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Cheap flights from Boston to Chicago O'Hare Intl Airport from ₹ 5,678

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 28/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
10 Nov — 17 Nov1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or January, booked 74 days in advance, depart on a Wednesday or Friday and return on a Tuesday

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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 11 October 2025.

Sat 8/1116:10BOS - ORD
Nonstop2h 57mDelta
Thu 13/1107:10ORD - BOS
Nonstop2h 26mDelta
Deal found 10/10₹ 11,267
Fri 24/1015:17BOS - ORD
Nonstop2h 50mUnited Airlines
Mon 27/1006:15ORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 9/10₹ 11,799
Mon 20/1020:47BOS - ORD
Nonstop2h 48mUnited Airlines
Tue 28/1013:55ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/10₹ 11,976
Sat 1/1105:05BOS - ORD
1 stop7h 45mSouthwest
Sat 1/1113:30ORD - BOS
1 stop4h 20mSouthwest
Deal found 9/10₹ 12,154
Fri 7/1118:23BOS - ORD
Nonstop3h 00mUnited Airlines
Fri 14/1121:25ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/10₹ 12,242
Sun 16/1106:00BOS - ORD
Nonstop3h 00mUnited Airlines
Tue 18/1107:15ORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 9/10₹ 12,420
Thu 30/1006:55BOS - ORD
2 stops10h 30mSouthwest
Sat 1/1112:40ORD - BOS
1 stop7h 10mSouthwest
Deal found 9/10₹ 12,597
Fri 24/1020:47BOS - ORD
Nonstop2h 48mUnited Airlines
Sun 26/1007:15ORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 10/10₹ 12,863
Sat 22/1118:23BOS - ORD
Nonstop3h 00mUnited Airlines
Mon 24/1121:25ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 9/10₹ 12,952
Fri 14/1119:55BOS - ORD
Nonstop3h 00mDelta
Wed 19/1119:15ORD - BOS
Nonstop2h 30mDelta
Deal found 9/10₹ 13,041
Thu 11/1210:40BOS - ORD
Nonstop3h 00mUnited Airlines
Mon 15/1207:10ORD - BOS
1 stop4h 23mUnited Airlines
Deal found 9/10₹ 13,484
Sun 9/1108:30BOS - ORD
Nonstop3h 05mJetBlue
Tue 11/1118:55ORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/10₹ 13,573

Cheap 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 11 October 2025.

Round-trip from

₹ 11,267

One-way from

₹ 5,678

Popular in

November

Cheapest in

September

Average price

₹ 21,912

Good round-trip deal

₹ 19,248 or less
Delta
  • Delta
  • 8/11-11/11
  • Nonstop
  • 5h 23m total
  • Boston to Chicago
Search Deals
United Airlines
  • United Airlines
  • 11/11
  • 1 total stop
  • 7h 40m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (₹ 159,249 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (₹ 23,145 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
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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 11 October 2025.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/11

16:10-18:07

Nonstop2h 57m

Chicago O'Hare Intl

Tue 11/11

07:10-10:36

Nonstop2h 26m

₹ 11,267

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/11

19:30-21:19

Nonstop2h 49m

Chicago O'Hare Intl

Sat 8/11

07:05-10:29

Nonstop2h 24m

₹ 11,267

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/11

16:10-18:07

Nonstop2h 57m

Chicago O'Hare Intl

Wed 12/11

07:10-10:36

Nonstop2h 26m

₹ 11,267

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 30/10

08:30-10:35

Nonstop3h 05m

Chicago O'Hare Intl

Fri 31/10

18:55-22:27

Nonstop2h 32m

₹ 11,976

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/3

20:10-22:15

Nonstop3h 05m

Chicago O'Hare Intl

Wed 11/3

10:10-13:40

Nonstop2h 30m

₹ 12,154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/11

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Sun 9/11

06:15-09:30

Nonstop2h 15m

₹ 12,242

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 30/10

06:55-16:25

2 stops10h 30m

Chicago O'Hare Intl

Sat 1/11

12:40-20:50

1 stop7h 10m

₹ 12,597

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 14/11

19:55-21:55

Nonstop3h 00m

Chicago O'Hare Intl

Sat 15/11

07:10-10:36

Nonstop2h 26m

₹ 13,041

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 3/12

12:03-16:04

1 stop5h 01m

Chicago O'Hare Intl

Mon 8/12

16:05-19:25

Nonstop2h 20m

₹ 13,484

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 13/12

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Mon 15/12

07:10-12:33

1 stop4h 23m

₹ 13,484

Flights are sorted by cheapest return flights first.

Deals found on 9/10

Showing 1-10 of 24 results
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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?

Use this chart to determine the optimal time to book a return flight from Boston to O'Hare Intl. Price data was last updated on 3 October 2025.

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 74 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, November is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 7,629). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of ₹ 11,976). 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 11 October 2025.

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 afternoon could potentially save you up to 52% on airfare.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated 11 October 2025.
Check out reviews from past customers who have flown with Delta and American Airlines from Boston to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,974 reviews
Check prices

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very Good
7,974 reviews
Delta
8.0
Very Good
7,974 reviews
Check prices

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,047 reviews
Delta
8.0
Very Good
7,974 reviews
Check prices

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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. 2 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 64 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 2h 57m. There are 1390 km between Boston and Chicago O'Hare Intl Airport. Most flights are nonstop.

  • What are the cheapest airlines flying from Boston to Chicago O'Hare Intl Airport round-trip?

    Flying on Delta is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at ₹ 7,850. Another option worth looking into is American Airlines, starting at ₹ 18,371 round trip. You may be able to fly from Boston to Chicago O'Hare Intl Airport for 64% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Boston to Chicago O'Hare Intl Airport one-way?

    ₹ 6,121 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on JetBlue and United Airlines, with prices starting from ₹ 6,121 and ₹ 7,807, respectively.

  • 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 Icelandair(90%), Avianca(87%) or TAP AIR PORTUGAL(87%), 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 ₹ 6,924. On average you can expect to pay ₹ 21,782. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for ₹ 11,267.

  • 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, November is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 7,629). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of ₹ 11,976). 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
DeKalb

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Top 2 airlines flying from Boston to O'Hare Intl

Discover the top 2 airlines that operate flights from Boston to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 454,620 searches. Data last updated 11 October 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest₹ 7,850Average₹ 21,996FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest₹ 18,371Average₹ 29,370FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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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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