$110+ Cheap flights from Boston (BOS) to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Illinois with Cheapflights
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Cheapest flights from Boston to IllinoisExplore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/20![Frontier logo]()
$212
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop7h 15m
Tue 11/171:00 pm -
Nonstop2h 49m
Deal found 10/20![Multiple Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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.
Thu 12/35:55 pm -
Nonstop2h 45m
Sun 12/61:00 pm -
Nonstop2h 10m
Deal found 10/21![Southwest logo]()
$213
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/195:45 am -
Nonstop3h 06m
Mon 12/219:49 pm -
Nonstop2h 29m
Deal found 10/21![United Airlines logo]()
$213
This Frontier deal was found by Cheapflights users on 10/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/21![Frontier logo]()
$214
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/1212:12 pm -
Nonstop3h 06m
Sun 11/156:00 am -
Nonstop2h 29m
Deal found 10/21![American Airlines logo]()
$214
This Frontier deal was found by Cheapflights users on 10/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 20m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/22![Frontier logo]()
$215
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Mon 12/75:48 am -
Nonstop3h 11m
Mon 12/146:59 am -
Nonstop2h 33m
Deal found 10/23![American Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/177:10 am -
Nonstop2h 45m
Wed 11/189:40 am -
2 stops8h 25m
Deal found 10/23![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/195:20 am -
1 stop11h 10m
Mon 11/236:45 pm -
Nonstop2h 20m
Deal found 10/23![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/1010:00 am -
1 stop5h 23m
Sun 12/132:25 pm -
Nonstop2h 30m
Deal found 10/23![United Airlines logo]()
$217
This Priceline deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Thu 11/1212:39 pm -
1 stop7h 06m
Mon 11/168:15 pm -
Nonstop2h 44m
Deal found 10/23![Multiple Airlines logo]()
$218
Best flights from Boston to IllinoisDiscover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/35:05 pm -
1 stop5h 30m
Tue 12/151:15 pm -
Nonstop2h 05m
Deal found 10/23![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 11/129:15 am -
1 stop5h 44m
Sat 11/144:40 pm -
Nonstop2h 23m
Deal found 10/21![Delta logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/255:00 pm -
1 stop6h 15m
Thu 12/314:00 pm -
Nonstop2h 29m
Deal found 10/23![United Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/175:51 am -
1 stop5h 25m
Sun 1/175:44 pm -
1 stop5h 11m
Deal found 10/23![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/21. 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.
Wed 1/1312:55 pm -
1 stop4h 42m
Thu 1/217:00 am -
Nonstop2h 28m
Deal found 10/21![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/20. 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 11/175:55 pm -
Nonstop2h 45m
Wed 11/189:40 am -
2 stops8h 25m
Deal found 10/20![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/22. 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.
Sat 12/196:15 pm -
Nonstop3h 11m
Mon 1/412:15 pm -
1 stop5h 09m
Deal found 10/22![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/21. 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.
Mon 11/167:10 am -
Nonstop2h 45m
Wed 11/189:55 am -
2 stops8h 10m
Deal found 10/21![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/22. 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 12/109:05 am -
1 stop4h 56m
Sat 12/129:37 am -
1 stop5h 17m
Deal found 10/22![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/297:49 pm -
1 stop5h 12m
Sun 1/39:49 pm -
Nonstop2h 29m
Deal found 10/20![United Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/53:05 pm -
1 stop5h 35m
Tue 12/151:20 pm -
2 stops7h 35m
Deal found 10/23![Southwest logo]()
$238
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/111:00 pm -
1 stop6h 23m
Sun 12/137:45 pm -
Nonstop2h 32m
Deal found 10/23![Delta logo]()
$253
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/2010:42 am -
Nonstop3h 04m
Sun 11/226:00 pm -
Nonstop2h 30m
Deal found 10/24![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 11/78:10 am -
1 stop8h 25m
Mon 11/96:45 pm -
Nonstop2h 20m
Deal found 10/20![Southwest logo]()
$284
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/45:45 pm -
2 stops7h 30m
Sun 12/66:00 am -
2 stops7h 44m
Deal found 10/23![American Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:00 am -
1 stop5h 48m
Sun 11/156:15 am -
Nonstop2h 19m
Deal found 10/21![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 10/22. 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 11/122:00 pm -
1 stop6h 25m
Sun 11/157:05 am -
Nonstop2h 27m
Deal found 10/22![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 12/156:00 am -
2 stops9h 55m
Fri 12/189:49 pm -
Nonstop2h 29m
Deal found 10/20![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 10/20. 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 12/191:04 pm -
1 stop4h 56m
Sun 1/1010:35 am -
1 stop4h 48m
Deal found 10/20![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/1512:20 pm -
2 stops8h 05m
Mon 1/186:30 am -
1 stop6h 45m
Deal found 10/23![Southwest logo]()
$311
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/56:00 am -
2 stops8h 58m
Mon 11/92:34 pm -
1 stop7h 08m
Deal found 10/21![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/126:00 am -
1 stop5h 05m
Sat 11/143:39 pm -
2 stops7h 20m
Deal found 10/21![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 10/20. 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.
Thu 12/172:25 pm -
2 stops6h 45m
Sun 12/205:15 am -
2 stops8h 05m
Deal found 10/20![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/65:58 pm -
1 stop7h 01m
Sat 11/142:34 pm -
1 stop5h 52m
Deal found 10/24![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/258:40 pm -
Nonstop2h 56m
Mon 11/302:37 pm -
1 stop6h 48m
Deal found 10/23![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sat 11/217:10 pm -
1 stop6h 15m
Mon 11/307:00 pm -
Nonstop2h 25m
Deal found 10/22![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/257:15 am -
2 stops8h 53m
Wed 12/307:18 pm -
1 stop5h 00m
Deal found 10/23![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/1910:17 am -
1 stop5h 14m
Thu 11/265:12 am -
1 stop5h 42m
Deal found 10/20![American Airlines logo]()
$491
This Southwest deal was found by Cheapflights users on 10/22. 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.
