$92+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Sep 11 — Sep 181
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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/9![Southwest logo]()
$166
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/38:45 pm -
Nonstop2h 36m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/11![Multiple Airlines logo]()
$171
This Jetabroad deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/88:24 pm -
Nonstop2h 34m
Tue 10/136:55 am -
Nonstop2h 51m
Deal found 8/10![JetBlue logo]()
$174
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:18 pm -
1 stop5h 41m
Wed 9/912:15 pm -
Nonstop2h 49m
Deal found 8/11![Delta logo]()
$175
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:50 pm -
1 stop4h 50m
Mon 11/165:55 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$175
This Travelocity deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:38 am -
Nonstop2h 28m
Fri 10/239:15 am -
1 stop15h 40m
Deal found 8/10![Multiple Airlines logo]()
$176
This Frontier deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/57:44 pm -
1 stop12h 25m
Thu 9/1011:17 am -
1 stop12h 42m
Deal found 8/9![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/69:36 am -
1 stop11h 28m
Deal found 8/7![Frontier logo]()
$178
This Trip.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 8/12![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:50 am -
2 stops7h 15m
Wed 9/27:15 pm -
Nonstop2h 35m
Deal found 8/11![Southwest logo]()
$180
This Vliegwinkel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 pm -
Nonstop2h 36m
Mon 9/75:01 am -
1 stop4h 50m
Deal found 8/11![JetBlue logo]()
$181
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/107:55 pm -
1 stop11h 05m
Thu 9/178:20 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$181
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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/217:55 pm -
1 stop11h 05m
Thu 9/246:40 pm -
Nonstop2h 45m
Deal found 8/11![Southwest logo]()
$181
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/310:30 am -
Nonstop2h 29m
Sat 11/79:00 am -
1 stop5h 09m
Deal found 8/10![United Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/262:29 pm -
1 stop6h 55m
Fri 10/3012:00 pm -
1 stop7h 20m
Deal found 8/11![Delta logo]()
$207
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:38 am -
Nonstop2h 28m
Tue 10/275:35 am -
1 stop9h 04m
Deal found 8/7![JetBlue logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:36 pm -
1 stop11h 44m
Wed 10/2111:05 am -
1 stop8h 51m
Deal found 8/10![Multiple Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:28 pm -
1 stop5h 26m
Sat 9/265:45 pm -
1 stop7h 23m
Deal found 8/7![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/66:25 pm -
Nonstop2h 20m
Tue 9/87:15 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/186:10 am -
Nonstop2h 23m
Sun 9/207:05 am -
Nonstop2h 58m
Deal found 8/11![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/193:10 pm -
Nonstop2h 25m
Tue 9/222:45 pm -
1 stop7h 05m
Deal found 8/10![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:05 pm -
Nonstop2h 39m
Tue 11/31:35 pm -
Nonstop2h 52m
Deal found 8/8![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:30 am -
Nonstop2h 31m
Sun 10/45:45 am -
1 stop4h 53m
Deal found 8/11![United Airlines logo]()
$219
This JetBlue deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:24 pm -
Nonstop2h 45m
Fri 10/27:00 am -
Nonstop2h 48m
Deal found 8/7![JetBlue logo]()
$255
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 10/149:10 am -
Nonstop2h 20m
Sat 10/177:40 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/277:55 am -
Nonstop2h 29m
Sun 8/307:30 am -
Nonstop2h 56m
Deal found 8/11![Delta logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/123:00 pm -
1 stop7h 39m
Sun 9/136:19 am -
1 stop8h 26m
Deal found 8/8![JetBlue logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:24 pm -
Nonstop2h 30m
Sun 10/47:01 am -
Nonstop2h 59m
Deal found 8/7![United Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/236:40 am -
Nonstop2h 15m
Sat 9/267:05 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$247
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/102:32 pm -
2 stops7h 09m
Mon 11/167:14 am -
1 stop7h 43m
Deal found 8/10![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:35 pm -
Nonstop2h 44m
Thu 9/248:31 pm -
Nonstop2h 58m
Deal found 8/7![United Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:24 pm -
Nonstop2h 30m
Mon 9/287:55 am -
Nonstop2h 56m
Deal found 8/7![United Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/25:30 am -
Nonstop2h 25m
Mon 10/510:00 pm -
Nonstop2h 35m
Deal found 8/8![Southwest logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/2511:41 am -
1 stop4h 53m
Sat 8/294:14 pm -
1 stop5h 14m
Deal found 8/10![American Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/912:06 pm -
1 stop7h 17m
Tue 11/179:05 am -
1 stop7h 30m
Deal found 8/8![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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.
