$79+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
May 23 — May 301
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 April 23, 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 April 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 8/510:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/21![JetBlue logo]()
$146
This Delta deal was found by Cheapflights users on 4/20. 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
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 4/20. 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 5/197:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/20![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 4/20. 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 5/287:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 4/20. 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 5/297:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/18:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/20![Delta logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
Thu 6/48:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/22![JetBlue logo]()
$151
This Southwest deal was found by Cheapflights users on 4/20. 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/20![Southwest logo]()
$151
This JetBlue deal was found by Cheapflights users on 4/22. 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 8/48:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/22![JetBlue logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/21![JetBlue logo]()
$153
This JetBlue deal was found by Cheapflights users on 4/22. 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 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/22![JetBlue logo]()
$154
This United Airlines deal was found by Cheapflights users on 4/22. 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 8/207:33 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Wed 8/2612:30 pm
BOS
- ORD
Nonstop2h 51m
United Airlines
Deal found 4/22![United Airlines logo]()
$155
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 April 23, 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 April 23, 2026.
This Delta deal was found by Cheapflights users on 4/21. 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 5/2911:26 am
ORD
- BOS
1 stop5h 29m
Delta
Tue 6/22:00 pm
BOS
- ORD
1 stop6h 09m
Delta
Deal found 4/21![Delta logo]()
$169
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Mon 5/256:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 5/286:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/19![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 4/21. 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 5/291:55 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/211:40 am
BOS
- MDW
1 stop5h 35m
Southwest
Deal found 4/21![Southwest logo]()
$190
This JetBlue deal was found by Cheapflights users on 4/18. 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 4/289:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/18![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 4/21. 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 5/296:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Tue 6/25:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/21![Delta logo]()
$169
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/52:28 pm
CMI
- BOS
1 stop6h 40m
American Airlines
Sat 5/94:32 pm
BOS
- CMI
1 stop6h 03m
American Airlines
Deal found 4/20![American Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 4/21. 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 5/227:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/21![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 4/18. 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 5/123:00 pm
MDW
- BOS
1 stop6h 30m
Southwest
Sat 5/167:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/18![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/226:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Fri 5/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/22![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 4/21. 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 5/187:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/209:05 am
BOS
- ORD
1 stop4h 56m
Delta
Deal found 4/21![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 4/21. 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 5/301:55 pm
ORD
- BOS
1 stop7h 10m
Southwest
Wed 6/38:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Deal found 4/21![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 4/18. 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 6/297:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/305:50 am
BOS
- MDW
1 stop5h 55m
Southwest
Deal found 4/18![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 4/21. 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 6/27:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Thu 6/117:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/21![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/19. 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 5/249:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Mon 5/256:00 am
BOS
- ORD
2 stops9h 41m
United Airlines
Deal found 4/19![United Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 4/22. 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 5/203:00 pm
MDW
- BOS
1 stop6h 30m
Southwest
Sun 5/248:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/22![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/18. 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 7/156:30 am
CMI
- BOS
2 stops7h 10m
United Airlines
Wed 7/227:19 am
BOS
- CMI
1 stop6h 31m
United Airlines
Deal found 4/18![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/66:05 am
CMI
- BOS
1 stop4h 27m
American Airlines
Sat 5/96:30 am
BOS
- CMI
1 stop8h 17m
American Airlines
Deal found 4/22![American Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 4/22. 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 5/223:50 pm
ORD
- BOS
Nonstop2h 37m
Delta
Tue 5/262:00 pm
BOS
- ORD
1 stop7h 26m
Delta
Deal found 4/22![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 4/19. 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 5/285:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Sun 5/315:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 4/19![Southwest logo]()
$247
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/62:38 pm
CMI
- BOS
1 stop5h 34m
American Airlines
Sun 5/106:30 am
BOS
- CMI
1 stop8h 17m
American Airlines
Deal found 4/21![American Airlines logo]()
$350
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.
Wed 6/37:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Mon 6/85:30 am
BOS
- ORD
1 stop6h 15m
Delta
Deal found 4/17![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 4/19. 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 6/115:20 pm
MDW
- BOS
1 stop5h 45m
Southwest
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/19![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 4/18. 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 5/1911:57 am
MLI
- BOS
1 stop4h 25m
United Airlines
Tue 5/267:19 am
BOS
- MLI
1 stop6h 21m
United Airlines
Deal found 4/18![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/82:17 pm
CMI
- BOS
1 stop7h 11m
American Airlines
Mon 5/114:32 pm
BOS
- CMI
1 stop6h 03m
American Airlines
Deal found 4/22![American Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 4/20. 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 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 6/112:20 pm
BOS
- MDW
1 stop8h 00m
Southwest
Deal found 4/20![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 4/22. 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 7/167:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Sun 7/195:40 am
BOS
- ORD
1 stop5h 57m
Delta
Deal found 4/22![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 4/21. 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 6/202:31 pm
MLI
- BOS
1 stop6h 25m
United Airlines
Thu 6/258:15 pm
BOS
- MLI
1 stop5h 09m
United Airlines
Deal found 4/21![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/511:16 am
BMI
- BOS
1 stop6h 34m
American Airlines
Sat 5/96:30 am
BOS
- BMI
1 stop5h 16m
American Airlines
Deal found 4/20![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Mon 6/299:49 am
CMI
- BOS
1 stop5h 40m
United Airlines
Fri 7/35:45 am
BOS
- CMI
2 stops8h 05m
United Airlines
Deal found 4/19![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 4/21. 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 7/82:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 7/128:15 pm
BOS
- MDW
1 stop4h 25m
Southwest
Deal found 4/21![Southwest logo]()
$277
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated April 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 5/165:35 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 4/21![American Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 4/20. 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/20![Southwest logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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.
