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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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$133
(Kissandfly.com)

One-way from

$69
(Delta)

Popular in

February

Cheapest in

September

Average price

$218

Good round-trip deal

$166 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. 7% potential increase in price ($17 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 August 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 August 18, 2025.

This Kissandfly.com deal was found by Cheapflights users on 8/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:30 amORD - BOS
Nonstop2h 26mJetBlue
Sun 8/316:00 amBOS - ORD
Nonstop2h 55mJetBlue
Deal found 8/16$133
This Priceline deal was found by Cheapflights users on 8/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1011:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Thu 9/118:47 amBOS - ORD
1 stop9h 04mMultiple Airlines
Deal found 8/15$135
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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.
Sat 9/611:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/1012:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/17$136
This JetBlue deal was found by Cheapflights users on 8/17. 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 10/119:42 amORD - BOS
Nonstop2h 28mJetBlue
Sun 10/124:05 pmBOS - ORD
Nonstop2h 50mJetBlue
Deal found 8/17$137
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amORD - BOS
1 stop6h 44mSpirit Airlines
Tue 10/283:00 pmBOS - ORD
1 stop11h 03mSpirit Airlines
Deal found 8/16$138
This Flightnetwork deal was found by Cheapflights users on 8/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/111:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 10/86:11 amBOS - ORD
1 stop13h 13mSpirit Airlines
Deal found 8/17$140
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:40 pmORD - BOS
1 stop15h 18mMultiple Airlines
Wed 9/106:10 amBOS - ORD
1 stop12h 29mMultiple Airlines
Deal found 8/17$142
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1011:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Fri 9/1210:53 amBOS - ORD
1 stop14h 17mMultiple Airlines
Deal found 8/16$143
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1311:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/1712:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/16$146
This Southwest deal was found by Cheapflights users on 8/18. 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.
Thu 9/41:50 pmORD - BOS
1 stop7h 25mSouthwest
Mon 9/87:30 amBOS - ORD
1 stop6h 15mSouthwest
Deal found 8/18$147
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Tue 10/146:00 amORD - BOS
1 stop6h 44mSpirit Airlines
Wed 10/1512:31 pmBOS - ORD
1 stop10h 02mSpirit Airlines
Deal found 8/17$148

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 August 18, 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

Fri 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Sun 9/21

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/16

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sun 10/19

8:47 pm-10:35 pm

Nonstop2h 48m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/10

7:00 am-10:30 am

Nonstop2h 30m

Boston Logan Intl

Fri 9/12

7:30 pm-9:15 pm

Nonstop2h 45m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/20

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Wed 12/31

7:45 am-9:49 am

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/27

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

Sat 10/4

7:25 am-9:15 am

Nonstop2h 50m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

Sun 11/9

8:30 am-10:35 am

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/11

3:50 pm-7:23 pm

Nonstop2h 33m

Boston Logan Intl

Wed 10/15

4:10 pm-6:10 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/6

9:51 am-1:20 pm

Nonstop2h 29m

Boston Logan Intl

Wed 9/10

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/18

9:15 pm-12:45 am

Nonstop2h 30m

Boston Logan Intl

Thu 9/25

6:00 am-7:56 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 12/22

9:12 pm-12:45 am

Nonstop2h 33m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

Showing 1-10 of 18 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 8, 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 August 18, 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 23% 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 August 17, 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.

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 August 18, 2025.

The most flights from ORD to BOS are scheduled on a Monday (80 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (31 on average).

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 August 18, 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
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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
2,915 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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
8,038 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

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 51 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 26m. JetBlue 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, Spirit Airlines ($31), JetBlue ($77), and Delta ($92) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Spirit Airlines is currently priced 86% below the average price you’ll pay for this route.

  • 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 (95%), Etihad Airways (83%), Alaska 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 $68. On average you can expect to pay $394. 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
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
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Saugus
Burlington
Braintree

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$33Average$101FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$188FlexibilityNo cancel feeOn-time62%
DeltaCheapest$91Average$220FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$121Average$233FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$130Average$283FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$241FlexibilityNo cancel feeOn-time63%

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