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$69+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 82 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 September 11, 2025.

Round-trip from

$132
(JetBlue)

One-way from

$69
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$187

Good round-trip deal

$165 or less

Good one-way deal

$114 or less
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. 6% potential increase in price ($16 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 September 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 September 11, 2025.

This JetBlue deal was found by Cheapflights users on 9/9. 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.
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/9$132
This JetBlue deal was found by Cheapflights users on 9/11. 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.
Wed 10/17:50 pmORD - BOS
Nonstop2h 35mJetBlue
Tue 10/77:09 amBOS - ORD
Nonstop3h 13mJetBlue
Deal found 9/11$133
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/249:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/10$135
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1111:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Tue 10/142:15 pmBOS - ORD
1 stop8h 18mSpirit Airlines
Deal found 9/9$136
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 9/172:15 pmORD - BOS
Nonstop2h 31mUnited Airlines
Fri 9/1911:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 9/10$137
This American Airlines deal was found by Cheapflights users on 9/9. 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.
Sat 9/205:36 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Sat 9/272:40 pmBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 9/9$138
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:25 pmORD - BOS
Nonstop2h 29mAmerican Airlines
Sun 10/265:24 amBOS - ORD
Nonstop3h 01mAmerican Airlines
Deal found 9/11$139
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/223:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Deal found 9/11$140
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:55 pmORD - BOS
Nonstop2h 32mJetBlue
Sun 11/168:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 9/10$141
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sun 9/217:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/10$142
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 11/66:05 amORD - BOS
Nonstop2h 24mAmerican Airlines
Sun 11/96:45 amBOS - ORD
Nonstop3h 07mAmerican Airlines
Deal found 9/10$143
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:30 pmORD - BOS
1 stop4h 20mSouthwest
Sat 11/15:05 amBOS - ORD
1 stop7h 45mSouthwest
Deal found 9/10$144

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 September 11, 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 10/25

4:09 pm-1:13 am

1 stop8h 04m

Boston Logan Intl

Sat 11/1

5:40 am-12:16 pm

1 stop7h 36m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Wed 11/12

4:05 pm-6:13 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/18

10:30 am-1:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 11/23

7:30 am-9:35 am

Nonstop3h 05m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

1:55 pm-5:15 pm

Nonstop2h 20m

Boston Logan Intl

Sun 11/16

5:30 am-9:46 am

1 stop5h 16m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:37 am

Nonstop2h 27m

Boston Logan Intl

Sun 12/7

5:45 am-11:48 am

1 stop7h 03m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/25

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sat 10/25

5:19 pm-9:44 pm

1 stop5h 25m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/30

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Sat 11/1

5:40 am-12:16 pm

1 stop7h 36m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

7:13 pm-10:46 pm

Nonstop2h 33m

Boston Logan Intl

Sun 10/26

8:30 am-10:35 am

Nonstop3h 05m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

7:10 pm-10:45 pm

Nonstop2h 35m

Boston Logan Intl

Tue 10/28

6:00 am-12:17 pm

1 stop7h 17m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 10/6

4:45 pm-11:55 pm

1 stop6h 10m

Boston Logan Intl

Thu 10/9

5:40 am-4:25 pm

2 stops11h 45m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 24 results
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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

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 August 29, 2025.

Booking 82 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 September 11, 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 24% 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 September 7, 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.

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 September 11, 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
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 52 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 20m. Delta provides one of the quickest options available for as low as $149. 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 ($35), JetBlue ($78), and Delta ($95) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Spirit Airlines is currently priced 84% 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 United Airlines and JetBlue, 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 (94%), Air France (88%), Etihad Airways( 84%).

  • 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 $68. On average you can expect to pay $434. 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, 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 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
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$141FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$183FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$225FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$231FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$132Average$284FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$231FlexibilityNo cancel feeOn-time63%

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