$111+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 19 — Nov 261
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 October 20, 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 October 20, 2026.
This Delta deal was found by Cheapflights users on 10/19. 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 11/216:15 pm -
1 stop5h 53m
Mon 11/304:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/96:00 am -
2 stops28h 30m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/19![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:55 am -
2 stops8h 05m
Tue 11/102:25 pm -
1 stop5h 40m
Deal found 10/15![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/178:10 am -
2 stops6h 40m
Mon 11/234:20 pm -
Nonstop2h 45m
Deal found 10/19![Southwest logo]()
$228
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:16 pm -
Nonstop2h 33m
Sat 11/74:41 pm -
Nonstop3h 14m
Deal found 10/15![American Airlines logo]()
$229
This CheapOair deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:35 am -
1 stop27h 36m
Sat 12/511:08 am -
1 stop15h 00m
Deal found 10/16![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 11/2411:06 am -
1 stop9h 41m
Deal found 10/15![Frontier logo]()
$230
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 am -
1 stop4h 55m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/14![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 10/19. 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 11/149:59 am -
1 stop7h 28m
Mon 11/166:00 pm -
1 stop5h 18m
Deal found 10/19![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/1210:20 am -
1 stop5h 50m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/19![Southwest logo]()
$233
This deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:15 pm -
Nonstop2h 44m
Fri 11/65:05 pm -
Nonstop3h 12m
Deal found 10/15![JetBlue logo]()
$234
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 October 20, 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 October 20, 2026.
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 11/257:05 am -
Nonstop2h 27m
Mon 11/3012:00 pm -
1 stop7h 22m
Deal found 10/19![Delta logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:15 am -
Nonstop2h 19m
Wed 11/258:25 pm -
Nonstop3h 04m
Deal found 10/17![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:30 am -
Nonstop2h 30m
Sat 11/216:55 pm -
Nonstop2h 45m
Deal found 10/16![Southwest logo]()
$311
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 1/142:52 pm -
1 stop7h 05m
Mon 1/187:03 am -
2 stops8h 19m
Deal found 10/19![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 10/19. 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 11/145:05 pm -
1 stop5h 49m
Tue 11/174:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 11/612:00 pm -
Nonstop2h 32m
Wed 11/187:30 am -
Nonstop3h 05m
Deal found 10/19![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:10 pm -
1 stop4h 45m
Sun 11/85:10 am -
1 stop10h 00m
Deal found 10/14![Southwest logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:50 am -
Nonstop2h 27m
Sun 1/35:45 am -
Nonstop3h 06m
Deal found 10/16![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:35 am -
Nonstop2h 24m
Sun 11/228:40 pm -
Nonstop2h 56m
Deal found 10/17![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/271:25 pm -
Nonstop2h 10m
Fri 1/295:40 am -
2 stops10h 05m
Deal found 10/14![Southwest logo]()
$328
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 11/55:39 pm -
1 stop4h 52m
Wed 11/1112:33 pm -
1 stop5h 34m
Deal found 10/19![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:40 pm -
Nonstop2h 23m
Mon 11/238:40 pm -
Nonstop2h 56m
Deal found 10/15![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:30 am -
1 stop6h 24m
Tue 12/86:00 am -
1 stop5h 10m
Deal found 10/16![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:15 am -
2 stops8h 05m
Mon 12/287:00 am -
Nonstop2h 45m
Deal found 10/15![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 pm -
1 stop5h 05m
Fri 11/276:00 am -
1 stop5h 08m
Deal found 10/15![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
1 stop4h 27m
Mon 11/97:40 pm -
1 stop5h 19m
Deal found 10/17![American Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:25 pm -
Nonstop2h 20m
Thu 12/105:55 pm -
Nonstop2h 45m
Deal found 10/18![Southwest logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:25 am -
2 stops7h 07m
Mon 11/96:00 am -
1 stop5h 08m
Deal found 10/15![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:35 am -
Nonstop2h 24m
Sat 11/147:45 am -
Nonstop3h 10m
Deal found 10/16![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:30 am -
Nonstop2h 30m
Mon 12/712:50 pm -
Nonstop2h 50m
Deal found 10/17![Southwest logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:30 pm -
1 stop5h 29m
Tue 11/35:58 pm -
1 stop7h 01m
Deal found 10/15![American Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:25 am -
Nonstop2h 35m
Fri 11/134:35 pm -
Nonstop3h 09m
Deal found 10/17![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:25 am -
1 stop6h 34m
Wed 11/1111:55 am -
1 stop5h 52m
Deal found 10/16![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:40 pm -
Nonstop2h 15m
Mon 12/75:20 am -
1 stop7h 45m
Deal found 10/16![Southwest logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:00 am -
2 stops9h 06m
Wed 11/47:14 am -
1 stop7h 44m
Deal found 10/16![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:05 am -
Nonstop2h 27m
Wed 12/27:30 am -
Nonstop3h 08m
Deal found 10/16![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/19. 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 3/126:07 pm -
1 stop4h 46m
Mon 3/155:42 pm -
1 stop7h 26m
Deal found 10/19![American Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:04 am -
1 stop6h 40m
