$113+ Cheap flights from Illinois to Boston (BOS)
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 19 — Oct 261
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 September 19, 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 September 19, 2026.
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:38 am -
Nonstop2h 28m
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 9/17![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/2611:47 am -
1 stop30h 16m
Deal found 9/17![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 10/116:10 am -
Nonstop2h 23m
Tue 10/135:45 am -
1 stop4h 53m
Deal found 9/17![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 9/17. 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 10/38:25 am -
1 stop5h 20m
Wed 10/76:45 am -
1 stop5h 35m
Deal found 9/17![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/197:25 am -
Nonstop2h 35m
Sun 10/257:30 am -
Nonstop2h 54m
Deal found 9/16![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 9/17. 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 10/174:25 pm -
Nonstop2h 25m
Mon 10/1910:00 pm -
Nonstop2h 40m
Deal found 9/17![Southwest logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/16. 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.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/245:12 pm -
Nonstop3h 02m
Deal found 9/16![JetBlue logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/38:25 am -
1 stop5h 20m
Mon 10/510:00 pm -
Nonstop2h 40m
Deal found 9/18![Southwest logo]()
$225
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:50 pm -
1 stop10h 51m
Thu 11/267:55 am -
Nonstop3h 04m
Deal found 9/17![Multiple Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
Nonstop2h 25m
Thu 11/52:30 pm -
1 stop8h 30m
Deal found 9/14![Southwest logo]()
$226
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Tue 10/136:55 am -
Nonstop2h 52m
Deal found 9/18![Multiple Airlines logo]()
$227
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 September 19, 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 September 19, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:29 am -
Nonstop2h 31m
Mon 10/127:01 am -
Nonstop2h 59m
Deal found 9/16![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/191:27 pm -
1 stop5h 22m
Thu 10/225:39 am -
1 stop4h 53m
Deal found 9/16![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/38:10 am -
2 stops9h 10m
Mon 10/57:30 pm -
1 stop5h 25m
Deal found 9/18![Southwest logo]()
$240
This JetBlue deal was found by Cheapflights users on 9/18. 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.
Wed 10/710:59 am -
1 stop5h 25m
Sun 10/116:55 am -
Nonstop2h 52m
Deal found 9/18![JetBlue logo]()
$242
This American Airlines deal was found by Cheapflights users on 9/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm -
1 stop5h 06m
Thu 10/224:48 pm -
1 stop8h 22m
Deal found 9/18![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/15. 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 10/246:44 pm -
1 stop4h 15m
Thu 10/295:30 am -
1 stop5h 33m
Deal found 9/15![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/1711:55 am -
2 stops8h 45m
Sat 10/249:20 am -
2 stops9h 35m
Deal found 9/18![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 12/176:30 am -
1 stop6h 15m
Sun 1/241:10 pm -
Nonstop2h 45m
Deal found 9/15![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 12/27:00 am -
1 stop4h 27m
Thu 12/32:58 pm -
Nonstop3h 02m
Deal found 9/16![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/16. 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 10/75:29 pm -
1 stop5h 30m
Thu 10/156:00 am -
1 stop8h 08m
Deal found 9/16![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/69:24 pm -
Nonstop2h 30m
Wed 10/146:00 am -
2 stops9h 42m
Deal found 9/17![United Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:45 pm -
Nonstop2h 20m
Fri 11/2712:45 pm -
Nonstop2h 45m
Deal found 9/16![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 9/15. 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 10/319:59 am -
1 stop6h 12m
Sun 11/15:50 am -
1 stop6h 50m
Deal found 9/15![Delta logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 pm -
1 stop5h 06m
Sun 11/17:40 pm -
1 stop5h 23m
Deal found 9/14![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 11/146:49 am -
1 stop5h 53m
Sun 11/155:40 pm -
1 stop7h 14m
Deal found 9/16![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/18. 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.
Wed 11/115:20 am -
2 stops8h 10m
Mon 11/1611:20 am -
2 stops9h 25m
Deal found 9/18![Southwest logo]()
$290
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:10 pm -
Nonstop2h 31m
Fri 10/304:40 pm -
1 stop4h 44m
Deal found 9/18![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 11/126:25 am -
1 stop5h 21m
Sun 11/156:00 am -
1 stop5h 08m
Deal found 9/17![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 9/18. 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.
Wed 11/254:05 pm -
Nonstop2h 15m
Tue 12/17:10 am -
Nonstop2h 45m
Deal found 9/18![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 9/17. 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.
