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Cheap flights from Boston to Chicago O'Hare Intl Airport from £51

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 23/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
20 8월 — 27 8월1
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 Thursday or Saturday and return on a Saturday

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 15 8월 2025.

Round-trip from

£101

One-way from

£51

Popular in

November

Cheapest in

September

Average price

£166

Good one-way deal

£194 or less
United Airlines
  • United Airlines
  • 11/9-16/9
  • Nonstop
  • 5h 25m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 24/9
  • Nonstop
  • 2h 50m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£9 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 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 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 15 8월 2025.

목 11/909:43BOS - ORD
Nonstop2h 50mUnited Airlines
화 16/909:13ORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 14/8£101
목 4/914:55BOS - ORD
Nonstop2h 57mDelta
일 7/907:00ORD - BOS
Nonstop2h 30mDelta
Deal found 14/8£102
수 10/906:00BOS - ORD
1 stop5h 35mUnited Airlines
일 14/906:30ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 13/8£103
토 30/816:27BOS - ORD
Nonstop2h 54mUnited Airlines
금 26/921:20ORD - BOS
Nonstop2h 30mUnited Airlines
Deal found 14/8£105
월 6/1016:10BOS - ORD
Nonstop3h 00mDelta
목 4/1207:00ORD - BOS
Nonstop2h 30mDelta
Deal found 13/8£108
수 8/1016:05BOS - ORD
Nonstop2h 50mJetBlue
월 8/1220:00ORD - BOS
Nonstop2h 16mJetBlue
Deal found 13/8£109
토 20/906:10BOS - ORD
1 stop12h 29mSpirit Airlines
수 24/911:57ORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 13/8£111
토 27/917:05BOS - ORD
Nonstop3h 00mDelta
토 4/1014:00ORD - BOS
Nonstop2h 39mDelta
Deal found 13/8£113
월 15/906:10BOS - ORD
Nonstop2h 55mUnited Airlines
화 16/915:48ORD - BOS
Nonstop2h 31mUnited Airlines
Deal found 14/8£114
목 25/1215:27BOS - ORD
Nonstop2h 52mJetBlue
수 7/109:50ORD - BOS
Nonstop2h 26mJetBlue
Deal found 14/8£116
금 21/1106:00BOS - ORD
Nonstop3h 00mUnited Airlines
월 24/1108:50ORD - BOS
1 stop4h 39mUnited Airlines
Deal found 13/8£117
목 2/1016:40BOS - ORD
Nonstop3h 15mJetBlue
일 5/1019:02ORD - BOS
Nonstop2h 33mJetBlue
Deal found 13/8£117

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 15 8월 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

토 20/9

07:25-09:15

Nonstop2h 50m

Chicago O'Hare Intl

토 20/9

14:00-17:39

Nonstop2h 39m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

목 28/8

06:00-07:55

Nonstop2h 55m

Chicago O'Hare Intl

토 6/9

09:51-13:20

Nonstop2h 29m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

목 20/11

10:40-12:40

Nonstop3h 00m

Chicago O'Hare Intl

일 23/11

07:15-10:34

Nonstop2h 19m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

화 9/9

16:20-18:25

Nonstop3h 05m

Chicago O'Hare Intl

화 16/9

10:15-13:49

Nonstop2h 34m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

월 3/11

20:30-22:30

Nonstop3h 00m

Chicago O'Hare Intl

월 10/11

21:25-00:45

Nonstop2h 20m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

토 13/9

17:05-19:05

Nonstop3h 00m

Chicago O'Hare Intl

화 16/9

14:05-17:44

Nonstop2h 39m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

금 21/11

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

월 24/11

21:25-00:45

Nonstop2h 20m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

수 17/9

19:30-21:15

Nonstop2h 45m

Chicago O'Hare Intl

월 22/9

07:25-10:55

Nonstop2h 30m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

목 1/1

06:01-08:05

Nonstop3h 04m

Chicago O'Hare Intl

월 5/1

21:15-00:48

Nonstop2h 33m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

금 19/9

19:30-21:15

Nonstop2h 45m

Chicago O'Hare Intl

월 22/9

07:25-10:55

Nonstop2h 30m

£101

Flights are sorted by cheapest return flights first.

Deals found on 13/8

Showing 1-10 of 23 results
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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, 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 15 8월 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 67% 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 15 8월 2025.

The most flights from BOS to ORD are scheduled on a Friday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 15 8월 2025.
Read through reviews of airlines operating flights from Boston to Chicago O'Hare Intl Airport, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews
Check prices

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews
Check prices

Crew

8.0

Boarding

7.5

Food

6.5

Comfort

7.2

Entertainment

6.9

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap

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

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

    Currently priced at £72, American Airlines will fly you from Boston to Chicago O'Hare Intl Airport and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. This flight start at 60% lower than the current average price 3 months from now.

  • 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?

    While on average a flight from Boston to Chicago O'Hare Intl Airport is generally £212, our data shows the cheapest flight currently is £103. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £73 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

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
Downers Grove
Elk Grove Village
Rosemont

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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 15 8월 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£72Average£114FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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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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