HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$79+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to O'Hare Intl with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or August, booked 57 days in advance, depart on a Wednesday or Friday and return on a Wednesday

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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Mytrip)

One-way from

$79
(Delta)

Popular in

May

Cheapest in

September

Average price

$233

Good round-trip deal

$249 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago O'Hare Intl flights.
Search Deals
From Boston Logan Intl to Chicago O'Hare Intl
Search Deals
One-way flight from Boston Logan Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago O'Hare Intl.
Search Deals

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 February 21, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/28:59 amBOS - ORD
2 stops24h 45mSpirit Airlines
Sat 4/51:48 pmORD - BOS
1 stop7h 40mSpirit Airlines
Deal found 2/19$151
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sun 5/256:00 amBOS - ORD
1 stop6h 32mMultiple Airlines
Wed 5/286:00 amORD - BOS
1 stop8h 30mMultiple Airlines
Deal found 2/20$153
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:10 amBOS - ORD
1 stop6h 40mFrontier
Sun 3/98:10 amORD - BOS
1 stop24h 01mFrontier
Deal found 2/20$155
This Delta deal was found by Cheapflights users on 2/20. 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 2/277:15 amBOS - ORD
Nonstop3h 06mDelta
Sat 3/17:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 2/20$157
This American Airlines deal was found by Cheapflights users on 2/20. 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 2/276:34 amBOS - ORD
Nonstop3h 05mAmerican Airlines
Mon 3/37:00 pmORD - BOS
Nonstop2h 23mAmerican Airlines
Deal found 2/20$161
This JetBlue deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/105:20 amBOS - ORD
1 stop6h 39mJetBlue
Thu 3/271:00 pmORD - BOS
Nonstop2h 20mJetBlue
Deal found 2/20$167
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/46:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Sun 4/67:10 amORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 2/20$168
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 3/105:35 amBOS - ORD
2 stops8h 10mSouthwest
Wed 3/124:00 pmORD - BOS
1 stop6h 00mSouthwest
Deal found 2/20$240

Find flights from Boston to O'Hare Intl within your budget

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 February 21, 2025.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/2

8:59 am-8:44 am

2 stops24h 45m

Chicago O'Hare Intl

Sat 4/5

1:48 pm-10:28 pm

1 stop7h 40m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/25

6:00 am-11:32 am

1 stop6h 32m

Chicago O'Hare Intl

Wed 5/28

6:00 am-3:30 pm

1 stop8h 30m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/6

5:10 am-10:50 am

1 stop6h 40m

Chicago O'Hare Intl

Sun 3/9

8:10 am-9:11 am

1 stop24h 01m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/4

7:15 am-9:21 am

Nonstop3h 06m

Chicago O'Hare Intl

Wed 3/12

10:55 am-2:12 pm

Nonstop2h 17m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/3

6:34 am-8:39 am

Nonstop3h 05m

Chicago O'Hare Intl

Wed 3/5

8:05 am-11:18 am

Nonstop2h 13m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/10

5:20 am-10:59 am

1 stop6h 39m

Chicago O'Hare Intl

Thu 3/27

1:00 pm-4:20 pm

Nonstop2h 20m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 4/6

7:10 am-10:38 am

Nonstop2h 28m

$168

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/10

5:35 am-12:45 pm

2 stops8h 10m

Chicago O'Hare Intl

Wed 3/12

4:00 pm-11:00 pm

1 stop6h 00m

$240

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/24

2:30 pm-4:30 pm

Nonstop3h 00m

$79

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/16

12:48 pm-11:11 pm

1 stop11h 23m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 18 results
1
2

Compare providers for flights from Boston to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to O'Hare Intl in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
FareScanPrice Accuracy-Trust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from 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.

Travel insights for flights from Boston to O'Hare Intl

Get recent, data-driven insights about flights from Boston to O'Hare Intl including ideal travel times, pricing trends, and more.

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 February 14, 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 57 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 February 21, 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 33% 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 February 16, 2025.

Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport flight should consider departing on Saturday 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 February 21, 2025.

The most flights from BOS to ORD are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 21, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Boston to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 39 outbound flights to Chicago O'Hare Intl per day from 6 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 Spirit Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $151. Additional round-trip tickets that might be worth considering are offered by Frontier and Delta, with the lowest prices starting at $155 and $157, respectively. Spirit Airlines is priced at 39% 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 Delta. According to our data, you can fly for as low as $79. Users have also found prices from $80 and $81 on Spirit Airlines and Frontier, 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 Air France (100%), Japan Airlines (90%) or KLM (90%) 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 $78. On average you can expect to pay $795. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $85.

  • 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Naperville
Rosemont
Schaumburg
Beloit
Racine
Hoffman Estates
Rockford
Tinley Park
Skokie
Arlington Heights
Northbrook
Joliet
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Evanston
Des Plaines
Elgin

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Boston to O'Hare Intl

Discover the top 6 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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$109FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$250FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$139FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$155Average$301FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.