$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 7 — Nov 141
Round-trip
1 adult, Economy
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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 8, 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 8, 2026.
This Orbitz deal was found by Cheapflights users on 10/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/7![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 10/6. 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.
Thu 11/58:36 am -
1 stop4h 49m
Tue 11/101:45 pm -
1 stop6h 20m
Deal found 10/6![Delta logo]()
$221
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop6h 40m
Thu 11/125:30 am -
1 stop5h 16m
Deal found 10/7![Delta logo]()
$221
This CheapOair deal was found by Cheapflights users on 10/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:46 am -
1 stop25h 16m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 10/7![Frontier logo]()
$222
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:00 am -
1 stop3h 55m
Mon 11/26:25 pm -
1 stop6h 32m
Deal found 10/7![Delta logo]()
$223
This JetBlue deal was found by Cheapflights users on 10/6. 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.
Fri 10/236:10 am -
1 stop7h 19m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 10/6![JetBlue logo]()
$225
This Super.com deal was found by Cheapflights users on 10/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:24 pm -
Nonstop2h 44m
Mon 11/25:05 pm -
Nonstop3h 12m
Deal found 10/5![JetBlue logo]()
$226
This Southwest deal was found by Cheapflights users on 10/7. 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.
Thu 11/510:20 am -
1 stop5h 50m
Thu 11/122:25 pm -
2 stops7h 05m
Deal found 10/7![Southwest logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:15 pm -
Nonstop2h 44m
Tue 11/179:59 am -
Nonstop3h 01m
Deal found 10/7![JetBlue logo]()
$227
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 11/128:25 pm -
1 stop10h 40m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/6![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:50 pm -
2 stops36h 39m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/6![Multiple Airlines logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/219:23 pm -
1 stop10h 17m
Mon 1/1110:24 am -
1 stop10h 18m
Deal found 10/7![Frontier logo]()
$228
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 8, 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 8, 2026.
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:36 am -
1 stop4h 49m
Thu 11/1212:00 pm -
1 stop7h 22m
Deal found 10/7![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 10/7. 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.
Tue 11/171:20 pm -
2 stops7h 35m
Wed 11/187:55 am -
1 stop7h 45m
Deal found 10/7![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:31 pm -
1 stop5h 59m
Mon 11/96:36 pm -
1 stop5h 23m
Deal found 10/6![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/126:02 am -
2 stops7h 40m
Sun 11/157:40 pm -
1 stop5h 23m
Deal found 10/4![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:00 am -
1 stop5h 58m
Mon 12/72:00 pm -
1 stop5h 23m
Deal found 10/7![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 11/257:00 pm -
Nonstop2h 25m
Fri 11/277:05 am -
Nonstop2h 45m
Deal found 10/7![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:30 am -
1 stop7h 24m
Thu 10/299:15 am -
1 stop4h 55m
Deal found 10/7![Delta logo]()
$221
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 am -
1 stop5h 21m
Mon 11/166:00 pm -
1 stop5h 18m
Deal found 10/7![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 11/56:45 pm -
Nonstop2h 20m
Tue 11/105:55 pm -
Nonstop2h 45m
Deal found 10/6![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 10/5. 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.
Sat 11/146:44 pm -
1 stop4h 10m
Wed 11/185:30 am -
1 stop5h 16m
Deal found 10/5![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sun 11/87:50 am -
Nonstop2h 20m
Fri 11/136:30 pm -
Nonstop2h 45m
Deal found 10/6![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/217:18 pm -
1 stop5h 00m
Tue 12/295:45 am -
1 stop5h 15m
Deal found 10/4![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/7. 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 1/142:52 pm -
1 stop7h 05m
Mon 1/187:03 am -
2 stops8h 19m
Deal found 10/7![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:30 pm -
1 stop5h 49m
Mon 11/26:25 pm -
1 stop6h 32m
Deal found 10/7![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 10/5. 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.
Mon 11/233:35 pm -
Nonstop2h 15m
Fri 11/277:05 am -
Nonstop2h 45m
Deal found 10/5![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 10/295:00 am -
2 stops7h 31m
Sat 10/314:56 pm -
1 stop5h 26m
Deal found 10/4![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/146:00 am -
2 stops7h 37m
Sat 1/168:04 am -
2 stops10h 10m
Deal found 10/7![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/6. 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.
Fri 11/135:50 pm -
1 stop4h 27m
Mon 11/161:00 pm -
1 stop7h 25m
Deal found 10/6![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 10/6. 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.
Sat 10/244:25 pm -
Nonstop2h 25m
Thu 10/2910:00 pm -
Nonstop2h 40m
Deal found 10/6![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:43 am -
2 stops6h 51m
Sun 11/159:12 am -
1 stop5h 41m
Deal found 10/7![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 -
2 stops8h 24m
Sun 11/16:00 am -
2 stops8h 58m
Deal found 10/4![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:45 pm -
Nonstop2h 29m
Wed 12/302:55 pm -
Nonstop3h 06m
Deal found 10/7![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/136:45 pm -
Nonstop2h 20m
Sun 11/157:30 pm -
1 stop5h 40m
Deal found 10/7![Southwest logo]()
$296
This American Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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 11/125:00 am -
2 stops8h 42m
Sat 11/146:00 am -
2 stops8h 58m
Deal found 10/4![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 10/5. 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.
