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$59+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or August, booked 82 days in advance, depart on a Wednesday or Thursday 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 April 29, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$114
(Trip.com)

One-way from

$59
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$283

Good round-trip deal

$162 or less

Good one-way deal

$90 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. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Trip.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/710:05 amORD - BOS
Nonstop2h 29mDelta
Tue 5/278:20 pmBOS - ORD
Nonstop2h 54mDelta
Deal found 4/27$114
This Cheapflightsfares deal was found by Cheapflights users on 4/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/299:55 amORD - BOS
1 stop12h 34mSpirit Airlines
Tue 6/33:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 4/26$116
This JetBlue deal was found by Cheapflights users on 4/28. 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 5/98:45 amORD - BOS
Nonstop2h 28mJetBlue
Sun 5/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/28$118
This United Airlines deal was found by Cheapflights users on 4/27. 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 7/238:05 pmORD - BOS
Nonstop2h 27mUnited Airlines
Tue 7/296:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Deal found 4/27$123
This Southwest deal was found by Cheapflights users on 4/28. 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.
Wed 8/271:50 pmORD - BOS
1 stop4h 30mSouthwest
Sun 8/316:50 amBOS - ORD
1 stop8h 25mSouthwest
Deal found 4/28$136
This American Airlines deal was found by Cheapflights users on 4/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:35 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Wed 5/288:51 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
Deal found 4/26$142
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Wed 5/213:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/26$166
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:15 pmORD - BOS
1 stop7h 29mFrontier
Sun 5/116:00 amBOS - ORD
1 stop18h 32mFrontier
Deal found 4/28$219

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 April 29, 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

Wed 5/7

10:05 am-1:34 pm

Nonstop2h 29m

Boston Logan Intl

Tue 5/27

8:20 pm-10:14 pm

Nonstop2h 54m

$114

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/29

9:55 am-11:29 pm

1 stop12h 34m

Boston Logan Intl

Tue 6/3

3:49 pm-11:04 pm

1 stop8h 15m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/9

8:45 am-12:13 pm

Nonstop2h 28m

Boston Logan Intl

Sun 5/11

6:00 am-8:00 am

Nonstop3h 00m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/23

8:05 pm-11:32 pm

Nonstop2h 27m

Boston Logan Intl

Tue 7/29

6:59 pm-11:37 pm

1 stop5h 38m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/24

6:35 pm-10:07 pm

Nonstop2h 32m

Boston Logan Intl

Wed 5/28

8:51 pm-10:52 pm

Nonstop3h 01m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Wed 5/21

3:49 pm-11:04 pm

1 stop8h 15m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/6

1:50 pm-9:05 pm

1 stop6h 15m

Boston Logan Intl

Sun 5/11

5:45 am-11:50 am

1 stop7h 05m

$186

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/9

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Sun 5/11

6:00 am-11:32 pm

1 stop18h 32m

$219

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/9

9:20 pm-12:45 am

Nonstop2h 25m

$59

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/4

7:37 am-9:50 pm

1 stop13h 13m

$60

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 18 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 starsTrust Score*2 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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.

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, use the free shuttle train between terminals at ORD, especially if your flight is from United's Terminal 1.

Read more about ORDby Ramsey Qubein
BOS

BOS offers easy access to downtown Boston via rideshares, public transit, and even a scenic water taxi service.

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

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 April 25, 2025.

Booking 73 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $218). Flying from Chicago O'Hare Intl Airport to Boston in July is currently the most expensive (average of $311). 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 April 29, 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 36% on your trip compared to booking a flight in the afternoon.

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 March 30, 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. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Boston

Explore weekly flight availability from O'Hare Intl to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 29, 2025.

The most flights from ORD to BOS are scheduled on a Monday (68 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (23 on average).

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 April 29, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Boston. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,292 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 46 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.

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

    According to our current data, Delta ($114), Spirit Airlines ($116), and JetBlue ($118) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Delta is currently priced 52% 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 United Airlines, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Spirit Airlines and Southwest, 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: Air France (100%), Iberia (91%), Virgin Atlantic( 88%).

  • 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 $50. On average you can expect to pay $616. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $112.

  • 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $218). Flying from Chicago O'Hare Intl Airport to Boston in July is currently the most expensive (average of $311). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Marlborough
Warwick
Cambridge
Waltham
Framingham
Chestnut Hill
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Lincoln
Salem
Chelsea
Seabrook

Browse thousands of different options on Cheapflights for your next trip

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$95FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$79Average$212FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$231FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$243FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$140Average$292FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$293FlexibilityNo cancel feeOn-time63%

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