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Cheap flights from Chicago to Boston from £92

CHI — BOS
5 Dec — 12 Dec1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Chicago to Boston Logan Intl are usually found in January or February, booked 68 days in advance, depart on a Friday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Boston

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Boston

Thu 19/1111:00 -
Nonstop2h 24m
Mon 23/1107:55 -
Nonstop3h 04m
Deal found 4/11£183
Thu 17/1207:50 -
Nonstop2h 20m
Thu 17/1212:45 -
Nonstop2h 45m
Deal found 5/11£183
Thu 19/1111:00 -
Nonstop2h 24m
Sun 22/1107:55 -
Nonstop3h 04m
Deal found 4/11£184
Fri 13/1115:16 -
1 stop16h 03m
Tue 17/1112:15 -
1 stop6h 32m
Deal found 2/11£202
Fri 20/1117:30 -
Nonstop2h 29m
Sun 22/1114:40 -
Nonstop3h 00m
Deal found 5/11£204
Fri 18/1219:55 -
Nonstop2h 26m
Sun 20/1216:45 -
Nonstop3h 13m
Deal found 4/11£209
Thu 19/1110:35 -
Nonstop2h 24m
Sun 22/1120:40 -
Nonstop2h 56m
Deal found 2/11£213
Wed 23/1216:05 -
Nonstop2h 15m
Mon 28/1222:25 -
Nonstop3h 00m
Deal found 3/11£213
Thu 19/1107:35 -
1 stop5h 10m
Tue 1/1212:50 -
Nonstop2h 50m
Deal found 5/11£215
Thu 17/1215:35 -
Nonstop2h 15m
Mon 18/106:55 -
Nonstop2h 50m
Deal found 5/11£216
Fri 13/1107:55 -
1 stop24h 34m
Tue 17/1112:15 -
1 stop7h 15m
Deal found 2/11£217
Fri 20/1107:00 -
Nonstop2h 19m
Sun 22/1118:05 -
1 stop5h 13m
Deal found 4/11£220

Find flight deals from Chicago to Boston

Round-trip from

£183

One-way from

£92

Popular in

October

Cheapest in

January

Average price

£222

Good one-way deal

£299 or less
JetBlue
  • JetBlue
  • 19/11-23/11
  • Nonstop
  • 5h 28m total
  • Chicago to Boston
Search Deals
JetBlue
  • JetBlue
  • 21/12-31/12
  • Nonstop
  • 2h 26m total
  • Chicago to Boston
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£21 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in November 2026
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Price to beat on a one-way flight from Chicago (CHI) to Boston Logan Intl.
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Cheapflights Fare Finder

 
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 Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Mon 21/12

19:55-23:21

Nonstop2h 26m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£92

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Sun 22/11

07:50-14:30

2 stops5h 40m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£103

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sat 2/1

07:05-10:33

Nonstop2h 28m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£107

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Fri 20/11

19:45-23:08

Nonstop2h 23m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£107

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sat 21/11

16:40-20:03

Nonstop2h 23m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£107

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Wed 23/12

06:00-13:26

1 stop6h 26m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£114

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Fri 18/12

18:10-23:59

1 stop4h 49m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£114

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Mon 4/1

18:10-23:55

1 stop4h 45m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£114

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sun 22/11

08:50-14:32

1 stop4h 42m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£114
Fastest return journey

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Fri 19/2

07:40-10:55

Nonstop2h 15m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£117

Flights are sorted by cheapest return flights first.

Deals found on 4/11

Showing 1-10 of 43 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

Cheapflights Insights

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

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 £149). Flying from Chicago to Boston in October is currently the most expensive (average of £245). 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?

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 80% versus a flight at midday.

Weekly flight availability from Chicago to Boston

The most flights from CHI to BOS are scheduled on a Wednesday (62 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (26 on average).

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

Airfare is typical for this route at the moment.
Chicago to Boston flights typically cost between £172 and £289 in November.
The cheapest return price found within the last 5 days was £183 on JetBlue (19 Nov–23 Nov).

How often are flights from Chicago to Boston delayed?

About 26% of weekly flights between Chicago and Boston have experienced delays in the past year, with the average delay time being 155 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 Monday 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, Delta have had the lowest number of delays on this route, with just 22% of flights being delayed.

How far ahead should I book a flight from Chicago to Boston?

Booking 60 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.

Related info for your journey

  • 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 35 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 857 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 Avianca (91%), ITA Airways (90%) or Envoy Air (86%) 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 £299. On average you can expect to pay £324. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £220.

  • 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 £149). Flying from Chicago to Boston in October is currently the most expensive (average of £245). 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
North Truro
Warwick
Waltham
Cambridge
Wellfleet
Peabody
Revere
Somerville
Chelmsford
Quincy
Raynham

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Boston

O'Hare Intl to Boston flights

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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.

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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.

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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.

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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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