$78+ Cheap flights from Boston (BOS) to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
May 28 — Jun 41
Round-trip
1 adult, Economy
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Cheapest flights from Boston to IllinoisExplore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
Explore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/196:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/23![American Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:51 am
BOS
- MDW
1 stop8h 28m
Delta
Tue 6/25:15 pm
MDW
- BOS
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Sat 6/66:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
BOS
- MDW
1 stop4h 03m
Delta
Mon 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/23![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
BOS
- ORD
1 stop5h 49m
Delta
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Mon 8/175:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/23![Southwest logo]()
$159
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/196:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Wed 5/2012:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$160
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/94:32 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Tue 5/1210:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Deal found 4/24![American Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Wed 7/155:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 7/2110:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 4/28![JetBlue logo]()
$162
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:45 am
BOS
- ORD
1 stop4h 48m
United Airlines
Mon 8/177:33 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 4/23![United Airlines logo]()
$163
Best flights from Boston to IllinoisDiscover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
Discover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/185:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 4/25![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/228:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/249:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 4/25![United Airlines logo]()
$191
This KAYAK deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/27![Delta logo]()
$237
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/17:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/49:49 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 4/24![JetBlue logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:45 am
BOS
- RFD
1 stop29h 02m
Multiple Airlines
Sun 5/1011:50 am
RFD
- BOS
1 stop21h 53m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:05 am
BOS
- BMI
1 stop6h 56m
American Airlines
Tue 7/711:27 am
BMI
- BOS
1 stop7h 32m
American Airlines
Deal found 4/23![American Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 5/305:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Deal found 4/25![Southwest logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/123:00 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Fri 5/158:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/28![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/206:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 8/37:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/25![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:00 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/109:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 4/23![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/266:30 pm
BOS
- ORD
1 stop5h 06m
Delta
Wed 6/33:50 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/24![Delta logo]()
$241
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/25:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Wed 7/86:00 am
ORD
- BOS
1 stop4h 21m
JetBlue
Deal found 4/24![JetBlue logo]()
$260
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/245:40 am
BOS
- ORD
1 stop5h 57m
Delta
Mon 7/277:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 4/23![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/255:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 5/317:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 4/25![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/117:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 6/125:05 pm
MDW
- BOS
1 stop6h 05m
Southwest
Deal found 4/27![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Sun 7/1911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/77:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 5/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/26![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Multiple Airlines
Thu 7/911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Sun 7/199:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/23![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/1012:50 pm
BOS
- MDW
1 stop7h 15m
Southwest
Wed 6/177:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Deal found 4/27![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Mon 7/207:50 pm
RFD
- BOS
1 stop26h 48m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$308
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/65:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/92:45 pm
MDW
- BOS
1 stop7h 40m
Southwest
Deal found 4/24![Southwest logo]()
$247
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:05 am
BOS
- BMI
1 stop6h 56m
American Airlines
Wed 7/85:54 pm
BMI
- BOS
1 stop5h 05m
American Airlines
Deal found 4/23![American Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/512:33 pm
BOS
- RFD
1 stop20h 44m
Multiple Airlines
Sun 6/711:27 am
RFD
- BOS
1 stop11h 27m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 am
BOS
- MLI
1 stop5h 54m
Delta
Fri 7/105:07 pm
MLI
- BOS
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/811:35 am
BOS
- MDW
2 stops6h 25m
Southwest
Sun 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 4/26![Southwest logo]()
$256
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/243:05 pm
BOS
- BMI
2 stops9h 54m
American Airlines
Sun 5/316:02 pm
BMI
- BOS
1 stop5h 13m
American Airlines
Deal found 4/26![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/812:30 pm
BOS
- PIA
1 stop5h 28m
United Airlines
Mon 7/135:33 pm
PIA
- BOS
1 stop6h 35m
United Airlines
Deal found 4/28![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/56:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 5/115:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 4/26![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:30 am
BOS
- MLI
1 stop5h 54m
Delta
Wed 7/85:00 pm
MLI
- BOS
1 stop7h 20m
Delta
Deal found 4/23![Delta logo]()
$392
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated April 28, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Tue 5/1912:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/27![Frontier logo]()
