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Cheap flights from Chicago O'Hare Intl Airport to Boston 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 23/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
23 May — 30 May1
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 65 days in advance, depart on a Saturday or Tuesday and return on a Friday

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 23 April 2026.

Sat 30/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Wed 3/605:35
BOS
-
ORD
1 stop5h 41m
Delta
Deal found 20/4£109
Sat 30/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Mon 1/618:00
BOS
-
ORD
1 stop5h 36m
Delta
Deal found 20/4£110
Thu 28/510:25
ORD
-
BOS
Nonstop2h 24m
Delta
Mon 1/618:00
BOS
-
ORD
1 stop5h 36m
Delta
Deal found 20/4£110
Wed 10/621:26
ORD
-
BOS
Nonstop2h 33m
United Airlines
Tue 16/610:55
BOS
-
ORD
Nonstop2h 53m
United Airlines
Deal found 20/4£112
Tue 4/820:20
ORD
-
BOS
Nonstop2h 31m
JetBlue
Wed 12/808:10
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 22/4£112
Sat 23/513:56
ORD
-
BOS
Nonstop2h 31m
JetBlue
Mon 25/506:00
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 22/4£114
Thu 20/807:33
ORD
-
BOS
Nonstop2h 34m
United Airlines
Wed 26/812:30
BOS
-
ORD
Nonstop2h 51m
United Airlines
Deal found 22/4£115
Wed 20/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Sun 24/517:05
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 21/4£115
Thu 28/506:00
ORD
-
BOS
1 stop6h 20m
Delta
Tue 2/613:00
BOS
-
ORD
1 stop6h 07m
Delta
Deal found 21/4£117
Fri 29/519:16
ORD
-
BOS
Nonstop2h 34m
Delta
Tue 2/614:00
BOS
-
ORD
1 stop7h 26m
Delta
Deal found 21/4£118

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 23 April 2026.

Round-trip from

£109

One-way from

£58

Popular in

April

Cheapest in

September

Average price

£201
Delta
  • Delta
  • 23/5-27/5
  • 1 total stop
  • 8h 10m total
  • Chicago to Boston
Search Deals
Delta
  • Delta
  • 6/6
  • 1 total stop
  • 5h 10m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£9 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 2026
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 23 April 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

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 25/8

20:20-23:51

Nonstop2h 31m

Boston Logan Intl

Wed 26/8

17:20-19:25

Nonstop3h 05m

£112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 23/5

13:56-17:27

Nonstop2h 31m

Boston Logan Intl

Sun 24/5

06:00-08:00

Nonstop3h 00m

£128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 23/6

15:15-18:53

Nonstop2h 38m

Boston Logan Intl

Wed 24/6

07:30-09:28

Nonstop2h 58m

£142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/5

07:00-12:51

1 stop4h 51m

Boston Logan Intl

Sat 22/8

08:10-10:08

Nonstop2h 58m

£142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 30/6

06:00-11:16

1 stop4h 16m

Boston Logan Intl

Fri 3/7

06:00-07:58

Nonstop2h 58m

£161

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/6

17:19-23:29

1 stop5h 10m

Boston Logan Intl

Sat 13/6

18:20-20:29

Nonstop3h 09m

£161

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 30/5

13:55-22:05

1 stop7h 10m

Boston Logan Intl

Wed 3/6

08:10-12:50

1 stop5h 40m

£164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 22/5

19:16-22:50

Nonstop2h 34m

Boston Logan Intl

Tue 26/5

07:35-09:27

Nonstop2h 52m

£164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 23/5

18:20-21:56

Nonstop2h 36m

Boston Logan Intl

Mon 25/5

07:19-09:17

Nonstop2h 58m

£175
Fastest return journey

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/5

06:50-10:11

Nonstop2h 21m

Boston Logan Intl

Fri 8/5

07:35-09:27

Nonstop2h 52m

£175

Flights are sorted by cheapest return flights first.

Deals found on 21/4

Showing 1-10 of 23 resultsSorted by cheapest first
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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?

Booking 90 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 £145). Flying from Chicago O'Hare Intl Airport to Boston in April is currently the most expensive (average of £201). 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 23 April 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 81% on your trip compared to booking a flight in the afternoon.

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

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 49 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 £112, JetBlue can have you in Boston from Chicago O'Hare Intl Airport in 2h 31m. 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: Avianca (88%), Envoy Air (78%), Iberia (74%).

  • 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 £145). Flying from Chicago O'Hare Intl Airport to Boston in April is currently the most expensive (average of £201). 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
Waltham
Warwick
Cambridge
Peabody
Somerville
Quincy
Chelmsford

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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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