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Cheap flights from Boston to Chicago O'Hare Intl Airport from £62

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 20/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
11 Mar — 18 Mar1
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 Friday 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 6 March 2025.

Round-trip from

£121

One-way from

£62

Popular in

May

Cheapest in

September

Average price

£193

Good round-trip deal

£76 or less

Good one-way deal

£77 or less
United Airlines
  • United Airlines
  • 24/5-29/5
  • Nonstop
  • 5h 27m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 20/3
  • 1 total stop
  • 5h 08m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£18 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 March 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 6 March 2025.

Sat 24/506:00BOS - ORD
Nonstop2h 58mUnited Airlines
Thu 29/521:30ORD - BOS
Nonstop2h 29mUnited Airlines
Deal found 5/3£121
Wed 2/411:14BOS - ORD
3 stops19h 32mSpirit Airlines
Tue 8/418:25ORD - BOS
2 stops11h 58mSpirit Airlines
Deal found 5/3£122
Thu 1/506:00BOS - ORD
Nonstop3h 05mJetBlue
Tue 6/519:30ORD - BOS
Nonstop2h 29mJetBlue
Deal found 5/3£126
Thu 27/307:25BOS - ORD
Nonstop3h 09mDelta
Sun 30/307:00ORD - BOS
Nonstop2h 25mDelta
Deal found 5/3£128
Tue 24/606:59BOS - ORD
Nonstop3h 01mAmerican Airlines
Sun 29/620:40ORD - BOS
Nonstop2h 40mAmerican Airlines
Deal found 5/3£157
Tue 8/406:05BOS - ORD
2 stops7h 40mSouthwest
Wed 9/416:00ORD - BOS
1 stop5h 05mSouthwest
Deal found 4/3£165
Tue 24/610:11BOS - ORD
1 stop22h 45mFrontier
Sun 29/609:01ORD - BOS
1 stop23h 08mFrontier
Deal found 5/3£199
Sat 19/406:30BOS - ORD
1 stop15h 24mSun Country Air
Thu 24/419:15ORD - BOS
1 stop15h 48mSun Country Air
Deal found 5/3£226

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 6 March 2025.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 24/5

06:00-07:58

Nonstop2h 58m

Chicago O'Hare Intl

Thu 29/5

21:30-00:59

Nonstop2h 29m

£121

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/4

11:14-05:46

3 stops19h 32m

Chicago O'Hare Intl

Tue 8/4

18:25-07:23

2 stops11h 58m

£122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/5

06:00-08:05

Nonstop3h 05m

Chicago O'Hare Intl

Tue 6/5

19:30-22:59

Nonstop2h 29m

£126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 27/3

07:25-09:34

Nonstop3h 09m

Chicago O'Hare Intl

Sun 30/3

07:00-10:25

Nonstop2h 25m

£128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 24/6

06:59-09:00

Nonstop3h 01m

Chicago O'Hare Intl

Sun 29/6

20:40-00:20

Nonstop2h 40m

£157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/4

06:05-12:45

2 stops7h 40m

Chicago O'Hare Intl

Wed 9/4

16:00-22:05

1 stop5h 05m

£165

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 24/6

10:11-07:56

1 stop22h 45m

Chicago O'Hare Intl

Sun 29/6

09:01-09:09

1 stop23h 08m

£199

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 19/4

06:30-20:54

1 stop15h 24m

Chicago O'Hare Intl

Thu 24/4

19:15-12:03

1 stop15h 48m

£226

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 20/3

05:30-09:38

1 stop5h 08m

£62

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/4

07:00-09:02

Nonstop3h 02m

£69

Flights are sorted by cheapest return flights first.

Deals found on 5/3

Showing 1-10 of 14 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 28 February 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 6 March 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 69% versus a flight at midday.

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 6 March 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
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very Good
4,321 reviews
Southwest
8.1
Very Good
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very Good
9,708 reviews
Southwest
8.1
Very Good
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very Good
8,044 reviews
Southwest
8.1
Very Good
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,655 reviews
Southwest
8.1
Very Good
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

JetBlue
7.3
Good
2,998 reviews
Southwest
8.1
Very Good
4,321 reviews
Check prices

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 19 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 £121, United Airlines will fly you from Boston to Chicago O'Hare Intl Airport and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and JetBlue - these airlines can fly you to your destination from £122 and £126, 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 United Airlines. According to our data, you can fly for as low as £62. Users have also found prices from £69 and £78 on Delta 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%), LATAM Airlines (100%) or Virgin Atlantic (91%) 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 £171, our data shows the cheapest flight currently is £61. When looking at the most popular route, (Boston Logan Intl - Chicago O'Hare Intl), you can expect to pay £185 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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