:15

Nonstop3h 03m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£102

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Mon 21/9

05:15-09:58

1 stop5h 43m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£102

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 17/9

16:30-18:28

Nonstop2h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£102

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 22/9

16:30-18:28

Nonstop2h 58m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£107

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 27/9

06:00-07:59

Nonstop2h 59m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£122

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 11/10

05:45-09:38

1 stop4h 53m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£133

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 3/1

05:45-11:37

1 stop6h 52m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£137

Flights are sorted by cheapest return flights first.

Deals found on 2/9

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Boston to Chicago

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

Cheapflights Insights

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

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

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £145). Flying from Boston to Chicago in June is currently the most expensive (average of £204). 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 BOS to CHI?

When flying from Boston to Chicago, 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 64% versus a flight in the afternoon.

Weekly flight availability from Boston to Chicago

The most flights from BOS to CHI are scheduled on a Wednesday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

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

Airfare is typical for this route at the moment.
Boston to Chicago flights typically cost between £121 and £225 in October.
The cheapest return price found within the last 5 days was £141 on Frontier (1 Oct–3 Oct).

How often are flights from Boston to Chicago delayed?

About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 171 minutes.

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

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

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

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

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

Over the past year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.

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

The best time to book flights from Boston to Chicago is 14 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

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

    Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 43 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

  • How long is the flight from Boston to Chicago?

    A quick flight from Boston to Chicago can take about 2h 54m. Delta provides one of the quickest options available for as low as £161. Airlines will cover a distance of 864 mi. All flights are typically direct.

  • What are the most reliable airlines from Boston to Chicago?

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Japan Airlines (84%), Republic Airways (77%) or Cathay Pacific (77%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is £77. On average you can expect to pay £143. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £161.

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

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

  • How can I find direct flights from Boston to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Boston to Chicago 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 Boston to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £145). Flying from Boston to Chicago in June is currently the most expensive (average of £204). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Boston to Chicago

Boston to O'Hare Intl flights

Fly with Cheapflights

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!

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

Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.