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Cheap flights from Chicago to Boston from £84

CHI — BOS
13 Nov — 20 Nov1
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 57 days in advance, depart on a Friday or Wednesday 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

Wed 4/1109:55 -
1 stop6h 15m
Mon 9/1119:30 -
1 stop5h 40m
Deal found 13/10£167
Wed 4/1108:30 -
Nonstop2h 30m
Sat 7/1108:10 -
2 stops10h 15m
Deal found 13/10£168
Wed 11/1113:15 -
2 stops7h 40m
Wed 18/1105:20 -
1 stop7h 45m
Deal found 12/10£171
Fri 13/1107:05 -
Nonstop2h 27m
Sat 14/1107:45 -
Nonstop3h 10m
Deal found 13/10£173
Fri 6/1118:45 -
Nonstop2h 20m
Mon 9/1118:30 -
Nonstop2h 45m
Deal found 13/10£173
Wed 11/1113:15 -
2 stops7h 40m
Mon 16/1111:20 -
2 stops9h 25m
Deal found 13/10£175
Tue 3/1116:40 -
Nonstop2h 41m
Wed 4/1119:10 -
Nonstop2h 56m
Deal found 11/10£178
Tue 10/1117:47 -
1 stop4h 26m
Tue 17/1112:33 -
Nonstop3h 07m
Deal found 12/10£181
Thu 5/1120:15 -
Nonstop2h 44m
Thu 12/1117:05 -
Nonstop3h 12m
Deal found 12/10£183
Mon 23/1115:05 -
Nonstop2h 24m
Thu 26/1113:35 -
Nonstop2h 55m
Deal found 13/10£184
Fri 13/1118:45 -
Nonstop2h 20m
Mon 16/1113:20 -
2 stops7h 25m
Deal found 13/10£184
Mon 2/1116:40 -
Nonstop2h 41m
Fri 6/1119:10 -
Nonstop2h 56m
Deal found 10/10£188

Find flight deals from Chicago to Boston

Round-trip from

£167

One-way from

£84

Popular in

September

Cheapest in

January

Average price

£222

Good one-way deal

£217 or less
Southwest
  • Southwest
  • 4/11-9/11
  • 2 total stops
  • 11h 55m total
  • Chicago to Boston
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United Airlines
  • United Airlines
  • 3/11-31/12
  • 1 total stop
  • 4h 51m total
  • Chicago to Boston
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Highest demand for flights based on searches. 11% potential increase in price (£18 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 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.

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Route

Depart

Return

Price

Cheapest return flight

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Tue 3/11

05:00-10:51

1 stop4h 51m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£84

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Mon 9/11

20:15-08:20

1 stop11h 05m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£88

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Sat 12/12

10:05-19:25

2 stops8h 20m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£88

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

£109

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sat 12/12

07:05-10:36

Nonstop2h 31m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119
Fastest return journey

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Thu 7/1

09:00-12:15

Nonstop2h 15m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Thu 31/12

08:30-12:00

Nonstop2h 30m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Tue 29/12

07:45-11:00

Nonstop2h 15m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119

ChicagoBoston

ORD Chicago O'Hare Intl - BOS Boston Logan Intl

ORDBOS

Chicago O'Hare Intl

Sun 8/11

10:30-13:59

Nonstop2h 29m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119

ChicagoBoston

MDW Chicago Midway - BOS Boston Logan Intl

MDWBOS

Chicago Midway

Sat 10/4

15:45-19:05

Nonstop2h 20m

Boston Logan Intl

Wed 31/12

00:00-23:00

Nonstop0h 00m

£119

Flights are sorted by cheapest return flights first.

Deals found on 14/10

Showing 1-10 of 40 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 £152). Flying from Chicago to Boston in September is currently the most expensive (average of £237). 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 Monday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 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 £167 and £292 in November.
The cheapest return price found within the last 5 days was £167 on Southwest (4 Nov–9 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 64 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 27m. 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 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 Envoy Air (94%), ITA Airways (77%) or Royal Jordanian (77%) 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 £104. On average you can expect to pay £226. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for £152.

  • 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 £152). Flying from Chicago to Boston in September is currently the most expensive (average of £237). 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
Waltham
Warwick
Cambridge
Wellfleet
Peabody
Revere
Somerville
Quincy
Chelmsford
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.

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.

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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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