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O'Hare Intl

$64+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Massachusetts to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) 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 enero 21, 2025.

Round-trip from

$147
(Mytrip)

One-way from

$64
(Mytrip)

Good round-trip deal

$260 or less

Good one-way deal

$133 or less
From Massachusetts to Chicago O'Hare Intl
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One-way flight from Massachusetts to Chicago O'Hare Intl
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Price to beat on a round-trip flight from Massachusetts to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Massachusetts to Chicago O'Hare Intl.
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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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/1010:21 pmBOS - ORD
2 stops16h 18mSpirit Airlines
mié. 3/126:45 amORD - BOS
1 stop8h 25mSpirit Airlines
Deal found 1/21$147
This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/76:00 amBOS - ORD
1 stop15h 57mFrontier
lun. 2/104:41 pmORD - BOS
1 stop6h 58mFrontier
Deal found 1/21$148
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/105:10 amBOS - ORD
1 stop12h 21mMultiple Airlines
lun. 3/176:45 amORD - BOS
1 stop8h 25mMultiple Airlines
Deal found 1/21$149
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/218:20 pmBOS - ORD
Nonstop2h 59mDelta
mié. 2/267:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 1/21$157
This JetBlue deal was found by Cheapflights users on 1/21. 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.
lun. 2/2410:00 amBOS - ORD
Nonstop3h 00mJetBlue
sáb. 3/112:38 pmORD - BOS
Nonstop2h 20mJetBlue
Deal found 1/21$167
This United Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 3/104:17 pmBOS - ORD
1 stop6h 43mUnited Airlines
mié. 3/1211:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 1/21$183
This American Airlines deal was found by Cheapflights users on 1/21. 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.
jue. 2/135:20 amBOS - ORD
Nonstop3h 01mAmerican Airlines
dom. 2/168:05 amORD - BOS
Nonstop2h 14mAmerican Airlines
Deal found 1/21$189
This American Airlines deal was found by Cheapflights users on 1/20. 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.
jue. 2/202:15 pmORH - ORD
1 stop21h 31mAmerican Airlines
mié. 2/264:16 pmORD - ORH
1 stop20h 27mAmerican Airlines
Deal found 1/20$197
This Southwest deal was found by Cheapflights users on 1/21. 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.
jue. 2/135:45 amBOS - ORD
1 stop9h 15mSouthwest
mar. 2/1811:25 amORD - BOS
1 stop5h 20mSouthwest
Deal found 1/21$227
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/14:15 pmORH - ORD
1 stop7h 28mDelta
mar. 4/87:15 amORD - ORH
1 stop6h 46mDelta
Deal found 1/19$232
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/137:20 amBDL - ORD
1 stop7h 29mDelta
lun. 2/176:59 amORD - BDL
1 stop4h 11mDelta
Deal found 1/21$277
This Mytrip deal was found by Cheapflights users on 1/20. 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.
sáb. 2/88:00 amBDL - ORD
3 stops16h 32mMultiple Airlines
lun. 2/106:15 pmORD - BDL
1 stop17h 50mMultiple Airlines
Deal found 1/20$278

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

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

10:21 pm-1:39 pm

2 stops16h 18m

Chicago O'Hare Intl

mié. 3/12

6:45 am-4:10 pm

1 stop8h 25m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 2/24

5:10 am-4:51 pm

1 stop12h 41m

Chicago O'Hare Intl

jue. 2/27

12:59 pm-11:54 am

1 stop21h 55m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

5:10 am-4:31 pm

1 stop12h 21m

Chicago O'Hare Intl

lun. 3/17

6:45 am-4:10 pm

1 stop8h 25m

$149

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 2/21

8:20 pm-10:19 pm

Nonstop2h 59m

Chicago O'Hare Intl

mar. 2/25

2:35 pm-6:06 pm

Nonstop2h 31m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 2/24

10:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 3/1

12:38 pm-3:58 pm

Nonstop2h 20m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

4:17 pm-10:00 pm

1 stop6h 43m

Chicago O'Hare Intl

mié. 3/12

11:15 am-2:34 pm

Nonstop2h 19m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 2/13

5:20 am-7:21 am

Nonstop3h 01m

Chicago O'Hare Intl

mar. 2/18

7:00 am-10:21 am

Nonstop2h 21m

$187

WorcesterChicago

ORH - ORD

ORHORD

Worcester

mié. 4/23

2:18 pm-11:05 am

1 stop21h 47m

Chicago O'Hare Intl

jue. 4/24

5:10 pm-1:47 pm

1 stop19h 37m

$218

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 2/13

5:45 am-2:00 pm

1 stop9h 15m

Chicago O'Hare Intl

dom. 2/16

7:00 am-2:00 pm

1 stop6h 00m

$227

WorcesterChicago

ORH - ORD

ORHORD

Worcester

vie. 2/28

4:00 pm-7:55 pm

1 stop4h 55m

Chicago O'Hare Intl

dom. 3/9

7:15 am-2:54 pm

1 stop6h 39m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 55 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.

Travel insights for flights from Massachusetts to O'Hare Intl

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

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 $320). 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 enero 21, 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 enero 21, 2025.

The most flights from USMA to ORD are scheduled on a Monday (49 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 enero 21, 2025.
Peruse reviews from past customers who have flown with American Airlines, Delta and Frontier 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.
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Qatar Airways
7.5
Good
3,754 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Food

7.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $64. Spirit Airlines flights start at $74 while deals on Delta start at $79 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: Air France (100%), Spirit Airlines (100%), Cathay Pacific( 96%).

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

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Boston Logan Intl - Chicago O'Hare Intl) can be booked for $113 on average our data indicates $892 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 $320). 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
Naperville
Rosemont
Beloit
Racine
Hoffman Estates
Schaumburg
Rockford
Skokie
Tinley Park
Arlington Heights
Northbrook
Evanston
Des Plaines
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Gurnee
Willowbrook

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.
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Philadelphia to Midway flights
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Hobby to Midway flights
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Boston to Midway flights
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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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$109FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$316FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$139FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$266FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$154Average$301FlexibilityNo cancel feeOn-time69%
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