Cheap flights from Chicago (CHI) to Massachusetts (MA)

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How to find the cheapest flight from
Chicago (CHI) to Massachusetts

All the information you need to plan the best CHI to BOS flight in 2022: compare Chicago to Massachusetts flight prices with the expected peak season, weather and rainfall in Massachusetts.
When is the cheapest time to fly from Chicago to Massachusetts (CHI - MA)?

When flying from Chicago to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Massachusetts in June, July 2022

The best prices found for CHI to Massachusetts flights for June, July
6 Jul - 13 Jul
$114pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
4 Jul - 7 Jul
$121pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
4 Jul - 7 Jul
$126pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Massachusetts 2022 flight deals

Cheap flights to Massachusetts from Chicago found for this year
25 Oct - 29 Oct
$114pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
4 Jul - 7 Jul
$121pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
4 Jul - 7 Jul
$126pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Massachusetts from Chicago

Save time with Chicago to Massachusetts direct flight deals
25 Oct - 29 Oct
$114pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
5 Nov - 12 Nov
$121pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Delta
Non-Stop
ORD
Chicago O'Hare Intl
21 Sep - 24 Sep
$128pp
ORD
Chicago O'Hare Intl
Delta
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Delta
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Massachusetts

Late deals on round-trip flights to Massachusetts from Chicago, departing today and this week
6 Jul - 13 Jul
$114pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
6 Jul - 12 Jul
$128pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
7 Jul - 13 Jul
$133pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Massachusetts from Chicago

The cheapest one-way flights from Chicago to Massachusetts
3:45 pm - 7:11 pm
JetBlue
Nonstop
2h 26m
ORD - BOS
JetBlue
7:05 am - 3:46 pm
Spirit Airlines
1 Stop
7h 41m
ORD - BOS
Spirit Airlines
$88
Kiwi.com
3:13 am - 10:41 am
Allegiant Air
1 Stop
6h 28m
MDW - BOS
Allegiant Air
$107
Gotogate

Related info for your journey

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

Flight FAQs

From Chicago to Massachusetts

Which airlines flying from Chicago to Massachusetts have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Massachusetts that may be offering flexible cancellation policies are American Airlines, United Airlines, and JetBlue. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Massachusetts for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Massachusetts for under $200. The cheapest flight booked recently is on JetBlue for just $114, but on average you can expect to pay $140.

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

Cheapflights has at least 20 direct flights from Chicago to Massachusetts under $200. A good price for a nonstop flight from Chicago to Massachusetts is less than $153.

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

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

What days are nonstop flights available from Chicago to Massachusetts?

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

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

15 flight departures from Chicago to Massachusetts per day on average.
Early Morning (Midnight to 6am) - 20% of flight departures
Morning (6am - Noon) - 20% of flight departures
Afternoon (Noon - 6pm) - 47% of flight departures
Evening (6pm - Midnight) - 13% of flight departures

How long is the flight from Chicago to Massachusetts?

There are many flights that can get you from Chicago to Massachusetts in 2h 16m. Fly via JetBlue, American Airlines, or United Airlines to get the fastest option. The distance between Chicago and Massachusetts is about 869 mi. This flight may include one or multiple stops.

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

The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $57. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Chicago to Massachusetts for a low price.

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

Major Airline, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Massachusetts.

What are the most reliable airlines from Chicago to Massachusetts?

Before booking your flight to Massachusetts from Chicago, check out the most reliable airlines to get you to your destination on time: Virgin Atlantic (91%), KLM (91%), Korean Air( 91%).

What are the cheapest flights from Chicago to Massachusetts?

Looking at all options, your cheapest flight can be booked for $74. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $114 on average our data indicates $446 when flying from Chicago to Massachusetts.

What are the most popular routes from Chicago to Massachusetts?

When deciding which route to take from Chicago to Massachusetts consider Chicago O'Hare Intl - Boston Logan Intl, Chicago Midway - Boston Logan Intl or Chicago O'Hare Intl - Nantucket Memorial as they are the most popular.

COVID Restrictions

View COVID Travel Restrictions for Massachusetts (MA)

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

Information is based on travel restrictions for travel to Massachusetts within the United States

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

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Massachusetts.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Massachusetts.

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

Returning to Chicago from Massachusetts

COVID-19 testing requirements
Visitors from Massachusetts are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Massachusetts are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Massachusetts (MA)

Destination points for flights from Chicago to Massachusetts

Select to see more specific information for flights from Chicago to all places in Massachusetts.
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Destination information for Massachusetts

Things to know before you go - useful duration and weather info for your trip from Chicago to Massachusetts.
Flight duration from Chicago to Massachusetts
2h 39m

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing

Bedford Hanscom Field (BED)
Boston Harbor SPB (BNH)
Boston (BOS)
Beverly (BVY)
New Bedford Regional (EWB)
Hyannis Barnstable (HYA)

Top 7 airlines flying from Chicago to Massachusetts

The chart below displays the airlines Cheapflights users traveling from Chicago to Massachusetts 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
$14 $21 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
$56 $145 No cancel fee 65%
JetBlue
$58 $208 No cancel fee 62%
Delta
$74 $318 No cancel fee N/A
United Airlines
$82 $335 No cancel fee 69%
American Airlines
$97 $408 No cancel fee 71%
Alaska Airlines
$192 $303 No cancel fee 75%
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