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Cheap flights from Boston to Chicago O'Hare Intl Airport from £64

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
9 Feb — 16 Feb1
1 adult

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 Wednesday or Friday 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 4 February 2025.

Round-trip from

£126

One-way from

£64

Popular in

May

Cheapest in

September

Average price

£181

Good round-trip deal

£240 or less

Good one-way deal

£71 or less
Delta
  • Delta
  • 7/5-9/5
  • Nonstop
  • 5h 21m total
  • Boston to Chicago
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Delta
  • Delta
  • 10/2
  • Nonstop
  • 2h 59m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£21 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 February 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 4 February 2025.

Mon 10/220:20BOS - ORD
Nonstop2h 59mDelta
Mon 17/207:10ORD - BOS
Nonstop2h 33mDelta
Deal found 3/2£126
Mon 10/316:17BOS - ORD
1 stop6h 43mUnited Airlines
Tue 11/316:00ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 3/2£132
Mon 3/315:00BOS - ORD
Nonstop3h 00mJetBlue
Thu 6/317:15ORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/2£135
Fri 4/405:50BOS - ORD
1 stop9h 10mSouthwest
Tue 8/416:00ORD - BOS
1 stop5h 05mSouthwest
Deal found 2/2£176

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

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 4 February 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/5

20:10-22:05

Nonstop2h 55m

Chicago O'Hare Intl

Fri 9/5

07:00-10:26

Nonstop2h 26m

£126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/3

16:17-22:00

1 stop6h 43m

Chicago O'Hare Intl

Tue 11/3

16:00-19:20

Nonstop2h 20m

£132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/3

15:00-17:00

Nonstop3h 00m

Chicago O'Hare Intl

Thu 6/3

17:15-20:44

Nonstop2h 29m

£135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

05:50-14:00

1 stop9h 10m

Chicago O'Hare Intl

Tue 8/4

16:00-22:05

1 stop5h 05m

£176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/7

06:30-19:11

1 stop13h 41m

Chicago O'Hare Intl

Mon 7/7

20:10-10:37

1 stop13h 27m

£239

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/2

20:20-22:19

Nonstop2h 59m

£64

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 9/3

05:30-09:38

1 stop5h 08m

£68

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/4

06:10-12:29

1 stop7h 19m

£80

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

05:50-14:00

1 stop9h 10m

£88

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/3

06:00-16:31

2 stops11h 31m

£97

Flights are sorted by cheapest return flights first.

Deals found on 4/2

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.

Travel insights for flights from Boston to O'Hare Intl

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

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 31 January 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 4 February 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 70% versus a flight in the afternoon.

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 4 February 2025.

The most flights from BOS 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 (27 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 4 February 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
4,564 reviews
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
9,681 reviews
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,415 reviews
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
3,138 reviews
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

United Airlines
7.4
Good
8,892 reviews
Southwest
8.1
Very Good
4,564 reviews
Check prices

Comfort

8.1

Overall

8.1

Food

7.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 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 38 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 £126, Delta will fly you from Boston to Chicago O'Hare Intl Airport and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and JetBlue - these airlines can fly you to your destination from £132 and £135, respectively. These flights start at 37% 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 Delta. According to our data, you can fly for as low as £64. Users have also found prices from £68 and £72 on United Airlines and JetBlue, 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 Air France (100%), Spirit Airlines (100%) or Avianca (92%) 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 £232, our data shows the cheapest flight currently is £56. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £181 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.

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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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