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

$62+ Cheap flights from Massachusetts 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts 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.

Cheap flight deals from Massachusetts to O'Hare Intl

Keep the following information in mind while searching for Massachusetts to O'Hare Intl flight deals. Data was last updated October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Delta)

One-way from

$62
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$210 or less

Good one-way deal

$136 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Chicago O'Hare Intl
Search Deals
One-way flight from Massachusetts to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago O'Hare Intl.
Search Deals

Find flight deals from Massachusetts to O'Hare Intl

Cheapest flights from Massachusetts to O'Hare Intl
Explore the most affordable flight options available from Massachusetts to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 22, 2025.

This JetBlue deal was found by Cheapflights users on 10/21. 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 11/17:00 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 11/1211:20 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 10/21$117
This JetBlue deal was found by Cheapflights users on 10/21. 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 12/45:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 10/21$118
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/256:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Wed 1/79:13 amORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/21$120
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Mon 11/179:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mon 11/249:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/21$122
This Kissandfly.com deal was found by Cheapflights users on 10/21. 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.
Tue 11/188:30 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 11/197:00 amORD - BOS
Nonstop2h 25mJetBlue
Deal found 10/21$123
This Expedia deal was found by Cheapflights users on 10/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:10 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 11/176:55 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/21$125
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/314:36 pmBOS - ORD
Nonstop3h 27mAmerican Airlines
Mon 1/56:22 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Deal found 10/21$126
This Delta deal was found by Cheapflights users on 10/22. 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 12/44:05 pmBOS - ORD
Nonstop2h 57mDelta
Mon 12/810:36 amORD - BOS
1 stop4h 35mDelta
Deal found 10/22$127
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sun 12/75:00 amBOS - ORD
1 stop8h 15mSouthwest
Tue 12/91:45 pmORD - BOS
1 stop7h 30mSouthwest
Deal found 10/21$128
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/27:14 pmBOS - ORD
Nonstop3h 06mAmerican Airlines
Sat 12/68:52 amORD - BOS
Nonstop2h 34mAmerican Airlines
Deal found 10/20$129
This Delta deal was found by Cheapflights users on 10/22. 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.
Fri 12/55:29 amBOS - ORD
1 stop5h 31mDelta
Sun 12/77:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/22$131
This United Airlines deal was found by Cheapflights users on 10/22. 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.
Sun 11/236:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Thu 11/276:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 10/22$133

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 October 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Massachusetts

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/4

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 12/8

12:35 pm-5:53 pm

1 stop4h 18m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 12/8

6:30 pm-10:30 pm

1 stop5h 00m

Chicago O'Hare Intl

Thu 12/11

10:35 am-1:59 pm

Nonstop2h 24m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

5:29 am-10:00 am

1 stop5h 31m

Chicago O'Hare Intl

Sun 1/18

7:00 am-10:33 am

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/15

12:00 pm-4:17 pm

1 stop5h 17m

Chicago O'Hare Intl

Sun 1/18

7:00 am-10:33 am

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

4:40 pm-8:35 pm

1 stop4h 55m

Chicago O'Hare Intl

Fri 12/12

7:10 pm-10:34 pm

Nonstop2h 24m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

4:05 pm-8:14 pm

1 stop5h 09m

Chicago O'Hare Intl

Tue 1/20

9:13 am-12:46 pm

Nonstop2h 33m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/19

6:00 am-8:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 3/22

9:10 pm-12:30 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/8

4:10 pm-6:07 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 11/9

7:10 am-10:36 am

Nonstop2h 26m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/10

4:10 pm-6:10 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 3/11

10:10 am-1:40 pm

Nonstop2h 30m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

5:30 am-9:35 am

1 stop5h 05m

Chicago O'Hare Intl

Tue 1/20

6:00 am-12:23 pm

1 stop5h 23m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Massachusetts to O'Hare Intl

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

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

Currently, November is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $87). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $135). 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 MA to ORD?

Find hourly flight availability from Massachusetts 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 October 22, 2025.

It’s typically best to fly out from Massachusetts to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 66% on the flight price compared to flying in the afternoon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to O'Hare Intl. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Chicago O'Hare Intl Airport flight should consider departing on Tuesday mornings 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 Massachusetts to Chicago O'Hare Intl Airport

Explore weekly flight availability from Massachusetts 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 October 22, 2025.

The most flights from USMA to ORD are scheduled on a Monday (72 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Massachusetts to Chicago O'Hare Intl Airport?

Related info for your journey

Find useful and relevant information for your journey from Massachusetts 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.

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

    A quick flight from Massachusetts to Chicago O'Hare Intl Airport can take about 2h 54m. Delta provides one of the quickest options available for as low as $235. The distance between Massachusetts and Chicago O'Hare Intl Airport is about 780 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $69. JetBlue flights start at $69 while deals on United Airlines start at $73 one-way.

  • What are the most popular routes from Massachusetts to Chicago O'Hare Intl Airport?

    The most popular route from Massachusetts to Chicago O'Hare Intl Airport is Boston Logan Intl - Chicago O'Hare Intl. You may also consider Hartford Bradley Intl - Chicago O'Hare Intl or Albany Intl - Chicago O'Hare Intl.

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

    Before booking your flight to Chicago O'Hare Intl Airport from Massachusetts, check out the most reliable airlines to get you to your destination on time: TAP AIR PORTUGAL (88%), Icelandair (88%), Avianca( 85%).

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

    Looking at all options, your cheapest flight can be booked for $59. While the most popular route (Boston Logan Intl - Chicago O'Hare Intl) can be booked for $91 on average, our data indicates $673 when flying from Massachusetts to Chicago O'Hare Intl Airport.

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

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

  • How can I find direct flights from Massachusetts 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 Massachusetts to O'Hare Intl.

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

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

    Currently, November is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $87). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $135). 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
Des Plaines
Gurnee
Hoffman Estates
Elgin
Oak Brook
Elk Grove Village
Beloit
Rockford
Naperville
Racine
Downers Grove
Orland Park
Merrillville
Bridgeview
Warrenville
Joliet
Waukegan

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.

Alternative routes for Massachusetts to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
LaGuardia to Midway flights
Minneapolis to O'Hare Intl flights
Atlanta to Midway flights
Newark to Midway flights
Hobby to Midway flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Minneapolis to Midway flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Dulles Intl to Midway flights
Baltimore to Midway flights
Denver to Midway flights
George Bush Intcntl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Hobby to O'Hare Intl flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Portland to O'Hare Intl flights
San Jose to O'Hare Intl flights
Seattle to Midway flights
Love Field to O'Hare Intl flights
Orlando to Midway flights
San Diego to O'Hare Intl flights
Hartford to O'Hare Intl flights
Reagan-National to Midway flights
Cleveland to O'Hare Intl flights
San Francisco to Midway flights
Miami to O'Hare Intl flights
Los Angeles to Midway flights
Philadelphia to Midway flights
Columbus to O'Hare Intl flights

Top 7 airlines flying from Massachusetts to O'Hare Intl

Discover the top 7 airlines that operate flights from Massachusetts 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$69Average$248FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$196FlexibilityNo cancel feeOn-time62%
FrontierCheapest$89Average$116FlexibilityNo cancel feeOn-time62%
DeltaCheapest$115Average$256FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$130Average$278FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$137Average$256FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$203FlexibilityNo cancel feeOn-time63%

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.