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$79+ Cheap flights from O'Hare Intl (ORD) to Massachusetts

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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Mar 19 — Mar 261
Wed 3/19
Wed 3/26
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Massachusetts

Keep the following information in mind while searching for O'Hare Intl to Massachusetts flight deals. Data was last updated March 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$156
(Flightnetwork)

One-way from

$79
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$273

Good round-trip deal

$201 or less

Good one-way deal

$113 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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From Chicago O'Hare Intl to Massachusetts
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One-way flight from Chicago O'Hare Intl to Massachusetts
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Highest demand for flights based on searches. 15% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Massachusetts.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Massachusetts.
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Find flight deals from O'Hare Intl to Massachusetts

Cheapest flights from O'Hare Intl to Massachusetts
Explore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 14, 2025.

This Mytrip deal was found by Cheapflights users on 3/11. 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.
Mon 3/318:33 pmORD - BOS
2 stops24h 55mSpirit Airlines
Thu 4/32:59 pmBOS - ORD
1 stop9h 38mSpirit Airlines
Deal found 3/11$155
This Flightnetwork deal was found by Cheapflights users on 3/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Wed 5/145:42 pmBOS - ORD
1 stop6h 47mMultiple Airlines
Deal found 3/12$156
This JetBlue Airways deal was found by Cheapflights users on 3/13. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:10 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 4/95:15 pmBOS - ORD
Nonstop3h 12mJetBlue
Deal found 3/13$157
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/14:15 pmORD - BOS
1 stop7h 50mFrontier
Mon 5/512:58 pmBOS - ORD
1 stop11h 13mFrontier
Deal found 3/13$160
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/17:00 amORD - BOS
Nonstop2h 26mDelta
Tue 5/67:30 amBOS - ORD
Nonstop3h 00mDelta
Deal found 3/13$167
This American Airlines deal was found by Cheapflights users on 3/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/307:05 amORD - BOS
Nonstop2h 30mAmerican Airlines
Sun 5/46:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Deal found 3/12$168
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Tue 3/259:20 amORD - BOS
Nonstop2h 23mUnited Airlines
Mon 3/316:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 3/12$193
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:00 amORD - ACK
1 stop4h 24mDelta
Tue 6/33:45 pmACK - ORD
1 stop7h 56mDelta
Deal found 3/13$206
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/54:00 pmORD - BOS
1 stop7h 15mSouthwest
Wed 4/96:05 amBOS - ORD
2 stops7h 40mSouthwest
Deal found 3/12$212
This Delta deal was found by Cheapflights users on 3/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/167:15 amORD - ORH
1 stop6h 51mDelta
Tue 4/224:00 pmORH - ORD
1 stop7h 23mDelta
Deal found 3/13$212
This CheapOair deal was found by Cheapflights users on 3/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:14 pmORD - BDL
1 stop25h 17mFrontier
Sun 5/253:56 pmBDL - ORD
1 stop9h 21mFrontier
Deal found 3/13$220
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1911:00 amORD - BDL
3 stops31h 03mSpirit Airlines
Wed 5/2110:22 amBDL - ORD
1 stop15h 02mSpirit Airlines
Deal found 3/13$221

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

Customize your flight search to find flights from O'Hare Intl to Massachusetts 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 March 14, 2025.

Fly from

O'Hare Intl

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/31

8:33 pm-10:28 pm

2 stops24h 55m

Boston Logan Intl

Thu 4/3

2:59 pm-11:37 pm

1 stop9h 38m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/9

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Wed 5/14

5:42 pm-11:29 pm

1 stop6h 47m

$156

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/4

4:00 pm-7:28 pm

Nonstop2h 28m

Boston Logan Intl

Mon 4/7

12:25 pm-2:22 pm

Nonstop2h 57m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/2

6:30 pm-10:09 pm

Nonstop2h 39m

Boston Logan Intl

Sun 5/4

6:00 am-8:05 am

Nonstop3h 05m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/1

4:15 pm-1:05 am

1 stop7h 50m

Boston Logan Intl

Mon 5/5

12:58 pm-11:11 pm

1 stop11h 13m

$160

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/30

7:05 am-10:35 am

Nonstop2h 30m

Boston Logan Intl

Sun 5/4

6:10 am-8:18 am

Nonstop3h 08m

$168

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/8

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Wed 4/16

9:05 am-4:11 pm

1 stop8h 06m

$196

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 6/3

6:00 am-11:24 am

1 stop4h 24m

Nantucket Memorial

Tue 6/3

3:45 pm-10:41 pm

1 stop7h 56m

$206

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/5

4:00 pm-12:15 am

1 stop7h 15m

Boston Logan Intl

Wed 4/9

6:05 am-12:45 pm

2 stops7h 40m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/16

7:15 am-3:06 pm

1 stop6h 51m

Worcester

Tue 4/22

4:00 pm-10:23 pm

1 stop7h 23m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 60 results
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Best time to book a flight from O'Hare Intl to Massachusetts

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

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $218). Flying from Chicago O'Hare Intl Airport to Massachusetts in July is currently the most expensive (average of $311). 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 ORD to MA?

Find hourly flight availability from O'Hare Intl to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 14, 2025.

When flying from Chicago O'Hare Intl Airport to Massachusetts, 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 Chicago O'Hare Intl Airport to Massachusetts

Explore weekly flight availability from O'Hare Intl to Massachusetts. 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 March 14, 2025.

The most flights from ORD to USMA are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, 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 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated March 14, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta from Chicago to Massachusetts to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,292 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very good
9,734 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,944 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Qatar Airways
7.4
Good
3,545 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,623 reviews
Southwest
8.1
Very good
4,292 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Food

7.1

Crew

8.7

Comfort

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Massachusetts. 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 Chicago O'Hare Intl Airport to Massachusetts one-way?

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $79. Frontier flights start at $80 while deals on Spirit Airlines start at $81 one-way.

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

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

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

    Consider Air France (100%), LATAM Airlines (92%) or Iberia (91%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Massachusetts.

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

    The cheapest flight price from Chicago O'Hare Intl Airport to Massachusetts is $78. On average you can expect to pay $591. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $105.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Massachusetts.

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $218). Flying from Chicago O'Hare Intl Airport to Massachusetts in July is currently the most expensive (average of $311). 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.

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Alternative routes for O'Hare Intl to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Las Vegas flights
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Midway to Orlando flights
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Midway to LaGuardia flights
O'Hare Intl to Charlotte flights
Midway to San Francisco flights
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Midway to Tampa flights
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Top 7 airlines flying from O'Hare Intl to Massachusetts

Discover the top 7 airlines that operate flights from O'Hare Intl to Massachusetts. 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 March 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$460FlexibilityNo cancel feeOn-time62%
DeltaCheapest$89Average$238FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$142Average$436FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$435FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$280FlexibilityNo cancel feeOn-time63%
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