$95+ Cheap flights from Boston (BOS) to Chicago (CHI)
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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Chicago 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.Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 89 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from Boston to Chicago
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Cheapest flights from Boston to ChicagoExplore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:00 pm -
Nonstop2h 40m
Mon 10/195:30 am -
Nonstop2h 25m
Deal found 9/14![Southwest logo]()
$216
This Priceline deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:39 pm -
1 stop7h 06m
Sun 11/88:15 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$216
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/17![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 -
Nonstop2h 35m
Tue 10/209:40 am -
2 stops6h 30m
Deal found 9/13![Southwest logo]()
$218
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:35 am -
1 stop11h 41m
Sun 12/139:21 pm -
1 stop10h 19m
Deal found 9/16![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:20 am -
2 stops8h 05m
Mon 11/912:55 pm -
2 stops8h 40m
Deal found 9/15![Southwest logo]()
$219
This KAYAK deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:10 pm -
Nonstop2h 56m
Wed 11/47:25 am -
Nonstop2h 35m
Deal found 9/16![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:15 am -
2 stops13h 45m
Tue 10/278:10 am -
1 stop5h 45m
Deal found 9/16![Southwest logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1812:39 pm -
1 stop12h 08m
Sun 11/228:42 pm -
1 stop12h 29m
Deal found 9/16![Frontier logo]()
$221
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:47 am -
1 stop21h 04m
Mon 10/268:24 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:39 am -
1 stop4h 53m
Sat 10/106:44 pm -
1 stop4h 15m
Deal found 9/16![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:10 am -
1 stop4h 49m
Wed 10/710:05 am -
1 stop7h 23m
Deal found 9/16![Delta logo]()
$222
Best flights from Boston to ChicagoDiscover carefully curated flight deals from Boston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Boston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:30 am -
2 stops8h 45m
Sat 11/710:25 am -
2 stops10h 40m
Deal found 9/16![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:59 pm -
1 stop5h 16m
Mon 10/57:35 am -
Nonstop2h 33m
Deal found 9/15![Delta logo]()
$252
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:45 am -
1 stop4h 53m
Sat 10/109:24 pm -
Nonstop2h 30m
Deal found 9/15![United Airlines logo]()
$252
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/54:10 pm -
1 stop6h 50m
Tue 10/67:05 am -
1 stop6h 24m
Deal found 9/16![JetBlue logo]()
$253
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/192:20 pm -
Nonstop2h 50m
Mon 2/228:05 am -
Nonstop2h 20m
Deal found 9/14![Southwest logo]()
$229
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/14![JetBlue logo]()
$256
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:20 pm -
Nonstop2h 45m
Sun 11/87:50 am -
Nonstop2h 20m
Deal found 9/15![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:40 am -
1 stop4h 27m
Mon 10/57:01 pm -
1 stop3h 57m
Deal found 9/15![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/79:45 am -
1 stop6h 32m
Sat 1/92:20 pm -
Nonstop2h 29m
Deal found 9/14![United Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 2/2310:24 am -
1 stop28h 38m
Sun 2/285:25 pm -
1 stop14h 54m
Deal found 9/13![Multiple Airlines logo]()
$614
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:40 am -
Nonstop2h 35m
Mon 10/196:45 pm -
Nonstop2h 20m
Deal found 9/14![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:30 am -
Nonstop2h 54m
Tue 10/206:00 am -
1 stop4h 23m
Deal found 9/16![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:30 pm -
Nonstop2h 59m
Sun 10/47:29 am -
Nonstop2h 31m
Deal found 9/16![United Airlines logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/176:55 am -
Nonstop2h 52m
Mon 10/196:10 am -
1 stop7h 19m
Deal found 9/13![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 pm -
Nonstop2h 45m
Sun 11/157:50 am -
Nonstop2h 20m
Deal found 9/14![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:30 am -
Nonstop2h 54m
Tue 10/273:05 pm -
Nonstop2h 39m
Deal found 9/12![Delta logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/165:12 pm -
Nonstop3h 02m
Wed 10/2112:38 pm -
1 stop7h 11m
Deal found 9/12![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/165:35 pm -
1 stop4h 55m
Sun 11/226:30 am -
1 stop6h 15m
Deal found 9/15![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:50 am -
Nonstop2h 58m
Mon 10/263:05 pm -
Nonstop2h 39m
Deal found 9/14![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/295:40 am -
2 stops10h 10m
Sun 1/317:50 am -
1 stop7h 55m
Deal found 9/16![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop7h 46m
Sat 10/249:59 am -
1 stop7h 55m
Deal found 9/16![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/25:30 am -
1 stop4h 30m
Thu 12/241:20 pm -
2 stops7h 30m
Deal found 9/13![Southwest logo]()
$277
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:50 am -
Nonstop2h 35m
Mon 10/266:45 pm -
Nonstop2h 20m
Deal found 9/12![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:35 am -
2 stops9h 20m
Tue 10/203:05 pm -
2 stops6h 40m
Deal found 9/16![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 10/66:45 am -
1 stop5h 35m
Tue 10/63:15 pm -
Nonstop2h 20m
Deal found 9/12![Southwest logo]()
$305
Last-minute flights from Boston to ChicagoDiscover last-minute flight deals from Boston to Chicago. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Chicago. Data last updated September 17, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
Nonstop2h 48m
Mon 10/57:00 am -
1 stop6h 29m
Deal found 9/17![JetBlue logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
1 stop12h 23m
Tue 10/68:24 pm -
Nonstop2h 59m
Deal found 9/16![Multiple Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:10 am -
1 stop4h 49m
Wed 10/710:05 am -
1 stop7h 23m
Deal found 9/16![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:39 am -
1 stop4h 53m
Sat 10/106:44 pm -
1 stop4h 15m
Deal found 9/16![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1510:00 pm -
Nonstop2h 40m
Mon 10/195:30 am -
Nonstop2h 25m
Deal found 9/14![Southwest logo]()
$216
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 -
Nonstop2h 35m
Tue 10/209:40 am -
2 stops6h 30m
Deal found 9/13![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:40 pm -
Nonstop2h 51m
Mon 10/265:29 pm -
1 stop5h 30m
Deal found 9/14![Delta logo]()
