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 Tuesday or Wednesday and return on a Tuesday

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 2022: 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
Rainfall
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

Average price

$127

Average for round-trip flights in May 2022

Round-trip from

$70

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 in the morning. Doing so could potentially save you 10% 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 December

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 May, June 2022

The best prices found for CHI to BOS flights for May, June
21 May - 22 May
$150pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
21 May - 25 May
$154pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
21 May - 24 May
$156pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Boston 2022 flight deals

Cheap flights to Boston from Chicago found for this year
12 Nov - 12 Nov
$144pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
21 May - 25 May
$150pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
12 Nov - 12 Nov
$153pp
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals
12 Nov - 12 Nov
$144pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
8 Nov - 10 Nov
$150pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
9 Aug - 17 Aug
$160pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
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
28 May - 7 Jun
$159pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 May - 1 Jun
$168pp
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
25 May - 7 Jun
$172pp
ORD
Chicago O'Hare Intl
Multiple 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
7:56 am - 3:28 pm
American Airlines
1 Stop
6h 32m
ORD - BOS
American Airlines
1:55 pm - 7:19 pm
United Airlines
1 Stop
4h 24m
ORD - BOS
United Airlines
$102
United
3:13 am - 10:41 am
Allegiant Air
1 Stop
6h 28m
MDW - BOS
Allegiant Air
$103
Gotogate

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 59 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 10 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 JetBlue 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 $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Boston for under $200. The cheapest flight booked recently is on American Airlines for just $144, but on average you can expect to pay $163.

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 $183.

Are there last-minute flights available from Chicago to Boston for under $200?

There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than $200.

What days are nonstop flights available from Chicago to Boston?

Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

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

On average, you can expect to see 31 flights from Chicago to Boston a day.
Morning (6am - Noon) - 23% of flight departures
Afternoon (Noon - 6pm) - 58% of flight departures
Evening (6pm - Midnight) - 19% of flight departures

How long is the flight from Chicago to Boston?

A quick flight from Chicago to Boston can take about 2h 15m. American Airlines provides one of the quickest options available for as low as $144. Airlines will cover a distance of 869 mi. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Chicago to Boston round-trip?

Cheapflights users have booked flights from Chicago to Boston round-trip from $144. Other airlines that can offer you cheap pricing are JetBlue, from $165, and Delta, from $168.

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

For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $75. Users have also found prices from $77 and $81 on Spirit Airlines and Allegiant Air, respectively.

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: Azul (92%), Korean Air (87%), Republic Airways( 86%).

What are the cheapest flights from Chicago to Boston?

On average you can expect to pay $381 for a flight from Chicago to Boston. The cheapest flight overall is $82 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $150.

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 Alaska Airlines.

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 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) 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 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) 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.

Destination information for Boston

Things to know before you go - useful duration and weather info for your trip from Chicago to Boston.
Flight duration from Chicago to BOS
2h 38m
Average temperature for May in Boston
68.0 °F
Avg rainfall for May in Boston
3.7 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Boston

Top 7 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
Juneyao Airlines
$11 $17 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Spirit Airlines
$50 $115 No cancel fee 65%
JetBlue
$58 $208 No cancel fee 62%
Delta
$70 $245 No cancel fee N/A
United Airlines
$82 $213 No cancel fee 69%
American Airlines
$90 $274 No cancel fee 71%
Alaska Airlines
$192 $303 No cancel fee 75%

Hourly flight availability from Chicago to Boston

See what time of day planes typically take off from Chicago towards Boston.
Afternoon Noon to 6 PM 43% of CHI to BOS departures
Morning 6 AM to noon 40% of CHI to BOS departures
Early morning Midnight to 6 AM 11% of CHI to BOS departures
Evening 6 PM to midnight 6% 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
51 daily flights
Monday
68 daily flights
Tuesday
71 daily flights
Wednesday
73 daily flights
Thursday
59 daily flights
Friday
64 daily flights
Saturday
29 daily flights
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