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O'Hare Intl

$69+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
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 September or August, booked 50 days in advance, depart on a Friday or Thursday 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 July 28, 2025.

Round-trip from

$137
(United Airlines)

One-way from

$69
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$257

Good round-trip deal

$218 or less

Good one-way deal

$133 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. 5% potential increase in price ($15 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 July 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 July 28, 2025.

This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/119:43 amBOS - ORD
Nonstop2h 50mUnited Airlines
Sun 9/146:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 7/27$137
This FlightHub deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2610:34 amBOS - ORD
1 stop12h 48mSpirit Airlines
Tue 9/28:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Deal found 7/27$138
This Trip.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:00 amBOS - ORD
Nonstop2h 55mJetBlue
Thu 8/214:27 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 7/28$142
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:45 pmBOS - ORD
1 stop10h 20mSouthwest
Mon 9/87:30 amORD - BOS
1 stop9h 15mSouthwest
Deal found 7/28$146
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:20 amBOS - ORD
Nonstop2h 55mDelta
Sun 9/77:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 7/28$155
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:33 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
Sun 9/77:10 amORD - BOS
Nonstop2h 19mAmerican Airlines
Deal found 7/27$166
This CheapOair deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:00 amBOS - ORD
1 stop14h 12mMultiple Airlines
Tue 8/198:12 pmORD - BOS
1 stop14h 06mMultiple Airlines
Deal found 7/26$167

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 July 28, 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

Thu 9/11

9:43 am-11:33 am

Nonstop2h 50m

Chicago O'Hare Intl

Sun 9/14

6:30 am-9:56 am

Nonstop2h 26m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/26

10:34 am-10:22 pm

1 stop12h 48m

Chicago O'Hare Intl

Tue 9/2

8:12 pm-11:18 am

1 stop14h 06m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/21

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 8/21

4:27 pm-8:00 pm

Nonstop2h 33m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

1:45 pm-11:05 pm

1 stop10h 20m

Chicago O'Hare Intl

Mon 9/8

7:30 am-5:45 pm

1 stop9h 15m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/30

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 9/2

7:00 am-10:30 am

Nonstop2h 30m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

12:33 pm-2:34 pm

Nonstop3h 01m

Chicago O'Hare Intl

Sun 9/7

7:10 am-10:29 am

Nonstop2h 19m

$166

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/16

6:00 am-7:12 pm

1 stop14h 12m

Chicago O'Hare Intl

Wed 8/20

8:12 pm-11:18 am

1 stop14h 06m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/4

7:00 am-8:56 am

Nonstop2h 56m

$69

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/9

3:00 pm-10:48 pm

1 stop8h 48m

$70

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/12

7:04 pm-11:41 pm

1 stop5h 37m

$74

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 13 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 July 25, 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 50 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 July 28, 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 28% 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 July 27, 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.

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

Explore weekly flight availability from Boston to O'Hare Intl. 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 July 28, 2025.

The most flights from BOS to ORD are scheduled on a Monday (78 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (42 on average).

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 July 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,892 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 60 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.

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

    Flying on United Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $137. Additional round-trip tickets that might be worth considering are offered by American Airlines and Spirit Airlines, with the lowest prices starting at $138 and $139, respectively. United Airlines is priced at 43% 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 $70 and $74 on Spirit Airlines and United 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 Avianca (95%), TAP AIR PORTUGAL (95%) or Icelandair (94%) 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 $68. On average you can expect to pay $1,340. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $117.

  • 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
Beloit
Hoffman Estates
Skokie
Naperville
Arlington Heights
Des Plaines
Elgin
Orland Park
Elk Grove Village
Racine
Rockford
Tinley Park
Merrillville
Evanston
Lake Geneva
Gurnee
Joliet
Waukegan

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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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$128FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$71Average$202FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$239FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$116FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$251FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$138Average$280FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$212FlexibilityNo cancel feeOn-time63%

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