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O'Hare Intl

$55+ 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
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Mytrip)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

September

Average price

$256

Good round-trip deal

$249 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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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Highest demand for flights based on searches. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:12 pmBOS - ORD
3 stops18h 52mSpirit Airlines
Mon 4/2810:19 amORD - BOS
2 stops27h 36mSpirit Airlines
Deal found 2/19$151
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/216:00 amBOS - ORD
1 stop12h 26mFrontier
Mon 3/245:47 pmORD - BOS
1 stop5h 57mFrontier
Deal found 2/20$152
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/108:31 pmBOS - ORD
1 stop12h 33mMultiple Airlines
Mon 4/148:55 amORD - BOS
1 stop14h 52mMultiple Airlines
Deal found 2/19$153
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/277:15 amBOS - ORD
Nonstop3h 06mDelta
Fri 2/287:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 2/20$157
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Mon 4/76:35 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 2/19$161
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:30 amBOS - ORD
1 stop5h 08mUnited Airlines
Wed 3/124:05 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 2/19$163
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/75:37 amBOS - ORD
1 stop6h 22mJetBlue
Thu 3/131:15 pmORD - BOS
Nonstop2h 24mJetBlue
Deal found 2/20$177
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 3/312:10 pmORH - ORD
1 stop21h 41mAmerican Airlines
Fri 4/45:10 pmORD - ORH
1 stop18h 58mAmerican Airlines
Deal found 2/20$214
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 3/911:36 amBDL - ORD
2 stops21h 45mSpirit Airlines
Tue 3/115:55 amORD - BDL
2 stops27h 46mSpirit Airlines
Deal found 2/20$224
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/25:45 amBOS - ORD
1 stop9h 15mSouthwest
Tue 3/47:00 amORD - BOS
1 stop4h 35mSouthwest
Deal found 2/19$231
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 3/74:00 pmORH - ORD
1 stop7h 36mDelta
Tue 3/117:15 amORD - ORH
1 stop6h 39mDelta
Deal found 2/19$232
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 4/251:59 pmBDL - ORD
2 stops19h 05mMultiple Airlines
Mon 4/2810:26 pmORD - BDL
3 stops34h 14mMultiple Airlines
Deal found 2/20$236

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 February 20, 2025.

Fly from

Massachusetts

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/24

2:12 pm-8:04 am

3 stops18h 52m

Chicago O'Hare Intl

Mon 4/28

10:19 am-2:55 pm

2 stops27h 36m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/21

6:00 am-5:26 pm

1 stop12h 26m

Chicago O'Hare Intl

Mon 3/24

5:47 pm-12:44 am

1 stop5h 57m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/10

8:31 pm-8:04 am

1 stop12h 33m

Chicago O'Hare Intl

Mon 4/14

8:55 am-12:47 am

1 stop14h 52m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/4

7:15 am-9:21 am

Nonstop3h 06m

Chicago O'Hare Intl

Wed 3/5

7:10 am-10:43 am

Nonstop2h 33m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 3/15

7:30 am-9:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Tue 3/18

7:30 am-10:49 am

Nonstop2h 19m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

8:59 pm-10:57 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 4/7

6:35 pm-10:06 pm

Nonstop2h 31m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/7

6:00 am-8:01 am

Nonstop3h 01m

Chicago O'Hare Intl

Fri 5/9

1:12 pm-6:38 pm

1 stop4h 26m

$167

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/31

2:10 pm-10:51 am

1 stop21h 41m

Chicago O'Hare Intl

Fri 4/4

5:10 pm-1:08 pm

1 stop18h 58m

$214

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/6

5:40 pm-9:30 pm

1 stop4h 50m

Chicago O'Hare Intl

Fri 3/14

7:00 am-5:50 pm

2 stops9h 50m

$216

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 5/10

8:20 am-4:45 pm

2 stops9h 25m

Chicago O'Hare Intl

Wed 5/14

1:50 pm-7:45 pm

1 stop4h 55m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 59 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 $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 February 20, 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 February 20, 2025.

The most flights from USMA to ORD are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Qatar Airways
7.4
Good
3,609 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $55. Spirit Airlines flights start at $70 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%), Japan Airlines (90%), KLM( 90%).

  • 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 $85 on average our data indicates $795 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
Naperville
Rosemont
Schaumburg
Beloit
Racine
Hoffman Estates
Rockford
Tinley Park
Skokie
Arlington Heights
Northbrook
Joliet
Orland Park
Merrillville
Kenosha
Lake Geneva
New Buffalo
Evanston
Des Plaines
Elgin

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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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Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
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Minneapolis to Midway flights
Philadelphia to Midway flights
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Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford to O'Hare Intl 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$109FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$315FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$139FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$263FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$155Average$301FlexibilityNo cancel feeOn-time69%
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