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Cheap flights from Boston to Chicago O'Hare Intl Airport from £77

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
6 Sep — 13 Sep1
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 44 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 7 August 2026.

Thu 10/912:54 -
1 stop6h 29m
Sat 12/915:50 -
1 stop18h 08m
Deal found 4/8£130
Sun 6/912:45 -
1 stop8h 19m
Wed 9/915:50 -
1 stop17h 32m
Deal found 3/8£131
Wed 23/917:00 -
Nonstop3h 01m
Tue 29/909:38 -
Nonstop2h 28m
Deal found 6/8£154
Wed 7/1019:40 -
Nonstop2h 51m
Wed 14/1019:10 -
Nonstop2h 43m
Deal found 6/8£161
Fri 30/1016:25 -
Nonstop2h 55m
Sat 31/1007:25 -
Nonstop2h 35m
Deal found 3/8£168
Tue 15/912:15 -
Nonstop2h 49m
Wed 23/910:29 -
Nonstop2h 36m
Deal found 7/8£168
Sat 12/918:00 -
Nonstop2h 59m
Mon 14/919:30 -
Nonstop2h 39m
Deal found 4/8£171
Sat 12/907:00 -
Nonstop2h 48m
Sun 13/920:24 -
Nonstop2h 45m
Deal found 4/8£172
Wed 2/912:45 -
1 stop8h 23m
Thu 3/919:44 -
1 stop12h 25m
Deal found 4/8£173
Sat 5/917:01 -
Nonstop2h 59m
Sun 6/918:24 -
Nonstop2h 35m
Deal found 3/8£174
Fri 11/920:50 -
Nonstop2h 42m
Wed 23/910:29 -
Nonstop2h 36m
Deal found 7/8£175

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 7 August 2026.

Round-trip from

£130

One-way from

£77

Popular in

April

Cheapest in

January

Average price

£180

Good one-way deal

£147 or less
Frontier
  • Frontier
  • 10/9-12/9
  • 2 total stops
  • 24h 37m total
  • Boston to Chicago
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Delta
  • Delta
  • 7/11
  • Nonstop
  • 2h 45m 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).
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Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in August 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 7 August 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 Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 6/9

07:30-09:26

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/9

15:05-18:52

Nonstop2h 47m

£168

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Thu 24/9

20:50-22:32

Nonstop2h 42m

Chicago O'Hare Intl

Sat 26/9

11:30-15:15

Nonstop2h 45m

£171
Fastest return journey

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 12/9

13:35-15:26

Nonstop2h 51m

Chicago O'Hare Intl

Sun 13/9

07:35-11:08

Nonstop2h 33m

£172

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 19/9

14:45-23:08

1 stop9h 23m

Chicago O'Hare Intl

Wed 23/9

20:24-00:09

Nonstop2h 45m

£174

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 19/9

17:00-19:01

Nonstop3h 01m

Chicago O'Hare Intl

Sat 26/9

15:00-23:39

1 stop7h 39m

£174

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 4/10

05:45-09:38

1 stop4h 53m

Chicago O'Hare Intl

Wed 7/10

07:30-11:01

Nonstop2h 31m

£179

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 20/12

18:33-20:38

Nonstop3h 05m

Chicago O'Hare Intl

Mon 4/1

21:20-00:55

Nonstop2h 35m

£182

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 5/12

20:25-22:29

Nonstop3h 04m

Chicago O'Hare Intl

Wed 9/12

12:50-16:26

Nonstop2h 36m

£182

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 5/9

07:30-09:26

Nonstop2h 56m

Chicago O'Hare Intl

Tue 8/9

15:05-18:52

Nonstop2h 47m

£186

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Wed 2/9

05:10-13:39

1 stop9h 29m

Chicago O'Hare Intl

Sat 5/9

13:49-17:59

Nonstop3h 10m

£188

Flights are sorted by cheapest return flights first.

Deals found on 5/8

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 43 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 £145). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of £209). 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 7 August 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 66% versus a flight in the afternoon.

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

Airfare is below average for this route at the moment.

Boston to Chicago O'Hare Intl Airport flights typically cost between £144 and £235 in September.
The cheapest return price found within the last 5 days was £130 on Frontier (10 Sept–12 Sept).

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 53 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, United Airlines, and JetBlue can get you from Boston to Chicago O'Hare Intl Airport in just under 2h 56m. Your travel time will be generally consistent. The distance from Boston to Chicago O'Hare Intl Airport is about 864 mi. All flights are typically direct.

  • 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 Japan Airlines (90%), Cathay Pacific (89%) or Envoy Air (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 £155, our data shows the cheapest flight currently is £106. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £171 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 £145). Flying from Boston to Chicago O'Hare Intl Airport in April is currently the most expensive (average of £209). 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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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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