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O'Hare Intl

$63+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
gen. 14 — gen. 211
dc. 1/14
dc. 1/21
1 adult, Economy
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Cheap 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 desembre 15, 2025.

This JetBlue deal was found by Cheapflights users on 12/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 12/254:31 pmBOS - ORD
Nonstop3h 15mJetBlue
dl. 12/297:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/15$132
This United Airlines deal was found by Cheapflights users on 12/14. 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.
ds. 12/207:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
dl. 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/14$137
This United Airlines deal was found by Cheapflights users on 12/13. 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.
dt. 12/166:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
dt. 12/161:55 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 12/13$157
This Super.com deal was found by Cheapflights users on 12/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dj. 12/184:31 pmBOS - ORD
Nonstop3h 15mJetBlue
dg. 12/217:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/13$158
This United Airlines deal was found by Cheapflights users on 12/14. 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.
dj. 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
ds. 12/209:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/14$162
This United Airlines deal was found by Cheapflights users on 12/12. 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.
dc. 12/316:45 amBOS - ORD
1 stop6h 20mUnited Airlines
dt. 1/69:13 amORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/12$167
This Priceline deal was found by Cheapflights users on 12/13. 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.
dj. 12/254:31 pmBOS - ORD
Nonstop3h 15mMultiple Airlines
dl. 1/124:49 pmORD - BOS
1 stop7h 30mMultiple Airlines
Deal found 12/13$170
This American Airlines deal was found by Cheapflights users on 12/14. 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.
dl. 12/291:45 pmORH - ORD
1 stop21h 18mAmerican Airlines
dv. 1/28:45 pmORD - ORH
1 stop15h 32mAmerican Airlines
Deal found 12/14$173
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dc. 12/244:47 pmBDL - ORD
1 stop8h 15mDelta
dc. 12/317:00 amORD - BDL
1 stop3h 59mDelta
Deal found 12/15$177
This American Airlines deal was found by Cheapflights users on 12/13. 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.
dc. 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
dt. 1/68:18 pmORD - BOS
Nonstop2h 26mAmerican Airlines
Deal found 12/13$177
This United Airlines deal was found by Cheapflights users on 12/13. 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.
dj. 12/187:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
dv. 12/197:45 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/13$178
This United Airlines deal was found by Cheapflights users on 12/14. 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.
dj. 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
dj. 12/186:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/14$182

Find 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 desembre 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$120
(Flysmarter)

One-way from

$63
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$253

Good round-trip deal

$229 or less

Good one-way deal

$138 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. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 desembre 15, 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

dj. 12/25

4:31 pm-6:46 pm

Nonstop3h 15m

Chicago O'Hare Intl

dl. 12/29

7:41 pm-11:10 pm

Nonstop2h 29m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dj. 2/26

5:27 am-6:52 pm

1 stop14h 25m

Chicago O'Hare Intl

dt. 3/3

5:15 am-5:15 pm

1 stop11h 00m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dv. 1/30

4:16 pm-6:16 pm

Nonstop3h 00m

Chicago O'Hare Intl

dg. 2/1

7:30 am-10:52 am

Nonstop2h 22m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ds. 1/24

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

dg. 1/25

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dt. 2/3

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

dv. 2/6

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dl. 2/23

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

ds. 3/7

10:00 am-1:23 pm

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dt. 1/27

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

dt. 2/3

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dc. 1/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

dv. 1/16

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dc. 3/25

7:55 am-10:05 am

Nonstop3h 10m

Chicago O'Hare Intl

dg. 3/29

6:22 pm-9:55 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dc. 3/11

7:00 am-9:09 am

Nonstop3h 09m

Chicago O'Hare Intl

dg. 3/15

6:22 pm-9:55 pm

Nonstop2h 33m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 60 results
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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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $89). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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 desembre 15, 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 65% 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 desembre 15, 2025.

The most flights from USMA to ORD are scheduled on a Monday (67 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (15 on average).

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 3h 05m. JetBlue provides one of the quickest options available for as low as $132. The distance between Massachusetts and Chicago O'Hare Intl Airport is about 864 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $46. Frontier flights start at $47 while deals on JetBlue start at $58 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: ANA (84%), TAP AIR PORTUGAL (83%), JetBlue( 81%).

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

    Looking at all options, your cheapest flight can be booked for $64. While the most popular route (Boston Logan Intl - Chicago O'Hare Intl) can be booked for $127 on average, our data indicates $828 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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $89). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

Browse thousands of different options on Cheapflights for your next trip

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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
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Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
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Los Angeles to Midway flights
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Boston to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to Midway flights
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Santa Ana to O'Hare Intl flights
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Austin to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Orlando to O'Hare Intl flights
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Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
LaGuardia to Midway flights
Hobby to Midway flights
Raleigh to O'Hare Intl flights
Nashville to O'Hare Intl flights
Dulles Intl to Midway flights
San Francisco to Midway flights
Orlando to Midway flights
Minneapolis to Midway flights
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Detroit to O'Hare Intl flights
Baltimore to Midway flights
Denver to Midway flights
Philadelphia to Midway flights
Las Vegas to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Newark to Midway flights

Top 6 airlines flying from Massachusetts to O'Hare Intl

Discover the top 6 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 desembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$75Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$308FlexibilityNo cancel feeOn-time65%
DeltaCheapest$112Average$261FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$123Average$270FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$128Average$255FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$196FlexibilityNo cancel feeOn-time63%

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