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Cheap flights from Chicago to Boston 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
23 Apr — 30 Apr1
1 adult

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or August, booked 52 days in advance, depart on a Wednesday or Friday and return on a Thursday

Cheap flight deals from Chicago to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). 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 18 April 2025.

Round-trip from

£88

One-way from

£51

Popular in

April

Cheapest in

September

Average price

£218

Good one-way deal

£44 or less
JetBlue
  • JetBlue
  • 2/5-4/5
  • Nonstop
  • 5h 44m total
  • Chicago to Boston
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Southwest
  • Southwest
  • 6/5
  • 1 total stop
  • 4h 20m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (£17 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£4 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.
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Find flight deals from Chicago to Boston

Cheapest flights from Chicago to Boston
Explore the most affordable flight options available from Chicago to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 18 April 2025.

Fri 2/518:30ORD - BOS
Nonstop2h 39mJetBlue
Sun 4/506:00BOS - ORD
Nonstop3h 05mJetBlue
Deal found 17/4£88
Sun 25/506:30ORD - BOS
Nonstop2h 26mUnited Airlines
Sun 29/618:59BOS - ORD
1 stop5h 38mUnited Airlines
Deal found 16/4£93
Tue 6/516:00ORD - BOS
1 stop5h 05mSouthwest
Sun 11/505:45BOS - ORD
1 stop7h 05mSouthwest
Deal found 17/4£103
Tue 29/407:00ORD - BOS
Nonstop2h 26mDelta
Sun 4/507:30BOS - ORD
Nonstop3h 00mDelta
Deal found 16/4£126
Wed 23/415:10ORD - BOS
1 stop5h 14mAmerican Airlines
Wed 30/413:48BOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 17/4£231

Cheapflights Fare Finder

Customise your flight search to find flights from Chicago to Boston 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 18 April 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Chicago

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/5

18:30-22:09

Nonstop2h 39m

Boston Logan Intl

Sun 4/5

06:00-08:05

Nonstop3h 05m

£88

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 25/5

06:30-09:56

Nonstop2h 26m

Boston Logan Intl

Sun 29/6

18:59-23:37

1 stop5h 38m

£93

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/5

16:00-22:05

1 stop5h 05m

Boston Logan Intl

Sun 11/5

05:45-11:50

1 stop7h 05m

£103

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 29/4

07:00-10:26

Nonstop2h 26m

Boston Logan Intl

Sun 4/5

07:30-09:30

Nonstop3h 00m

£126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/5

13:50-19:10

1 stop4h 20m

£51

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 15/5

06:15-11:42

1 stop4h 27m

£52

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 17/5

12:50-16:17

Nonstop2h 27m

£60

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 25/5

10:05-13:34

Nonstop2h 29m

£68

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 13/10

11:41-10:41

1 stop22h 00m

£134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/6

07:00-00:06

2 stops16h 06m

£164

Flights are sorted by cheapest return flights first.

Deals found on 17/4

Best time to book a flight from Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago 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 Chicago to Boston

How far ahead should I book a flight from Chicago to Boston?

Use this chart to determine the optimal time to book a return flight from Chicago to Boston. Price data was last updated on 11 April 2025.

Booking 52 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Boston?

Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). 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 CHI to BOS?

Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 18 April 2025.

When flying from Chicago to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 82% versus a flight in the afternoon.

Weekly flight availability from Chicago to Boston

Explore weekly flight availability from Chicago to Boston. 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 18 April 2025.

The most flights from CHI to BOS are scheduled on a Thursday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 78.0 - 101.0 inches per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Boston when rainfall is around 78.0 mm.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, 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 -1.0 C).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated 18 April 2025.
Read through reviews of airlines operating flights from Chicago to Boston, such as Alaska Airlines, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very Good
9,887 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very Good
4,280 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very Good
7,917 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,928 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Food

7.1

Comfort

7.9

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Chicago to Boston. 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 into for flights to Boston from Chicago?

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Chicago. On average, Logan Intl has 44 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • What are the cheapest airlines flying from Chicago to Boston round-trip?

    Flying on JetBlue is currently your cheapest option to Boston, with prices starting at £88. Additional return tickets that might be worth considering are offered by United Airlines and Southwest, with the lowest prices starting at £93 and £103, respectively. You may be able to fly from Chicago to Boston for 50% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Boston one-way?

    One-way options have recently been found by users for as low as £51 on Southwest. Other airlines that offer cheap prices include JetBlue from £52 and United Airlines from £60 one-way.

  • What are the most reliable airlines from Chicago to Boston?

    No one likes to see their flight delayed. When booking a flight from Chicago to Boston consider choosing Air France (100%), Iberia (91%) or Virgin Atlantic (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Boston?

    The cheapest flight price from Chicago to Boston is £37. On average you can expect to pay £44. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £143.

  • Can I find deals for flights from Chicago to Boston that include hotel bookings?

    Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.

  • Can I find deals for business class flights from Chicago to Boston?

    Yes. Cheapflights offers flight deals from Chicago to Boston 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 Chicago to Boston?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Boston (average of £10). Flying from Chicago to Boston in July is currently the most expensive (average of £724). 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?

Book flights to Chicago if you plan to visit one of these locations
Cambridge
Somerville
Quincy
Chelmsford
Burlington
Kittery

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Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights

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Deals for Chicago to Boston flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Boston.

Can Cheapflights find flights from Chicago to Boston with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Boston, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

Yes! Start tracking prices for Chicago to Boston flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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