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Cheap flights from Chicago O'Hare Intl Airport to Boston from £51

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
12 Oct — 19 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or January, booked 82 days in advance, depart on a Monday or Friday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Boston

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Boston (BOS). 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 12 September 2025.

Round-trip from

£98

One-way from

£51

Popular in

February

Cheapest in

September

Average price

£138

Good round-trip deal

£123 or less

Good one-way deal

£139 or less
United Airlines
  • United Airlines
  • 12/10-15/10
  • Nonstop
  • 5h 22m total
  • Chicago to Boston
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Delta
  • Delta
  • 20/1
  • 1 total stop
  • 5h 23m total
  • Chicago to Boston
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Highest demand for flights based on searches. 6% potential increase in price (£8 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 September 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Boston Logan Intl.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Boston Logan Intl.
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Find flight deals from O'Hare Intl to Boston

Cheapest flights from O'Hare Intl to Boston
Explore the most affordable flight options available from O'Hare Intl to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 September 2025.

Tue 30/907:30ORD - BOS
Nonstop2h 32mUnited Airlines
Wed 1/1011:02BOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 10/9£98
Sat 4/1007:30ORD - BOS
Nonstop2h 32mUnited Airlines
Mon 6/1020:47BOS - ORD
Nonstop2h 48mUnited Airlines
Deal found 12/9£100
Sat 20/909:51ORD - BOS
Nonstop2h 29mJetBlue
Mon 22/916:40BOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/9£101
Thu 23/1006:30ORD - BOS
Nonstop2h 26mUnited Airlines
Mon 27/1020:30BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 11/9£103
Tue 21/1006:00ORD - BOS
1 stop6h 20mSpirit Airlines
Wed 29/1015:00BOS - ORD
1 stop11h 03mSpirit Airlines
Deal found 11/9£103
Thu 13/1118:55ORD - BOS
Nonstop2h 32mJetBlue
Sun 16/1108:30BOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/9£104
Fri 19/919:50ORD - BOS
Nonstop2h 35mJetBlue
Sun 21/907:00BOS - ORD
Nonstop2h 56mJetBlue
Deal found 10/9£105
Sat 25/1013:30ORD - BOS
1 stop4h 20mSouthwest
Sat 1/1105:05BOS - ORD
1 stop7h 45mSouthwest
Deal found 10/9£106
Tue 28/1015:10ORD - BOS
1 stop6h 05mSouthwest
Wed 29/1005:30BOS - ORD
2 stops8h 15mSouthwest
Deal found 10/9£107
Fri 7/1118:55ORD - BOS
Nonstop2h 32mJetBlue
Thu 13/1108:30BOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/9£109
Fri 3/1019:50ORD - BOS
Nonstop2h 35mJetBlue
Tue 7/1007:09BOS - ORD
Nonstop3h 13mJetBlue
Deal found 11/9£109
Sat 11/1007:30ORD - BOS
Nonstop2h 32mUnited Airlines
Sat 11/1017:19BOS - ORD
1 stop5h 22mUnited Airlines
Deal found 10/9£110

Cheapflights Fare Finder

 
Customise your flight search to find flights from O'Hare Intl to Boston 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 12 September 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Boston that are best for you.

Fly from

O'Hare Intl

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 15/12

10:46-16:00

1 stop4h 14m

Boston Logan Intl

Thu 1/1

05:55-11:48

1 stop6h 53m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/11

18:55-22:27

Nonstop2h 32m

Boston Logan Intl

Mon 10/11

08:30-10:35

Nonstop3h 05m

£109

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 18/11

10:30-13:59

Nonstop2h 29m

Boston Logan Intl

Sun 23/11

07:30-09:35

Nonstop3h 05m

£109

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/10

10:41-16:22

1 stop4h 41m

Boston Logan Intl

Tue 14/10

16:25-18:20

Nonstop2h 55m

£110

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 14/11

13:55-17:15

Nonstop2h 20m

Boston Logan Intl

Sun 16/11

05:30-09:46

1 stop5h 16m

£110

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/12

07:10-10:37

Nonstop2h 27m

Boston Logan Intl

Sun 7/12

05:45-11:48

1 stop7h 03m

£110

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 30/10

07:05-10:29

Nonstop2h 24m

Boston Logan Intl

Sat 1/11

05:40-12:16

1 stop7h 36m

£113

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 24/10

19:10-22:45

Nonstop2h 35m

Boston Logan Intl

Tue 28/10

06:00-12:17

1 stop7h 17m

£116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 29/10

15:10-22:15

1 stop6h 05m

Boston Logan Intl

Tue 4/11

09:05-21:50

2 stops13h 45m

£117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 29/10

07:15-10:34

Nonstop2h 19m

Boston Logan Intl

Tue 4/11

14:21-18:30

1 stop5h 09m

£119

Flights are sorted by cheapest return flights first.

Deals found on 11/9

Showing 1-10 of 23 results
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Best time to book a flight from O'Hare Intl to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from O'Hare Intl 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 Chicago O'Hare Intl Airport to Boston

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

Use this chart to determine the optimal time to book a return flight from O'Hare Intl to Boston. Price data was last updated on 29 August 2025.

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £10). Flying from Chicago O'Hare Intl Airport to Boston in July is currently the most expensive (average of £724). 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 ORD to BOS?

Find hourly flight availability from O'Hare Intl to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 September 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 83% on your trip compared to booking a flight in the afternoon.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Boston. 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 into for flights to Boston from Chicago O'Hare Intl?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago O'Hare Intl. On average, Logan Intl has 54 inbound flights from Chicago O'Hare Intl per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    For as low as £101, Delta can have you in Boston from Chicago O'Hare Intl Airport in 2h 24m. There are 864 mi between Chicago O'Hare Intl Airport and Boston. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    One-way options have recently been found by users for as low as £51 on JetBlue. Other airlines that offer cheap prices include Delta from £51 and United Airlines from £51 one-way.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago O'Hare Intl Airport to Boston on time: Envoy Air (94%), Air France (88%), Etihad Airways (84%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Boston?

    Looking at all options, your cheapest flight can be booked for £77. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £106 on average, our data indicates £157 when flying from Chicago O'Hare Intl Airport to Boston.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £10). Flying from Chicago O'Hare Intl Airport to Boston in July is currently the most expensive (average of £724). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Burlington
Peabody
Cambridge
Somerville
Quincy
Chelmsford

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Fly with Cheapflights

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

Cheapflights makes it easy to find O'Hare Intl to Boston flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Boston from O'Hare Intl.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from O'Hare Intl to Boston, users can toggle the no change fees filter when performing a flight search.

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

Yes, Cheapflights offers price alerts on O'Hare Intl to Boston flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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