$225
This Expedia deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:47 am -
1 stop21h 04m
Mon 10/268:24 pm -
Nonstop2h 44m
Deal found 9/16![Multiple Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:30 pm -
1 stop5h 25m
Mon 10/262:50 pm -
2 stops5h 30m
Deal found 9/16![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:15 am -
2 stops13h 45m
Tue 10/278:10 am -
1 stop5h 45m
Deal found 9/16![Southwest logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:39 pm -
1 stop7h 06m
Sat 10/318:24 pm -
Nonstop2h 44m
Deal found 9/17![Multiple Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:30 am -
2 stops8h 45m
Sat 11/710:25 am -
2 stops10h 40m
Deal found 9/16![Southwest logo]()
$225
One-way flights from Boston to ChicagoSearch for one-way flight options from Boston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Boston to Chicago. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/131:10 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$95
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/119:35 am -
1 stop11h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:15 am -
2 stops13h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$116
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:39 am -
1 stop4h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:00 am -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/112:40 pm -
Nonstop3h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$119
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:30 am -
Nonstop2h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:00 pm -
Nonstop2h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$121
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:43 pm -
Nonstop2h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$121
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/267:45 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$123
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/265:15 am -
1 stop5h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![JetBlue logo]()
$124
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:57 pm -
1 stop11h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$125
Find flight deals from Boston to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $216 (Southwest) |
One-way from | $95 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $254 |
Good round-trip deal | $280 or less |
Good one-way deal | $162 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 10/24
5:50 am-11:47 am
1 stop6h 57m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 11/12
7:00 am-1:08 pm
1 stop7h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 1/31
1:10 pm-2:55 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Mon 11/23
6:30 pm-8:15 pm
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sun 10/25
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - RFD Chicago Greater Rockford
BOSRFD
Boston Logan Intl
Sat 10/24
10:19 am-9:30 am
1 stop24h 11m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Mon 11/2
6:00 am-2:54 pm
2 stops9h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 10/24
6:00 am-2:42 pm
2 stops9h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 9/29
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$152
BostonChicago
BOS Boston Logan Intl - RFD Chicago Greater Rockford
BOSRFD
Boston Logan Intl
Sat 11/7
10:19 am-9:40 am
1 stop24h 21m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
Showing 1-10 of 55 resultsSorted by cheapest first
Compare providers for flights from Boston to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Boston-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Boston-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Boston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.
BOS-CHI
BOS-MDW
BOS-ORD
BOS-RFD
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 Chicago
BOS-CHI
BOS-MDW
BOS-ORD
BOS-RFD
What is the cheapest month to book a flight from Boston to Chicago?
Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of $197). Flying from Boston to Chicago in June is currently the most expensive (average of $275). 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 CHI?
Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 17% on flights from Boston to Chicago by exploring options for tickets in the evening.
Weekly flight availability from Boston to Chicago
Explore weekly flight availability from Boston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2026.
The most flights from BOS to CHI are scheduled on a Monday (73 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 Boston to Chicago?
Airfare is typical for this route at the moment.
Boston to Chicago flights typically cost between $204 and $330 in October.The cheapest round-trip price found within the last 5 days was $216 on Southwest (Oct 15-Oct 19).
How often are flights from Boston to Chicago delayed?
About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 172 minutes.
What is the most punctual flight time for Boston to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Boston to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
How far ahead should I book a flight from Boston to Chicago?
The best time to book flights from Boston to Chicago is 14 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 Chicago?
Use this chart to determine the cheapest time to fly round-trip from Boston to Chicago. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Boston to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Boston to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 17, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Chicago 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
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
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 Chicago. 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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Complete your trip
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Boston and Chicago flights
Browse other Boston and Chicago flight options. Last updated on September 17, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on September 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Boston to Chicago
Discover the top 5 airlines that operate flights from Boston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$326 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$132 | Average$284 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$139 | Average$307 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$143 | Average$249 | FlexibilityNo cancel fee | On-time71% |