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Cheap flights from Chicago to Boston from £64

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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
27 Jan — 3 Feb1
1 adult

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 Wednesday

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 22 January 2025.

Round-trip from

£128

One-way from

£64

Popular in

April

Cheapest in

September

Average price

£178

Good round-trip deal

£298 or less

Good one-way deal

£162 or less
Delta
  • Delta
  • 20/2-27/2
  • Nonstop
  • 5h 34m total
  • Chicago to Boston
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Delta
  • Delta
  • 12/2
  • Nonstop
  • 2h 33m total
  • Chicago to Boston
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Highest demand for flights based on searches. 15% potential increase in price (£28 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 January 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Boston Logan Intl.
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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 22 January 2025.

Thu 20/207:10ORD - BOS
Nonstop2h 33mDelta
Thu 27/211:45BOS - ORD
Nonstop3h 01mDelta
Deal found 21/1£128
Fri 28/212:50ORD - BOS
Nonstop2h 23mJetBlue
Sat 1/314:00BOS - ORD
Nonstop3h 05mJetBlue
Deal found 21/1£136
Mon 17/321:30ORD - BOS
Nonstop2h 20mUnited Airlines
Thu 20/305:30BOS - ORD
1 stop5h 08mUnited Airlines
Deal found 21/1£149
Sat 1/305:15ORD - BOS
2 stops11h 17mSpirit Airlines
Mon 10/317:27BOS - ORD
1 stop17h 02mSpirit Airlines
Deal found 21/1£150
Thu 13/207:00ORD - BOS
1 stop6h 00mSouthwest
Fri 14/208:20BOS - ORD
1 stop6h 40mSouthwest
Deal found 21/1£178
Mon 9/614:45ORD - BOS
Nonstop2h 18mAmerican Airlines
Fri 13/605:30BOS - ORD
Nonstop2h 55mAmerican Airlines
Deal found 20/1£183
Fri 25/419:35ORD - BOS
1 stop14h 00mSun Country Air
Mon 28/411:31BOS - ORD
1 stop7h 35mSun Country Air
Deal found 21/1£260

Find flights from Chicago to Boston within your budget

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 22 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 20/2

07:10-10:43

Nonstop2h 33m

Boston Logan Intl

Thu 27/2

11:45-13:46

Nonstop3h 01m

£128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 28/2

12:50-16:13

Nonstop2h 23m

Boston Logan Intl

Sat 1/3

14:00-16:05

Nonstop3h 05m

£136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 17/3

21:30-00:50

Nonstop2h 20m

Boston Logan Intl

Thu 20/3

05:30-09:38

1 stop5h 08m

£149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/3

05:15-17:32

2 stops11h 17m

Boston Logan Intl

Mon 10/3

17:27-09:29

1 stop17h 02m

£150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 13/2

07:00-14:00

1 stop6h 00m

Boston Logan Intl

Fri 14/2

08:20-14:00

1 stop6h 40m

£178

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 9/6

14:45-18:03

Nonstop2h 18m

Boston Logan Intl

Fri 13/6

05:30-07:25

Nonstop2h 55m

£183

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/7

20:05-10:37

1 stop13h 32m

Boston Logan Intl

Mon 7/7

06:30-19:11

1 stop13h 41m

£256

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/2

07:10-10:43

Nonstop2h 33m

£64

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/2

10:35-14:01

Nonstop2h 26m

£72

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/5

08:50-12:18

Nonstop2h 28m

£81

Flights are sorted by cheapest return flights first.

Deals found on 21/1

Showing 1-10 of 14 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.

Travel insights for flights from Chicago to Boston

Get recent, data-driven insights about flights from Chicago to Boston including ideal travel times, pricing trends, and more.

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 17 January 2025.

Booking 83 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 22 January 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 85% 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 22 January 2025.

The most flights from CHI to BOS are scheduled on a Tuesday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 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 22 January 2025.
Read through reviews of airlines operating flights from Chicago to Boston, such as Delta, JetBlue and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very Good
4,662 reviews
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very Good
9,706 reviews
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very Good
8,521 reviews
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very Good
4,662 reviews
Check prices

Comfort

8.1

Crew

8.7

Food

7.2

Entertainment

7.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 40 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 Delta is currently your cheapest option to Boston, with prices starting at £128. Additional return tickets that might be worth considering are offered by JetBlue and United Airlines, with the lowest prices starting at £136 and £149, respectively. You may be able to fly from Chicago to Boston for 35% 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 £64 on Delta. Other airlines that offer cheap prices include JetBlue from £72 and Southwest from £86 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 Korean Air (92%), Etihad Airways (89%) or Scandinavian Airlines (85%) 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 £84. On average you can expect to pay £232. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £98.

  • 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
Chelsea
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Chelmsford
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Alternative routes for Chicago to Boston

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O'Hare Intl to Boston flights

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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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