$139+ Cheap flights from Hartford (BDL) 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Oct 21 — Oct 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Hartford 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 Hartford Bradley Intl to Chicago are usually found in January or December, booked 85 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from Hartford to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Hartford to ChicagoExplore the most affordable flight options available from Hartford to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 2026.
Explore the most affordable flight options available from Hartford to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 21, 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.
Wed 10/215:35 am -
2 stops8h 50m
Sat 10/246:45 am -
2 stops7h 15m
Deal found 9/16![Southwest logo]()
$287
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm -
Nonstop2h 48m
Sat 10/242:52 pm -
1 stop5h 31m
Deal found 9/16![American Airlines logo]()
$287
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:40 pm -
1 stop4h 51m
Tue 10/137:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$288
This KAYAK deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
1 stop5h 59m
Sat 10/242:55 pm -
1 stop8h 03m
Deal found 9/18![JetBlue logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:02 pm -
1 stop7h 32m
Sat 10/173:37 pm -
1 stop6h 59m
Deal found 9/17![American Airlines logo]()
$291
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:25 pm -
Nonstop2h 30m
Thu 11/128:00 am -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$292
This KAYAK deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Sat 10/242:55 pm -
1 stop8h 03m
Deal found 9/18![JetBlue logo]()
$292
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:45 am -
Nonstop2h 30m
Sat 12/53:40 pm -
Nonstop2h 00m
Deal found 9/17![Southwest logo]()
$293
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:05 am -
Nonstop2h 45m
Fri 10/237:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$293
Best flights from Hartford to ChicagoDiscover carefully curated flight deals from Hartford to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
Discover carefully curated flight deals from Hartford to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
1 stop6h 33m
Wed 12/96:20 pm -
Nonstop2h 20m
Deal found 9/17![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop6h 54m
Mon 10/196:44 pm -
1 stop3h 48m
Deal found 9/18![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/125:40 pm -
1 stop6h 35m
Sat 11/1410:05 am -
2 stops6h 30m
Deal found 9/20![Southwest logo]()
$322
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/316:00 am -
Nonstop2h 51m
Tue 11/31:30 pm -
1 stop4h 12m
Deal found 9/20![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/22:30 pm -
1 stop6h 40m
Wed 11/49:55 am -
2 stops8h 50m
Deal found 9/20![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:23 am -
1 stop5h 09m
Fri 10/166:44 pm -
1 stop3h 48m
Deal found 9/19![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:37 am -
1 stop7h 23m
Sat 11/1410:32 am -
1 stop7h 12m
Deal found 9/20![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:50 am -
Nonstop2h 20m
Tue 10/205:45 am -
1 stop6h 00m
Deal found 9/19![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:50 pm -
1 stop7h 04m
Fri 11/277:05 am -
1 stop4h 07m
Deal found 9/20![Delta logo]()
$333
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.
Fri 1/296:00 am -
1 stop6h 40m
Mon 2/18:40 am -
1 stop4h 09m
Deal found 9/16![United Airlines logo]()
$331
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:05 pm -
1 stop6h 20m
Mon 10/264:30 pm -
2 stops6h 25m
Deal found 9/17![Southwest logo]()
$356
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:16 pm -
1 stop17h 38m
Sun 10/2510:20 am -
2 stops23h 40m
Deal found 9/17![Multiple Airlines logo]()
$442
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.
Wed 1/136:00 am -
1 stop6h 40m
Wed 5/56:20 pm -
Nonstop2h 02m
Deal found 9/16![United Airlines logo]()
$340
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.
Wed 10/215:35 am -
2 stops8h 50m
Sun 10/257:20 pm -
Nonstop2h 10m
Deal found 9/16![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:17 am -
1 stop5h 20m
Sun 12/135:12 pm -
1 stop6h 03m
Deal found 9/19![Delta logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:10 am -
1 stop27h 04m
Sun 10/2510:20 am -
2 stops36h 24m
Deal found 9/19![Multiple Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:01 pm -
Nonstop2h 51m
Sat 12/192:30 pm -
Nonstop2h 18m
Deal found 9/19![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:57 pm -
1 stop6h 07m
Sun 11/156:44 pm -
1 stop3h 57m
Deal found 9/19![Delta logo]()
$412
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:20 pm -
Nonstop2h 20m
Sun 10/257:45 am -
Nonstop2h 10m
Deal found 9/20![Southwest logo]()
$376
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.
Mon 10/196:05 am -
Nonstop2h 45m
Wed 10/2111:06 am -
Nonstop2h 23m
Deal found 9/16![United Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/153:16 pm -
1 stop17h 43m
Mon 10/196:13 pm -
1 stop19h 48m
Deal found 9/20![Multiple Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:50 am -
2 stops8h 50m
Sun 10/257:45 am -
Nonstop2h 10m
Deal found 9/19![Southwest logo]()
$391
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:02 am -
Nonstop2h 53m
Sun 12/62:15 pm -
Nonstop2h 18m
Deal found 9/17![United Airlines logo]()
$395
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:55 pm -
1 stop4h 10m
Sun 10/187:45 am -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:10 am -
1 stop27h 04m
Fri 10/168:49 am -
2 stops12h 37m
Deal found 9/19![Multiple Airlines logo]()
$544
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 1/135:04 pm -
Nonstop2h 56m
Mon 1/186:18 pm -
Nonstop2h 21m
Deal found 9/20![United Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/213:10 pm -
1 stop19h 41m
Sun 10/2510:20 am -
2 stops23h 40m
Deal found 9/20![Multiple Airlines logo]()
$548
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:16 pm -
1 stop18h 36m
Fri 9/255:05 pm -
1 stop16h 51m
Deal found 9/16![Multiple Airlines logo]()
$643
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:10 pm -
1 stop20h 55m
Sun 9/273:53 pm -
2 stops21h 00m
Deal found 9/16![Multiple Airlines logo]()
$645
Last-minute flights from Hartford to ChicagoDiscover last-minute flight deals from Hartford to Chicago. Data last updated September 21, 2026 and is based on user searches.
