$78+ Cheap flights from Chicago (CHI) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
May 17 — May 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Massachusetts
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to MassachusettsExplore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Orbitz deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Sat 5/912:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/15![Frontier logo]()
$144
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/16![JetBlue logo]()
$146
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/16![JetBlue logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Sat 5/912:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/13![Frontier logo]()
$151
This flygcity.se deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:50 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/12![JetBlue logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:50 am
ORD
- BOS
1 stop26h 26m
Frontier
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Deal found 4/12![Frontier logo]()
$153
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:39 pm
ORD
- BOS
Nonstop2h 33m
American Airlines
Thu 4/306:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:41 am
MDW
- BOS
1 stop23h 31m
Frontier
Wed 5/612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/12![Frontier logo]()
$156
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Deal found 4/13![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/206:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/14![Frontier logo]()
$160
Best flights from Chicago to MassachusettsDiscover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:46 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Tue 9/88:10 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/13![United Airlines logo]()
$167
This JetBlue deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/268:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/16![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1210:30 am
ORD
- BOS
Nonstop2h 27m
Delta
Sat 5/165:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 4/16![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/911:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 5/132:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/14![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:00 am
ORD
- ORH
1 stop10h 53m
American Airlines
Mon 6/295:18 pm
ORH
- ORD
1 stop8h 16m
American Airlines
Deal found 4/14![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Thu 5/146:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/12![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:00 pm
ORD
- BOS
Nonstop2h 35m
Delta
Thu 9/107:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/14![Delta logo]()
$186
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Sat 8/298:22 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/16![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:45 pm
ORD
- ORH
1 stop19h 29m
American Airlines
Mon 5/182:39 pm
ORH
- ORD
1 stop21h 59m
American Airlines
Deal found 4/13![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sat 8/227:00 pm
BOS
- ORD
1 stop5h 16m
United Airlines
Deal found 4/16![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/265:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Sat 8/15:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/13![Southwest logo]()
$227
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:40 am
ORD
- ORH
1 stop9h 13m
American Airlines
Mon 6/295:18 pm
ORH
- ORD
1 stop8h 16m
American Airlines
Deal found 4/14![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 5/245:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/14![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Tue 5/267:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 4/16![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 5/167:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/15![Southwest logo]()
$234
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:30 am
ORD
- ORH
1 stop4h 44m
American Airlines
Mon 5/42:39 pm
ORH
- ORD
1 stop21h 02m
American Airlines
Deal found 4/15![American Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:10 am
ORD
- ORH
2 stops8h 33m
Delta
Mon 5/45:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/15![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Sat 5/167:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/15![United Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:50 pm
MDW
- BOS
1 stop6h 25m
Southwest
Mon 6/85:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/16![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:15 pm
ORD
- ORH
1 stop17h 59m
American Airlines
Sat 5/22:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Deal found 4/12![American Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Wed 9/236:42 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/13![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:10 pm
MDW
- BOS
2 stops6h 40m
Southwest
Sun 5/106:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/13![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:45 am
ORD
- ORH
1 stop4h 58m
Delta
Mon 5/45:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/16![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Mon 6/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/13![United Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:35 am
ORD
- ORH
1 stop6h 08m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 55m
Delta
Deal found 4/17![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/172:35 pm
MDW
- BOS
1 stop7h 05m
Southwest
Sat 6/275:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/14![Southwest logo]()
$257
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:00 am
ORD
- HYA
1 stop6h 24m
American Airlines
Sat 7/113:02 pm
HYA
- ORD
1 stop7h 22m
American Airlines
Deal found 4/12![American Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:20 am
MDW
- BOS
1 stop6h 45m
Southwest
Tue 9/297:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/16![Southwest logo]()
$262
This JetBlue deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:12 am
ORD
- MVY
1 stop4h 57m
JetBlue
Wed 7/85:05 pm
MVY
- ORD
1 stop5h 22m
JetBlue
