$94+ Cheap flights from Illinois to Boston (BOS)
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 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jul 18 — Jul 251
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to BostonExplore the most affordable flight options available from Illinois to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.
Explore the most affordable flight options available from Illinois to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.
This Jetabroad deal was found by Cheapflights users on 6/16. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/35:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 6/16![JetBlue logo]()
$176
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Wed 7/2212:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 6/16![JetBlue logo]()
$177
This Delta deal was found by Cheapflights users on 6/17. 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.
Sat 9/57:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/17![Delta logo]()
$178
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:12 am
ORD
- BOS
1 stop7h 37m
JetBlue
Sat 7/115:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
Deal found 6/17![JetBlue logo]()
$179
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 7/155:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:43 am
ORD
- BOS
1 stop4h 57m
United Airlines
Sat 7/117:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$180
This Jetabroad deal was found by Cheapflights users on 6/14. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Tue 7/712:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 6/14![JetBlue logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
ORD
- BOS
1 stop4h 21m
JetBlue
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 10m
JetBlue
Deal found 6/16![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 6/13. 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.
Mon 6/299:20 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 7/45:40 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 6/13![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/15. 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.
Sat 7/116:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 7/137:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/15![Delta logo]()
$183
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 7/117:55 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$183
Best flights from Illinois to BostonDiscover carefully curated flight deals from Illinois to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2026.
Discover carefully curated flight deals from Illinois to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2026.
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 7/184:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/17![JetBlue logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Sun 7/56:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Fri 7/108:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/12![United Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 6/15. 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.
Mon 8/177:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 8/227:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/15![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 7/65:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/12![Southwest logo]()
$230
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 7/311:37 am
CMI
- BOS
1 stop6h 09m
American Airlines
Sat 7/115:10 am
BOS
- CMI
1 stop6h 57m
American Airlines
Deal found 6/15![American Airlines logo]()
$306
This JetBlue deal was found by Cheapflights users on 6/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Thu 9/105:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 6/14![JetBlue logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Fri 7/38:33 am
EVV
- BOS
2 stops23h 17m
Multiple Airlines
Tue 7/710:04 am
BOS
- EVV
1 stop30h 45m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$409
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 9/511:05 am
BOS
- ORD
Nonstop2h 54m
JetBlue
Deal found 6/12![JetBlue logo]()
$197
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Thu 10/17:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Mon 10/59:23 am
BOS
- ORD
Nonstop2h 52m
United Airlines
Deal found 6/16![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:50 pm
ORD
- BOS
Nonstop2h 35m
Delta
Mon 10/268:10 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/13![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 6/15. 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 7/155:30 pm
MDW
- BOS
1 stop4h 55m
Southwest
Sat 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/15![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1011:41 am
EVV
- BOS
1 stop21h 28m
Allegiant Air
Sun 7/1210:40 am
BOS
- EVV
2 stops25h 11m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$490
This JetBlue deal was found by Cheapflights users on 6/15. 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.
Tue 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sat 7/44:43 pm
BOS
- ORD
1 stop5h 47m
JetBlue
Deal found 6/15![JetBlue logo]()
$211
This Delta deal was found by Cheapflights users on 6/16. 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 6/304:00 pm
ORD
- BOS
Nonstop2h 43m
Delta
Sat 7/45:05 pm
BOS
- ORD
Nonstop3h 12m
Delta
Deal found 6/16![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 7/135:20 pm
BOS
- MDW
1 stop5h 40m
Southwest
Deal found 6/16![Southwest logo]()
$244
This JetBlue deal was found by Cheapflights users on 6/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/181:09 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Wed 7/225:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/14![JetBlue logo]()
$213
This Southwest deal was found by Cheapflights users on 6/16. 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.
Sat 8/87:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 8/106:35 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/16![Southwest logo]()
$256
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/46:04 am
CMI
- BOS
1 stop7h 34m
American Airlines
Tue 7/79:37 am
BOS
- CMI
2 stops9h 29m
American Airlines
Deal found 6/15![American Airlines logo]()
$312
This JetBlue deal was found by Cheapflights users on 6/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Mon 7/135:10 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 6/12![JetBlue logo]()
$214
This American Airlines deal was found by Cheapflights users on 6/15. 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 7/166:04 pm
BMI
- BOS
1 stop5h 01m
American Airlines
Thu 7/236:30 pm
BOS
- BMI
1 stop7h 05m
American Airlines
Deal found 6/15![American Airlines logo]()
$319
This JetBlue deal was found by Cheapflights users on 6/16. 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 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Fri 7/38:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/16![JetBlue logo]()
$220
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 7/118:00 am
MDW
- BOS
2 stops7h 20m
Southwest
Sat 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/13![Southwest logo]()
$269
This United Airlines deal was found by Cheapflights users on 6/13. 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 7/16:45 pm
DEC
- BOS
1 stop5h 29m
United Airlines
Tue 7/712:30 pm
BOS
- DEC
1 stop6h 26m
United Airlines
Deal found 6/13![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:25 pm
MDW
- BOS
1 stop6h 33m
Delta
Sun 11/15:30 am
BOS
- MDW
1 stop4h 15m
Delta
Deal found 6/13![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 7/96:04 pm
BMI
- BOS
1 stop5h 01m
American Airlines
Tue 7/1411:33 am
BOS
- BMI
2 stops7h 01m
American Airlines
Deal found 6/13![American Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 9/135:30 am
BOS
- MDW
1 stop5h 25m
Southwest
Deal found 6/12![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 7/35:43 pm
PIA
- BOS
1 stop6h 31m
United Airlines
Thu 7/99:50 am
BOS
- PIA
1 stop5h 07m
United Airlines
Deal found 6/14![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 6/14. 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.
