$83+ Cheap flights from Illinois 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jun 7 — Jun 141
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to MassachusettsExplore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
Explore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/3. 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.
Tue 7/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 7/288:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/3![JetBlue logo]()
$165
This Jetabroad deal was found by Cheapflights users on 5/5. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2410:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/5![JetBlue logo]()
$166
This Delta deal was found by Cheapflights users on 5/6. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/6![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 5/3. 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 6/166:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 7/11:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/178:59 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 6/247:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/3![American Airlines logo]()
$168
This Priceline deal was found by Cheapflights users on 5/4. 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.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Super.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$170
This Delta deal was found by Cheapflights users on 5/5. 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.
Sat 5/304:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/5![Delta logo]()
$172
This Southwest deal was found by Cheapflights users on 5/4. 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 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sun 5/316:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Fri 6/55:00 am
BOS
- ORD
Nonstop2h 58m
American Airlines
Deal found 5/4![American Airlines logo]()
$176
Best flights from Illinois to MassachusettsDiscover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 2026.
Discover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 8, 2026.
This JetBlue deal was found by Cheapflights users on 5/5. 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.
Thu 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/125:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/5![JetBlue logo]()
$172
This Delta deal was found by Cheapflights users on 5/4. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/4![Delta logo]()
$174
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/59:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Mon 6/88:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/5![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/3. 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 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 6/95:50 am
BOS
- MDW
1 stop5h 55m
Southwest
Deal found 5/3![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 5/4. 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 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 7/135:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$177
This KAYAK deal was found by Cheapflights users on 5/4. 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 5/198:15 am
ORD
- ALB
Nonstop2h 12m
American Airlines
Thu 5/211:27 pm
ALB
- ORD
Nonstop2h 43m
American Airlines
Deal found 5/4![American Airlines logo]()
$361
This JetBlue deal was found by Cheapflights users on 5/6. 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 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/6![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 5/3. 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 7/166:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Tue 7/215:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/3![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 5/5. 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 7/146:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 7/165:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/5![Southwest logo]()
$187
This Sun Country Air deal was found by Cheapflights users on 5/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:19 pm
ORD
- BDL
1 stop13h 18m
Sun Country Air
Mon 6/1511:37 am
BDL
- ORD
1 stop6h 52m
Sun Country Air
Deal found 5/3![Sun Country Air logo]()
$425
This United Airlines deal was found by Cheapflights users on 5/7. 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 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 6/105:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/7![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 5/3. 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 5/3012:05 pm
MDW
- BOS
1 stop10h 35m
Southwest
Sun 5/316:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/3![Southwest logo]()
$188
This United Airlines deal was found by Cheapflights users on 5/7. 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 6/36:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 6/56:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/7![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 5/7. 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 6/19:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/105:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/7![Southwest logo]()
$192
This JetBlue deal was found by Cheapflights users on 5/7. 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.
Sun 7/58:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Fri 7/105:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/7![JetBlue logo]()
$246
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/57:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sun 6/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/3![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 5/5. 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 6/307:05 am
ORD
- ACK
1 stop7h 43m
Delta
Fri 7/312:06 pm
ACK
- ORD
1 stop5h 39m
Delta
Deal found 5/5![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 5/4. 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 7/169:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/195:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/4![United Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 5/6. 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 6/122:45 pm
MDW
- BOS
1 stop7h 40m
Southwest
Mon 6/155:35 am
BOS
- MDW
1 stop5h 25m
Southwest
Deal found 5/6![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 5/5. 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.
Wed 7/15:22 pm
ORD
- ALB
1 stop5h 02m
Delta
Tue 7/712:25 pm
ALB
- ORD
1 stop6h 38m
Delta
Deal found 5/5![Delta logo]()
$325
This United Airlines deal was found by Cheapflights users on 5/7. 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 8/156:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Wed 8/196:42 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/7![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 5/5. 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 7/232:30 pm
MDW
- BOS
1 stop8h 35m
Southwest
Mon 7/278:00 pm
BOS
- MDW
1 stop5h 05m
Southwest
Deal found 5/5![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 5/3. 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 6/246:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 7/115:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/3![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 5/5. 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.
Sat 6/273:25 pm
ORD
- ALB
1 stop7h 34m
Delta
Wed 7/15:45 am
ALB
- ORD
1 stop4h 29m
Delta
Deal found 5/5![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 5/3. 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 7/256:21 pm
ORD
- MVY
1 stop18h 03m
American Airlines
Sat 8/15:08 pm
MVY
- ORD
1 stop7h 22m
American Airlines
Deal found 5/3![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 5/5. 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.
Sat 6/273:25 pm
ORD
- ALB
1 stop7h 34m
Delta
Tue 6/3012:27 pm
ALB
- ORD
1 stop5h 18m
Delta
Deal found 5/5![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 5/5. 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 8/136:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 8/188:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Deal found 5/5![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 5/5. 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 7/216:00 am
ORD
- ACK
1 stop4h 32m
Delta
Wed 7/2912:13 pm
ACK
- ORD
2 stops7h 16m
Delta
Deal found 5/5![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 5/5. 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 6/47:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 6/145:50 am
BOS
- MDW
1 stop5h 20m
Southwest
Deal found 5/5![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 5/7. 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 6/237:30 am
ORD
- ALB
Nonstop2h 13m
United Airlines
Tue 6/307:30 pm
ALB
- ORD
1 stop5h 01m
United Airlines
Deal found 5/7![United Airlines logo]()
$315
Last-minute flights from Illinois to MassachusettsDiscover last-minute flight deals from Illinois to Massachusetts. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Massachusetts. Data last updated May 8, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 5/4. 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.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Tue 5/269:12 am
BOS
- ORD
1 stop11h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 5/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$164
This Super.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/3![JetBlue logo]()
$170
This Delta deal was found by Cheapflights users on 5/6. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/6![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 5/5. 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.