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/21![JetBlue logo]()
$153
This Southwest deal was found by Cheapflights users on 4/20. 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 5/197:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/20![Southwest logo]()
$148
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/206:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Sun 5/245:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/21![United Airlines logo]()
$156
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This JetBlue deal was found by Cheapflights users on 4/22. 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 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/22![JetBlue logo]()
$154
This Delta deal was found by Cheapflights users on 4/20. 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 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Jetabroad deal was found by Cheapflights users on 4/21. 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.
Thu 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/21![JetBlue logo]()
$152
This SmartFares deal was found by Cheapflights users on 4/20. 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.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/20![JetBlue logo]()
$155
This Delta deal was found by Cheapflights users on 4/20. 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 5/297:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/18:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/20![Delta logo]()
$150
This Delta deal was found by Cheapflights users on 4/20. 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
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
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 April 23, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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 8/1210:35 am
ORD
- BOS
1 stop4h 51m
Delta
Deal found 4/20![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/20. 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 6/66:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/20![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/20. 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 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/20![Delta logo]()
$80
This Delta deal was found by Cheapflights users on 4/21. 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 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/21![Delta logo]()
$80
This United Airlines deal was found by Cheapflights users on 4/20. 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 5/236:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/20![United Airlines logo]()
$81
This Southwest deal was found by Cheapflights users on 4/20. 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 5/197:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/20![Southwest logo]()
$81
This SmartFares deal was found by Cheapflights users on 4/21. 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.
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/21![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 7/148:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/21![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 4/20. 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 9/23:00 pm
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/20![Delta logo]()
$84
This Southwest deal was found by Cheapflights users on 4/19. 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/19![Southwest logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/20. 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 4/20![American Airlines logo]()
$85
This Jetabroad deal was found by Cheapflights users on 4/20. 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.
Thu 5/147:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 4/20![JetBlue logo]()
$87
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 April 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (Cheapflightsfares) |
One-way from | $79 (Delta) |
Popular in | April |
Cheapest in | January |
Average price | $273 |
Good round-trip deal | $209 or less |
Good one-way deal | $110 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 April 23, 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
Fri 5/29
11:26 am-5:55 pm
1 stop5h 29m
Boston Logan Intl
Tue 6/2
2:00 pm-7:09 pm
1 stop6h 09m
$169
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/29
6:36 pm-11:29 pm
1 stop3h 53m
Boston Logan Intl
Tue 6/2
5:40 am-8:43 am
1 stop4h 03m
$169
Quickest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 5/25
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Thu 5/28
6:00 am-7:58 am
Nonstop2h 58m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/22
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/27
8:40 pm-10:35 pm
Nonstop2h 55m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 5/18
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/20
9:05 am-1:01 pm
1 stop4h 56m
$187
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/29
1:55 pm-5:10 pm
Nonstop2h 15m
Boston Logan Intl
Tue 6/2
11:40 am-4:15 pm
1 stop5h 35m
$190
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 5/12
3:00 pm-10:30 pm
1 stop6h 30m
Boston Logan Intl
Sat 5/16
7:15 am-9:05 am
Nonstop2h 50m
$202
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/28
9:41 am-1:07 pm
Nonstop2h 26m
Boston Logan Intl
Thu 4/30
7:02 am-8:59 am
Nonstop2h 57m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/2
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Thu 6/11
7:30 am-9:28 am
Nonstop2h 58m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
1:55 pm-10:05 pm
1 stop7h 10m
Boston Logan Intl
Wed 6/3
8:10 am-12:50 pm
1 stop5h 40m
$222
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
MLI-BOS
PIA-BOS
CMI-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
MLI-BOS
PIA-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 $182). Flying from Illinois to Boston 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 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 April 23, 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 19% versus a flight at noon.
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 April 18, 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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 23, 2026.
The most flights from USIL to BOS are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).
How much does it cost to fly round-trip from Illinois to Boston?
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 locationsMedford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
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
Boston flight routes
Complete your trip
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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 April 23, 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 April 23, 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 6 airlines flying from Illinois to Boston
Discover the top 6 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 April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$164 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$225 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$400 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$118 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$126 | Average$249 | FlexibilityNo cancel fee | On-time63% |