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Cheap flights from Boston to Chicago O'Hare Intl Airport from £50

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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
23 Feb — 2 Mar1
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 66 days in advance, depart on a Wednesday or Monday 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 January 2026.

Thu 26/207:00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Mon 2/306:04
ORD
-
BOS
1 stop7h 12m
JetBlue
Deal found 24/1£97
Sat 21/216:49
BOS
-
ORD
Nonstop3h 16m
American Airlines
Sat 28/207:18
ORD
-
BOS
Nonstop2h 28m
American Airlines
Deal found 24/1£98
Fri 30/106:00
BOS
-
ORD
Nonstop3h 04m
United Airlines
Sat 31/109:13
ORD
-
BOS
Nonstop2h 33m
United Airlines
Deal found 23/1£100
Sat 7/217:15
BOS
-
ORD
Nonstop3h 11m
Delta
Mon 9/207:05
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 24/1£101
Tue 24/207:00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Fri 6/306:04
ORD
-
BOS
1 stop7h 31m
JetBlue
Deal found 22/1£103
Fri 6/212:08
BOS
-
ORD
1 stop5h 48m
United Airlines
Sun 8/207:30
ORD
-
BOS
Nonstop2h 22m
United Airlines
Deal found 22/1£105
Thu 13/806:00
BOS
-
ORD
Nonstop2h 50m
United Airlines
Sat 15/821:37
ORD
-
BOS
Nonstop2h 32m
United Airlines
Deal found 22/1£109
Mon 9/317:32
BOS
-
ORD
1 stop6h 28m
JetBlue
Mon 16/312:20
ORD
-
BOS
1 stop8h 05m
JetBlue
Deal found 23/1£109
Sat 7/213:40
BOS
-
ORD
1 stop6h 51m
JetBlue
Mon 9/207:40
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 23/1£111

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 January 2026.

Round-trip from

£97

One-way from

£50

Popular in

April

Cheapest in

January

Average price

£153

Good one-way deal

£120 or less
JetBlue
  • JetBlue
  • 26/2-2/3
  • 1 total stop
  • 10h 22m total
  • Boston to Chicago
Search Deals
United Airlines
  • United Airlines
  • 26/3
  • Nonstop
  • 3h 06m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (£8 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
Search Deals
Average for round-trip flights in January 2026
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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 January 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

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/3

06:10-11:54

1 stop6h 44m

Chicago O'Hare Intl

Fri 13/3

11:00-14:24

Nonstop2h 24m

£97

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 21/2

16:25-18:30

Nonstop3h 05m

Chicago O'Hare Intl

Sat 28/2

13:02-19:08

1 stop5h 06m

£105

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 6/2

19:07-23:39

1 stop5h 32m

Chicago O'Hare Intl

Wed 11/2

13:55-17:19

Nonstop2h 24m

£105

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/2

13:40-19:31

1 stop6h 51m

Chicago O'Hare Intl

Mon 9/2

07:40-11:05

Nonstop2h 25m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 26/5

08:15-10:12

Nonstop2h 57m

Chicago O'Hare Intl

Fri 29/5

19:40-23:16

Nonstop2h 36m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/6

06:00-07:50

Nonstop2h 50m

Chicago O'Hare Intl

Sun 7/6

06:00-09:24

Nonstop2h 24m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 28/5

06:50-08:45

Nonstop2h 55m

Chicago O'Hare Intl

Mon 8/6

20:21-23:56

Nonstop2h 35m

£116

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 27/5

05:45-09:36

1 stop4h 51m

Chicago O'Hare Intl

Wed 27/5

21:26-00:59

Nonstop2h 33m

£119

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 27/4

06:52-08:51

Nonstop2h 59m

Chicago O'Hare Intl

Thu 30/4

15:15-21:24

1 stop5h 09m

£120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 23/2

07:45-09:50

Nonstop3h 05m

Chicago O'Hare Intl

Wed 25/2

13:57-17:19

Nonstop2h 22m

£122

Flights are sorted by cheapest return flights first.

Deals found on 22/1

Showing 1-10 of 22 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 16 January 2026.

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 66 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, April is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £66). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £99). 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 January 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 at midday, which can drop the price by up to 82% versus a flight in the afternoon.

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

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 24 January 2026.
Read through reviews of airlines operating flights from Boston to Chicago O'Hare Intl Airport, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,193 reviews
Check prices

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
11,193 reviews
American Airlines
7.2
Good
11,193 reviews
Check prices

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

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 42 flights from Logan Intl to Chicago O'Hare Intl per day from 1 airline.

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

    JetBlue, United Airlines, and Delta can get you from Boston to Chicago O'Hare Intl Airport in just under 3h 04m. Your travel time can differ by up to 3h 24m. The distance from Boston to Chicago O'Hare Intl Airport is about 864 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Boston to Chicago O'Hare Intl Airport round-trip?

    Currently priced at £72, American Airlines will fly you from Boston to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. This flight start at 60% lower than the current average price 3 months from now.

  • 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 (88%), Envoy Air (84%) or Emirates (82%) 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 £158, our data shows the cheapest flight currently is £69. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £72 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, April is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £66). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £99). 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Boston to O'Hare Intl

Discover the top airline 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 858,174 searches. Data last updated 24 January 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£72Average£108FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Boston to O'Hare Intl?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Boston to O'Hare Intl. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights simply makes it quick and affordable to book flights from Boston to O'Hare Intl by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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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