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Cheap flights from Boston to Chicago O'Hare Intl Airport from £58

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
24 May — 31 May1
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 Saturday

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 24 April 2026.

Thu 28/507:35
BOS
-
ORD
Nonstop2h 52m
Delta
Fri 29/519:16
ORD
-
BOS
Nonstop2h 34m
Delta
Deal found 20/4£111
Tue 12/518:47
BOS
-
ORD
Nonstop3h 06m
JetBlue
Tue 26/520:30
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 21/4£113
Sat 30/511:00
BOS
-
ORD
Nonstop3h 01m
JetBlue
Mon 1/620:30
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 22/4£114
Tue 9/606:00
BOS
-
ORD
Nonstop2h 58m
United Airlines
Sat 13/618:20
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 21/4£116
Wed 3/605:51
BOS
-
ORD
1 stop6h 56m
Delta
Sat 6/617:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£116
Sat 30/506:00
BOS
-
ORD
1 stop7h 16m
Delta
Mon 1/617:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£117
Thu 28/505:51
BOS
-
ORD
1 stop6h 56m
Delta
Mon 1/617:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£118
Fri 28/807:30
BOS
-
ORD
Nonstop2h 58m
Delta
Mon 31/817:45
ORD
-
BOS
1 stop4h 47m
Delta
Deal found 20/4£119
Sat 9/506:00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Tue 12/507:30
ORD
-
BOS
Nonstop2h 31m
United Airlines
Deal found 21/4£119
Sat 9/517:30
BOS
-
ORD
Nonstop3h 03m
Delta
Tue 12/510:30
ORD
-
BOS
Nonstop2h 27m
Delta
Deal found 20/4£120
Sat 9/512:00
BOS
-
ORD
Nonstop2h 54m
Delta
Mon 11/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 20/4£121
Fri 15/518:39
BOS
-
ORD
Nonstop3h 01m
United Airlines
Tue 19/513:55
ORD
-
BOS
Nonstop2h 27m
United Airlines
Deal found 22/4£122

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 24 April 2026.

Round-trip from

£111

One-way from

£58

Popular in

April

Cheapest in

January

Average price

£211

Good round-trip deal

£138 or less

Good one-way deal

£130 or less
Delta
  • Delta
  • 28/5-29/5
  • Nonstop
  • 5h 26m total
  • Boston to Chicago
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Southwest
  • Southwest
  • 20/5
  • 1 total stop
  • 5h 40m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£10 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in April 2026
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
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Price to beat on a one-way 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 858,174 searches. Data last updated 24 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 20/5

14:00-20:26

1 stop7h 26m

Chicago O'Hare Intl

Wed 27/5

09:36-16:28

1 stop5h 52m

£116

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 30/5

09:00-13:21

1 stop5h 21m

Chicago O'Hare Intl

Mon 1/6

17:19-23:29

1 stop5h 10m

£117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/5

19:27-23:44

1 stop5h 17m

Chicago O'Hare Intl

Sat 16/5

21:30-00:59

Nonstop2h 29m

£120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 21/7

08:15-10:12

Nonstop2h 57m

Chicago O'Hare Intl

Mon 27/7

19:42-23:18

Nonstop2h 36m

£128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/6

07:35-09:39

Nonstop3h 04m

Chicago O'Hare Intl

Tue 9/6

06:00-12:23

1 stop5h 23m

£139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Thu 14/5

21:30-00:59

Nonstop2h 29m

£139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/6

07:35-09:27

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/6

17:22-23:54

1 stop5h 32m

£139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 19/7

07:56-09:53

Nonstop2h 57m

Chicago O'Hare Intl

Wed 22/7

20:20-23:51

Nonstop2h 31m

£142
Fastest return journey

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

£152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/7

05:45-11:58

1 stop7h 13m

Chicago O'Hare Intl

Sat 11/7

19:42-23:18

Nonstop2h 36m

£165

Flights are sorted by cheapest return flights first.

Deals found on 22/4

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 £146). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of £211). 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 24 April 2026.

When flying from Boston to Chicago O'Hare Intl Airport, 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 65% versus a flight at midday.

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?

    If you book a flight to Chicago O'Hare Intl from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 49 flights from Logan Intl to Chicago O'Hare Intl per day from 0 different airlines.

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

    Delta and United Airlines can get you from Boston to Chicago O'Hare Intl Airport in just under 5h 17m. Your travel time can differ by up to 2h 09m. The distance from Boston to Chicago O'Hare Intl Airport is about 864 mi. This flight may include one or multiple stops.

  • 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?

    While on average a flight from Boston to Chicago O'Hare Intl Airport is generally £163, our data shows the cheapest flight currently is £102. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £131 for that flight.

  • 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 £146). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of £211). 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
Elk Grove Village

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Why should you use Cheapflights to find cheap flight tickets from Boston to O'Hare Intl?

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

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

Can Cheapflights notify me if prices for flights from Boston to O'Hare Intl become cheaper?

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

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