Deal found 4/15![JetBlue logo]()
$426
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:15 am
ORD
- ORH
2 stops10h 28m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/17![Delta logo]()
$266
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated April 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:39 pm
ORD
- BOS
Nonstop2h 33m
American Airlines
Thu 4/306:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Deal found 4/13![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:50 am
ORD
- BOS
1 stop26h 26m
Frontier
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Deal found 4/12![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:41 am
MDW
- BOS
1 stop23h 31m
Frontier
Wed 5/612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/12![Frontier logo]()
$156
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Sat 5/912:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/13![Frontier logo]()
$151
This Orbitz deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Sat 5/912:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/15![Frontier logo]()
$144
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/16![JetBlue logo]()
$151
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/16![JetBlue logo]()
$146
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$154
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/206:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/14![Frontier logo]()
$160
This flygcity.se deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:50 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/12![JetBlue logo]()
$152
One-way flights from Chicago to MassachusettsSearch for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/14![Frontier logo]()
$78
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 4/14![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$79
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$80
This Super.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/12![JetBlue logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 4/15![Frontier logo]()
$81
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$82
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/13![United Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/13![Southwest logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/15![American Airlines logo]()
$85
This Super.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/15![JetBlue logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- BOS
1 stop26h 16m
Frontier
Deal found 4/14![Frontier logo]()
$86
Find flight deals from Chicago to Massachusetts
Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $144 (Orbitz) |
One-way from | $78 (Expedia) |
Popular in | April |
Cheapest in | January |
Average price | $272 |
Good round-trip deal | $198 or less |
Good one-way deal | $112 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/2
7:46 pm-11:20 pm
Nonstop2h 34m
Boston Logan Intl
Tue 9/8
8:10 am-10:08 am
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/25
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Wed 8/26
8:10 am-10:06 am
Nonstop2h 56m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/12
10:30 am-1:57 pm
Nonstop2h 27m
Boston Logan Intl
Sat 5/16
5:30 pm-7:33 pm
Nonstop3h 03m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/9
11:25 am-2:45 pm
Nonstop2h 20m
Boston Logan Intl
Wed 5/13
2:25 pm-4:05 pm
Nonstop2h 40m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/7
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Thu 5/14
6:00 am-8:00 am
Nonstop3h 00m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 5/10
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sat 8/29
8:22 pm-10:19 pm
Nonstop2h 57m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
6:23 pm-9:59 pm
Nonstop2h 36m
Boston Logan Intl
Sat 8/22
7:00 pm-11:16 pm
1 stop5h 16m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
3:55 pm-7:30 pm
Nonstop2h 35m
Boston Logan Intl
Sun 5/24
5:45 am-9:36 am
1 stop4h 51m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/1
3:00 pm-6:35 pm
Nonstop2h 35m
Boston Logan Intl
Thu 9/10
7:30 am-9:28 am
Nonstop2h 58m
$186
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/14
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Sat 5/16
7:30 am-9:30 am
Nonstop3h 00m
$194
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
MDW-BOS
ORD-BOS
ORD-ORH
ORD-HYA
ORD-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Massachusetts
CHI-USMA
MDW-BOS
ORD-BOS
ORD-ORH
ORD-HYA
What is the cheapest month to book a flight from Chicago to Massachusetts?
Currently, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $182). Flying from Chicago to Massachusetts in December is currently the most expensive (average of $283). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to MA?
Find hourly flight availability from Chicago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.
What is the cheapest day to fly from Chicago to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Massachusetts
Explore weekly flight availability from Chicago to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 17, 2026.
The most flights from CHI to USMA are scheduled on a Thursday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).
How much does it cost to fly round-trip from Chicago to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated April 17, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Chicago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Massachusetts by cabin class
Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Massachusetts flights
Browse other Chicago and Massachusetts flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Massachusetts flights
Consider these flights traveling from Chicago to Massachusetts.
Top 6 airlines flying from Chicago to Massachusetts
Discover the top 6 airlines that operate flights from Chicago to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$65 | Average$366 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$86 | Average$257 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$250 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$118 | Average$383 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$126 | Average$251 | FlexibilityNo cancel fee | On-time63% |