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Cheap flights from Boston to Chicago from £61

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 31/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
5 nov. — 12 nov.1
1 adult

The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 51 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Find flights from Boston to Chicago within your budget

Customise your flight search to find flights from Boston to Chicago 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 1,010,473 searches. Data last updated 31 oktober 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

fre. 31/1

07:00-09:11

Nonstop3h 11m

£61

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ons. 6/11

06:00-08:06

Nonstop3h 06m

£62

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ons. 1/1

06:02-08:05

Nonstop3h 03m

£72

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ons. 6/11

08:55-14:00

1 stop6h 05m

£81

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lør. 14/12

11:37-11:35

1 stop24h 58m

£85

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

tir. 10/12

17:23-23:47

1 stop31h 24m

£129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

ons. 13/11

19:50-21:51

Nonstop3h 01m

Chicago O'Hare Intl

lør. 16/11

12:40-16:01

Nonstop2h 21m

£90

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

fre. 13/12

06:00-08:06

Nonstop3h 06m

Chicago O'Hare Intl

tir. 14/1

09:05-12:23

Nonstop2h 18m

£92

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

tor. 14/11

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

søn. 17/11

07:22-10:41

Nonstop2h 19m

£125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lør. 23/11

20:59-15:19

1 stop19h 20m

Chicago O'Hare Intl

man. 25/11

16:45-20:04

Nonstop2h 19m

£133

Flights are sorted by cheapest first

Deals found on 31/10

Showing 1-10 of 11 results
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Cheap flight deals from Boston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). 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 oktober 2024.

Round-trip from

£90

One-way from

£61

Popular in

April

Cheapest in

September
Delta
  • Delta
  • 13/11-16/11
  • Nonstop
  • 5h 22m total
  • Boston to Chicago
Delta
  • Delta
  • 31/1
  • Nonstop
  • 3h 11m total
  • Boston to Chicago
High demand for flights, 18% potential price rise
Best time to find cheap flights, 25% potential price drop

Find flight deals from Boston to Chicago

Cheapest flights from Boston to Chicago
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 oktober 2024.

ons. 13/1119:50BOS - ORD
Nonstop3h 01mDelta
lør. 16/1112:40ORD - BOS
Nonstop2h 21mDelta
Deal found 30/10£90
fre. 13/1206:00BOS - ORD
Nonstop3h 06mJetBlue
tor. 9/109:10ORD - BOS
Nonstop2h 30mJetBlue
Deal found 30/10£92
tor. 14/1106:00BOS - ORD
Nonstop2h 56mUnited Airlines
søn. 17/1107:22ORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 30/10£125
lør. 23/1120:59BOS - ORD
1 stop19h 20mSpirit Airlines
man. 25/1116:45ORD - BOS
Nonstop2h 19mSpirit Airlines
Deal found 30/10£133
tir. 19/1106:00BOS - ORD
2 stops8h 00mSouthwest
tir. 19/1115:10ORD - BOS
1 stop6h 15mSouthwest
Deal found 30/10£182

Best time to book a flight from Boston to Chicago

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

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

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

Use this chart to determine the optimal time to book a return flight from Boston to Chicago. Price data was last updated on 25 October 2024.

The best time to book flights from Boston to Chicago is 51 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?

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £601). Flying from Boston to Chicago in July is currently the most expensive (average of £774). 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 CHI?

Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 31 oktober 2024.

When flying from Boston to Chicago, 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 13% versus a flight at midday.

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago 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 when rainfall is around 43.0 mm.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 31 oktober 2024.
Read reviews from past customers who have flown United Airlines, Delta and JetBlue from Boston to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

Reviews

1 / 10

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

8.1
Very Good
5,116 reviews
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

Reviews

1 / 10

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

8.0
Very Good
9,420 reviews
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

Reviews

1 / 10

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

8.0
Very Good
8,836 reviews
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

Reviews

1 / 10

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

7.5
Good
3,514 reviews
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

Reviews

1 / 10

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

7.4
Good
9,240 reviews
8.1
Very Good
5,116 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.3

Overall

8.1

Food

7.2

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 Boston to Chicago. 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?

    Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 14 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

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

    Currently priced at £90, Delta will fly you from Boston to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from JetBlue and United Airlines - these airlines can fly you to your destination from £92 and £125, respectively. These flights start at 52% lower than the current average price 3 months from now.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as £61. However, be on the lookout for offers from JetBlue and United Airlines, as they are both options that can get you from Boston to Chicago for a low price.

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

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Republic Airways (100%), Avianca (100%) or Japan Airlines (95%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is £64. On average you can expect to pay £112. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £128.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Boston to Chicago 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?

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £601). Flying from Boston to Chicago in July is currently the most expensive (average of £774). 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 Boston to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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

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

Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.

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

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.

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