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$62+ Cheap flights from O'Hare Intl (ORD) to Boston (BOS)

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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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 Thursday or Wednesday and return on a Friday

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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$123
(United Airlines)

One-way from

$62
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$237

Good round-trip deal

$167 or less

Good one-way deal

$102 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Boston Logan Intl flights.
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From Chicago O'Hare Intl to Boston Logan Intl
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One-way flight from Chicago O'Hare Intl to Boston Logan Intl
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Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 16, 2025.

This Trip.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:13 pmORD - BOS
Nonstop2h 33mJetBlue
Sat 10/257:09 amBOS - ORD
Nonstop3h 13mJetBlue
Deal found 10/15$122
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Wed 10/2910:25 amBOS - ORD
1 stop7h 40mUnited Airlines
Deal found 10/16$123
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:10 amORD - BOS
Nonstop2h 25mDelta
Fri 12/57:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/14$127
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:44 amORD - BOS
1 stop21h 38mFrontier
Sun 12/711:28 amBOS - ORD
1 stop11h 56mFrontier
Deal found 10/15$128
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Sun 11/97:30 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/15$133
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:21 pmORD - BOS
Nonstop2h 28mUnited Airlines
Tue 12/26:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/14$134
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:55 pmORD - BOS
Nonstop2h 32mJetBlue
Tue 11/43:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/14$135
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:30 amORD - BOS
1 stop8h 25mSouthwest
Thu 10/309:00 amBOS - ORD
1 stop8h 25mSouthwest
Deal found 10/16$137
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Fri 10/246:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 10/14$138
This Mytrip deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/123:26 pmORD - BOS
1 stop7h 33mSpirit Airlines
Sat 11/151:36 pmBOS - ORD
1 stop10h 30mSpirit Airlines
Deal found 10/14$139
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:50 pmORD - BOS
Nonstop2h 20mUnited Airlines
Sun 11/166:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/15$140

Cheapflights Fare Finder

 
Customize 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 2,558,603 searches. Data last updated October 16, 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

Thu 12/11

1:45 pm-10:15 pm

1 stop7h 30m

Boston Logan Intl

Sun 12/14

5:00 am-12:15 pm

1 stop8h 15m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/22

5:15 pm-1:00 am

1 stop6h 45m

Boston Logan Intl

Sun 11/23

5:00 am-12:15 pm

1 stop8h 15m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Fri 12/12

5:29 pm-7:43 pm

Nonstop3h 14m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/28

3:10 pm-10:15 pm

1 stop6h 05m

Boston Logan Intl

Thu 10/30

6:55 am-4:25 pm

2 stops10h 30m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

2:50 pm-9:35 pm

1 stop5h 45m

Boston Logan Intl

Tue 10/28

7:50 am-5:55 pm

2 stops11h 05m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/1

6:21 pm-9:49 pm

Nonstop2h 28m

Boston Logan Intl

Mon 11/3

10:40 am-12:40 pm

Nonstop3h 00m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/7

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

Sun 11/9

7:30 am-9:30 am

Nonstop3h 00m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/19

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sun 1/18

8:30 am-10:40 am

Nonstop3h 10m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/7

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Thu 12/11

5:30 am-9:36 am

1 stop5h 06m

$152

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/10

6:00 am-12:33 pm

1 stop5h 33m

Boston Logan Intl

Thu 12/11

6:00 am-8:00 am

Nonstop3h 00m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 22 results
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Compare providers for flights from O'Hare Intl to Boston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Boston in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 round-trip 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 round-trip flight from O'Hare Intl to Boston. Price data was last updated on October 10, 2025.

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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $71). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of $138). 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 October 16, 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 27% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Boston?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Boston. Price data was last updated on October 12, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Chicago O'Hare Intl Airport to Boston flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago O'Hare Intl Airport to Boston trip
Airlines
United Airlines

United's Economy Plus offers extra legroom; ideal for comfort on short flights.


United's MileagePlus allows pooling miles, great for family travel.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for short flights.


Spirit's self-service bag drop saves time; print your boarding pass to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
ORD

For a quick departure from ORD, consider using the 'L' train. It’s often faster than taxis during peak traffic.

Read more about ORDby Ramsey Qubein
BOS

Upon arrival at BOS, use the Silver Line 1 (SL1) bus for a free ride to downtown Boston’s South Station.

Read more about BOSby Paul Rubio
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on BOS

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated October 16, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Boston to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,984 reviews
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,982 reviews
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,043 reviews
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
JetBlue
7.2
Good
2,908 reviews
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,097 reviews
Delta
8.0
Very good
7,984 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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?

    Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Boston. You should not have trouble finding flights to Logan Intl from Chicago O'Hare Intl; the airport handles an average of 57 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago O'Hare Intl. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

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

    A quick flight from Chicago O'Hare Intl Airport to Boston can take about 2h 28m. Southwest provides one of the quickest options available for as low as $142. Chicago O'Hare Intl Airport and Boston are separated by a distance of 864 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Boston round-trip?

    According to our current data, Spirit Airlines ($58), JetBlue ($79), and Delta ($97) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Spirit Airlines is currently priced 75% below the average price you’ll pay for this route.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Southwest and United Airlines, as they are both options that can get you from Chicago O'Hare Intl Airport to Boston for a low price.

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

    Before booking your flight to Boston from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: Etihad Airways (83%), TAP AIR PORTUGAL (83%), Envoy Air( 80%).

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

    The cheapest flight price from Chicago O'Hare Intl Airport to Boston is $58. On average you can expect to pay $540. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $117.

  • 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 vacation 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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $71). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of $138). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 7 airlines flying from O'Hare Intl to Boston

Discover the top 7 airlines that operate flights from O'Hare Intl to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$58Average$158FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$79Average$183FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$228FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$231FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$125Average$275FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$144Average$216FlexibilityNo cancel feeOn-time63%

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