Thu 12/241:20 pm -
2 stops7h 25m
Mon 12/284:20 pm -
1 stop6h 10m
Deal found 10/22![Southwest logo]()
$360
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/57:31 am -
1 stop7h 03m
Mon 11/96:25 am -
1 stop5h 21m
Deal found 10/21![United Airlines logo]()
$399
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated October 25, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:15 pm -
1 stop7h 15m
Tue 11/171:00 pm -
Nonstop2h 49m
Deal found 10/20![Multiple Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/123:01 pm -
Nonstop3h 04m
Sun 11/157:00 am -
Nonstop2h 19m
Deal found 10/20![United Airlines logo]()
$213
This American Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/1212:12 pm -
Nonstop3h 06m
Sun 11/156:00 am -
Nonstop2h 29m
Deal found 10/21![American Airlines logo]()
$214
This Priceline deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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.
Thu 11/1212:39 pm -
1 stop7h 06m
Mon 11/168:15 pm -
Nonstop2h 44m
Deal found 10/23![Multiple Airlines logo]()
$218
This Frontier deal was found by Cheapflights users on 10/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/21![Frontier logo]()
$214
This Frontier deal was found by Cheapflights users on 10/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop7h 20m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 10/22![Frontier logo]()
$215
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:39 pm -
1 stop12h 08m
Thu 11/196:42 pm -
1 stop11h 59m
Deal found 10/20![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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.
Mon 11/167:10 am -
Nonstop2h 45m
Wed 11/181:15 pm -
Nonstop2h 05m
Deal found 10/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/177:10 am -
Nonstop2h 45m
Wed 11/189:40 am -
2 stops8h 25m
Deal found 10/23![Southwest logo]()
$216
This CheapOair deal was found by Cheapflights users on 10/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:59 am -
Nonstop3h 01m
Wed 11/255:12 pm -
1 stop15h 59m
Deal found 10/21![Multiple Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/195:20 am -
1 stop11h 10m
Mon 11/236:45 pm -
Nonstop2h 20m
Deal found 10/23![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/213:41 pm -
1 stop7h 37m
Thu 11/267:00 am -
Nonstop2h 19m
Deal found 10/21![United Airlines logo]()
$219
One-way flights from Boston to IllinoisSearch for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/1312:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$110
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/97:30 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$111
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates ” 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 11/93:41 pm -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$111
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/3010:25 pm -
Nonstop3h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$113
This Trip.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:39 pm -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 1/1010:01 am -
1 stop10h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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.
Fri 12/411:57 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/1011:20 am -
2 stops9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$116
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/85:45 am -
1 stop4h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$116
This Delta deal was found by Cheapflights users on 10/21. 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.
Sat 11/219:15 am -
1 stop4h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/129:00 am -
1 stop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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.
Sat 11/711:27 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$118
Find flight deals from Boston to Illinois
Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $212 (Trip.com) |
One-way from | $110 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $340 |
Good round-trip deal | $328 or less |
Good one-way deal | $188 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Illinois 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 7,457,451 searches. Data last updated October 25, 2026.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 11/12
7:30 pm-12:10 am
1 stop5h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Thu 11/26
5:45 am-10:25 am
1 stop5h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 1/12
8:50 am-2:15 pm
1 stop6h 25m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 11/21
9:15 am-12:51 pm
1 stop4h 36m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 12/4
7:33 pm-11:29 pm
1 stop4h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 12/12
5:27 am-9:37 am
1 stop5h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 12/5
1:05 pm-4:17 pm
1 stop4h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 11/23
5:05 pm-9:42 pm
1 stop5h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 1/5
11:00 am-4:12 pm
1 stop6h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 11/12
2:00 pm-8:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Boston with our price prediction graph.
BOS-ORD
BOS-MDW
BOS-BMI
BOS-PIA
BOS-MLI
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 Boston to Illinois
BOS-USIL
BOS-ORD
BOS-MDW
BOS-BMI
BOS-PIA
What is the cheapest month to book a flight from Boston to Illinois?
Currently, January is the cheapest month in which you can book a flight from Boston to Illinois (average of $198). Flying from Boston to Illinois in October is currently the most expensive (average of $348). 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 BOS to IL?
Find hourly flight availability from Boston to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 25, 2026.
One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 13% on airfare.
Weekly flight availability from Boston to Illinois
Explore weekly flight availability from Boston to Illinois. 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 October 25, 2026.
The most flights from BOS to USIL are scheduled on a Saturday (63 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from Boston to Illinois?
Airfare is below average for this route at the moment.
Boston to Illinois flights typically cost between $242 and $422 in November.The cheapest round-trip price found within the last 5 days was $212 on Multiple Airlines (Nov 10-Nov 17).
How far ahead should I book a flight from Boston to Illinois?
The best time to book flights from Boston to Illinois is 59 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Boston to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Boston to Illinois. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Boston to Illinois flight should consider departing on Friday evenings 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.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated October 25, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Food
7.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Boston to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Boston to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Illinois by cabin class
Find flights from Boston to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Illinois flights
Browse other Boston and Illinois flight options. Last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Illinois flights
Consider these flights traveling from Boston to Illinois.
Top 5 airlines flying from Boston to Illinois
Discover the top 5 airlines that operate flights from Boston to Illinois. 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 7,457,451 searches. Data last updated October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$237 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$362 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$147 | Average$311 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$150 | Average$447 | FlexibilityNo cancel fee | On-time71% |