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Cheap flights from Chicago to Boston from £45

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 15/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
25 Dec — 1 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in September or July, booked 89 days in advance, depart on a Saturday or Thursday and return on a Thursday

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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 25 November 2025.

Thu 4/1211:25ORD - BOS
Nonstop2h 24mJetBlue
Thu 4/1217:29BOS - ORD
Nonstop3h 14mJetBlue
Deal found 23/11£93
Fri 5/1216:05ORD - BOS
Nonstop2h 20mUnited Airlines
Sun 7/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 24/11£97
Sat 13/1216:05ORD - BOS
Nonstop2h 20mUnited Airlines
Sat 10/116:49BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 23/11£101
Fri 19/1207:10ORD - BOS
Nonstop2h 26mDelta
Wed 7/113:50BOS - ORD
Nonstop3h 07mDelta
Deal found 24/11£105
Tue 2/1218:17ORD - BOS
Nonstop2h 28mUnited Airlines
Thu 4/1206:00BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 23/11£111
Sat 20/1217:15ORD - BOS
1 stop6h 45mSouthwest
Sat 10/105:10BOS - ORD
1 stop8h 05mSouthwest
Deal found 24/11£118
Fri 12/1220:38ORD - BOS
Nonstop2h 28mJetBlue
Tue 16/1215:40BOS - ORD
1 stop7h 12mJetBlue
Deal found 24/11£118
Thu 25/1218:21ORD - BOS
1 stop4h 33mUnited Airlines
Thu 1/107:45BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 24/11£120
Sat 13/1218:17ORD - BOS
Nonstop2h 28mUnited Airlines
Mon 15/1205:30BOS - ORD
1 stop5h 06mUnited Airlines
Deal found 24/11£124
Wed 3/1206:00ORD - BOS
1 stop5h 33mUnited Airlines
Wed 3/1218:23BOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 24/11£127
Wed 24/1213:55ORD - BOS
Nonstop2h 22mUnited Airlines
Wed 31/1206:01BOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 24/11£128
Thu 4/1220:38ORD - BOS
Nonstop2h 28mJetBlue
Mon 8/1215:40BOS - ORD
1 stop7h 12mJetBlue
Deal found 24/11£131

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 25 November 2025.

Round-trip from

£89

One-way from

£45

Popular in

April

Cheapest in

September

Average price

£196

Good round-trip deal

£486 or less
Delta
  • Delta
  • 17/1-20/1
  • Nonstop
  • 5h 38m total
  • Chicago to Boston
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United Airlines
  • United Airlines
  • 18/1
  • Nonstop
  • 2h 33m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (£7 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 November 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Boston Logan Intl.
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Cheapflights Fare Finder

 
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 858,174 searches. Data last updated 25 November 2025.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Chicago

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/12

11:25-14:49

Nonstop2h 24m

Boston Logan Intl

Thu 4/12

17:29-19:43

Nonstop3h 14m

£93

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/12

16:05-19:25

Nonstop2h 20m

Boston Logan Intl

Sun 7/12

06:00-08:00

Nonstop3h 00m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 15/1

07:05-10:40

Nonstop2h 35m

Boston Logan Intl

Sat 17/1

17:15-19:26

Nonstop3h 11m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/12

20:38-00:06

Nonstop2h 28m

Boston Logan Intl

Mon 8/12

08:30-10:35

Nonstop3h 05m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

20:38-00:06

Nonstop2h 28m

Boston Logan Intl

Sun 14/12

17:29-19:43

Nonstop3h 14m

£97

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 18/2

10:00-13:23

Nonstop2h 23m

Boston Logan Intl

Mon 23/2

07:00-09:10

Nonstop3h 10m

£101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 15/1

07:05-10:40

Nonstop2h 35m

Boston Logan Intl

Thu 22/1

16:10-18:19

Nonstop3h 09m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 23/1

16:15-19:39

Nonstop2h 24m

Boston Logan Intl

Mon 26/1

16:16-18:16

Nonstop3h 00m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/1

11:00-14:28

Nonstop2h 28m

Boston Logan Intl

Tue 13/1

07:30-09:41

Nonstop3h 11m

£105

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 18/2

10:00-13:23

Nonstop2h 23m

Boston Logan Intl

Tue 24/2

17:32-22:54

1 stop6h 22m

£108

Flights are sorted by cheapest return flights first.

Deals found on 23/11

Showing 1-10 of 23 results
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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.

Cheapflights Insights

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

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 21 November 2025.

Booking 89 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.

What is the cheapest month to book a flight from Chicago to Boston?

Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £69). Flying from Chicago to Boston in February is currently the most expensive (average of £105). 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 25 November 2025.

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 evening, which can drop the price by up to 72% 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 25 November 2025.

The most flights from CHI to BOS are scheduled on a Monday (60 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 on average).

How much does it cost for a return flight from Chicago to Boston?

How often are flights from Chicago to Boston delayed?

About 21% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 147 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon 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 Chicago to Boston flights?

Over the past year, TezJet have had the lowest number of delays on this route, with no flights being classified as delayed.

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 49 inbound flights from Chicago per day from 0 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How long is the flight from Chicago to Boston?

    Departing from Chicago to Boston will take you 2h 20m. Chicago and Boston are separated by a distance of 864 mi. Generally, flights for this route are direct.

  • 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 WestJet (73%), Virgin Atlantic (71%) or Envoy Air (71%) 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 £276. On average you can expect to pay £684. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £167.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Boston (average of £69). Flying from Chicago to Boston in February is currently the most expensive (average of £105). 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

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Burlington
Cambridge
Peabody
Somerville
Quincy
Waltham
Chelmsford

Browse thousands of different options on Cheapflights for your next trip

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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

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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