$160
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:28 pm
BOS
- ORD
1 stop5h 12m
United Airlines
Wed 5/136:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/23![United Airlines logo]()
$165
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/23![JetBlue logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/196:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/23![American Airlines logo]()
$156
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2310:16 am
BOS
- ORD
1 stop7h 40m
Delta
Wed 5/279:36 am
ORD
- BOS
1 stop5h 52m
Delta
Deal found 4/23![Delta logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Wed 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sat 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/27![JetBlue logo]()
$162
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:51 am
BOS
- MDW
1 stop8h 28m
Delta
Tue 6/25:15 pm
MDW
- BOS
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
BOS
- MDW
1 stop4h 03m
Delta
Mon 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/23![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
BOS
- ORD
1 stop5h 49m
Delta
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$158
One-way flights from Boston to IllinoisSearch for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Deal found 4/23![Southwest logo]()
$78
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/23![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/205:40 am
BOS
- ORD
1 stop5h 49m
Delta
Deal found 4/23![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/285:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/24![Delta logo]()
$80
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/23![Southwest logo]()
$81
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:39 pm
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 4/23![United Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/269:12 am
BOS
- STL
1 stop24h 43m
Frontier
Deal found 4/27![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/2311:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 4/24![JetBlue logo]()
$82
This Super.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/27![JetBlue logo]()
$83
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$84
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/78:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 4/27![Delta logo]()
$84
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/246:00 am
BOS
- STL
1 stop12h 33m
Frontier
Deal found 4/27![Frontier logo]()
$86
Find flight deals from Boston to Illinois
Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated April 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (American Airlines) |
One-way from | $78 (Southwest) |
Popular in | April |
Cheapest in | September |
Average price | $260 |
Good round-trip deal | $232 or less |
Good one-way deal | $133 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/18
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Sun 6/21
5:15 am-8:25 am
Nonstop2h 10m
$191
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/22
8:20 pm-10:20 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/24
9:15 am-12:57 pm
Nonstop2h 42m
$191
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/23
1:50 pm-3:30 pm
Nonstop2h 40m
Chicago Midway
Sat 5/30
5:25 pm-11:40 pm
1 stop5h 15m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/12
3:00 pm-4:58 pm
Nonstop2h 58m
Chicago O'Hare Intl
Fri 5/15
8:00 pm-11:35 pm
Nonstop2h 35m
$192
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 7/20
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Mon 8/3
7:35 pm-10:50 pm
Nonstop2h 15m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/7
3:00 pm-4:58 pm
Nonstop2h 58m
Chicago O'Hare Intl
Sun 5/10
9:30 pm-12:59 am
Nonstop2h 29m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
8:40 pm-10:35 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
$237
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 5/26
6:30 pm-10:36 pm
1 stop5h 06m
Chicago O'Hare Intl
Wed 6/3
3:50 pm-7:27 pm
Nonstop2h 37m
$241
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/25
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sun 5/31
7:33 am-11:05 am
Nonstop2h 32m
$241
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/11
7:30 am-9:10 am
Nonstop2h 40m
Chicago Midway
Fri 6/12
5:05 pm-12:10 am
1 stop6h 05m
$242
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Boston with our price prediction graph.
BOS-MDW
BOS-ORD
BOS-STL
BOS-RFD
BOS-BMI
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 Boston to Illinois
BOS-USIL
BOS-MDW
BOS-ORD
BOS-STL
BOS-RFD
How far ahead should I book a flight from Boston to Illinois?
The best time to book flights from Boston to Illinois is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Boston to Illinois?
Currently, September is the cheapest month in which you can book a flight from Boston to Illinois (average of $166). Flying from Boston to Illinois in April is currently the most expensive (average of $295). 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 BOS to IL?
Find hourly flight availability from Boston to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 28, 2026.
One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 23% on airfare.
What is the cheapest day to fly from Boston to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Boston to Illinois. Price data was last updated on April 25, 2026.
Travelers seeking maximum savings on their Boston to Illinois flight should consider departing on Thursday evenings 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.
Weekly flight availability from Boston to Illinois
Explore weekly flight availability from Boston to Illinois. 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 April 28, 2026.
The most flights from BOS to USIL are scheduled on a Tuesday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Boston to Illinois?
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated April 28, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Boston to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Boston to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Illinois by cabin class
Find flights from Boston to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Illinois flights
Browse other Boston and Illinois flight options. Last updated on April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Illinois flights
Consider these flights traveling from Boston to Illinois.
Top 6 airlines flying from Boston to Illinois
Discover the top 6 airlines that operate flights from Boston to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$322 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$95 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$125 | Average$217 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$132 | Average$413 | FlexibilityNo cancel fee | On-time71% |