$101+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 26 — Sep 21
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Illinois 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Illinois
Cheapest
Best
Last-minute
One-way
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 July 27, 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 July 27, 2026.
This SmartFares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Sun 9/137:00 am
ORD
- BOS
1 stop5h 44m
JetBlue
Deal found 7/22![JetBlue logo]()
$193
This Flysmarter deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:09 pm
BOS
- ORD
1 stop6h 49m
JetBlue
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Deal found 7/22![JetBlue logo]()
$198
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Tue 8/256:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$201
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Sun 9/137:00 am
ORD
- BOS
1 stop5h 44m
JetBlue
Deal found 7/22![JetBlue logo]()
$203
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Sat 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/22![JetBlue logo]()
$207
This Super.com deal was found by Cheapflights users on 7/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Thu 8/209:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/23![JetBlue logo]()
$211
This Super.com deal was found by Cheapflights users on 7/24. 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.
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Thu 8/209:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/24![JetBlue logo]()
$212
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/22![JetBlue logo]()
$213
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
BOS
- ORD
Nonstop2h 48m
JetBlue
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Deal found 7/22![JetBlue logo]()
$215
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:19 pm
BOS
- ORD
Nonstop3h 19m
American Airlines
Sat 9/129:00 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Deal found 7/22![American Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 7/26. 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 9/93:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/168:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. 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.
Sat 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$222
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 July 27, 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 July 27, 2026.
This Delta deal was found by Cheapflights users on 7/23. 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 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Wed 9/237:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/23![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. 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.
Thu 10/155:50 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/206:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Wed 10/148:31 pm
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 10/187:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 7/25![United Airlines logo]()
$222
This JetBlue deal was found by Cheapflights users on 7/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 9/157:05 am
ORD
- BOS
1 stop6h 22m
JetBlue
Deal found 7/25![JetBlue logo]()
$233
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 8/253:53 pm
BOS
- CMI
1 stop5h 35m
American Airlines
Tue 9/111:41 am
CMI
- BOS
1 stop5h 59m
American Airlines
Deal found 7/26![American Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 10/1010:19 am
BOS
- RFD
1 stop24h 21m
Multiple Airlines
Mon 10/1210:39 am
RFD
- BOS
1 stop22h 30m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/234:30 pm
BOS
- ORD
Nonstop2h 58m
Delta
Mon 9/287:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/26![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Thu 9/173:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Tue 9/221:55 pm
ORD
- BOS
Nonstop2h 41m
United Airlines
Deal found 7/25![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 7/26. 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.
Fri 9/1112:40 pm
BOS
- MDW
Nonstop2h 30m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/26![Southwest logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:00 am
BOS
- ORD
Nonstop2h 54m
JetBlue
Tue 9/811:01 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 7/25![JetBlue logo]()
$235
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Wed 9/93:05 pm
ORD
- BOS
Nonstop2h 47m
Delta
Deal found 7/26![Delta logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 12/189:28 am
BOS
- RFD
2 stops9h 27m
Allegiant Air
Thu 1/2111:23 am
RFD
- BOS
1 stop21h 44m
Allegiant Air
Deal found 7/24![Allegiant Air logo]()
$498
This United Airlines deal was found by Cheapflights users on 7/25. 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 10/166:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 10/186:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 7/25![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 7/26. 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.
Sat 10/179:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 10/1911:00 am
MDW
- BOS
1 stop5h 20m
Southwest
Deal found 7/26![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:36 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sun 9/277:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/23![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/84:05 pm
BOS
- ORD
Nonstop2h 56m
Delta
Thu 9/107:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/26![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Sun 9/206:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/23![Southwest logo]()
$235
This KAYAK deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Thu 10/221:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/22![JetBlue logo]()
$280
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/48:31 pm
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 9/66:24 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 7/23![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 am
BOS
- MDW
1 stop5h 00m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/22![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sat 8/226:14 am
BOS
- CMI
1 stop5h 57m
American Airlines
Sat 8/2911:41 am
CMI
- BOS
1 stop4h 53m
American Airlines
Deal found 7/26![American Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 7/25. 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.
Fri 9/44:30 pm
BOS
- MDW
1 stop7h 55m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$237
This American Airlines deal was found by Cheapflights users on 7/23. 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 10/217:00 am
BOS
- BMI
1 stop7h 57m
American Airlines
Sat 10/242:30 pm
BMI
- BOS
1 stop5h 29m
American Airlines
Deal found 7/23![American Airlines logo]()
$329
This Southwest deal was found by Cheapflights users on 7/25. 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.
Fri 8/218:40 am
BOS
- MDW
2 stops9h 25m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$242
This American Airlines deal was found by Cheapflights users on 7/24. 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.
