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

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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago O'Hare Intl to Boston Logan Intl are usually found in September or January, booked 73 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap flight deals from O'Hare Intl to Boston

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Boston (BOS). 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$153
(Mytrip)

One-way from

$79
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$198 or less

Good one-way deal

$111 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Boston Logan Intl flights.
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From Chicago O'Hare Intl to Boston Logan Intl
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One-way flight from Chicago O'Hare Intl to Boston Logan Intl
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Highest demand for flights based on searches. 11% potential increase in price ($29 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 Chicago O'Hare Intl to Boston Logan Intl.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Boston Logan Intl.
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Find flight deals from O'Hare Intl to Boston

Cheapest flights from O'Hare Intl to Boston
Explore the most affordable flight options available from O'Hare Intl to Boston. 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.
Wed 3/510:25 amORD - BOS
3 stops33h 55mSpirit Airlines
Wed 3/125:00 pmBOS - ORD
2 stops15h 44mSpirit Airlines
Deal found 2/19$151
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/13:25 pmORD - BOS
1 stop8h 05mMultiple Airlines
Wed 3/511:14 amBOS - ORD
1 stop13h 42mMultiple Airlines
Deal found 2/19$152
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/57:10 amORD - BOS
Nonstop2h 33mDelta
Sun 3/97:00 amBOS - ORD
Nonstop3h 09mDelta
Deal found 2/20$155
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.
Sat 4/53:13 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Mon 4/78:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 2/20$158
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/274:21 pmORD - BOS
1 stop7h 23mFrontier
Thu 3/275:10 amBOS - ORD
1 stop6h 40mFrontier
Deal found 2/19$162
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:30 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 5/46:00 amBOS - ORD
Nonstop3h 01mJetBlue
Deal found 2/19$167
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.
Thu 4/37:10 amORD - BOS
Nonstop2h 28mUnited Airlines
Sun 4/67:43 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 2/19$168
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.
Tue 3/47:00 amORD - BOS
1 stop4h 35mSouthwest
Thu 3/65:10 amBOS - ORD
1 stop8h 35mSouthwest
Deal found 2/19$226

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

Customize your flight search to find flights from O'Hare Intl to Boston 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

O'Hare Intl

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/5

10:25 am-9:20 pm

3 stops33h 55m

Boston Logan Intl

Wed 3/12

5:00 pm-7:44 am

2 stops15h 44m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/17

9:20 am-12:47 am

1 stop14h 27m

Boston Logan Intl

Mon 4/21

9:31 pm-8:04 am

1 stop11h 33m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/7

7:10 am-10:43 am

Nonstop2h 33m

Boston Logan Intl

Mon 3/10

7:25 am-9:34 am

Nonstop3h 09m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/5

3:13 pm-6:37 pm

Nonstop2h 24m

Boston Logan Intl

Mon 4/7

8:59 pm-10:57 pm

Nonstop2h 58m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 3/9

8:10 am-9:11 am

1 stop24h 01m

Boston Logan Intl

Sun 3/16

6:00 am-7:44 am

1 stop26h 44m

$162

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/6

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Mon 3/10

5:30 am-9:35 am

1 stop5h 05m

$164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/1

6:30 pm-9:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 5/4

6:00 am-8:01 am

Nonstop3h 01m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/4

7:00 am-12:35 pm

1 stop4h 35m

Boston Logan Intl

Thu 3/6

5:10 am-12:45 pm

1 stop8h 35m

$226

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/29

7:00 am-10:25 am

Nonstop2h 25m

$79

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/4

1:58 pm-11:20 am

2 stops20h 22m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 17 results
1
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Compare providers for flights from O'Hare Intl to Boston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Boston in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
FlightnetworkPrice Accuracy-Trust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston 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 Boston

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

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Boston?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Boston. Price data was last updated on February 14, 2025.

Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Boston (average of $218). Flying from Chicago O'Hare Intl Airport to Boston 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 BOS?

Find hourly flight availability from O'Hare Intl to Boston. 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.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Boston?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Boston. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Boston flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Boston

Explore weekly flight availability from O'Hare Intl to Boston. 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 ORD to BOS are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

Rainfall in Boston by month

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

In terms of precipitation, rainfall in Boston 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 Boston when rainfall is around 3.1 in.

Temperature in Boston by month

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

If weather is an important factor for your trip to Boston, 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 Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Chicago to Boston. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Food

7.1

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 O'Hare Intl to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Boston from Chicago O'Hare Intl?

    Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Boston. You should not have trouble finding flights to Logan Intl from Chicago O'Hare Intl; the airport handles an average of 43 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago O'Hare Intl. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Boston round-trip?

    According to our current data, Frontier ($153), Spirit Airlines ($154), and Delta ($155) offers the cheapest pricing from Chicago O'Hare Intl Airport to Boston. Frontier is currently priced 36% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Boston one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Spirit Airlines and Frontier, as they are both options that can get you from Chicago O'Hare Intl Airport to Boston for a low price.

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

    Before booking your flight to Boston from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: WestJet (100%), Air France (100%), Korean Air( 91%).

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

    The cheapest flight price from Chicago O'Hare Intl Airport to Boston is $78. On average you can expect to pay $680. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $91.

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

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

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

    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 Boston.

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

    Yes. Cheapflights offers flight deals from O'Hare Intl to Boston 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 Boston?

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

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
Warwick
Marlborough
Brockton
Waltham
Cambridge
Sturbridge
Framingham
Somerville
Chestnut Hill
Seekonk
Randolph
Lowell
Watertown
West Yarmouth
Woburn
Saco
Seabrook
Salem
Brookline
Fall River

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Top 7 airlines flying from O'Hare Intl to Boston

Discover the top 7 airlines that operate flights from O'Hare Intl to Boston. 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$38Average$96FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$85Average$237FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$238FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$111FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$254FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$296FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$280FlexibilityNo cancel feeOn-time63%
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