Menu

Cheap flights from Illinois (IL) 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
Add another flight clear all

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

Home North America USA Massachusetts Cheap flights from Illinois to Massachusetts

How to find the cheapest flight from
Illinois to Massachusetts

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

Travelers have found it’s best to book a flight 26 days in advance to save up to 23% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 26 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Illinois to Massachusetts 1-2 weeks in advance for as low as $270, or $316 for flights within the next 24 hours.

Cheap flights from Illinois to Massachusetts in July, August 2020

The best prices found for Illinois to Massachusetts flights for July, August
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Illinois to Massachusetts 2020 flight deals

Cheap flights to Massachusetts from Illinois found for this year
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Massachusetts from Illinois

Save time with Illinois to Massachusetts direct flight deals
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 29 Jul
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Illinois to Massachusetts

Late deals on round-trip flights to Massachusetts from Illinois, departing today and this week
27 Jun - 11 Jul
$95pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Jun - 11 Jul
$96pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
27 Jun - 12 Jul
$104pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Massachusetts from Illinois

The cheapest one-way flights from Illinois to Massachusetts
2:45 pm - 6:17 pm
British Airways
Nonstop
2h 32m
ORD - BOS
British Airways
$51
Ovago
2:16 pm - 5:33 pm
JetBlue
Nonstop
2h 17m
ORD - BOS
JetBlue
$63
1:10 pm - 4:36 pm
Major Airline
Nonstop
2h 26m
ORD - BOS
Major Airline
$64
StudentUniverse

Related info for your journey

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

Flight FAQs

From Illinois to Massachusetts

Are flight prices decreasing from Illinois 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 Illinois 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.

Can I find flights from Illinois to Massachusetts for under $100 on Cheapflights?

Yes, there are multiple flights from Illinois to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $32, but on average you can expect to pay $45.

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

Cheapflights has at least 20 direct flights from Illinois to Massachusetts under $100. A good price for a nonstop flight from Illinois to Massachusetts is less than $47.

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

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

What days are nonstop flights available from Illinois to Massachusetts?

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

How popular is this flight route?

This flight path from Illinois to Massachusetts was viewed by 207 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

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

When booking a flight from Illinois to Massachusetts, you may want to consider flying on Endeavor Airlines, JetBlue or Delta as they are the most popular for this route.

What are the most popular routes from Illinois to Massachusetts?

Most travelers choose Chicago O'Hare Intl - Boston Logan Intl, Chicago O'Hare Intl - West Tisbury Martha's Vineyard or Greater Peoria - Boston Logan Intl when deciding on the best route from Illinois to Massachusetts.

What are the cheapest Flights from Illinois to Massachusetts?

Looking at all options, your cheapest flight can be booked for $77. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $32 on average our data indicates $174 when flying from Illinois to Massachusetts

What are the most reliable airlines from Illinois to Massachusetts?

Consider Japan Airlines (100%), Icelandair (100%) or Emirates (100%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Massachusetts.

Related searches

Flights to Massachusetts from Illinois
Flights to Illinois Flights to Massachusetts

Rent a Car

Car Rentals in Massachusetts Car Rentals at Logan Intl Car Rentals at Nantucket Memorial

Destination points for flights from Illinois to Massachusetts

Show more

Destination information for Massachusetts

Things to know before you go. Useful info for your trip from Illinois to Massachusetts
Flight duration
2h 37m

Airports servicing

Belleville (BLV)
Bloomington (BMI)
Champaign (CMI)
Decatur (DEC)
Moline (MLI)
Marion (MWA)

Airports servicing

Laurence G. Hanscom Field (BED)
Boston (BOS)
Beverly (BVY)
New Bedford (EWB)
Hyannis (HYA)
West Tisbury Martha's Vineyard (MVY)

Popular flight searches

Check out other popular destinations found by fellow travelers