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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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
12 Apr — 19 Apr1
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 72 days in advance, depart on a Saturday or Tuesday and return on a Monday

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 13 March 2026.

Sat 11/407:00
ORD
-
BOS
Nonstop2h 25m
Delta
Tue 14/419:35
BOS
-
ORD
Nonstop2h 54m
Delta
Deal found 8/3£94
Tue 28/409:41
ORD
-
BOS
Nonstop2h 26m
JetBlue
Tue 19/519:35
BOS
-
ORD
Nonstop3h 01m
JetBlue
Deal found 8/3£102
Fri 1/506:00
ORD
-
BOS
Nonstop2h 15m
JetBlue
Sun 3/506:52
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 9/3£102
Sat 11/413:55
ORD
-
BOS
1 stop7h 10m
Southwest
Tue 14/408:10
BOS
-
ORD
1 stop5h 40m
Southwest
Deal found 8/3£109
Tue 17/311:00
ORD
-
BOS
Nonstop2h 24m
JetBlue
Tue 24/308:00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 8/3£110
Wed 20/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Sun 24/509:50
BOS
-
ORD
Nonstop2h 53m
United Airlines
Deal found 8/3£111
Sat 9/521:30
ORD
-
BOS
Nonstop2h 29m
United Airlines
Wed 13/505:45
BOS
-
ORD
1 stop4h 52m
United Airlines
Deal found 8/3£112
Tue 28/409:41
ORD
-
BOS
Nonstop2h 26m
JetBlue
Thu 14/506:52
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 8/3£113
Tue 21/417:39
ORD
-
BOS
Nonstop2h 33m
American Airlines
Fri 24/419:40
BOS
-
ORD
Nonstop3h 10m
American Airlines
Deal found 9/3£114
Sat 9/513:55
ORD
-
BOS
2 stops8h 45m
Southwest
Tue 12/506:20
BOS
-
ORD
2 stops10h 45m
Southwest
Deal found 8/3£117
Mon 20/409:50
ORD
-
BOS
Nonstop2h 25m
JetBlue
Sun 26/407:00
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 11/3£117
Thu 2/408:55
ORD
-
BOS
Nonstop2h 32m
JetBlue
Mon 6/406:05
BOS
-
ORD
Nonstop3h 03m
JetBlue
Deal found 11/3£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 13 March 2026.

Round-trip from

£94

One-way from

£51

Popular in

March

Cheapest in

September

Average price

£193

Good round-trip deal

£133 or less

Good one-way deal

£156 or less
Delta
  • Delta
  • 11/4-14/4
  • Nonstop
  • 5h 19m total
  • Chicago to Boston
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Southwest
  • Southwest
  • 11/4
  • 1 total stop
  • 7h 10m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (£11 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 March 2026
Search Deals
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 13 March 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 21/4

14:40-22:30

1 stop6h 50m

Boston Logan Intl

Fri 24/4

05:15-15:00

1 stop10h 45m

£117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/6

18:20-21:56

Nonstop2h 36m

Boston Logan Intl

Sun 7/6

05:45-09:36

1 stop4h 51m

£132
Fastest return journey

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 11/5

06:00-09:25

Nonstop2h 25m

Boston Logan Intl

Mon 22/6

06:00-07:58

Nonstop2h 58m

£138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/5

08:31-14:16

1 stop4h 45m

Boston Logan Intl

Tue 12/5

19:35-21:36

Nonstop3h 01m

£140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/4

14:40-22:30

1 stop6h 50m

Boston Logan Intl

Wed 15/4

05:35-15:00

1 stop10h 25m

£140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 26/7

07:00-10:28

Nonstop2h 28m

Boston Logan Intl

Tue 4/8

16:10-18:07

Nonstop2h 57m

£147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 25/3

06:45-14:24

1 stop6h 39m

Boston Logan Intl

Thu 2/4

06:05-08:05

Nonstop3h 00m

£162

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/8

16:00-19:37

Nonstop2h 37m

Boston Logan Intl

Wed 5/8

07:00-08:58

Nonstop2h 58m

£162

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

14:40-23:15

1 stop7h 35m

Boston Logan Intl

Mon 13/4

05:30-12:50

2 stops8h 20m

£166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/8

19:40-23:16

Nonstop2h 36m

Boston Logan Intl

Tue 11/8

06:00-13:14

2 stops8h 14m

£177

Flights are sorted by cheapest return flights first.

Deals found on 10/3

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?

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 6 March 2026.

Booking 72 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 £68). Flying from Chicago O'Hare Intl Airport to Boston in January is currently the most expensive (average of £88). 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 13 March 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 85% 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 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 £132, Southwest can have you in Boston from Chicago O'Hare Intl Airport in 2h 36m. 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 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 (83%), WestJet (83%), Royal Jordanian (83%).

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

    Looking at all options, your cheapest flight can be booked for £81. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for £117 on average, our data indicates £236 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 £68). Flying from Chicago O'Hare Intl Airport to Boston in January is currently the most expensive (average of £88). 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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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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