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Cheap flights from Chicago to Boston from £58

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
26 May — 2 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in January or September, booked 86 days in advance, depart on a Saturday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Boston

Enter your travel dates to find the best prices.

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 26 April 2026.

Tue 4/820:20
ORD
-
BOS
Nonstop2h 31m
JetBlue
Wed 12/808:10
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 22/4£112
Sat 23/513:56
ORD
-
BOS
Nonstop2h 31m
JetBlue
Mon 25/506:00
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 22/4£114
Thu 20/807:33
ORD
-
BOS
Nonstop2h 34m
United Airlines
Wed 26/812:30
BOS
-
ORD
Nonstop2h 51m
United Airlines
Deal found 22/4£115
Wed 20/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Sun 24/509:50
BOS
-
ORD
Nonstop2h 53m
United Airlines
Deal found 22/4£115
Sat 30/517:19
ORD
-
BOS
1 stop5h 10m
Delta
Tue 2/614:00
BOS
-
ORD
1 stop7h 26m
Delta
Deal found 23/4£116
Thu 28/507:05
ORD
-
BOS
1 stop5h 15m
Delta
Sat 30/505:40
BOS
-
ORD
1 stop5h 49m
Delta
Deal found 21/4£117
Mon 11/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Fri 15/518:39
BOS
-
ORD
Nonstop3h 01m
United Airlines
Deal found 22/4£117
Fri 29/511:26
ORD
-
BOS
1 stop5h 29m
Delta
Mon 1/620:40
BOS
-
ORD
Nonstop2h 55m
Delta
Deal found 23/4£118
Wed 13/506:00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Tue 19/519:26
BOS
-
ORD
1 stop5h 11m
United Airlines
Deal found 23/4£119
Wed 5/807:05
ORD
-
BOS
Nonstop2h 31m
Delta
Tue 11/815:00
BOS
-
ORD
1 stop6h 45m
Delta
Deal found 22/4£120
Wed 13/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Thu 14/507:35
BOS
-
ORD
Nonstop2h 52m
Delta
Deal found 24/4£120
Fri 8/506:00
ORD
-
BOS
Nonstop2h 14m
JetBlue
Tue 12/518:47
BOS
-
ORD
Nonstop3h 06m
JetBlue
Deal found 23/4£123

Find 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 26 April 2026.

Round-trip from

£112

One-way from

£58

Popular in

April

Cheapest in

January

Average price

£201
JetBlue
  • JetBlue
  • 4/8-12/8
  • Nonstop
  • 5h 27m total
  • Chicago to Boston
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Delta
  • Delta
  • 2/9
  • 1 total stop
  • 5h 30m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (£7 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in April 2026
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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 26 April 2026.
Use the filters below to find and compare flights from Chicago to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 25/8

20:20-23:51

Nonstop2h 31m

Boston Logan Intl

Wed 26/8

17:20-19:25

Nonstop3h 05m

£112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 28/5

07:05-13:20

1 stop5h 15m

Boston Logan Intl

Sat 30/5

05:40-10:29

1 stop5h 49m

£117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 6/9

07:33-11:07

Nonstop2h 34m

Boston Logan Intl

Sat 12/9

18:42-20:39

Nonstop2h 57m

£126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 23/5

13:56-17:27

Nonstop2h 31m

Boston Logan Intl

Sun 24/5

06:00-08:00

Nonstop3h 00m

£128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 22/5

19:16-22:50

Nonstop2h 34m

Boston Logan Intl

Tue 26/5

12:00-18:07

1 stop7h 07m

£138
Fastest return journey

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/5

16:30-20:03

Nonstop2h 33m

Boston Logan Intl

Tue 12/5

07:35-09:27

Nonstop2h 52m

£138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 26/9

16:00-19:37

Nonstop2h 37m

Boston Logan Intl

Thu 1/10

07:30-09:28

Nonstop2h 58m

£151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 30/6

06:00-11:16

1 stop4h 16m

Boston Logan Intl

Fri 3/7

06:00-07:58

Nonstop2h 58m

£160

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/6

17:19-23:29

1 stop5h 10m

Boston Logan Intl

Sat 13/6

18:20-20:29

Nonstop3h 09m

£160

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 15/5

19:16-22:50

Nonstop2h 34m

Boston Logan Intl

Mon 18/5

07:35-09:27

Nonstop2h 52m

£165

Flights are sorted by cheapest return flights first.

Deals found on 22/4

Showing 1-10 of 24 resultsSorted by cheapest first
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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?

Booking 71 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of £134). Flying from Chicago to Boston in December is currently the most expensive (average of £209). 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 26 April 2026.

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 78% 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 26 April 2026.

The most flights from CHI to BOS are scheduled on a Sunday (70 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (28 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 25% 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 Friday 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, JetBlue have had the lowest number of delays on this route, with just 21% of flights being 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 1 airline. 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 31m. Chicago and Boston are separated by a distance of 864 mi. Both multi-stop and direct flights can be found to your destination and back.

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

    Flying on American Airlines is currently your cheapest option to Boston, with prices starting at £116. You may be able to fly from Chicago to Boston for 30% less than the average price by searching for this airline.

  • 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 Avianca (88%), Envoy Air (78%) or Iberia (74%) as they are the most reliable in getting you off to your destination on time.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Boston (average of £134). Flying from Chicago to Boston in December is currently the most expensive (average of £209). 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
Canton
Waltham
Warwick
Cambridge
Peabody
Somerville
Quincy
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

Top airline flying from Chicago to Boston

Discover the top airline that operate flights from Chicago to Boston. 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 26 April 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest£116Average£127FlexibilityNo cancel feeOn-time71%
Search American Airlines 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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