$115+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Boston with Cheapflights
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 September 10, 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 10, 2026.
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1712:38 pm -
1 stop7h 28m
Mon 10/193:41 pm -
1 stop7h 29m
Deal found 9/5![JetBlue logo]()
$223
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Wed 10/1412:38 pm -
1 stop7h 11m
Sat 10/174:11 pm -
1 stop6h 59m
Deal found 9/5![JetBlue logo]()
$224
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1512:38 pm -
1 stop7h 11m
Mon 10/193:41 pm -
1 stop7h 29m
Deal found 9/5![JetBlue logo]()
$233
This deal was found by Cheapflights users on 9/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:20 pm -
Nonstop2h 56m
Thu 9/104:11 pm -
1 stop6h 47m
Deal found 9/8![JetBlue logo]()
$234
This Frontier deal was found by Cheapflights users on 9/9. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Wed 10/2812:39 pm -
1 stop6h 37m
Deal found 9/9![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/48:07 pm -
1 stop13h 55m
Sun 12/611:57 am -
1 stop8h 05m
Deal found 9/5![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/9. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/9![Frontier logo]()
$237
This CheapOair deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/303:50 pm -
1 stop17h 32m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 9/5![Frontier logo]()
$239
This Trip.com deal was found by Cheapflights users on 9/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/7![Frontier logo]()
$240
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Sun 10/47:00 am -
Nonstop2h 48m
Deal found 9/9![JetBlue logo]()
$241
This Super.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/248:46 am -
1 stop25h 16m
Wed 10/2812:39 pm -
1 stop6h 37m
Deal found 9/6![Frontier logo]()
$242
This lol.travel deal was found by Cheapflights users on 9/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:24 pm -
Nonstop2h 45m
Sun 10/47:00 am -
Nonstop2h 48m
Deal found 9/10![JetBlue logo]()
$243
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 10, 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 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:24 pm -
Nonstop2h 30m
Mon 10/58:05 am -
Nonstop2h 55m
Deal found 9/9![United Airlines logo]()
$249
This KAYAK deal was found by Cheapflights users on 9/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:38 am -
Nonstop2h 28m
Thu 9/247:00 am -
Nonstop2h 48m
Deal found 9/8![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:05 pm -
Nonstop2h 47m
Tue 10/65:50 am -
1 stop6h 50m
Deal found 9/10![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/5![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:29 pm -
1 stop5h 07m
Sat 10/3112:00 pm -
1 stop5h 59m
Deal found 9/8![American Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:36 pm -
1 stop14h 26m
Tue 10/1312:57 pm -
2 stops30h 59m
Deal found 9/8![Multiple Airlines logo]()
$476
This JetBlue deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:38 pm -
1 stop7h 11m
Fri 10/234:05 pm -
1 stop7h 05m
Deal found 9/6![JetBlue logo]()
$265
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:23 pm -
1 stop6h 45m
Wed 10/147:30 am -
Nonstop2h 54m
Deal found 9/9![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:10 am -
Nonstop2h 23m
Wed 10/218:05 am -
Nonstop2h 55m
Deal found 9/8![United Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/287:50 am -
Nonstop2h 20m
Fri 10/3010:00 pm -
Nonstop2h 40m
Deal found 9/9![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 9/8. 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 11/177:05 am -
Nonstop2h 27m
Mon 11/238:40 pm -
Nonstop2h 56m
Deal found 9/8![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/225:30 am -
Nonstop2h 25m
Sat 10/241:25 pm -
Nonstop2h 35m
Deal found 9/5![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:02 am -
1 stop4h 34m
Mon 11/97:40 pm -
1 stop5h 23m
Deal found 9/8![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 10/1510:24 am -
Nonstop2h 30m
Sat 10/177:40 pm -
Nonstop2h 51m
Deal found 9/8![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/8. 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.
Thu 10/225:30 am -
Nonstop2h 25m
Sun 10/2510:50 pm -
Nonstop2h 40m
Deal found 9/8![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 pm -
1 stop5h 05m
Fri 11/276:00 am -
1 stop5h 08m
Deal found 9/9![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:30 pm -
1 stop5h 29m
Tue 10/206:16 pm -
1 stop6h 43m
Deal found 9/6![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:30 am -
Nonstop2h 45m
Sat 10/107:40 pm -
Nonstop2h 51m
Deal found 9/9![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 11/76:35 am -
1 stop6h 45m
Tue 11/1012:50 pm -
Nonstop2h 50m
Deal found 9/8![Southwest logo]()
$285
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/65:00 am -
1 stop4h 33m
Wed 10/148:23 am -
1 stop6h 34m
Deal found 9/6![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 9/7. 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.
