$99+ Cheap flights from Illinois to Boston (BOS)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Sep 23 — Sep 301
Round-trip
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 24, 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 24, 2026.
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.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
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$183
This Super.com deal was found by Cheapflights users on 8/22. 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 Super.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
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Wed 10/2812:39 pm -
1 stop8h 05m
Deal found 8/19![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/93:50 pm -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/20![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Sat 9/128:24 pm -
Nonstop2h 45m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/21![Multiple Airlines logo]()
$197
This Expedia deal was found by Cheapflights users on 8/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:24 pm -
Nonstop2h 32m
Tue 11/1012:15 pm -
1 stop7h 30m
Deal found 8/21![Multiple Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/23. 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 10/25:30 am -
Nonstop2h 25m
Mon 10/510:00 pm -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/23. 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 9/147:55 pm -
1 stop11h 05m
Thu 9/173:55 pm -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$233
This Southwest deal was found by Cheapflights users on 8/22. 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.
Fri 10/166:45 pm -
Nonstop2h 15m
Mon 10/1910:00 pm -
Nonstop2h 35m
Deal found 8/22![Southwest logo]()
$235
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 24, 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 24, 2026.
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:24 pm -
Nonstop2h 32m
Tue 11/1711:15 am -
Nonstop3h 05m
Deal found 8/22![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 8/23. 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 9/175:45 am -
Nonstop2h 15m
Mon 9/216:45 pm -
Nonstop2h 45m
Deal found 8/23![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/23. 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 9/177:30 am -
Nonstop2h 31m
Sun 9/205:45 am -
1 stop4h 53m
Deal found 8/23![United Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 8/20. 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.
Sun 9/207:35 am -
Nonstop2h 33m
Mon 9/218:50 pm -
Nonstop2h 42m
Deal found 8/20![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 9/205:02 am -
1 stop4h 27m
Sat 9/266:00 am -
1 stop7h 49m
Deal found 8/20![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:00 pm -
1 stop7h 39m
Wed 10/146:55 am -
Nonstop2h 51m
Deal found 8/22![JetBlue logo]()
$249
This Southwest deal was found by Cheapflights users on 8/21. 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 10/295:30 am -
Nonstop2h 25m
Mon 11/28:40 am -
1 stop6h 00m
Deal found 8/21![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:07 am -
Nonstop2h 43m
Sun 9/136:00 am -
Nonstop2h 59m
Deal found 8/22![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/21. 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 9/127:30 am -
Nonstop2h 31m
Mon 9/148:50 pm -
Nonstop2h 42m
Deal found 8/21![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:35 am -
Nonstop2h 33m
Fri 9/118:50 pm -
Nonstop2h 42m
Deal found 8/20![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/23. 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 10/15:30 am -
Nonstop2h 25m
Mon 10/55:50 am -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/105:07 pm -
1 stop4h 38m
Sun 10/119:23 am -
Nonstop2h 52m
Deal found 8/21![United Airlines logo]()
$275
This JetBlue deal was found by Cheapflights users on 8/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:38 am -
Nonstop2h 28m
Sun 10/2511:15 am -
Nonstop3h 05m
Deal found 8/20![JetBlue logo]()
$275
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:30 pm -
Nonstop2h 39m
Sat 9/266:00 pm -
Nonstop2h 59m
Deal found 8/20![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/23. 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 9/215:45 am -
Nonstop2h 15m
Wed 9/231:20 pm -
2 stops6h 45m
Deal found 8/23![Southwest logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/23. 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 1/142:30 pm -
1 stop5h 29m
Mon 1/186:00 am -
2 stops8h 57m
Deal found 8/23![American Airlines logo]()
$334
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:00 pm -
1 stop6h 49m
Sun 10/2511:15 am -
Nonstop3h 05m
Deal found 8/19![JetBlue logo]()
$282
This Southwest deal was found by Cheapflights users on 8/23. 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 9/175:45 am -
Nonstop2h 15m
Sun 9/209:05 pm -
Nonstop2h 40m
Deal found 8/23![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:25 am -
Nonstop2h 35m
Fri 10/307:30 am -
Nonstop2h 54m
Deal found 8/19![Delta logo]()
$275
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:30 pm -
1 stop5h 29m
Mon 10/266:16 pm -
1 stop6h 43m
Deal found 8/22![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Wed 9/306:15 am -
1 stop6h 52m
Sat 10/36:00 am -
1 stop5h 06m
Deal found 8/20![United Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:30 am -
Nonstop2h 25m
Thu 10/85:50 am -
Nonstop2h 35m
Deal found 8/19![Southwest logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 9/98:13 am -
1 stop7h 14m
Sun 9/137:05 am -
1 stop6h 26m
Deal found 8/23![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Sun 9/66:00 am -
2 stops7h 26m
Fri 9/115:35 pm -
2 stops7h 30m
Deal found 8/23![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:16 pm -
1 stop7h 01m
Sat 10/105:30 am -
1 stop5h 48m
Deal found 8/19![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:16 pm -
1 stop7h 03m
Mon 9/145:30 am -
1 stop5h 43m
Deal found 8/21![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:50 pm -
1 stop4h 40m
Tue 10/1310:55 am -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/19![American Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/23. 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 9/83:35 pm -
1 stop5h 24m
Sat 9/129:00 am -
1 stop5h 39m
Deal found 8/23![United Airlines logo]()
$379
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated August 24, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated August 24, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/19![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/20. 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.
