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Cheap flights from Chicago to Boston from £57

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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
5 Apr — 12 Apr1
1 adult

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or August, booked 83 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 31 March 2025.

Round-trip from

£90

One-way from

£57

Popular in

April

Cheapest in

September

Average price

£216

Good one-way deal

£95 or less
Southwest
  • Southwest
  • 6/5-9/5
  • 2 total stops
  • 13h 00m total
  • Chicago to Boston
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United Airlines
  • United Airlines
  • 21/4
  • Nonstop
  • 2h 28m total
  • Chicago to Boston
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Highest demand for flights based on searches. 14% potential increase in price (£24 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 March 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 31 March 2025.

Tue 6/513:50ORD - BOS
1 stop4h 20mSouthwest
Fri 9/506:25BOS - ORD
1 stop8h 40mSouthwest
Deal found 31/3£90
Thu 8/508:45ORD - BOS
Nonstop2h 28mJetBlue
Sun 11/506:00BOS - ORD
Nonstop3h 00mJetBlue
Deal found 31/3£90
Tue 12/820:05ORD - BOS
Nonstop2h 27mUnited Airlines
Sat 16/807:44BOS - ORD
Nonstop2h 55mUnited Airlines
Deal found 30/3£96
Sat 31/507:00ORD - BOS
Nonstop2h 25mDelta
Sat 7/611:25BOS - ORD
Nonstop2h 49mDelta
Deal found 31/3£98
Wed 7/513:22ORD - BOS
Nonstop2h 26mAmerican Airlines
Thu 8/505:15BOS - ORD
Nonstop3h 00mAmerican Airlines
Deal found 30/3£107
Wed 7/512:41ORD - BOS
1 stop9h 48mSpirit Airlines
Thu 8/518:55BOS - ORD
2 stops22h 30mSpirit Airlines
Deal found 30/3£146

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 31 March 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

Tue 6/5

13:50-19:10

1 stop4h 20m

Boston Logan Intl

Fri 9/5

06:25-14:05

1 stop8h 40m

£90

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/5

08:45-12:13

Nonstop2h 28m

Boston Logan Intl

Sun 11/5

06:00-08:00

Nonstop3h 00m

£90

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/8

20:05-23:32

Nonstop2h 27m

Boston Logan Intl

Sat 16/8

07:44-09:39

Nonstop2h 55m

£96

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 31/5

07:00-10:25

Nonstop2h 25m

Boston Logan Intl

Sat 7/6

11:25-13:14

Nonstop2h 49m

£98

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/5

13:22-16:48

Nonstop2h 26m

Boston Logan Intl

Thu 8/5

05:15-07:15

Nonstop3h 00m

£107

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/5

12:41-23:29

1 stop9h 48m

Boston Logan Intl

Thu 8/5

18:55-16:25

2 stops22h 30m

£146

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 21/4

21:30-00:58

Nonstop2h 28m

£57

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 11/5

07:00-10:25

Nonstop2h 25m

£61

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 19/4

20:29-23:58

Nonstop2h 29m

£69

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 7/6

13:30-21:00

1 stop6h 30m

£91

Flights are sorted by cheapest return flights first.

Deals found on 31/3

Showing 1-10 of 13 results
1
2

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 28 March 2025.

Booking 79 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 31 March 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 31 March 2025.

The most flights from CHI to BOS are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 31 March 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
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very Good
9,818 reviews
Alaska Airlines
8.0
Very Good
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very Good
4,275 reviews
Alaska Airlines
8.0
Very Good
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very Good
7,899 reviews
Alaska Airlines
8.0
Very Good
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very Good
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very Good
9,818 reviews
Check prices

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 41 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 Southwest is currently your cheapest option to Boston, with prices starting at £90. Additional return tickets that might be worth considering are offered by JetBlue and United Airlines, with the lowest prices starting at £90 and £96, respectively. You may be able to fly from Chicago to Boston for 52% 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 £57 on United Airlines. Other airlines that offer cheap prices include Delta from £61 and JetBlue from £69 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%), WestJet (95%) or LATAM Airlines (93%) 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 £45. On average you can expect to pay £190. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £195.

  • 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
Chelsea
Burlington
Kittery

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Alternative routes for Chicago to Boston

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O'Hare Intl to Boston flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Boston?

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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