Sat 10/38:33 pm -
1 stop13h 25m
Tue 10/612:52 pm -
2 stops31h 04m
Deal found 8/9![Multiple Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:40 am -
2 stops8h 40m
Mon 10/1910:00 pm -
Nonstop2h 35m
Deal found 8/7![Southwest logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/111:19 pm -
1 stop5h 11m
Sun 9/137:00 am -
1 stop6h 49m
Deal found 8/11![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 11/1012:06 pm -
1 stop7h 17m
Tue 11/174:20 pm -
1 stop7h 00m
Deal found 8/8![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 11/1012:11 pm -
1 stop7h 40m
Mon 11/161:28 pm -
1 stop7h 52m
Deal found 8/10![American Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/3012:45 pm -
Nonstop2h 20m
Mon 11/24:20 pm -
Nonstop2h 45m
Deal found 8/8![Southwest logo]()
$270
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:11 pm -
1 stop5h 37m
Tue 12/17:14 am -
1 stop5h 30m
Deal found 8/7![American Airlines logo]()
$355
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated August 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/315:45 am -
Nonstop2h 15m
Tue 9/295:25 am -
1 stop7h 10m
Deal found 8/10![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:50 am -
2 stops7h 15m
Wed 9/27:15 pm -
Nonstop2h 35m
Deal found 8/11![Southwest logo]()
$180
This Frontier deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/38:45 pm -
Nonstop2h 36m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/11![Multiple Airlines logo]()
$171
This Vliegwinkel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 pm -
Nonstop2h 36m
Mon 9/75:01 am -
1 stop4h 50m
Deal found 8/11![JetBlue logo]()
$181
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm -
Nonstop2h 56m
Mon 9/78:15 am -
Nonstop2h 56m
Deal found 8/11![JetBlue logo]()
$184
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:50 pm -
1 stop6h 40m
Sat 10/36:00 pm -
Nonstop2h 59m
Deal found 8/12![Delta logo]()
$175
This Frontier deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/57:44 pm -
1 stop12h 25m
Thu 9/1011:17 am -
1 stop12h 42m
Deal found 8/9![Frontier logo]()
$177
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/10![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/107:55 pm -
1 stop11h 05m
Thu 9/178:20 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$181
This Trip.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:05 pm -
Nonstop2h 47m
Sat 9/191:35 pm -
Nonstop2h 51m
Deal found 8/12![Delta logo]()
$182
This Trip.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Sat 9/2612:54 pm -
1 stop6h 29m
Deal found 8/12![Frontier logo]()
$180
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 August 12, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/27:11 am -
1 stop25h 18m
Deal found 8/11![Multiple Airlines logo]()
$92
This Super.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/10![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 8/3110:30 am -
1 stop6h 20m
Deal found 8/10![Southwest logo]()
$93
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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.
Tue 10/139:33 pm -
1 stop12h 19m
Deal found 8/10![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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.
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/10![Frontier logo]()
$97
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:00 pm -
2 stops7h 10m
Deal found 8/12![Southwest logo]()
$98
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:15 am -
1 stop22h 36m
Deal found 8/11![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm -
Nonstop2h 56m
Deal found 8/11![JetBlue logo]()
$101
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:30 pm -
Nonstop2h 25m
Deal found 8/12![Southwest logo]()
$101
This Super.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 am -
1 stop6h 22m
Deal found 8/7![JetBlue logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:24 pm -
Nonstop2h 45m
Deal found 8/12![JetBlue logo]()
$103
This Frontier deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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.
Sun 10/189:33 pm -
1 stop12h 19m
Deal found 8/10![Frontier logo]()
$104
Find flight deals from Illinois to Boston
Keep the following information in mind while searching for Illinois to Boston flight deals. Data was last updated August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Southwest) |
One-way from | $92 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $268 |
Good round-trip deal | $233 or less |
Good one-way deal | $143 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 August 12, 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
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 9/21
7:55 pm-8:00 am
1 stop11h 05m
Boston Logan Intl
Thu 9/24
6:40 pm-8:25 pm
Nonstop2h 45m
$181
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 9/6
6:25 pm-9:45 pm
Nonstop2h 20m
Boston Logan Intl
Tue 9/8
7:15 pm-8:55 pm
Nonstop2h 40m
$205
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/3
10:30 am-1:59 pm
Nonstop2h 29m
Boston Logan Intl
Sat 11/7
9:00 am-1:09 pm
1 stop5h 09m
$206
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 9/19
3:10 pm-6:35 pm
Nonstop2h 25m
Boston Logan Intl
Tue 9/22
2:45 pm-8:50 pm
1 stop7h 05m
$206
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 10/26
2:29 pm-10:24 pm
1 stop6h 55m
Boston Logan Intl
Fri 10/30
12:00 pm-6:20 pm
1 stop7h 20m
$207
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/18
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Sun 9/20
7:05 am-9:03 am
Nonstop2h 58m
$209
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/1
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sun 10/4
5:45 am-9:38 am
1 stop4h 53m
$219
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 10/14
9:10 am-12:30 pm
Nonstop2h 20m
Boston Logan Intl
Sat 10/17
7:40 am-9:15 am
Nonstop2h 35m
$227
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 10/30
3:05 pm-6:44 pm
Nonstop2h 39m
Boston Logan Intl
Tue 11/3
1:35 pm-3:27 pm
Nonstop2h 52m
$236
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 10/21
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Tue 10/27
5:35 am-1:39 pm
1 stop9h 04m
$244
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.
MDW-BOS
ORD-BOS
PIA-BOS
STL-BOS
DEC-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
MDW-BOS
ORD-BOS
PIA-BOS
STL-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 $201). Flying from Illinois to Boston in June is currently the most expensive (average of $285). 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 August 12, 2026.
When flying from Illinois to Boston, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 11% versus a flight 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 August 12, 2026.
The most flights from USIL to BOS are scheduled on a Monday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 $196 and $359 in September.The cheapest round-trip price found within the last 5 days was $171 on Multiple Airlines (Sep 3-Sep 6).
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 August 8, 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
Cambridge
Concord
Brockton
Seekonk
Cranston
Dedham
Warwick
Peabody
Auburn
Chelsea
York Beach
Londonderry
Swansea
Revere
Fitchburg
North Falmouth
Braintree
Sandwich
Browse thousands of different options on Cheapflights for your next 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 August 12, 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 August 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Illinois to Boston flights
Consider these flights traveling from Illinois to Boston.
Top 5 airlines flying from Illinois to Boston
Discover the top 5 airlines that operate flights from Illinois to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$241 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$318 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$129 | Average$382 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$418 | FlexibilityNo cancel fee | On-time71% |