Sun 11/15:39 am -
1 stop4h 53m
Deal found 10/15![Delta logo]()
$355
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:01 pm -
1 stop5h 20m
Tue 12/87:47 am -
2 stops8h 03m
Deal found 10/17![American Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:10 am -
2 stops7h 15m
Sun 12/275:45 am -
1 stop5h 15m
Deal found 10/16![United Airlines logo]()
$445
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated October 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 am -
1 stop4h 55m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/14![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:55 am -
2 stops8h 05m
Tue 11/102:25 pm -
1 stop5h 40m
Deal found 10/15![Southwest logo]()
$226
This deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:15 pm -
Nonstop2h 44m
Fri 11/65:05 pm -
Nonstop3h 12m
Deal found 10/15![JetBlue logo]()
$234
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:16 pm -
Nonstop2h 33m
Sat 11/74:41 pm -
Nonstop3h 14m
Deal found 10/15![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 11/96:00 am -
2 stops28h 30m
Thu 11/1912:39 pm -
1 stop7h 06m
Deal found 10/19![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/1210:20 am -
1 stop5h 50m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/19![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 10/19. 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 11/145:42 pm -
1 stop5h 02m
Tue 11/177:00 pm -
1 stop5h 54m
Deal found 10/19![Delta logo]()
$233
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/178:10 am -
2 stops6h 40m
Mon 11/234:20 pm -
Nonstop2h 45m
Deal found 10/19![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 10/19. 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 11/216:15 pm -
1 stop5h 53m
Mon 11/304:35 pm -
Nonstop3h 09m
Deal found 10/19![Delta logo]()
$223
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 11/2411:06 am -
1 stop9h 41m
Deal found 10/15![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Thu 12/311:08 am -
1 stop28h 33m
Deal found 10/19![Frontier logo]()
$235
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
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 October 20, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:50 pm -
1 stop4h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Southwest logo]()
$111
This Super.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/258:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 10/19. 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.
Wed 11/255:05 pm -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 10/19. 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.
Wed 11/188:00 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$117
This Frontier deal was found by Cheapflights users on 10/19. 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 12/188:35 pm -
1 stop11h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Wed 12/910:00 am -
2 stops22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$124
This Super.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com 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 10/16![Frontier logo]()
$124
This Frontier deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/199:21 pm -
1 stop10h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 10/16![Allegiant Air logo]()
$126
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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Delta) |
One-way from | $111 (Southwest) |
Popular in | October |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $295 or less |
Good one-way deal | $174 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 October 20, 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 12/7
9:40 am-4:50 pm
1 stop6h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 12/5
10:20 am-7:25 pm
2 stops8h 05m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 11/19
7:00 am-12:25 pm
1 stop4h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 11/14
1:30 pm-6:57 pm
1 stop4h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 1/26
3:25 pm-8:50 pm
1 stop4h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 12/3
1:20 pm-9:55 pm
2 stops7h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 2/24
8:15 am-4:05 pm
2 stops6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sun 11/22
7:50 am-11:10 am
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
11:00 am-2:25 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/21
7:45 am-11:00 am
Nonstop2h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
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
CMI-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 $202). Flying from Illinois to Boston in October is currently the most expensive (average of $323). 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 October 20, 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 15% 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 October 20, 2026.
The most flights from USIL to BOS are scheduled on a Sunday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (55 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 $210 and $398 in November.The cheapest round-trip price found within the last 5 days was $223 on Delta (Nov 21-Dec 5).
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 October 17, 2026.
Travelers seeking maximum savings on their Illinois to Boston flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
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 October 20, 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 October 20, 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 October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$334 | FlexibilityNo cancel fee | On-time63% |