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Cheap flights from Boston to Chicago O'Hare Intl Airport

BOS — ORD
21 Aug — 28 Aug1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or January, booked 50 days in advance, depart on a Wednesday or Friday and return on a Thursday

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 August 2025.

Round-trip from

₹ 11,993

One-way from

₹ 6,040

Popular in

November

Cheapest in

September

Average price

₹ 19,696

Good round-trip deal

₹ 18,127 or less
JetBlue
  • JetBlue
  • 15/11-19/11
  • Nonstop
  • 5h 29m total
  • Boston to Chicago
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JetBlue
  • JetBlue
  • 12/1
  • Nonstop
  • 2h 54m total
  • Boston to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (₹ 137,867 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (₹ 25,565 potential savings vs. average return price).
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Average for round-trip flights in August 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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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 8 August 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, October is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 973). Flying from Boston to Chicago O'Hare Intl Airport in August is currently the most expensive (average of ₹ 1,277). 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 August 2025.

One of the essential ways to save on airfare from Boston to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at midday could potentially save you up to 50% on airfare.

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 August 2025.

The most flights from BOS to ORD are scheduled on a Friday (68 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 on average).

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 August 2025.
Check out reviews from past customers who have flown with Delta and American Airlines from Boston to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very Good
7,985 reviews
Check prices

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very Good
7,985 reviews
Delta
8.0
Very Good
7,985 reviews
Check prices

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very Good
7,985 reviews
Check prices

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Boston Logan Intl (BOS), located 4.2 km from the city centre, is the airport you fly out of when you book flights from Boston to Chicago O'Hare Intl. 2 airlines have flights from Logan Intl to Chicago O'Hare Intl on a regular basis. Booking flights from Boston Logan Intl to Chicago O'Hare Intl should not be difficult; the airport handles an average of 48 outbound flights to Chicago O'Hare Intl per day.

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

    Flying on Delta is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at ₹ 13,738. Another option worth looking into is American Airlines, starting at ₹ 18,127 round trip. You may be able to fly from Boston to Chicago O'Hare Intl Airport for 36% less than the average price by searching for these airlines.

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

    ₹ 6,040 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on United Airlines and Southwest, with prices starting from ₹ 6,478 and ₹ 6,915, 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 TAP AIR PORTUGAL(92%), Icelandair(91%) or Royal Jordanian(90%), 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?

    The cheapest flight price from Boston to Chicago O'Hare Intl Airport is ₹ 11,082. On average you can expect to pay ₹ 18,129. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for ₹ 13,481.

  • 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, October is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of ₹ 973). Flying from Boston to Chicago O'Hare Intl Airport in August is currently the most expensive (average of ₹ 1,277). 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

Travelling 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
Deerfield
DeKalb

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Top 2 airlines flying from Boston to O'Hare Intl

Discover the top 2 airlines 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 454,620 searches. Data last updated 16 August 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest₹ 13,738Average₹ 19,867FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest₹ 18,127Average₹ 28,981FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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

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

Certainly. Search results for flights to O'Hare Intl from Boston shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

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