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Cheap flights from Chicago O'Hare Intl Airport to Boston 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 13/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
26 Feb — 5 Mar1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or January, booked 43 days in advance, depart on a Friday or Tuesday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Boston

Enter your travel dates to find the best prices.

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 27 January 2026.

Sat 28/207:05
ORD
-
BOS
Nonstop2h 32m
Delta
Mon 2/319:45
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 26/1£99
Thu 19/207:05
ORD
-
BOS
Nonstop2h 32m
Delta
Tue 24/215:50
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 25/1£99
Thu 19/207:05
ORD
-
BOS
Nonstop2h 32m
Delta
Sun 22/207:15
BOS
-
ORD
Nonstop3h 13m
Delta
Deal found 26/1£100
Thu 12/311:00
ORD
-
BOS
Nonstop2h 24m
JetBlue
Thu 19/318:00
BOS
-
ORD
1 stop5h 56m
JetBlue
Deal found 26/1£103
Sat 31/109:02
ORD
-
BOS
1 stop5h 07m
United Airlines
Mon 9/218:21
BOS
-
ORD
Nonstop3h 04m
United Airlines
Deal found 24/1£104
Fri 13/207:30
ORD
-
BOS
Nonstop2h 19m
United Airlines
Wed 18/206:00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 26/1£105
Fri 22/521:26
ORD
-
BOS
Nonstop2h 33m
United Airlines
Sun 24/508:15
BOS
-
ORD
Nonstop2h 57m
United Airlines
Deal found 26/1£107
Sun 1/307:30
ORD
-
BOS
Nonstop2h 19m
United Airlines
Tue 3/306:00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 26/1£109
Sat 7/207:40
ORD
-
BOS
Nonstop2h 25m
JetBlue
Tue 10/212:15
BOS
-
ORD
1 stop8h 16m
JetBlue
Deal found 24/1£110
Wed 25/210:00
ORD
-
BOS
Nonstop2h 20m
JetBlue
Sat 28/217:25
BOS
-
ORD
1 stop6h 34m
JetBlue
Deal found 25/1£110
Fri 6/207:05
ORD
-
BOS
Nonstop2h 35m
Delta
Mon 9/220:25
BOS
-
ORD
Nonstop3h 04m
Delta
Deal found 26/1£111
Thu 12/306:26
ORD
-
BOS
Nonstop2h 28m
American Airlines
Thu 19/306:52
BOS
-
ORD
Nonstop3h 11m
American Airlines
Deal found 26/1£112

Find 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 27 January 2026.

Round-trip from

£99

One-way from

£50

Popular in

February

Cheapest in

September

Average price

£151

Good round-trip deal

£126 or less

Good one-way deal

£54 or less
Delta
  • Delta
  • 28/2-3/3
  • Nonstop
  • 5h 35m total
  • Chicago to Boston
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United Airlines
  • United Airlines
  • 1/2
  • Nonstop
  • 2h 24m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (£4 potential increase over avg. return price).
Search Deals
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 round-trip flight from Chicago O'Hare Intl to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Boston Logan Intl.
Search Deals

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 27 January 2026.
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

Sat 28/2

07:05-10:37

Nonstop2h 32m

Boston Logan Intl

Tue 3/3

15:50-17:53

Nonstop3h 03m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 14/2

14:07-17:26

Nonstop2h 19m

Boston Logan Intl

Sat 21/2

16:25-18:30

Nonstop3h 05m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 22/4

06:00-09:15

Nonstop2h 15m

Boston Logan Intl

Sat 9/5

19:35-21:36

Nonstop3h 01m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/3

18:05-21:28

Nonstop2h 23m

Boston Logan Intl

Wed 18/3

11:02-13:07

Nonstop3h 05m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 30/5

07:00-10:28

Nonstop2h 28m

Boston Logan Intl

Wed 3/6

07:00-08:58

Nonstop2h 58m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 25/2

10:00-13:20

Nonstop2h 20m

Boston Logan Intl

Sat 28/2

07:00-09:10

Nonstop3h 10m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 21/4

09:41-13:09

Nonstop2h 28m

Boston Logan Intl

Wed 13/5

06:52-08:51

Nonstop2h 59m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 17/3

10:40-14:04

Nonstop2h 24m

Boston Logan Intl

Fri 20/3

07:15-09:25

Nonstop3h 10m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/4

10:00-13:27

Nonstop2h 27m

Boston Logan Intl

Sat 11/4

07:10-09:10

Nonstop3h 00m

£99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/6

21:37-01:09

Nonstop2h 32m

Boston Logan Intl

Sun 7/6

06:00-07:50

Nonstop2h 50m

£110

Flights are sorted by cheapest return flights first.

Deals found on 27/1

Showing 1-10 of 22 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 23 January 2026.

Booking 43 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £67). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of £86). 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 27 January 2026.

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 86% on your trip compared to booking a flight at midday.

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 47 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 £99, Delta can have you in Boston from Chicago O'Hare Intl Airport in 2h 15m. There are 864 mi between Chicago O'Hare Intl Airport and Boston. Most flights are nonstop.

  • 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 (86%), WestJet (85%), Air France (80%).

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

    Looking at all options, your cheapest flight can be booked for £54. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £150 on average, our data indicates £93 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of £67). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of £86). 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
Canton
Warwick
Cambridge
Peabody
Somerville
Quincy
Waltham
Chelmsford

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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