Sun 10/256:20 am -
1 stop6h 50m
Thu 10/297:40 pm -
Nonstop2h 51m
Deal found 9/17![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 pm -
2 stops12h 40m
Mon 11/92:25 pm -
2 stops7h 05m
Deal found 9/16![Southwest logo]()
$298
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:13 pm -
1 stop5h 36m
Sun 11/85:43 am -
1 stop6h 56m
Deal found 9/17![American Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 9/17. 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 10/2811:19 am -
1 stop3h 56m
Sat 10/311:05 pm -
1 stop4h 21m
Deal found 9/17![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 11/79:40 am -
2 stops7h 05m
Tue 11/109:00 am -
2 stops7h 43m
Deal found 9/15![United Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:23 pm -
1 stop5h 07m
Mon 10/125:54 am -
1 stop7h 14m
Deal found 9/17![American Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 9/17. 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 11/252:44 pm -
1 stop4h 05m
Thu 11/261:35 pm -
Nonstop2h 55m
Deal found 9/17![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sun 11/17:50 am -
Nonstop2h 20m
Sun 11/87:05 am -
Nonstop2h 45m
Deal found 9/17![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/157:18 pm -
1 stop27h 06m
Thu 10/225:45 am -
2 stops13h 08m
Deal found 9/17![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:35 am -
1 stop9h 35m
Wed 11/1810:35 am -
2 stops10h 00m
Deal found 9/14![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:38 pm -
1 stop7h 21m
Tue 10/275:54 am -
1 stop7h 14m
Deal found 9/17![American Airlines logo]()
$486
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated September 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/38:25 am -
1 stop5h 20m
Wed 10/76:45 am -
1 stop5h 35m
Deal found 9/17![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/38:25 am -
1 stop5h 20m
Mon 10/510:00 pm -
Nonstop2h 40m
Deal found 9/18![Southwest logo]()
$225
This JetBlue deal was found by Cheapflights users on 9/16. 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.
Wed 10/710:59 am -
1 stop5h 25m
Tue 10/136:55 am -
1 stop5h 29m
Deal found 9/16![JetBlue logo]()
$226
This CheapOair deal was found by Cheapflights users on 9/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Tue 10/136:55 am -
Nonstop2h 52m
Deal found 9/18![Multiple Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 10/116:10 am -
Nonstop2h 23m
Tue 10/135:45 am -
1 stop4h 53m
Deal found 9/17![United Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:38 am -
Nonstop2h 28m
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 9/17![Multiple Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 9/17. 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 10/174:25 pm -
Nonstop2h 25m
Mon 10/1910:00 pm -
Nonstop2h 40m
Deal found 9/17![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/197:25 am -
Nonstop2h 35m
Thu 10/227:40 pm -
Nonstop2h 51m
Deal found 9/16![Delta logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/16. 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.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/245:12 pm -
Nonstop3h 02m
Deal found 9/16![JetBlue logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/2611:47 am -
1 stop30h 16m
Deal found 9/17![Frontier logo]()
$221
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
Nonstop2h 25m
Thu 11/52:30 pm -
1 stop8h 30m
Deal found 9/14![Southwest logo]()
$226
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 September 19, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This KAYAK deal was found by Cheapflights users on 9/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:24 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$113
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/267:00 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/261:27 pm -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:00 pm -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$119
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:50 pm -
2 stops5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$119
This Expedia deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$120
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$120
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:50 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$121
This Southwest deal was found by Cheapflights users on 9/15. 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 11/257:35 am -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 9/17. 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.
Thu 10/228:00 am -
2 stops7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$123
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop13h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:16 pm -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Allegiant Air logo]()
$124
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $220 (CheapOair) |
One-way from | $113 (KAYAK) |
Popular in | August |
Cheapest in | January |
Average price | $280 |
Good round-trip deal | $274 or less |
Good one-way deal | $157 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 7,457,451 searches. Data last updated September 19, 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 Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/31
8:05 am-2:54 pm
1 stop5h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 10/3
9:55 am-6:20 pm
1 stop7h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 11/2
6:10 pm-11:50 pm
1 stop4h 40m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 10/26
5:50 pm-11:35 pm
1 stop4h 45m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 11/27
11:56 am-5:27 pm
1 stop4h 31m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/24
6:00 am-11:24 am
1 stop4h 24m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/14
5:30 pm-11:48 pm
1 stop5h 18m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/28
7:00 am-2:27 pm
1 stop6h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 10/4
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 12/12
3:40 pm-6:55 pm
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
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
PIA-BOS
CMI-BOS
STL-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
PIA-BOS
CMI-BOS
What is the cheapest month to book a flight from Illinois to Boston?
Currently, January is the cheapest month in which you can book a flight from Illinois to Boston (average of $203). Flying from Illinois to Boston in September is currently the most expensive (average of $304). 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 September 19, 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 13% versus a flight in the afternoon.
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 September 19, 2026.
The most flights from USIL to BOS are scheduled on a Friday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from Illinois to Boston?
Airfare is below average for this route at the moment.
Illinois to Boston flights typically cost between $229 and $378 in October.The cheapest round-trip price found within the last 5 days was $220 on Multiple Airlines (Oct 17-Oct 21).
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 September 19, 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
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Revere
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
Sandwich
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 September 19, 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 September 19, 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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$196 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$250 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$324 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$138 | Average$410 | FlexibilityNo cancel fee | On-time71% |