Fri 11/610:10 am -
1 stop6h 30m
Sun 11/87:05 am -
Nonstop2h 45m
Deal found 10/5![Southwest logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:15 am -
1 stop5h 33m
Sun 10/256:00 am -
1 stop5h 08m
Deal found 10/6![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/6. 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.
Fri 12/46:00 am -
1 stop6h 21m
Fri 12/46:00 pm -
1 stop5h 13m
Deal found 10/6![Delta logo]()
$277
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:38 pm -
1 stop7h 21m
Sat 10/243:31 pm -
1 stop5h 54m
Deal found 10/5![American Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 10/5. 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 11/411:30 am -
1 stop4h 20m
Sun 11/87:30 pm -
1 stop5h 40m
Deal found 10/5![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 10/6. 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.
Fri 11/65:29 pm -
1 stop5h 30m
Fri 11/134:00 pm -
1 stop5h 45m
Deal found 10/6![Delta logo]()
$277
Last-minute flights from Illinois to BostonDiscover last-minute flight deals from Illinois to Boston. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Boston. Data last updated October 8, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop13h 51m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 10/7![Frontier logo]()
$238
This Frontier deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop13h 51m
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 10/7![Frontier logo]()
$242
This Kissandfly.com deal was found by Cheapflights users on 10/8. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:04 am -
1 stop5h 38m
Mon 11/212:39 pm -
1 stop12h 08m
Deal found 10/8![Frontier logo]()
$236
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 11/412:50 pm -
1 stop5h 15m
Sat 11/78:10 am -
2 stops10h 15m
Deal found 10/7![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:04 am -
1 stop6h 40m
Thu 11/125:30 am -
1 stop5h 16m
Deal found 10/7![Delta logo]()
$221
This Southwest deal was found by Cheapflights users on 10/7. 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.
Thu 11/510:20 am -
1 stop5h 50m
Thu 11/122:25 pm -
2 stops7h 05m
Deal found 10/7![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:00 pm -
Nonstop2h 10m
Mon 11/94:20 pm -
Nonstop2h 45m
Deal found 10/8![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 11/127:50 am -
2 stops5h 40m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/6![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 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
Sat 11/1411:27 am -
1 stop7h 20m
Deal found 10/6![Multiple Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/136:45 pm -
Nonstop2h 20m
Tue 11/173:30 pm -
1 stop7h 00m
Deal found 10/7![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/5. 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.
Fri 11/136:45 pm -
Nonstop2h 20m
Mon 11/165:45 pm -
1 stop6h 00m
Deal found 10/5![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 10/7. 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.
Wed 11/257:00 pm -
Nonstop2h 25m
Fri 11/277:05 am -
Nonstop2h 45m
Deal found 10/7![Southwest logo]()
$230
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 8, 2026.
Search for one-way flight options from Illinois to Boston. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Delta deal was found by Cheapflights users on 10/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:55 am -
1 stop4h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Delta logo]()
$111
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:27 pm -
1 stop5h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:24 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 10/6. 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.
Fri 12/49:43 pm -
1 stop11h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$113
This KAYAK deal was found by Cheapflights users on 10/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:40 pm -
Nonstop2h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$115
This Southwest deal was found by Cheapflights users on 10/7. 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.
Mon 11/98:15 pm -
1 stop11h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$116
This KAYAK deal was found by Cheapflights users on 10/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:10 pm -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Delta logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares 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 10/7![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/208:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$122
This JetBlue deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:38 pm -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![JetBlue logo]()
$125
This Trip.com deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” 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.
Mon 11/238:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 12/25:35 am -
1 stop27h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Frontier 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 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $220 (CheapOair) |
One-way from | $111 (Delta) |
Popular in | September |
Cheapest in | January |
Average price | $293 |
Good round-trip deal | $282 or less |
Good one-way deal | $157 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 8, 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 12/7
10:05 am-6:23 pm
1 stop7h 18m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 1/6
12:55 pm-7:08 pm
1 stop5h 13m
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
Thu 12/17
6:10 pm-11:50 pm
1 stop4h 40m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 11/5
5:27 am-1:44 pm
1 stop7h 17m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/3
8:36 am-3:23 pm
1 stop5h 47m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/24
6:00 am-2:21 pm
1 stop7h 21m
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
Wed 12/2
12:39 pm-6:58 pm
1 stop5h 19m
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
Mon 11/2
6:04 am-12:42 pm
1 stop5h 38m
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
Tue 10/27
9:29 am-4:15 pm
1 stop5h 46m
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 11/14
6:00 am-12:32 pm
1 stop5h 32m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
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
BMI-BOS
PIA-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
BMI-BOS
PIA-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 September is currently the most expensive (average of $318). 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 8, 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 14% 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 8, 2026.
The most flights from USIL to BOS are scheduled on a Tuesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 $233 and $397 in November.The cheapest round-trip price found within the last 5 days was $220 on Multiple Airlines (Nov 13-Nov 17).
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 3, 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
Auburn
Londonderry
York Beach
Revere
Fitchburg
North Falmouth
Chelsea
Swansea
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 October 8, 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 8, 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$249 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$385 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$422 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$330 | FlexibilityNo cancel fee | On-time63% |