Discover last-minute flight deals from Hartford to Chicago. Data last updated September 21, 2026 and is based on user searches.
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:16 pm -
1 stop8h 43m
Wed 10/73:50 pm -
1 stop21h 31m
Deal found 9/17![Frontier logo]()
$295
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:40 pm -
1 stop4h 51m
Tue 10/137:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$288
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:02 pm -
1 stop7h 32m
Sat 10/173:37 pm -
1 stop6h 59m
Deal found 9/17![American Airlines logo]()
$291
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 pm -
1 stop6h 33m
Tue 10/2012:49 pm -
1 stop7h 30m
Deal found 9/17![Delta logo]()
$291
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:25 pm -
Nonstop2h 20m
Fri 10/236:45 pm -
Nonstop2h 10m
Deal found 9/17![Southwest logo]()
$296
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.
Wed 10/215:35 am -
2 stops8h 50m
Sat 10/246:45 am -
2 stops7h 15m
Deal found 9/16![Southwest logo]()
$287
This KAYAK deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:25 am -
1 stop5h 59m
Sat 10/242:55 pm -
1 stop8h 03m
Deal found 9/18![JetBlue logo]()
$292
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:05 am -
Nonstop2h 45m
Fri 10/237:30 am -
Nonstop2h 19m
Deal found 9/17![United Airlines logo]()
$293
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm -
Nonstop2h 48m
Sat 10/242:52 pm -
1 stop5h 31m
Deal found 9/16![American Airlines logo]()
$287
This KAYAK deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
1 stop5h 59m
Mon 10/262:42 pm -
1 stop8h 17m
Deal found 9/18![JetBlue logo]()
$289
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:35 am -
2 stops9h 50m
Sat 10/318:30 am -
2 stops7h 55m
Deal found 9/17![Southwest logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:15 pm -
1 stop17h 39m
Thu 11/59:30 am -
2 stops24h 30m
Deal found 9/18![Multiple Airlines logo]()
$290
One-way flights from Hartford to ChicagoSearch for one-way flight options from Hartford to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
Search for one-way flight options from Hartford to Chicago. Find affordable one-way fares based on user searches. Data last updated September 21, 2026.
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.
Tue 10/277:00 am -
1 stop5h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$139
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$139
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.
Thu 10/156:25 am -
1 stop5h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$142
This Super.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/248:28 pm -
1 stop27h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$143
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.
Tue 10/275:35 am -
2 stops8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$144
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:16 pm -
1 stop17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$145
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:00 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:14 pm -
1 stop4h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$146
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:16 pm -
1 stop17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$147
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:25 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$149
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 10/2212:38 pm -
Nonstop2h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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.
Thu 11/193:15 pm -
1 stop29h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Frontier logo]()
$150
Find flight deals from Hartford to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Hartford (BDL) 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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Southwest) |
One-way from | $139 (Delta) |
Popular in | July |
Cheapest in | January |
Average price | $394 |
Cheapflights Fare Finder
Customize your flight search to find flights from Hartford 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 21, 2026.
Use the filters below to find and compare flights from Hartford to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Sat 10/10
5:23 am-10:24 am
1 stop6h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 11/14
5:33 pm-10:54 pm
1 stop6h 21m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Quickest round-trip
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/26
7:25 pm-8:45 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Thu 10/22
12:38 pm-2:23 pm
Nonstop2h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 11/10
6:25 pm-7:55 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/19
7:05 pm-12:25 am
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Wed 10/21
11:55 am-4:47 pm
1 stop5h 52m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Mon 10/26
5:20 pm-10:33 pm
1 stop6h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 10/27
4:15 pm-7:25 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 10/17
5:00 pm-10:33 pm
1 stop6h 33m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Showing 1-10 of 59 resultsSorted by cheapest first
Compare providers for flights from Hartford 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 Hartford to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Hartford-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hartford-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hartford-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Hartford-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 Hartford-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 Hartford to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Hartford with our price prediction graph.
BDL-CHI
BDL-MDW
BDL-ORD
BDL-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 Hartford to Chicago
BDL-CHI
BDL-MDW
BDL-ORD
BDL-RFD
What is the cheapest month to book a flight from Hartford to Chicago?
Currently, January is the cheapest month in which you can book a flight from Hartford to Chicago (average of $371). Flying from Hartford to Chicago in July is currently the most expensive (average of $473). 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 BDL to CHI?
Find hourly flight availability from Hartford 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 21, 2026.
It’s typically best to fly out from Hartford to Chicago at noon. Doing so could potentially save you 15% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from Hartford to Chicago
Explore weekly flight availability from Hartford 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 21, 2026.
The most flights from BDL to CHI are scheduled on a Friday (23 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Hartford to Chicago?
Airfare is below average for this route at the moment.
Hartford to Chicago flights typically cost between $329 and $472 in October.The cheapest round-trip price found within the last 5 days was $287 on Southwest (Oct 21-Oct 24).
How far ahead should I book a flight from Hartford to Chicago?
To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 84 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Hartford to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Hartford to Chicago. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 21, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Hartford to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
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 Hartford 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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Hartford to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 21, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Hartford to Chicago by cabin class
Find flights from Hartford to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hartford and Chicago flights
Browse other Hartford and Chicago flight options. Last updated on September 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Hartford to Chicago
Discover the top 5 airlines that operate flights from Hartford 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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$307 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$249 | Average$411 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$276 | Average$451 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$293 | Average$422 | FlexibilityNo cancel fee | On-time63% |