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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 16/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
22 Oct — 29 Oct1
1 adult

The best prices from Chicago to Boston Logan Intl are usually found in September or January, booked 83 days in advance, depart on a Tuesday or Thursday 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 17 October 2024.

Round-trip from

£77

One-way from

£57

Popular in

April

Cheapest in

September
Frontier
  • Frontier
  • 31/10-6/11
  • 2 total stops
  • 15h 14m total
  • Chicago to Boston
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JetBlue
  • JetBlue
  • 16/11
  • Nonstop
  • 2h 18m total
  • Chicago to Boston
Search Deals
High demand for flights, 18% potential price rise
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Best time to find cheap flights, 22% potential price drop
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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 17 October 2024.

Thu 31/1016:46ORD - BOS
1 stop6h 42mFrontier
Wed 6/1106:00BOS - ORD
1 stop8h 32mFrontier
Deal found 16/10£77
Sat 16/1109:56ORD - BOS
Nonstop2h 18mJetBlue
Tue 19/1114:14BOS - ORD
Nonstop2h 54mJetBlue
Deal found 15/10£113
Fri 13/1214:05ORD - BOS
Nonstop2h 29mDelta
Sun 12/107:00BOS - ORD
Nonstop3h 11mDelta
Deal found 15/10£121
Wed 6/1107:22ORD - BOS
Nonstop2h 19mUnited Airlines
Tue 12/1110:45BOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 16/10£125
Tue 12/1111:25ORD - BOS
1 stop9h 45mSouthwest
Wed 13/1106:00BOS - ORD
2 stops8h 00mSouthwest
Deal found 15/10£154
Thu 31/1007:30ORD - BOS
2 stops25h 38mSpirit Airlines
Wed 6/1109:14BOS - ORD
2 stops13h 53mSpirit Airlines
Deal found 16/10£157
Thu 31/1011:52ORD - BOS
1 stop4h 44mAmerican Airlines
Wed 6/1114:41BOS - ORD
Nonstop3h 02mAmerican Airlines
Deal found 16/10£164
Fri 13/1211:55ORD - BOS
1 stop21h 46mSun Country Air
Mon 16/1211:46BOS - ORD
1 stop23h 45mSun Country Air
Deal found 15/10£227

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 1,037,663 searches. Data last updated 17 October 2024.

Fly from

Any airport

Fly to

Any airport

Budget

£77 - £199

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 31/10

1 stop6h 42m

Boston Logan Intl

Wed 6/11

1 stop8h 32m

£77

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 19/11

Nonstop2h 22m

Boston Logan Intl

Tue 19/11

Nonstop2h 54m

£90

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/11

Nonstop2h 24m

Boston Logan Intl

Wed 13/11

Nonstop3h 01m

£102

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/11

Nonstop2h 21m

Boston Logan Intl

Tue 10/12

Nonstop2h 56m

£121

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 31/10

1 stop12h 48m

Boston Logan Intl

Wed 6/11

2 stops13h 53m

£135

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/12

2 stops9h 20m

Boston Logan Intl

Mon 9/12

2 stops11h 55m

£161

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 31/10

1 stop4h 44m

Boston Logan Intl

Wed 6/11

Nonstop3h 02m

£164

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/11

1 stop14h 29m

Boston Logan Intl

Sun 17/11

1 stop7h 31m

£199

Flights are sorted by cheapest first

Deals found on 16/10

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 11 October 2024.

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.

Find deals

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 £667). 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 17 October 2024.

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 afternoon, which can drop the price by up to 42% versus a flight at midday.

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 17 October 2024.

The most flights from CHI to BOS are scheduled on a Monday (69 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 17 October 2024.
Read through reviews of airlines operating flights from Chicago to Boston, such as American Airlines, Frontier and Spirit Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.2
Very Good
5,169 reviews
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very Good
9,412 reviews
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very Good
8,911 reviews
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,574 reviews
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,317 reviews
Southwest
8.2
Very Good
5,169 reviews
Check prices

Overall

8.2

Entertainment

7.7

Boarding

8.3

Crew

8.7

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 50 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 Frontier is currently your cheapest option to Boston, with prices starting at £77. Additional return tickets that might be worth considering are offered by JetBlue and Delta, with the lowest prices starting at £90 and £102, respectively. You may be able to fly from Chicago to Boston for 59% 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 JetBlue. Other airlines that offer cheap prices include Delta from £60 and United Airlines from £65 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 Republic Airways (95%), Icelandair (88%) or TAP AIR PORTUGAL (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 £38. On average you can expect to pay £76. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £114.

  • 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 £667). 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

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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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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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