Thu 8/202:00 pm
BOS
- MLI
1 stop5h 11m
American Airlines
Thu 8/276:00 am
MLI
- BOS
2 stops7h 42m
American Airlines
Deal found 7/24![American Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 8/1710:30 am
MDW
- BOS
1 stop6h 20m
Southwest
Deal found 7/22![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:30 am
BOS
- MLI
1 stop5h 55m
Delta
Tue 9/85:16 pm
MLI
- BOS
1 stop7h 01m
Delta
Deal found 7/25![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am
BOS
- CMI
1 stop6h 43m
American Airlines
Sat 10/314:05 pm
CMI
- BOS
1 stop6h 31m
American Airlines
Deal found 7/23![American Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:01 am
BOS
- PIA
1 stop5h 05m
United Airlines
Sat 8/1510:41 am
PIA
- BOS
1 stop4h 46m
United Airlines
Deal found 7/22![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:30 am
BOS
- MLI
1 stop5h 55m
Delta
Tue 9/85:16 pm
MLI
- BOS
1 stop7h 01m
Delta
Deal found 7/25![Delta logo]()
$329
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated July 27, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:52 am
BOS
- ORD
1 stop9h 01m
Multiple Airlines
Wed 8/58:25 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 7/22![Multiple Airlines logo]()
$241
This CheapOair deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:52 am
BOS
- ORD
1 stop9h 01m
Multiple Airlines
Fri 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:45 pm
BOS
- ORD
Nonstop3h 19m
American Airlines
Fri 8/73:00 pm
ORD
- BOS
Nonstop2h 40m
American Airlines
Deal found 7/22![American Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:10 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Sun 8/96:05 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Deal found 7/22![American Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 7/23. 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 8/117:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/1912:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/23![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 8/153:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/22![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 7/26. 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 8/127:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/175:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/26![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 8/1812:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/22![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/178:15 am
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/22![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 7/24. 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.
Tue 8/185:35 am
BOS
- MDW
1 stop9h 20m
Southwest
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 7/27. 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 8/207:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/27![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 9/12:00 pm
MDW
- BOS
1 stop7h 15m
Southwest
Deal found 7/22![Southwest logo]()
$245
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 July 27, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/22![JetBlue logo]()
$101
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/22![JetBlue logo]()
$102
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/22![JetBlue logo]()
$103
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:00 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 7/22![American Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 7/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:09 pm
BOS
- ORD
1 stop6h 49m
JetBlue
Deal found 7/25![JetBlue logo]()
$108
This Southwest deal was found by Cheapflights users on 7/24. 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.
Sat 9/198:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/24![Southwest logo]()
$109
This Delta deal was found by Cheapflights users on 7/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:35 pm
BOS
- ORD
Nonstop2h 51m
Delta
Deal found 7/26![Delta logo]()
$109
This Traveloka deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/22![JetBlue logo]()
$110
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:00 pm
BOS
- ORD
1 stop6h 56m
JetBlue
Deal found 7/22![JetBlue logo]()
$111
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:53 pm
BOS
- ORD
Nonstop3h 11m
American Airlines
Deal found 7/22![American Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 7/24. 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.
Thu 9/248:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/24![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/22![Southwest logo]()
$118
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 July 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $198 (Flysmarter) |
One-way from | $101 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $249 |
Good round-trip deal | $231 or less |
Good one-way deal | $151 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 July 27, 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
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/9
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 9/23
7:30 pm-11:09 pm
Nonstop2h 39m
$217
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 10/15
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Tue 10/20
6:10 pm-9:25 pm
Nonstop2h 15m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 10/14
8:31 pm-10:30 pm
Nonstop2h 59m
Chicago O'Hare Intl
Sun 10/18
7:30 am-11:01 am
Nonstop2h 31m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/23
4:30 pm-6:28 pm
Nonstop2h 58m
Chicago O'Hare Intl
Mon 9/28
7:30 pm-11:09 pm
Nonstop2h 39m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/17
3:13 pm-5:05 pm
Nonstop2h 52m
Chicago O'Hare Intl
Tue 9/22
1:55 pm-5:36 pm
Nonstop2h 41m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/3
12:25 pm-2:19 pm
Nonstop2h 54m
Chicago O'Hare Intl
Wed 9/9
3:05 pm-6:52 pm
Nonstop2h 47m
$222
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 9/11
12:40 pm-2:10 pm
Nonstop2h 30m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 10/16
6:00 am-7:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Sun 10/18
6:10 am-9:33 am
Nonstop2h 23m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/24
10:36 am-12:29 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:04 am
Nonstop2h 34m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 9/8
4:05 pm-6:01 pm
Nonstop2h 56m
Chicago O'Hare Intl
Thu 9/10
7:30 pm-11:09 pm
Nonstop2h 39m
$227
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-ORD
BOS-MDW
BOS-RFD
BOS-PIA
BOS-STL
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-ORD
BOS-MDW
BOS-RFD
BOS-PIA
What is the cheapest month to book a flight from Boston to Illinois?
Currently, January is the cheapest month in which you can book a flight from Boston to Illinois (average of $197). Flying from Boston to Illinois in June is currently the most expensive (average of $276). 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 July 27, 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 22% on airfare.
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 July 27, 2026.
The most flights from BOS to USIL are scheduled on a Sunday (77 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (51 on average).
How much does it cost to fly round-trip from Boston to Illinois?
Airfare is typical for this route at the moment.
Boston to Illinois flights typically cost between $185 and $318 in September.The cheapest round-trip price found within the last 5 days was $198 on JetBlue (Sep 5-Sep 12).
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 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 July 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.
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 July 27, 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
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 July 27, 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 5 airlines flying from Boston to Illinois
Discover the top 5 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 July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$322 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$134 | Average$284 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$393 | FlexibilityNo cancel fee | On-time71% |