Question 1

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

Accepted Answer

Currently priced at £100, 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 Spirit Airlines and Southwest - these airlines can fly you to your destination from £102 and £104, respectively. These flights start at 43% lower than the current average price 3 months from now.

Question 2

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

Accepted Answer

For one-way options, check prices for JetBlue. According to our data, you can fly for as low as £50. Users have also found prices from £54 and £58 on United Airlines and Southwest, respectively.

Question 3

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

Accepted Answer

The best time to book flights from Boston to Chicago O'Hare Intl Airport is 43 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.

Question 4

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

Accepted Answer

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.

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

The most flights from BOS to ORD are scheduled on a Monday (74 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (37 on average).

Question 7

E

Accepted Answer

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.

Question 8

E

Accepted Answer

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).

Question 9

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

Accepted Answer

While on average a flight from Boston to Chicago O'Hare Intl Airport is generally £247, our data shows the cheapest flight currently is £71. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £136 for that flight.

Question 10

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

Accepted Answer

No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing Avianca (93%), TAP AIR PORTUGAL (92%) or Icelandair (91%) as they are the most reliable in getting you off to your destination on time.

Question 11

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

Accepted Answer

Wednesday is generally a great day to depart. Flying on this day could help you save up to 202%.

Question 12

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

Accepted Answer

Find a great deal and save up to 63% by booking at least 50 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Boston to Chicago O'Hare Intl Airport within the next two weeks, with the cheapest ticket starting at £147.

Question 13

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

Accepted Answer

Our data shows that September tends to be the cheapest month to fly to Chicago O'Hare Intl Airport from Boston. Users have commonly found prices around £169 for the month, but tickets can be as low as £42. Due to multiple factors, prepare for potentially higher prices in March.

Question 14

What is the cheapest time of day to fly from BOS to ORD?

Accepted Answer

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 69% versus a flight at midday.

Question 15

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

Accepted Answer

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

Question 16

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

Accepted Answer

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

Question 17

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

Accepted Answer

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.

Question 18

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

Accepted Answer

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.

Question 19

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

Accepted Answer

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Boston to O'Hare Intl. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Question 20

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

Accepted Answer

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.

Question 21

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

Accepted Answer

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.

Question 22

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

Accepted Answer

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.

Round-trip from	£100
One-way from	£50
Popular in	December
Cheapest in	September
Average price	£176
Good one-way deal	£72 or less

Cheap flights from Boston to Chicago O'Hare Intl Airport from £50

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 8/7. Fares are subject to change and may not be available on all flights or dates of travel.

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 Saturday and return on a Saturday

Cheap flight deals from Boston to O'Hare Intl

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Find flight deals from Boston to O'Hare Intl

Cheapest flights from Boston to O'Hare IntlExplore 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 1 July 2025.

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 1 July 2025.

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Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

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.

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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 27 June 2025.

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

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 1 July 2025.

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 1 July 2025.

Reviews of airlines servicing O'Hare Intl

Read through reviews of airlines operating flights from Boston to Chicago O'Hare Intl Airport, such as Southwest, Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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?

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

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

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

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

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

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

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

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

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

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

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

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

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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 1 July 2025.