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Cheap flights from Boston to Chicago from £48

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 17/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
11 Jan — 18 Jan1
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 Monday and return on a Tuesday

Cheap flight deals from Boston to Chicago

Enter your travel dates to find the best prices.

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 12 December 2025.

Wed 31/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Mon 5/121:12ORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/12£99
Sun 14/1218:23BOS - ORD
Nonstop3h 00mUnited Airlines
Wed 17/1218:17ORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 11/12£102
Wed 17/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Wed 17/1216:05ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/12£108
Tue 16/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Thu 18/1218:11ORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/12£114
Wed 17/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Thu 18/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/12£116
Sun 14/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Tue 16/1211:00ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 11/12£117
Mon 15/1210:40BOS - ORD
Nonstop3h 00mUnited Airlines
Mon 22/1215:53ORD - BOS
1 stop5h 55mUnited Airlines
Deal found 11/12£125
Wed 17/1205:30BOS - ORD
1 stop5h 06mUnited Airlines
Sat 20/1221:12ORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 9/12£128
Tue 16/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Mon 5/118:21ORD - BOS
1 stop4h 33mUnited Airlines
Deal found 10/12£132
Sun 21/1216:31BOS - ORD
Nonstop3h 15mJetBlue
Sun 28/1206:45ORD - BOS
1 stop6h 27mJetBlue
Deal found 10/12£135
Mon 15/1209:40BOS - ORD
Nonstop3h 00mUnited Airlines
Wed 17/1208:45ORD - BOS
1 stop4h 44mUnited Airlines
Deal found 10/12£136
Sat 13/1205:30BOS - ORD
1 stop5h 06mUnited Airlines
Sun 14/1218:17ORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 10/12£140

Find 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 12 December 2025.

Round-trip from

£95

One-way from

£48

Popular in

March

Cheapest in

September

Average price

£184

Good round-trip deal

£188 or less

Good one-way deal

£125 or less
Delta
  • Delta
  • 17/1-20/1
  • Nonstop
  • 5h 46m total
  • Boston to Chicago
Search Deals
Delta
  • Delta
  • 17/1
  • Nonstop
  • 3h 11m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (£9 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
Search Deals
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 12 December 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

Sat 17/1

17:15-19:26

Nonstop3h 11m

Chicago O'Hare Intl

Wed 21/1

14:25-17:54

Nonstop2h 29m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 16/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Sun 18/1

07:45-11:10

Nonstop2h 25m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 31/3

16:25-18:31

Nonstop3h 06m

Chicago O'Hare Intl

Sat 4/4

07:00-10:27

Nonstop2h 27m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 6/2

15:35-17:44

Nonstop3h 09m

Chicago O'Hare Intl

Mon 9/2

07:45-11:10

Nonstop2h 25m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 14/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Sun 18/1

07:45-11:10

Nonstop2h 25m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 23/1

07:30-09:41

Nonstop3h 11m

Chicago O'Hare Intl

Sat 24/1

14:00-17:29

Nonstop2h 29m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 29/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/2

08:29-11:54

Nonstop2h 25m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 21/1

20:25-22:29

Nonstop3h 04m

Chicago O'Hare Intl

Wed 28/1

18:59-22:31

Nonstop2h 32m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 26/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/2

08:29-11:54

Nonstop2h 25m

£102

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 16/1

06:00-08:04

Nonstop3h 04m

Chicago O'Hare Intl

Sun 18/1

13:55-17:19

Nonstop2h 24m

£107

Flights are sorted by cheapest return flights first.

Deals found on 11/12

Showing 1-10 of 23 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 5 December 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, April is the cheapest month in which you can book a flight from Boston to Chicago (average of £66). Flying from Boston to Chicago in January is currently the most expensive (average of £89). 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 12 December 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 58% 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 12 December 2025.

The most flights from BOS to CHI are scheduled on a Thursday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

How often are flights from Boston to Chicago delayed?

About 13% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 168 minutes.

What is the most punctual flight time for Boston to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Boston to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.

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 51 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 3h 08m. Delta provides one of the quickest options available for as low as £99. 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 57% 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 ANA (84%), TAP AIR PORTUGAL (83%) or JetBlue (81%) 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 £47. On average you can expect to pay £245. 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, April is the cheapest month in which you can book a flight from Boston to Chicago (average of £66). Flying from Boston to Chicago in January is currently the most expensive (average of £89). 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£73Average£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?

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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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