Wed 9/93:50 pm -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/20![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/21. 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.
Sat 9/128:24 pm -
Nonstop2h 45m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/21![Multiple Airlines logo]()
$197
This Priceline deal was found by Cheapflights users on 8/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:38 am -
Nonstop2h 28m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/22![Multiple Airlines logo]()
$198
This CheapOair deal was found by Cheapflights users on 8/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/23![Frontier logo]()
$204
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/23. 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 9/147:55 pm -
1 stop11h 05m
Thu 9/173:55 pm -
Nonstop2h 35m
Deal found 8/23![Southwest logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:24 pm -
Nonstop2h 45m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/23![Multiple Airlines logo]()
$203
This Super.com deal was found by Cheapflights users on 8/22. 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 Super.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
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.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
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$183
This CheapOair deal was found by Cheapflights users on 8/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:24 pm -
Nonstop2h 45m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 8/23![Multiple Airlines logo]()
$199
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 24, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated August 24, 2026.
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/19![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 8/19![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Deal found 8/19![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 8/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:24 pm -
Nonstop2h 45m
Deal found 8/22![JetBlue logo]()
$105
This CheapOair deal was found by Cheapflights users on 8/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/22![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:24 pm -
Nonstop2h 34m
Deal found 8/21![JetBlue logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:56 pm -
2 stops21h 02m
Deal found 8/19![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 8/23. 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.
Tue 9/2210:29 am -
Nonstop2h 36m
Deal found 8/23![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/1512:50 pm -
Nonstop2h 20m
Deal found 8/21![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:56 pm -
2 stops21h 02m
Deal found 8/20![Frontier logo]()
$110
This Jetabroad deal was found by Cheapflights users on 8/22. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:00 am -
1 stop6h 26m
Deal found 8/22![JetBlue logo]()
$111
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:34 pm -
1 stop11h 42m
Deal found 8/19![Frontier logo]()
$115
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 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (Super.com) |
One-way from | $99 (CheapOair) |
Popular in | August |
Cheapest in | January |
Average price | $283 |
Good round-trip deal | $248 or less |
Good one-way deal | $158 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 August 24, 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
Mon 11/9
8:24 pm-11:56 pm
Nonstop2h 32m
Boston Logan Intl
Tue 11/17
11:15 am-1:20 pm
Nonstop3h 05m
$217
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Mon 9/21
6:45 pm-8:30 pm
Nonstop2h 45m
$217
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 9/12
7:40 am-11:00 am
Nonstop2h 20m
Boston Logan Intl
Mon 9/14
6:40 pm-8:25 pm
Nonstop2h 45m
$217
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
5:30 am-8:55 am
Nonstop2h 25m
Boston Logan Intl
Mon 11/2
8:40 am-1:40 pm
1 stop6h 00m
$227
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/1
5:30 am-8:55 am
Nonstop2h 25m
Boston Logan Intl
Mon 10/5
5:50 am-7:25 am
Nonstop2h 35m
$236
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 9/21
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Wed 9/23
1:20 pm-7:05 pm
2 stops6h 45m
$241
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 9/17
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sun 9/20
5:45 am-9:38 am
1 stop4h 53m
$246
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Sun 9/20
9:05 pm-10:45 pm
Nonstop2h 40m
$246
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/3
3:00 pm-11:39 pm
1 stop7h 39m
Boston Logan Intl
Wed 10/14
6:55 am-8:46 am
Nonstop2h 51m
$249
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 9/20
7:35 am-11:08 am
Nonstop2h 33m
Boston Logan Intl
Mon 9/21
8:50 pm-10:32 pm
Nonstop2h 42m
$255
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
MLI-BOS
BMI-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
MLI-BOS
BMI-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 August is currently the most expensive (average of $292). 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 24, 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 12% 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 24, 2026.
The most flights from USIL to BOS are scheduled on a Sunday (72 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (52 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 $188 and $340 in September.The cheapest round-trip price found within the last 5 days was $183 on Frontier (Sep 19-Sep 22).
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 22, 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
Seekonk
Cranston
Dedham
Warwick
Peabody
Auburn
Chelsea
York Beach
Londonderry
Revere
Fitchburg
Swansea
North Falmouth
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 August 24, 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 24, 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 August 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$187 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$243 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$131 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$409 | FlexibilityNo cancel fee | On-time71% |