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Cheap flights from Boston to Chicago 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
3 Sep — 10 Sep1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 90 days in advance, depart on a Thursday or Tuesday and return on a Saturday

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 29 August 2025.

Round-trip from

£101

One-way from

£51

Popular in

March

Cheapest in

September

Average price

£168

Good round-trip deal

£198 or less

Good one-way deal

£102 or less
United Airlines
  • United Airlines
  • 11/9-12/9
  • Nonstop
  • 5h 19m total
  • Boston to Chicago
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JetBlue
  • JetBlue
  • 4/10
  • Nonstop
  • 2h 56m total
  • Boston to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (£10 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
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Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
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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 29 August 2025.

Thu 4/915:15BOS - ORD
Nonstop2h 50mUnited Airlines
Sat 6/906:30ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 27/8£94
Fri 5/907:00BOS - ORD
Nonstop2h 56mJetBlue
Fri 12/919:50ORD - BOS
Nonstop2h 35mJetBlue
Deal found 29/8£101
Thu 4/914:55BOS - ORD
Nonstop2h 57mDelta
Sun 7/907:00ORD - BOS
Nonstop2h 30mDelta
Deal found 28/8£102
Wed 15/1006:11BOS - ORD
1 stop13h 25mSpirit Airlines
Wed 22/1006:00ORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 27/8£104
Wed 17/1208:30BOS - ORD
Nonstop2h 58mJetBlue
Sat 20/1220:12ORD - BOS
Nonstop2h 29mJetBlue
Deal found 27/8£107
Fri 17/1020:47BOS - ORD
Nonstop2h 48mUnited Airlines
Sun 19/1006:30ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 27/8£115
Sat 25/1016:05BOS - ORD
1 stop8h 00mSouthwest
Sat 1/1113:30ORD - BOS
1 stop4h 20mSouthwest
Deal found 26/8£116
Wed 15/1007:09BOS - ORD
Nonstop3h 13mJetBlue
Wed 22/1013:36ORD - BOS
1 stop6h 53mJetBlue
Deal found 27/8£119
Fri 12/905:00BOS - ORD
1 stop12h 25mSouthwest
Mon 15/913:50ORD - BOS
1 stop7h 25mSouthwest
Deal found 28/8£120
Wed 1/1012:10BOS - ORD
1 stop5h 25mUnited Airlines
Sun 5/1021:20ORD - BOS
Nonstop2h 30mUnited Airlines
Deal found 27/8£122
Thu 4/913:00BOS - ORD
1 stop5h 10mUnited Airlines
Thu 11/906:30ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 28/8£124

Cheapflights Fare Finder

 
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 858,174 searches. Data last updated 29 August 2025.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.

Fly from

Boston

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/12

16:55-19:05

Nonstop3h 10m

Chicago O'Hare Intl

Tue 9/12

11:30-14:46

Nonstop2h 16m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/12

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 7/12

07:30-10:49

Nonstop2h 19m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/11

16:10-18:07

Nonstop2h 57m

Chicago O'Hare Intl

Sat 8/11

10:25-13:55

Nonstop2h 30m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/9

16:40-18:55

Nonstop3h 15m

Chicago O'Hare Intl

Sat 13/9

09:51-13:20

Nonstop2h 29m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 24/9

12:30-14:20

Nonstop2h 50m

Chicago O'Hare Intl

Mon 29/9

07:30-11:02

Nonstop2h 32m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 13/9

17:05-19:05

Nonstop3h 00m

Chicago O'Hare Intl

Wed 17/9

07:25-10:55

Nonstop2h 30m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 13/12

06:00-08:05

Nonstop3h 05m

Chicago O'Hare Intl

Wed 17/12

11:30-14:46

Nonstop2h 16m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 17/11

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Thu 20/11

06:15-09:30

Nonstop2h 15m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 25/10

16:10-18:07

Nonstop2h 57m

Chicago O'Hare Intl

Tue 28/10

10:25-13:55

Nonstop2h 30m

£101

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/9

16:40-18:55

Nonstop3h 15m

Chicago O'Hare Intl

Thu 11/9

19:50-23:25

Nonstop2h 35m

£101

Flights are sorted by cheapest return flights first.

Deals found on 27/8

Showing 1-10 of 20 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago

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 22 August 2025.

The best time to book flights from Boston to Chicago is 90 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 £595). Flying from Boston to Chicago in July is currently the most expensive (average of £843). 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 29 August 2025.

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 62% versus a flight at midday.

Weekly flight availability from Boston to Chicago

Explore weekly flight availability from Boston to Chicago. 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 29 August 2025.

The most flights from BOS to CHI are scheduled on a Thursday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

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 49 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

  • How long is the flight from Boston to Chicago?

    A quick flight from Boston to Chicago can take about 2h 57m. JetBlue provides one of the quickest options available for as low as £101. Airlines will cover a distance of 864 mi. All flights are typically direct.

  • What is the cheapest airline to fly from Boston to Chicago round-trip?

    Currently priced at £73, American Airlines will fly you from Boston to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. This flight start at 58% lower than the current average price 3 months from now.

  • 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 Icelandair (91%), TAP AIR PORTUGAL (90%) or Avianca (89%) 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 £146. On average you can expect to pay £243. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £101.

  • 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 £595). Flying from Boston to Chicago in July is currently the most expensive (average of £843). 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.
Boston to O'Hare Intl flights

Top airline flying from Boston to Chicago

Discover the top airline that operate flights from Boston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 858,174 searches. Data last updated 29 August 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£73Average£115FlexibilityNo cancel feeOn-time71%
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Fly with Cheapflights

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!

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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