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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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 January or September, booked 72 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/9. 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.
Tue 12/166:50 amORD - BOS
Nonstop2h 27mAmerican Airlines
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 12/9$127
This American Airlines deal was found by Cheapflights users on 12/9. 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.
Fri 12/127:00 amORD - BOS
Nonstop2h 29mAmerican Airlines
Tue 12/166:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 12/9$132
This Trip.com deal was found by Cheapflights users on 12/9. 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 12/128:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 12/9$135
This JetBlue deal was found by Cheapflights users on 12/9. 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.
Sat 12/1311:25 amORD - BOS
Nonstop2h 24mJetBlue
Mon 1/123:35 pmBOS - ORD
Nonstop3h 08mJetBlue
Deal found 12/9$137
This United Airlines deal was found by Cheapflights users on 12/8. 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 12/197:45 amORD - BOS
Nonstop2h 22mUnited Airlines
Sat 1/104:49 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 12/8$142
This JetBlue deal was found by Cheapflights users on 12/9. 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.
Mon 12/1511:25 amORD - BOS
Nonstop2h 24mJetBlue
Mon 12/155:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 12/9$152
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/149:19 amORD - BOS
Nonstop2h 24mUnited Airlines
Tue 12/166:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 12/10$157
This Expedia deal was found by Cheapflights users on 12/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/187:41 pmORD - BOS
Nonstop2h 29mMultiple Airlines
Sat 1/106:00 amBOS - ORD
1 stop6h 35mMultiple Airlines
Deal found 12/9$161
This JetBlue deal was found by Cheapflights users on 12/11. 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.
Sun 12/148:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 1/191:40 pmBOS - ORD
1 stop6h 56mJetBlue
Deal found 12/11$162
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 12/157:00 amORD - BOS
Nonstop2h 29mAmerican Airlines
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 12/10$167
This American Airlines deal was found by Cheapflights users on 12/9. 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.
Thu 12/188:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Deal found 12/9$168
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Tue 12/239:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Wed 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/10$169

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 December 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$124
(Trip.com)

One-way from

$62
(Super.com)

Popular in

February

Cheapest in

January

Average price

$266

Good round-trip deal

$168 or less

Good one-way deal

$110 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Boston Logan Intl flight deals.
Search Deals
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
Search Deals
One-way flight from Chicago O'Hare Intl to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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

 
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 December 12, 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

Sat 1/17

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Tue 1/20

11:30 am-1:39 pm

Nonstop3h 09m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/28

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/1

3:20 pm-5:25 pm

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/22

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

Mon 1/26

4:16 pm-6:16 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/30

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/1

3:20 pm-5:25 pm

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/3

9:13 am-12:46 pm

Nonstop2h 33m

Boston Logan Intl

Tue 2/3

4:49 pm-6:49 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/24

2:00 pm-5:29 pm

Nonstop2h 29m

Boston Logan Intl

Sun 1/25

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/17

10:00 am-1:23 pm

Nonstop2h 23m

Boston Logan Intl

Sat 2/21

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/23

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

Mon 1/26

4:16 pm-6:16 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/26

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

Thu 1/29

4:10 pm-6:19 pm

Nonstop3h 09m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 24 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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 December 5, 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $88). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of $137). 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 December 12, 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 28% 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 December 6, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon 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

AI-powered summary based on content written by travel experts. AI can make mistakes.
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 December 12, 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
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,899 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,179 reviews
Delta
7.9
Good
8,008 reviews

Entertainment

7.9

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 54 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 25m. Delta provides one of the quickest options available for as low as $137. Chicago O'Hare Intl Airport and Boston are separated by a distance of 864 mi. Most flights are nonstop.

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

    According to our current data, Frontier ($57), JetBlue ($65), and Spirit Airlines ($79) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Frontier 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 Spirit Airlines, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from JetBlue 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: Envoy Air (79%), JetBlue (76%), Hawaiian Airlines( 76%).

  • 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 $60. On average you can expect to pay $519. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $127.

  • 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 $88). Flying from Chicago O'Hare Intl Airport to Boston in February is currently the most expensive (average of $137). 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
Cranston
Lincoln
Lowell
Smithfield
Peabody
Brockton
Quincy
York Beach
Warwick
Londonderry
Swansea
Old Orchard Beach
Waltham
Chelsea

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$78Average$178FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$104Average$225FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$233FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$262FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$144Average$206FlexibilityNo cancel feeOn-time63%

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