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Cheap flights from Boston to Chicago from £47

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 15/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
23 Nov — 30 Nov1
1 adult
1 adult, Economy, 0 bags

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 Saturday and return on a Monday

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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 24 October 2025.

Thu 4/1207:30BOS - ORD
Nonstop3h 03mDelta
Mon 8/1207:10ORD - BOS
Nonstop2h 26mDelta
Deal found 22/10£88
Wed 31/1207:45BOS - ORD
Nonstop3h 04mUnited Airlines
Mon 5/113:55ORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 23/10£89
Thu 20/1117:15BOS - ORD
Nonstop3h 12mJetBlue
Wed 26/1120:45ORD - BOS
Nonstop2h 28mJetBlue
Deal found 23/10£91
Tue 4/1115:55BOS - ORD
Nonstop3h 00mJetBlue
Thu 6/1107:45ORD - BOS
1 stop6h 10mJetBlue
Deal found 23/10£94
Fri 7/1118:23BOS - ORD
Nonstop3h 00mUnited Airlines
Sat 8/1107:15ORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 23/10£94
Wed 5/1106:00BOS - ORD
Nonstop3h 00mUnited Airlines
Sun 9/1106:15ORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 22/10£97
Fri 12/1205:29BOS - ORD
1 stop5h 31mDelta
Fri 12/1215:50ORD - BOS
Nonstop2h 24mDelta
Deal found 23/10£98
Thu 30/1006:35BOS - ORD
1 stop8h 25mSouthwest
Tue 4/1113:45ORD - BOS
1 stop7h 30mSouthwest
Deal found 23/10£99
Sat 15/1107:10BOS - ORD
Nonstop3h 05mJetBlue
Thu 20/1108:20ORD - BOS
1 stop7h 32mJetBlue
Deal found 23/10£100

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 24 October 2025.

Round-trip from

£88

One-way from

£47

Popular in

April

Cheapest in

September

Average price

£185

Good one-way deal

£115 or less
Delta
  • Delta
  • 14/1-21/1
  • Nonstop
  • 5h 38m total
  • Boston to Chicago
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JetBlue
  • JetBlue
  • 15/12
  • Nonstop
  • 2h 54m total
  • Boston to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (£12 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 October 2025
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Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
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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 24 October 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

19:52-21:47

Nonstop2h 55m

Chicago O'Hare Intl

Wed 10/12

06:00-13:15

1 stop6h 15m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/12

10:15-15:20

1 stop6h 05m

Chicago O'Hare Intl

Sat 13/12

07:10-10:36

Nonstop2h 26m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/12

16:05-18:02

Nonstop2h 57m

Chicago O'Hare Intl

Mon 22/12

18:02-23:57

1 stop4h 55m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 15/11

07:10-09:15

Nonstop3h 05m

Chicago O'Hare Intl

Thu 20/11

08:20-16:52

1 stop7h 32m

£100

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 11/1

05:45-09:43

1 stop4h 58m

Chicago O'Hare Intl

Thu 15/1

07:30-10:52

Nonstop2h 22m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 7/2

05:30-09:35

1 stop5h 05m

Chicago O'Hare Intl

Tue 10/2

09:35-15:17

1 stop4h 42m

£103

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/12

05:29-10:00

1 stop5h 31m

Chicago O'Hare Intl

Mon 8/12

10:45-16:03

1 stop4h 18m

£103

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 17/11

19:55-21:53

Nonstop2h 58m

Chicago O'Hare Intl

Mon 24/11

07:10-10:35

Nonstop2h 25m

£103

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/11

18:23-20:23

Nonstop3h 00m

Chicago O'Hare Intl

Sun 9/11

21:25-00:45

Nonstop2h 20m

£106

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 20/11

07:45-09:45

Nonstop3h 00m

£48

Flights are sorted by cheapest return flights first.

Deals found on 23/10

Showing 1-10 of 21 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 17 October 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, November is the cheapest month in which you can book a flight from Boston to Chicago (average of £65). Flying from Boston to Chicago in December is currently the most expensive (average of £94). 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 24 October 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 evening, which can drop the price by up to 50% versus a flight in the morning.

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 24 October 2025.

The most flights from BOS to CHI are scheduled on a Friday (77 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 39 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 55m. Delta provides one of the quickest options available for as low as £95. Airlines will cover a distance of 864 mi. This flight may include one or multiple stops.

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

    Currently priced at £74, 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 TAP AIR PORTUGAL (88%), Icelandair (88%) or Avianca (85%) 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 £78. On average you can expect to pay £178. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £70.

  • 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, November is the cheapest month in which you can book a flight from Boston to Chicago (average of £65). Flying from Boston to Chicago in December is currently the most expensive (average of £94). 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

Browse thousands of different options on Cheapflights for your next trip

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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 24 October 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£74Average£116FlexibilityNo cancel feeOn-time71%
Search American Airlines flights

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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