Menu

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

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

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

How far in advance should I book a flight from Chicago to Massachusetts?

To save up to 23% on this flight, we recommend booking at least 26 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Massachusetts from $270 1-2 weeks out and tickets from $316 for flights departing within the next 72 hours.

Cheap flights from Chicago to Massachusetts in October, November 2020

The best prices found for CHI to Massachusetts flights for October, November
11 Nov - 18 Nov
$48pp
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
10 Nov - 18 Nov
$59pp
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 - 10 Nov
$64pp
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 Massachusetts 2020 flight deals

Cheap flights to Massachusetts from Chicago found for this year
5 Dec - 8 Dec
$48pp
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
5 Dec - 8 Dec
$58pp
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
2 Dec - 9 Dec
$59pp
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 Massachusetts from Chicago

Save time with Chicago to Massachusetts direct flight deals
4 Nov - 7 Nov
$82pp
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
13 Nov - 15 Nov
$89pp
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
7 Dec - 7 Dec
$91pp
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
JetBlue
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
31 Oct - 7 Nov
$89pp
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
31 Oct - 3 Nov
$92pp
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
31 Oct - 14 Nov
$93pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Massachusetts from Chicago

The cheapest one-way flights from Chicago to Massachusetts
4:18 pm - 7:30 pm
JetBlue
Nonstop
2h 12m
ORD - BOS
JetBlue
8:59 am - 6:50 pm
Multiple Airlines
1 Stop
8h 51m
ORD - BOS
Multiple Airlines
$58
FlightNetwork
7:16 am - 5:13 pm
Delta
1 Stop
8h 57m
ORD - BOS
Delta
$65
Delta

Related info for your journey

Useful info, stats and facts about Chicago to Massachusetts flights.

Flight FAQs

From Chicago to Massachusetts

Are flight prices decreasing from Chicago to Massachusetts due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Massachusetts for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Chicago to Massachusetts to control the spread of COVID-19?

New policies can now be found on JetBlue, Southwest, and Delta to help keep travelers safe while flying. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Chicago to Massachusetts. Policies will vary by airline.

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 Spirit Airlines. 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 $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $48, but on average you can expect to pay $70.

Are there nonstop flights from Chicago to Massachusetts for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Massachusetts under $100. A good price for a nonstop flight from Chicago to Massachusetts is less than $111.

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

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

What days are nonstop flights available from Chicago to Massachusetts?

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

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

The most popular airlines flying from Chicago to Massachusetts are Major Airline, American Airlines and JetBlue. Something to consider prior to booking your flight.

What are the most popular routes from Chicago to Massachusetts?

While some choose either Chicago Midway - Boston Logan Intl or Chicago O'Hare Intl - Hyannis Barnstable, Chicago O'Hare Intl - Boston Logan Intl is the most popular route from Chicago to Massachusetts.

What are the cheapest Flights from Chicago to Massachusetts?

Looking for the cheapest flight from Chicago to Massachusetts? While on average our users pay $154, our data indicates the cheapest price to be $54. The most popular route (Chicago O'Hare Intl - Boston Logan Intl), is priced around $67.

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: Icelandair (100%), EL AL (100%), Royal Air Maroc( 100%).

How long is the flight from Chicago to Massachusetts?

JetBlue, Major Airline, and American Airlines can get you from Chicago to Massachusetts in just under 2h 10m. Your travel time will be generally consistent. All flights are typically nonstop.

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

Currently priced at $48, Spirit Airlines will fly you from Chicago to Massachusetts and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Major Airline and American Airlines - these airlines can fly you to your destination from $82 and $89, respectively.

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

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $24. United Airlines flights start at $41 while deals on Delta start at $53 one-way.

Arrival points for flights from Chicago to Massachusetts

Destination information for Massachusetts

Things to know before you go. Useful info for your trip from Chicago to Massachusetts
Flight duration
2h 38m

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

Boston (BOS)
Beverly (BVY)
New Bedford (EWB)
Hyannis (HYA)
West Tisbury Martha's Vineyard (MVY)
Home North America USA Massachusetts Cheap flights from Chicago to Massachusetts