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O'Hare Intl

$64+ Cheap flights from Boston (BOS) to O'Hare Intl (ORD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in January or September, booked 74 days in advance, depart on a Friday or Wednesday and return on a Thursday

Cheap flight deals from Boston to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to O'Hare Intl (ORD). 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 19, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$64
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$217

Good round-trip deal

$203 or less

Good one-way deal

$106 or less
From Boston Logan Intl to Chicago O'Hare Intl
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One-way flight from Boston Logan Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 3% potential increase in price ($8 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 Boston Logan Intl to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Boston Logan Intl to Chicago O'Hare Intl.
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Find flight deals from Boston to O'Hare Intl

Cheapest flights from Boston to O'Hare Intl
Explore the most affordable flight options available from Boston to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/18$126
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:47 pmBOS - ORD
Nonstop2h 48mUnited Airlines
Wed 10/227:30 amORD - BOS
Nonstop2h 32mUnited Airlines
Deal found 9/17$127
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/124:02 pmBOS - ORD
Nonstop3h 22mAmerican Airlines
Wed 11/266:35 pmORD - BOS
Nonstop2h 30mAmerican Airlines
Deal found 9/17$128
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:29 pmBOS - ORD
Nonstop2h 54mAmerican Airlines
Wed 10/17:10 amORD - BOS
Nonstop2h 19mAmerican Airlines
Deal found 9/17$129
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:15 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Sun 10/196:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 9/17$133
This JetBlue deal was found by Cheapflights users on 9/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:09 amBOS - ORD
Nonstop3h 13mJetBlue
Wed 10/157:13 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 9/18$135
This Trip.com deal was found by Cheapflights users on 9/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:00 amBOS - ORD
Nonstop2h 56mJetBlue
Mon 9/297:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 9/18$136
This JetBlue deal was found by Cheapflights users on 9/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:00 amBOS - ORD
Nonstop2h 56mJetBlue
Tue 9/309:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/18$137
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/237:00 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Wed 9/247:10 amORD - BOS
Nonstop2h 19mAmerican Airlines
Deal found 9/16$138
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Wed 10/86:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Wed 10/156:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/17$139
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:00 amBOS - ORD
Nonstop2h 55mUnited Airlines
Tue 10/216:14 pmORD - BOS
Nonstop2h 31mUnited Airlines
Deal found 9/17$140
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Fri 9/264:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Tue 9/309:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/17$142

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to O'Hare Intl 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 19, 2025.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/18

6:15 pm-8:09 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

7:15 am-12:45 pm

1 stop6h 30m

Chicago O'Hare Intl

Mon 10/27

2:50 pm-11:25 pm

1 stop7h 35m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/24

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

Sun 10/26

6:15 am-9:30 am

Nonstop2h 15m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Fri 10/24

7:13 pm-10:46 pm

Nonstop2h 33m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/16

5:30 am-9:36 am

1 stop5h 06m

Chicago O'Hare Intl

Tue 10/21

9:00 am-12:35 pm

Nonstop2h 35m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/22

6:00 am-10:38 am

1 stop5h 38m

Chicago O'Hare Intl

Wed 10/22

9:20 pm-12:50 am

Nonstop2h 30m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/25

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/29

12:00 pm-5:15 pm

1 stop4h 15m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/1

12:35 pm-2:25 pm

Nonstop2h 50m

Chicago O'Hare Intl

Thu 10/2

10:40 am-4:22 pm

1 stop4h 42m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 11/4

7:20 am-9:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Fri 11/7

7:05 am-10:29 am

Nonstop2h 24m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/18

11:45 am-1:40 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 10/25

7:05 am-10:29 am

Nonstop2h 24m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 23 results
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The best insider tips for Boston to Chicago O'Hare Intl Airport 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 Boston to Chicago O'Hare Intl Airport trip
Airlines
United Airlines

United's Economy Plus offers extra legroom and priority boarding, enhancing comfort on domestic flights.


Prepay for checked bags on United to save money. Avoid fees by using MileagePlus Premier benefits.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

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


Use Spirit's self-service bag drop for a faster airport experience. Print boarding pass beforehand to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
BOS

Use the FlyLogan App to pre-order meals and save time at BOS. Most restaurants participate in this convenient service.

Read more about BOSby Paul Rubio
ORD

Take the 'L' train from downtown Chicago to ORD to avoid traffic delays. It's a reliable public transport option.

Read more about ORDby Ramsey Qubein
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 Boston to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Boston 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 Boston to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Boston to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Boston to O'Hare Intl. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Chicago O'Hare Intl Airport, you should look to book at least 74 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Boston to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $245). Flying from Boston to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 BOS to ORD?

Find hourly flight availability from Boston to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 19, 2025.

It’s optimal to fly from Boston to Chicago O'Hare Intl Airport in the evening. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Boston to O'Hare Intl. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport flight should consider departing on Wednesday 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.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated September 19, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Boston to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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
8,926 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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
2,911 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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
8,030 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

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 Boston to O'Hare Intl. 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 from for flights from Boston to Chicago O'Hare Intl?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Chicago O'Hare Intl. On average, Logan Intl has 62 outbound flights to Chicago O'Hare Intl per day from 7 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    There are many flights that can get you from Boston to Chicago O'Hare Intl Airport in 2h 54m. Fly via United Airlines, Southwest, or JetBlue to get the fastest option. There are 864 mi between Boston and Chicago O'Hare Intl Airport. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on Spirit Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $50. Additional round-trip tickets that might be worth considering are offered by JetBlue and Frontier, with the lowest prices starting at $83 and $100, respectively. Spirit Airlines is priced at 79% lower than the current average price of a flight leaving 3 months from now.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $69 on United Airlines and American Airlines, respectively.

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

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing Icelandair (89%), TAP AIR PORTUGAL (87%) or Avianca (84%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Boston to Chicago O'Hare Intl Airport is $65. On average you can expect to pay $755. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $112.

  • Can I find deals for flights from Boston to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Boston to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to O'Hare Intl.

  • Can I find deals for business class flights from Boston to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Boston to O'Hare Intl 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 Boston to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $245). Flying from Boston to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Schaumburg
Rosemont
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

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Top 7 airlines flying from Boston to O'Hare Intl

Discover the top 7 airlines that operate flights from Boston to O'Hare Intl. 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 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$50Average$215FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$197FlexibilityNo cancel feeOn-time62%
FrontierCheapest$100Average$112FlexibilityNo cancel feeOn-time62%
DeltaCheapest$107Average$250FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$137Average$284FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$137Average$255FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$203FlexibilityNo cancel feeOn-time63%

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