O'Hare Intl

$59+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Apr 29 — May 61
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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 April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$118
(American Airlines)

One-way from

$59
(JetBlue)

Popular in

May

Cheapest in

September

Average price

$275

Good round-trip deal

$212 or less

Good one-way deal

$110 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
From Massachusetts to Chicago O'Hare Intl
One-way flight from Massachusetts to Chicago O'Hare Intl
Highest demand for flights based on searches. 9% potential increase in price ($26 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Massachusetts to Chicago O'Hare Intl.
Price to beat on a one-way flight from Massachusetts to Chicago O'Hare Intl.

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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 5/38:00 amBOS - ORD
Nonstop3h 07mAmerican Airlines
Mon 5/56:35 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Deal found 4/23$118
This Priceline deal was found by Cheapflights users on 4/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/43:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Wed 6/115:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Deal found 4/22$120
This United Airlines deal was found by Cheapflights users on 4/23. 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 6/306:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Fri 7/46:00 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 4/23$123
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Tue 6/104:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/23$136
This JetBlue deal was found by Cheapflights users on 4/23. 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 5/214:30 pmBOS - ORD
Nonstop3h 06mJetBlue
Sun 5/258:45 amORD - BOS
Nonstop2h 28mJetBlue
Deal found 4/23$148
This FlightHub deal was found by Cheapflights users on 4/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/22$153
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/61:46 pmORH - ORD
1 stop4h 48mAmerican Airlines
Fri 5/94:44 pmORD - ORH
1 stop20h 01mAmerican Airlines
Deal found 4/23$154
This Delta deal was found by Cheapflights users on 4/23. 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.
Mon 7/147:00 amBOS - ORD
Nonstop2h 59mDelta
Tue 7/227:00 amORD - BOS
Nonstop2h 28mDelta
Deal found 4/23$177
This Mytrip deal was found by Cheapflights users on 4/23. 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 5/156:00 amBOS - ORD
1 stop18h 32mFrontier
Sat 5/179:19 amORD - BOS
1 stop23h 05mFrontier
Deal found 4/23$192
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 10/74:00 pmORH - ORD
1 stop5h 44mDelta
Wed 10/228:30 amORD - ORH
1 stop5h 33mDelta
Deal found 4/23$212
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 7/14:45 pmALB - ORD
Nonstop2h 33mUnited Airlines
Sat 7/511:59 amORD - ALB
Nonstop2h 10mUnited Airlines
Deal found 4/23$267
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 5/316:00 amALB - ORD
1 stop4h 51mDelta
Mon 6/25:58 pmORD - ALB
1 stop5h 03mDelta
Deal found 4/23$271

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 April 24, 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

Sat 5/3

8:00 am-10:07 am

Nonstop3h 07m

Chicago O'Hare Intl

Mon 5/5

6:35 pm-10:07 pm

Nonstop2h 32m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/4

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 6/11

5:05 am-2:44 pm

1 stop8h 39m

$120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/30

6:59 pm-11:37 pm

1 stop5h 38m

Chicago O'Hare Intl

Fri 7/4

6:00 am-9:26 am

Nonstop2h 26m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Tue 6/10

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/21

4:30 pm-6:36 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 5/25

8:45 am-12:13 pm

Nonstop2h 28m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/14

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

$153

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 5/6

1:46 pm-5:34 pm

1 stop4h 48m

Chicago O'Hare Intl

Fri 5/9

4:44 pm-1:45 pm

1 stop20h 01m

$154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 7/14

7:00 am-8:59 am

Nonstop2h 59m

Chicago O'Hare Intl

Sat 7/19

7:00 am-10:28 am

Nonstop2h 28m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/15

6:00 am-11:32 pm

1 stop18h 32m

Chicago O'Hare Intl

Sat 5/17

9:19 am-9:24 am

1 stop23h 05m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/7

4:00 pm-8:44 pm

1 stop5h 44m

Chicago O'Hare Intl

Wed 10/22

8:30 am-3:03 pm

1 stop5h 33m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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, August is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $245). Flying from Massachusetts 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 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 April 24, 2025.

When flying from Massachusetts to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 April 24, 2025.

The most flights from USMA to ORD are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 April 24, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Massachusetts to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
8.0
Very good

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Boarding

8.2

Overall

8.0

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.
  • 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 JetBlue, which is currently one of the cheapest options available, starting at $59. American Airlines flights start at $60 while deals on United Airlines start at $64 one-way.

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

  • 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: Avianca (91%), ANA (89%), United Airlines( 87%).

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

    Looking at all options, your cheapest flight can be booked for $58. While the most popular route (Boston Logan Intl - Chicago O'Hare Intl) can be booked for $115 on average our data indicates $611 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, August is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $245). Flying from Massachusetts 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 Massachusetts?

Book flights to Massachusetts if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Racine
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Tinley Park
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Arlington Heights
Elgin
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Waukegan
Glenview

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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.

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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$220FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$244FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$134FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$261FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$290FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$182Average$378FlexibilityNo cancel feeOn-time63%

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