Wed 8/55:09 pm
MLI
- BOS
1 stop5h 32m
Delta
Wed 8/125:30 am
BOS
- MLI
1 stop5h 55m
Delta
Deal found 6/14![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Sun 7/2610:05 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 6/17![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:45 pm
DEC
- BOS
1 stop5h 29m
United Airlines
Mon 7/2012:30 pm
BOS
- DEC
1 stop6h 26m
United Airlines
Deal found 6/17![United Airlines logo]()
$350
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated June 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/13. 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.
Mon 6/299:20 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 7/45:40 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 6/13![Southwest logo]()
$182
This Jetabroad deal was found by Cheapflights users on 6/14. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Tue 7/712:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 6/14![JetBlue logo]()
$181
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:12 am
ORD
- BOS
1 stop7h 37m
JetBlue
Sat 7/115:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
Deal found 6/17![JetBlue logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:43 am
ORD
- BOS
1 stop4h 57m
United Airlines
Sat 7/117:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/71:55 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Fri 7/106:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/17![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 7/117:55 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 7/155:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$179
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 7/184:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/17![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/15. 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.
Sat 7/116:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 7/137:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/15![Delta logo]()
$183
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Wed 7/2212:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 6/16![JetBlue logo]()
$177
This Jetabroad deal was found by Cheapflights users on 6/16. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/35:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 6/16![JetBlue logo]()
$176
One-way flights from Illinois to BostonSearch for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Super.com deal was found by Cheapflights users on 6/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:21 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/17![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 6/17![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 6/307:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 6/15![United Airlines logo]()
$96
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:30 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$96
This Super.com deal was found by Cheapflights users on 6/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/13![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/17![JetBlue logo]()
$98
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 7/17:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 6/16![Delta logo]()
$101
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/2112:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Deal found 6/15![JetBlue logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/17![JetBlue logo]()
$103
This Delta deal was found by Cheapflights users on 6/15. 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.
Sun 9/207:30 am
ORD
- BOS
Nonstop2h 33m
Delta
Deal found 6/15![Delta logo]()
$104
Find flight deals from Illinois to Boston
Keep the following information in mind while searching for Illinois to Boston flight deals. Data was last updated June 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Jetabroad) |
One-way from | $94 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $258 |
Good round-trip deal | $224 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Boston 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 June 18, 2026.
Use the filters below to find and compare flights from Illinois to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/15
8:10 pm-11:41 pm
Nonstop2h 31m
Boston Logan Intl
Sat 7/18
4:43 pm-9:58 pm
1 stop6h 15m
$180
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/1
6:00 am-2:41 pm
1 stop7h 41m
Boston Logan Intl
Thu 9/10
5:00 pm-7:22 pm
Nonstop3h 22m
$188
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 7/5
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Fri 7/10
8:15 pm-10:15 pm
Nonstop3h 00m
$190
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/17
7:55 am-11:24 am
Nonstop2h 29m
Boston Logan Intl
Sat 8/22
7:30 am-9:26 am
Nonstop2h 56m
$192
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/1
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Sat 9/5
11:05 am-12:59 pm
Nonstop2h 54m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/30
6:00 am-2:22 pm
1 stop7h 22m
Boston Logan Intl
Sat 7/4
4:43 pm-9:30 pm
1 stop5h 47m
$211
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 7/18
1:09 pm-4:43 pm
Nonstop2h 34m
Boston Logan Intl
Wed 7/22
5:01 am-8:50 am
1 stop4h 49m
$213
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 7/11
6:00 am-2:24 pm
1 stop7h 24m
Boston Logan Intl
Mon 7/13
5:10 pm-7:15 pm
Nonstop3h 05m
$214
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/1
7:30 am-11:04 am
Nonstop2h 34m
Boston Logan Intl
Mon 10/5
9:23 am-11:15 am
Nonstop2h 52m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/30
6:00 am-2:22 pm
1 stop7h 22m
Boston Logan Intl
Fri 7/3
8:10 am-10:06 am
Nonstop2h 56m
$220
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
CMI-BOS
BMI-BOS
SPI-BOS
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 Boston
USIL-BOS
ORD-BOS
MDW-BOS
CMI-BOS
BMI-BOS
What is the cheapest month to book a flight from Illinois to Boston?
Currently, November is the cheapest month in which you can book a flight from Illinois to Boston (average of $181). Flying from Illinois to Boston in June is currently the most expensive (average of $324). 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 BOS?
Find hourly flight availability from Illinois to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 18, 2026.
When flying from Illinois to Boston, 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 11% versus a flight at noon.
Weekly flight availability from Illinois to Boston
Explore weekly flight availability from Illinois to Boston. 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 June 18, 2026.
The most flights from USIL to BOS are scheduled on a Wednesday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Illinois to Boston?
How far ahead should I book a flight from Illinois to Boston?
To ensure you get the cheapest price possible for a flight from Illinois to Boston, you should look to book at least 60 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 day to fly from Illinois to Boston?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Boston. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Illinois to Boston 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.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Cambridge
Concord
Brockton
Watertown
Hampton Beach
Seekonk
Cranston
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Dedham
Swansea
Old Orchard Beach
Lowell
Smithfield
Braintree
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
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Alternative routes for Illinois to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 18, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Boston by cabin class
Find flights from Illinois to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Boston flights
Browse other Illinois and Boston flight options. Last updated on June 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Illinois to Boston flights
Consider these flights traveling from Illinois to Boston.
Top 5 airlines flying from Illinois to Boston
Discover the top 5 airlines that operate flights from Illinois to Boston. 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$232 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$362 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$126 | Average$251 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$136 | Average$395 | FlexibilityNo cancel fee | On-time71% |