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Cheap flights from Boston to Chicago O'Hare Intl Airport from ₹ 7,440

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
28 May — 4 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in January or September, booked 42 days in advance, depart on a Friday or Wednesday and return on a Tuesday

Cheap flight deals from Boston to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from Boston to O'Hare Intl
Explore the most affordable flight options available from Boston to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 April 2026.

Sun 7/606:00
BOS
-
ORD
Nonstop2h 59m
JetBlue
Tue 9/620:30
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 23/4₹ 14,691
Sat 23/510:16
BOS
-
ORD
1 stop7h 40m
Delta
Wed 27/509:36
ORD
-
BOS
1 stop5h 52m
Delta
Deal found 23/4₹ 14,786
Sat 30/505:40
BOS
-
ORD
1 stop5h 49m
Delta
Mon 1/618:06
ORD
-
BOS
1 stop6h 22m
Delta
Deal found 23/4₹ 14,880
Tue 19/516:15
BOS
-
ORD
Nonstop3h 00m
Delta
Fri 29/517:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 23/4₹ 14,974
Fri 11/920:10
BOS
-
ORD
Nonstop2h 56m
Delta
Mon 14/906:00
ORD
-
BOS
1 stop7h 22m
Delta
Deal found 23/4₹ 15,068
Sat 16/519:10
BOS
-
ORD
1 stop5h 27m
United Airlines
Wed 20/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 23/4₹ 15,162
Tue 9/606:45
BOS
-
ORD
1 stop8h 31m
Delta
Tue 16/607:10
ORD
-
BOS
Nonstop2h 36m
Delta
Deal found 23/4₹ 15,256
Tue 11/805:45
BOS
-
ORD
1 stop4h 48m
United Airlines
Mon 17/807:33
ORD
-
BOS
Nonstop2h 34m
United Airlines
Deal found 23/4₹ 15,351
Tue 12/517:28
BOS
-
ORD
1 stop5h 12m
United Airlines
Wed 13/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 23/4₹ 15,539
Fri 8/507:02
BOS
-
ORD
Nonstop2h 57m
JetBlue
Tue 12/509:49
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 23/4₹ 15,633
Tue 9/608:15
BOS
-
ORD
Nonstop2h 57m
United Airlines
Tue 16/619:40
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 24/4₹ 15,727
Thu 21/507:35
BOS
-
ORD
Nonstop2h 52m
Delta
Thu 28/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 23/4₹ 15,822

Find flight deals from Boston to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 28 April 2026.

Round-trip from

₹ 14,691

One-way from

₹ 7,440

Popular in

April

Cheapest in

January

Average price

₹ 27,028

Good round-trip deal

₹ 49,977 or less
JetBlue
  • JetBlue
  • 7/6-9/6
  • Nonstop
  • 5h 28m total
  • Boston to Chicago
Search Deals
Delta
  • Delta
  • 27/5
  • 1 total stop
  • 6h 23m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (₹ 169,133 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (₹ 31,650 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from Boston to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 454,620 searches. Data last updated 28 April 2026.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 27/5

09:50-11:43

Nonstop2h 53m

Chicago O'Hare Intl

Thu 28/5

15:55-19:30

Nonstop2h 35m

₹ 16,198
Fastest return journey

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 20/8

10:51-12:42

Nonstop2h 51m

Chicago O'Hare Intl

Sun 23/8

06:00-09:23

Nonstop2h 23m

₹ 17,988

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 24/7

06:00-07:58

Nonstop2h 58m

Chicago O'Hare Intl

Sun 26/7

06:15-09:39

Nonstop2h 24m

₹ 19,306

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 25/9

06:00-07:50

Nonstop2h 50m

Chicago O'Hare Intl

Sun 27/9

06:00-09:24

Nonstop2h 24m

₹ 20,624

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 22/5

20:40-22:35

Nonstop2h 55m

Chicago O'Hare Intl

Sun 24/5

07:00-10:35

Nonstop2h 35m

₹ 21,378

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 25/5

05:45-09:36

1 stop4h 51m

Chicago O'Hare Intl

Sun 31/5

07:33-11:05

Nonstop2h 32m

₹ 22,696

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 25/8

17:20-19:25

Nonstop3h 05m

Chicago O'Hare Intl

Wed 26/8

06:00-11:21

1 stop4h 21m

₹ 23,073

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 25/9

06:00-10:00

1 stop5h 00m

Chicago O'Hare Intl

Mon 28/9

11:30-19:45

1 stop7h 15m

₹ 23,261

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 15/7

05:45-09:36

1 stop4h 51m

Chicago O'Hare Intl

Sun 19/7

21:35-01:08

Nonstop2h 33m

₹ 23,921

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 8/5

07:02-08:59

Nonstop2h 57m

Chicago O'Hare Intl

Sat 9/5

07:20-10:46

Nonstop2h 26m

₹ 24,203

Flights are sorted by cheapest return flights first.

Deals found on 27/4

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from Boston to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Boston with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago O'Hare Intl Airport

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

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 41 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.

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

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 18,553). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of ₹ 27,028). 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 ORD?

Find hourly flight availability from Boston to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 April 2026.

One of the essential ways to save on airfare from Boston to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are at midday tend to be the most expensive. A flight in the morning could potentially save you up to 40% on airfare.

How much does it cost for a return flight from Boston to Chicago O'Hare Intl Airport?

Related info for your journey

Find useful and relevant information for your journey from Boston to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Chicago O'Hare Intl?

    Boston Logan Intl (BOS), located 4.2 km from the city centre, is the airport you fly out of when you book flights from Boston to Chicago O'Hare Intl. 0 airlines have flights from Logan Intl to Chicago O'Hare Intl on a regular basis. Booking flights from Boston Logan Intl to Chicago O'Hare Intl should not be difficult; the airport handles an average of 44 outbound flights to Chicago O'Hare Intl per day.

  • How long is the flight from Boston to Chicago O'Hare Intl Airport?

    Departing from Boston to Chicago O'Hare Intl Airport will take you 3h. There are 1390 km between Boston and Chicago O'Hare Intl Airport. Most flights are nonstop.

  • What are the most reliable airlines from Boston to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing ANA(81%), Envoy Air(80%) or United Airlines(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 O'Hare Intl Airport?

    The cheapest flight price from Boston to Chicago O'Hare Intl Airport is ₹ 49,966. On average you can expect to pay ₹ 58,676. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for ₹ 17,988.

  • Can I find deals for flights from Boston to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Boston to O'Hare Intl flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Boston to O'Hare Intl?

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

  • Can I find deals for business class flights from Boston to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Boston to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 18,553). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of ₹ 27,028). 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

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Downers Grove
DeKalb

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Can Cheapflights find flights from Boston to O'Hare Intl with no change fees?

Certainly. Search results for flights to O'Hare Intl from Boston shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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