Sun 12/61:00 pm -
Nonstop2h 10m
Tue 12/85:45 pm -
1 stop5h 55m
Deal found 9/7![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1510:24 am -
Nonstop2h 30m
Thu 10/157:40 pm -
Nonstop2h 51m
Deal found 9/5![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/166:02 am -
2 stops7h 36m
Sun 12/205:47 am -
1 stop6h 05m
Deal found 9/6![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Thu 10/295:30 pm -
1 stop5h 06m
Mon 11/210:19 am -
2 stops7h 49m
Deal found 9/7![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:18 pm -
1 stop4h 36m
Sat 10/1712:45 pm -
1 stop6h 58m
Deal found 9/9![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/105:29 pm -
1 stop5h 30m
Thu 10/154:25 pm -
Nonstop2h 55m
Deal found 9/6![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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
Sat 10/103:10 pm -
1 stop4h 35m
Deal found 9/6![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:00 am -
2 stops8h 54m
Mon 11/97:40 pm -
1 stop5h 19m
Deal found 9/8![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/46:15 am -
1 stop5h 33m
Sat 10/106:00 am -
1 stop5h 06m
Deal found 9/5![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/105:29 pm -
1 stop5h 30m
Wed 10/145:39 am -
1 stop5h 50m
Deal found 9/6![Delta logo]()
$317
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated September 10, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 9/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/7![Frontier logo]()
$240
This CheapOair deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/303:50 pm -
1 stop17h 32m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 9/5![Frontier logo]()
$239
This KAYAK deal was found by Cheapflights users on 9/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:38 am -
Nonstop2h 28m
Sat 10/35:00 pm -
Nonstop3h 01m
Deal found 9/9![JetBlue logo]()
$245
This lol.travel deal was found by Cheapflights users on 9/10. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:24 pm -
Nonstop2h 45m
Sun 10/47:00 am -
Nonstop2h 48m
Deal found 9/10![JetBlue logo]()
$243
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Sun 10/47:00 am -
Nonstop2h 48m
Deal found 9/9![JetBlue logo]()
$241
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Wed 10/1412:38 pm -
1 stop7h 11m
Sat 10/174:11 pm -
1 stop6h 59m
Deal found 9/5![JetBlue logo]()
$224
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1512:38 pm -
1 stop7h 11m
Mon 10/193:41 pm -
1 stop7h 29m
Deal found 9/5![JetBlue logo]()
$233
This Southwest deal was found by Cheapflights users on 9/9. 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 10/155:30 am -
Nonstop2h 25m
Mon 10/1910:00 pm -
Nonstop2h 40m
Deal found 9/9![Southwest logo]()
$249
This Jetabroad deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1712:38 pm -
1 stop7h 28m
Mon 10/193:41 pm -
1 stop7h 29m
Deal found 9/5![JetBlue logo]()
$223
This Frontier deal was found by Cheapflights users on 9/9. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Wed 10/2812:39 pm -
1 stop6h 37m
Deal found 9/9![Frontier logo]()
$236
This Frontier deal was found by Cheapflights users on 9/9. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/9![Frontier logo]()
$237
This Super.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/248:46 am -
1 stop25h 16m
Wed 10/2812:39 pm -
1 stop6h 37m
Deal found 9/6![Frontier logo]()
$242
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 10, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 11/133:16 pm -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Allegiant Air logo]()
$115
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:50 pm -
1 stop17h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$116
This JetBlue deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![JetBlue logo]()
$119
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$121
This Super.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Sun 10/43:50 pm -
1 stop18h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$122
This Jetabroad deal was found by Cheapflights users on 9/10. 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.
Fri 9/258:24 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$123
This Frontier deal was found by Cheapflights users on 9/8. 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 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 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 11/228:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$124
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sun 9/276:00 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$125
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/23:50 pm -
1 stop17h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$126
This CheapOair deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Sun 11/225:12 pm -
1 stop15h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/22:59 pm -
2 stops17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$129
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Jetabroad) |
One-way from | $115 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $263 |
Good round-trip deal | $255 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 September 10, 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
Sun 10/25
6:00 am-9:17 am
Nonstop2h 17m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/24
8:50 am-2:55 pm
1 stop5h 05m
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
Fri 10/23
12:38 pm-8:37 pm
1 stop6h 59m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
Quickest round-trip
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 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/7
6:25 pm-9:40 pm
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 11/7
8:30 pm-11:58 pm
Nonstop2h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 9/23
6:40 am-9:55 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 10/11
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
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
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 10/4
5:00 am-8:25 am
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
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
STL-BOS
PIA-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
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 $203). Flying from Illinois to Boston in August is currently the most expensive (average of $298). 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 10, 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 September 10, 2026.
The most flights from USIL to BOS are scheduled on a Tuesday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).
How much does it cost to fly round-trip from Illinois to Boston?
Airfare is typical for this route at the moment.
Illinois to Boston flights typically cost between $208 and $346 in October.The cheapest round-trip price found within the last 5 days was $223 on JetBlue (Oct 17-Oct 19).
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 5, 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
Dedham
Cranston
Warwick
Pawtucket
Peabody
Auburn
Revere
York Beach
Londonderry
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 10, 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 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$189 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$91 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$319 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$409 | FlexibilityNo cancel fee | On-time71% |