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Cheap flights from Boston to Chicago O'Hare Intl Airport from £53

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
13 Apr — 20 Apr1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or August, booked 57 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap flight deals from Boston to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) 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 8 April 2025.

Round-trip from

£96

One-way from

£53

Popular in

May

Cheapest in

September

Average price

£221

Good round-trip deal

£396 or less

Good one-way deal

£46 or less
United Airlines
  • United Airlines
  • 29/7-5/8
  • 1 total stop
  • 8h 16m total
  • Boston to Chicago
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Southwest
  • Southwest
  • 1/5
  • 1 total stop
  • 7h 20m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£19 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Boston Logan Intl to Chicago O'Hare Intl.
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Find flight deals from Boston to O'Hare Intl

Cheapest flights from Boston to O'Hare Intl
Explore the most affordable flight options available from Boston to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 8 April 2025.

Tue 29/718:59BOS - ORD
1 stop5h 38mUnited Airlines
Tue 5/814:28ORD - BOS
Nonstop2h 38mUnited Airlines
Deal found 8/4£96
Thu 8/515:10BOS - ORD
1 stop7h 44mJetBlue
Mon 12/519:31ORD - BOS
Nonstop2h 29mJetBlue
Deal found 7/4£98
Wed 28/506:05BOS - ORD
1 stop6h 45mSouthwest
Sat 31/513:30ORD - BOS
1 stop8h 55mSouthwest
Deal found 6/4£111
Thu 21/811:00BOS - ORD
Nonstop2h 53mDelta
Sun 24/807:00ORD - BOS
Nonstop2h 28mDelta
Deal found 7/4£122
Thu 8/520:51BOS - ORD
Nonstop3h 01mAmerican Airlines
Sat 10/507:37ORD - BOS
Nonstop2h 35mAmerican Airlines
Deal found 7/4£129
Sat 19/406:30BOS - ORD
1 stop15h 24mSun Country Air
Thu 24/419:15ORD - BOS
1 stop14h 20mSun Country Air
Deal found 8/4£246

Cheapflights Fare Finder

Customise your flight search to find flights from Boston 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 858,174 searches. Data last updated 8 April 2025.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 29/7

18:59-23:37

1 stop5h 38m

Chicago O'Hare Intl

Tue 5/8

14:28-18:06

Nonstop2h 38m

£96

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sat 10/5

06:10-11:42

1 stop4h 32m

£98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 28/5

06:05-11:50

1 stop6h 45m

Chicago O'Hare Intl

Sat 31/5

13:30-23:25

1 stop8h 55m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 21/8

11:00-12:53

Nonstop2h 53m

Chicago O'Hare Intl

Sun 24/8

07:00-10:28

Nonstop2h 28m

£122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/5

20:51-22:52

Nonstop3h 01m

Chicago O'Hare Intl

Sat 10/5

07:37-11:12

Nonstop2h 35m

£129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 19/4

06:30-20:54

1 stop15h 24m

Chicago O'Hare Intl

Thu 24/4

19:15-10:35

1 stop14h 20m

£246

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/5

05:30-11:50

1 stop7h 20m

£53

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/5

17:30-21:54

1 stop5h 24m

£54

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 25/4

06:00-07:57

Nonstop2h 57m

£62

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 16/4

07:30-09:30

Nonstop3h 00m

£69

Flights are sorted by cheapest return flights first.

Deals found on 8/4

Showing 1-10 of 13 results
1
2

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

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Boston with our price prediction graph.
Estimated return 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 Boston to Chicago O'Hare Intl Airport

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

Use this chart to determine the optimal time to book a return flight from Boston to O'Hare Intl. Price data was last updated on 4 April 2025.

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £595). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £843). 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 BOS to ORD?

Find hourly flight availability from Boston 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 8 April 2025.

When flying from Boston to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 73% versus a flight at midday.

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

Explore weekly flight availability from Boston 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 8 April 2025.

The most flights from BOS to ORD are scheduled on a Monday (64 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (41 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 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 8 April 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Boston to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very Good
9,847 reviews
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very Good
4,277 reviews
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very Good
7,901 reviews
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,633 reviews
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very Good
9,847 reviews
Check prices

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

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

    If you book a flight to Chicago O'Hare Intl from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 51 flights from Logan Intl to Chicago O'Hare Intl per day from 0 different airlines.

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

    Currently priced at £96, United Airlines will fly you from Boston to Chicago O'Hare Intl Airport and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from JetBlue and Southwest - these airlines can fly you to your destination from £98 and £111, respectively. These flights start at 50% lower than the current average price 3 months from now.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as £53. Users have also found prices from £54 and £62 on JetBlue and United Airlines, respectively.

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

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing LATAM Airlines (100%), KLM (94%) or WestJet (91%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Boston to Chicago O'Hare Intl Airport is generally £249, our data shows the cheapest flight currently is £46. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £91 for that flight.

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of £595). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of £843). 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

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Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to O'Hare Intl from Boston today and book when prices fit your budget.

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