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Cheap flights from Boston to Chicago O'Hare Intl Airport from £44

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 30/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
21 Mai — 28 Mai1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or August, booked 50 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 16 Mai 2025.

Round-trip from

£88

One-way from

£44

Popular in

November

Cheapest in

September

Average price

£208

Good one-way deal

£119 or less
Delta
  • Delta
  • 14/6-17/6
  • Nonstop
  • 5h 42m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 30/6
  • 1 total stop
  • 5h 38m total
  • Boston to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (£11 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in May 2025
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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 16 Mai 2025.

Sa 14/618:10BOS - ORD
Nonstop3h 03mDelta
Sa 21/607:00ORD - BOS
Nonstop2h 31mDelta
Deal found 15/5£88
Mi 28/506:00BOS - ORD
Nonstop2h 58mUnited Airlines
Sa 31/519:45ORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 15/5£92
Mo 26/506:00BOS - ORD
Nonstop3h 00mJetBlue
Do 29/508:45ORD - BOS
Nonstop2h 28mJetBlue
Deal found 15/5£115
Fr 4/708:40BOS - ORD
1 stop9h 05mSouthwest
Di 8/716:00ORD - BOS
1 stop6h 55mSouthwest
Deal found 15/5£140
Fr 30/506:10BOS - ORD
3 stops18h 19mSpirit Airlines
Mo 2/619:35ORD - BOS
2 stops19h 49mSpirit Airlines
Deal found 16/5£193

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 16 Mai 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

Sa 14/6

18:10-20:13

Nonstop3h 03m

Chicago O'Hare Intl

Sa 21/6

07:00-10:31

Nonstop2h 31m

£88

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mi 28/5

06:00-07:58

Nonstop2h 58m

Chicago O'Hare Intl

Mi 4/6

15:40-19:10

Nonstop2h 30m

£92

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

So 27/7

06:00-07:55

Nonstop2h 55m

Chicago O'Hare Intl

Mi 30/7

08:40-12:05

Nonstop2h 25m

£105

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fr 4/7

08:40-16:45

1 stop9h 05m

Chicago O'Hare Intl

Di 8/7

16:00-23:55

1 stop6h 55m

£140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fr 30/5

06:10-23:29

3 stops18h 19m

Chicago O'Hare Intl

Mo 2/6

19:35-16:24

2 stops19h 49m

£193

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fr 30/5

19:21-23:08

1 stop4h 47m

Chicago O'Hare Intl

Mo 2/6

18:35-22:07

Nonstop2h 32m

£199

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mo 30/6

18:59-23:37

1 stop5h 38m

£44

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sa 16/8

05:20-11:50

1 stop7h 30m

£48

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

So 1/6

07:15-09:09

Nonstop2h 54m

£52

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mo 16/6

06:00-07:55

Nonstop2h 55m

£62

Flights are sorted by cheapest return flights first.

Deals found on 15/5

Showing 1-10 of 12 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 9 May 2025.

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 50 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 16 Mai 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 71% 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 16 Mai 2025.

The most flights from BOS to ORD are scheduled on a Friday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 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 16 Mai 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
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very Good
10,000 reviews
Alaska Airlines
8.0
Very Good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very Good
4,291 reviews
Alaska Airlines
8.0
Very Good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very Good
7,950 reviews
Alaska Airlines
8.0
Very Good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,730 reviews
Alaska Airlines
8.0
Very Good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,927 reviews
Alaska Airlines
8.0
Very Good
10,000 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 62 flights from Logan Intl to Chicago O'Hare Intl per day from 1 airline.

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

    Currently priced at £88, 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 £92 and £115, respectively. These flights start at 52% 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 United Airlines. According to our data, you can fly for as low as £44. Users have also found prices from £48 and £52 on Southwest and Delta, 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 Japan Airlines (93%), Avianca (90%) or ANA (89%) 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 £416, our data shows the cheapest flight currently is £44. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £178 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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Top airline flying from Boston to O'Hare Intl

Discover the top airline that operate flights from Boston 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 858,174 searches. Data last updated 16 Mai 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£59Average£114FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Boston to O'Hare Intl?

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Why should you use Cheapflights to find cheap flight tickets from Boston to O'Hare Intl?

Cheapflights simply makes it quick and affordable to book flights from Boston to O'Hare Intl by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Boston to O'Hare Intl with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to O'Hare Intl flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Boston to O'Hare Intl become cheaper?

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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