Sat 5/304:30 pm
ORD
- BOS
Nonstop2h 36m
Delta
Sun 5/317:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 5/5![Delta logo]()
$172
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sun 5/316:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Fri 6/55:00 am
BOS
- ORD
Nonstop2h 58m
American Airlines
Deal found 5/4![American Airlines logo]()
$176
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/49:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 6/116:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/5![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/4. 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 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/4![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 5/3. 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 6/166:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 7/11:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/3![Southwest logo]()
$167
This American Airlines deal was found by Cheapflights users on 5/3. 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 6/178:59 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 6/247:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/3![American Airlines logo]()
$168
This Jetabroad deal was found by Cheapflights users on 5/5. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2410:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Tue 6/308:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/5![JetBlue logo]()
$166
One-way flights from Illinois to MassachusettsSearch for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
Search for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This Super.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$83
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/36:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 5/5. 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 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/5![Southwest logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Tue 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/5![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/5. 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.
Tue 6/912:27 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 5/5![Frontier logo]()
$85
This Flysmarter deal was found by Cheapflights users on 5/4. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/131:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 5/4![JetBlue logo]()
$86
This Super.com deal was found by Cheapflights users on 5/5. 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.
Fri 5/298:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/5![JetBlue logo]()
$87
This United Airlines deal was found by Cheapflights users on 5/5. 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 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/5![United Airlines logo]()
$89
This Southwest deal was found by Cheapflights users on 5/6. 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 6/54:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/6![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 9/27:55 am
ORD
- ALB
1 stop25h 30m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$90
This Super.com deal was found by Cheapflights users on 5/5. 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.
Wed 5/209:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/5![JetBlue logo]()
$93
Find flight deals from Illinois to Massachusetts
Keep the following information in mind while searching for Illinois to Massachusetts flight deals. Data was last updated May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $83 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $227 |
Good round-trip deal | $208 or less |
Good one-way deal | $108 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 May 8, 2026.
Use the filters below to find and compare flights from Illinois 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
Thu 8/6
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Wed 8/12
5:20 pm-7:25 pm
Nonstop3h 05m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Sun 5/31
7:35 am-9:27 am
Nonstop2h 52m
$174
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Mon 6/8
8:15 am-10:12 am
Nonstop2h 57m
$177
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 6/6
5:45 pm-9:05 pm
Nonstop2h 20m
Boston Logan Intl
Tue 6/9
5:50 am-10:45 am
1 stop5h 55m
$177
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 7/11
5:25 am-8:40 am
Nonstop2h 15m
Boston Logan Intl
Mon 7/13
5:25 am-7:00 am
Nonstop2h 35m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
1:56 pm-5:27 pm
Nonstop2h 31m
Boston Logan Intl
Sun 5/31
6:00 am-8:00 am
Nonstop3h 00m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 7/16
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Tue 7/21
5:45 am-9:36 am
1 stop4h 51m
$182
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 7/14
6:05 pm-9:20 pm
Nonstop2h 15m
Boston Logan Intl
Thu 7/16
5:25 am-7:00 am
Nonstop2h 35m
$187
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/30
12:05 pm-11:40 pm
1 stop10h 35m
Boston Logan Intl
Sun 5/31
6:10 am-7:55 am
Nonstop2h 45m
$188
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 6/1
9:25 am-12:40 pm
Nonstop2h 15m
Boston Logan Intl
Wed 6/10
5:35 am-7:10 am
Nonstop2h 35m
$192
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
ORD-ALB
STL-ALB
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 Illinois to Massachusetts
USIL-USMA
ORD-BOS
MDW-BOS
ORD-ALB
STL-ALB
How far ahead should I book a flight from Illinois to Massachusetts?
To ensure you get the cheapest price possible for a flight from Illinois to Massachusetts, you should look to book at least 71 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Illinois to Massachusetts?
Currently, November is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $182). Flying from Illinois to Massachusetts in October is currently the most expensive (average of $293). 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 IL to MA?
Find hourly flight availability from Illinois 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 May 8, 2026.
When flying from Illinois to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 45% versus a flight in the morning.
What is the cheapest day to fly from Illinois to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Massachusetts. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Illinois to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Illinois to Massachusetts
Explore weekly flight availability from Illinois 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 May 8, 2026.
The most flights from USIL to USMA are scheduled on a Thursday (70 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 Illinois 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 May 8, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Illinois to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Illinois 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.
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Alternative routes for Illinois 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 Illinois to Massachusetts by cabin class
Find flights from Illinois to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Massachusetts flights
Browse other Illinois and Massachusetts flight options. Last updated on May 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Illinois after your stay in Massachusetts
Illinois to Massachusetts flights
Consider these flights traveling from Illinois to Massachusetts.
Top 6 airlines flying from Illinois to Massachusetts
Discover the top 6 airlines that operate flights from Illinois 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$413 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$87 | Average$228 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$356 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$121 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$126 | Average$250 | FlexibilityNo cancel fee | On-time63% |