Cheap flights from Chicago to Boston (CHI - BOS)

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The best prices from Chicago to Boston Logan Intl are usually found in August or July, booked 5 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Home North America USA Massachusetts Boston Cheap flights from Chicago to Boston

How to find the cheapest flight from
Chicago (CHI) to Boston (BOS)

All the information you need to plan the best CHI to BOS flight in 2021: compare Chicago to Boston flight prices with the expected peak season, weather and rainfall in Boston.
CHI - BOS
Price
$70 - $195
BOS
Temperature
30.2 - 73.4 °F
BOS
Precipitation
3.1 - 4 inches

Popular in

December

High demand for flights, 26% potential price rise

Cheapest in

August

Best time to find cheap flights, 51% potential price drop

Round-trip from

$70

From Chicago (CHI) to Boston Logan Intl

One-way from

$65

One-way flight from Chicago (CHI) to Boston Logan Intl

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from Chicago to Boston (CHI - BOS)?

It’s typically best to fly out from Chicago to Boston at noon. Doing so could potentially save you 32% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest month to fly from Chicago to Boston?

August is one of the best times of the year to fly to Boston from Chicago. Prices for August average $144 per person but you can even find prices for as low as $37. The most expensive prices can be found in the month of December. Opting for a August flight can save you 35% on your journey compared to booking in August

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

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Boston. Check prices with Cheapflights to find a great deal for your trip.

Cheap flights from Chicago to Boston in October, November 2021

The best prices found for CHI to BOS flights for October, November
26 Oct - 2 Nov
$78pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Nov - 16 Nov
$79pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Oct - 2 Nov
$86pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Boston 2021 flight deals

Cheap flights to Boston from Chicago found for this year
26 Oct - 2 Nov
$78pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Nov - 16 Nov
$79pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Oct - 2 Nov
$86pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals
4 Nov - 7 Nov
$128pp
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
12 Nov - 14 Nov
$132pp
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
12 Nov - 14 Nov
$134pp
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Boston

Late deals on round-trip flights to Boston from Chicago, departing today and this week
26 Oct - 2 Nov
$78pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 Oct - 28 Oct
$90pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
26 Oct - 2 Nov
$91pp
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Logan Intl from Chicago

The cheapest one-way flights from Chicago to Boston
6:45 am - 10:05 am
Major Airline
Nonstop
2h 20m
ORD - BOS
Major Airline
$65
StudentUniverse
3:05 pm - 6:32 pm
JetBlue
Nonstop
2h 27m
ORD - BOS
JetBlue
$70
3:00 am - 6:18 am
Delta
Nonstop
2h 18m
ORD - BOS
Delta
$71
Delta

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Boston</span> flights.

Flight FAQs

From Chicago to Boston

What airport do you fly into for flights to Boston from Chicago?

Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago to Boston. You should not have trouble finding flights to Logan Intl from Chicago; the airport handles an average of 53 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

Which airlines flying from Chicago to Boston Logan Intl have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Spirit Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Boston for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Boston for under $100. The cheapest flight booked recently is on Spirit Airlines for just $78, but on average you can expect to pay $97.

Are there nonstop flights from Chicago to Boston for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Boston under $200. A good price for a nonstop flight from Chicago to Boston is less than $155.

Are there last-minute flights available from Chicago to Boston for under $100?

There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than $100.

What days are nonstop flights available from Chicago to Boston?

Days when nonstop flights are available for this flight are: Tuesday, Wednesday, Thursday, Friday.

How many flights depart from Chicago to Boston on average per day?

On average, you can expect to see 12 flights from Chicago to Boston a day.
Morning (6am - Noon) - 33% of flight departures
Evening (6pm - Midnight) - 67% of flight departures

How long is the flight from Chicago to Boston?

A quick flight from Chicago to Boston can take about 14h 14m. Spirit Airlines provides one of the quickest options available for as low as $78. Airlines will cover a distance of 869 mi.

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

Cheapflights users have booked flights from Chicago to Boston round-trip from $78. This flight start at 45% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Chicago to Boston one-way?

For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $37. Users have also found prices from $65 and $70 on Major Airline and JetBlue, respectively.

What are the cheapest flights from Chicago to Boston?

On average you can expect to pay $313 for a flight from Chicago to Boston. The cheapest flight overall is $48 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $88.

What are the most reliable airlines from Chicago to Boston?

Before booking your flight to Boston from Chicago, check out the most reliable airlines to get you to your destination on time: Asiana Airlines (100%), TAP AIR PORTUGAL (97%), Icelandair( 96%).

What are the most popular airlines that fly from Chicago to Boston?

Before booking your flight from Chicago to Boston check out the most popular airlines for this route: Major Airline, American Airlines or JetBlue.

Related searches

Flights to Boston (BOS) from Chicago
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Rent a Car

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COVID Restrictions

View COVID Travel Restrictions for Boston, MA

Do I need a COVID test to fly to Boston from Chicago?

Information is based on travel restrictions for travel to Boston Logan Intl within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Boston Logan Intl.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Boston Logan Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Boston Logan Intl.

Do I need a test to fly back to Chicago from Boston?

Returning to Chicago from Boston Logan Intl

COVID-19 testing requirements
Visitors from Boston Logan Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Boston Logan Intl are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Boston, MA

Alternative routes for Chicago to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Bloomington Bloomington-Normal to Boston Logan Intl from $217 pp
Moline Quad-City to Boston Logan Intl from $217 pp
Greater Peoria to Boston Logan Intl from $240 pp
Champaign University-Willard to Boston Logan Intl from $423 pp

Destination information for Boston

Things to know before you go - useful duration and weather info for your trip from Chicago to Boston.
Average temperature for October in Boston
64.4 °F
Avg rainfall for October in Boston
3.7 ″

Airports servicing Chicago

O'Hare Intl (ORD)
Midway (MDW)
Rockford (RFD)

Airports servicing Boston

Boston (BOS)

Top 6 airlines flying from Chicago to Boston Logan Intl

The chart below displays the airlines Cheapflights users traveling from Chicago to Boston choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Delta 		$48 $268 No cancel fee N/A
Spirit Airlines 		$54 $132 No cancel fee 65%
JetBlue 		$71 $202 No cancel fee 62%
United Airlines 		$76 $247 No cancel fee 69%
American Airlines 		$76 $208 No cancel fee 71%
Southwest 		$189 $267 No cancel fee 63%

Popular flight searches

Check out other popular destinations found by fellow travelers in 2021.

Hourly flight availability from Chicago to Boston

See what time of day planes typically take off from Chicago towards Boston.
Morning 6 AM to noon 49% of CHI to BOS departures
Afternoon Noon to 6 PM 31% of CHI to BOS departures
Evening 6 PM to midnight 19% of CHI to BOS departures
Early morning Midnight to 6 AM 1% of CHI to BOS departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Boston
See how many times per day planes take to the skies headed from Chicago to Boston.
Sunday
46 daily flights
Monday
70 daily flights
Tuesday
67 daily flights
Wednesday
57 daily flights
Thursday
59 daily flights
Friday
53 daily flights
Saturday
21 daily flights
Home North America USA Massachusetts Boston Cheap flights from Chicago to Boston