$152+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Nov 6 — Nov 131
Round-trip
1 adult, Economy
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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 February, booked 85 days in advance, depart on a Wednesday or Saturday and return on a Saturday
Cheap flight deals from Hartford to Chicago
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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 October 7, 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 October 7, 2026.
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:10 pm -
Nonstop2h 55m
Sat 11/218:10 am -
Nonstop2h 10m
Deal found 10/5![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:25 pm -
Nonstop2h 20m
Wed 10/284:45 pm -
1 stop4h 35m
Deal found 10/7![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:50 am -
2 stops8h 00m
Mon 11/98:15 pm -
1 stop10h 40m
Deal found 10/5![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:37 am -
1 stop7h 00m
Fri 10/306:25 pm -
Nonstop2h 22m
Deal found 10/7![United Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:35 am -
2 stops9h 50m
Mon 11/98:15 pm -
1 stop10h 40m
Deal found 10/5![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:37 am -
1 stop7h 23m
Thu 11/57:25 am -
Nonstop2h 18m
Deal found 10/7![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:25 pm -
1 stop7h 40m
Sun 11/228:00 am -
Nonstop2h 10m
Deal found 10/6![Southwest logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:19 pm -
Nonstop3h 01m
Sun 11/224:56 pm -
1 stop5h 40m
Deal found 10/7![American Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:40 pm -
Nonstop2h 25m
Mon 11/98:00 am -
Nonstop2h 10m
Deal found 10/5![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:37 pm -
Nonstop2h 52m
Tue 11/101:30 pm -
1 stop4h 12m
Deal found 10/7![United Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:54 pm -
1 stop5h 07m
Mon 11/911:00 am -
Nonstop2h 18m
Deal found 10/7![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:37 am -
1 stop7h 23m
Sun 11/2210:25 am -
1 stop7h 17m
Deal found 10/7![United Airlines logo]()
$308
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 October 7, 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 October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:30 pm -
1 stop5h 55m
Sun 11/228:00 am -
Nonstop2h 10m
Deal found 10/4![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:20 am -
1 stop4h 30m
Fri 1/16:00 am -
1 stop5h 23m
Deal found 10/6![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop4h 40m
Tue 12/299:30 pm -
Nonstop2h 22m
Deal found 10/6![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:40 am -
Nonstop2h 30m
Mon 11/166:20 pm -
Nonstop2h 05m
Deal found 10/6![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
2 stops6h 29m
Tue 11/36:04 am -
1 stop7h 00m
Deal found 10/7![United Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:20 am -
1 stop5h 29m
Fri 1/16:00 am -
1 stop5h 23m
Deal found 10/6![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 11/197:45 am -
Nonstop2h 30m
Sat 11/216:45 pm -
Nonstop2h 05m
Deal found 10/2![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
2 stops8h 04m
Mon 11/96:05 pm -
1 stop4h 54m
Deal found 10/5![United Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/307:25 pm -
Nonstop2h 25m
Mon 1/46:10 pm -
1 stop4h 35m
Deal found 10/6![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:43 am -
1 stop4h 16m
Tue 10/2712:30 pm -
1 stop4h 55m
Deal found 10/5![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:25 pm -
Nonstop2h 25m
Fri 11/278:00 am -
Nonstop2h 10m
Deal found 10/5![Southwest logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop6h 33m
Thu 12/32:15 pm -
Nonstop2h 18m
Deal found 10/5![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:45 pm -
2 stops8h 40m
Thu 11/128:00 am -
Nonstop2h 10m
Deal found 10/7![Southwest logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 11/810:44 am -
1 stop7h 16m
Sat 11/1410:32 am -
1 stop7h 12m
Deal found 10/2![United Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 12/76:25 pm -
Nonstop2h 30m
Wed 12/96:20 pm -
Nonstop2h 00m
Deal found 10/2![Southwest logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:37 pm -
Nonstop2h 52m
Mon 11/96:25 pm -
Nonstop2h 22m
Deal found 10/4![United Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:00 am -
Nonstop2h 51m
Mon 11/237:25 am -
Nonstop2h 18m
Deal found 10/6![United Airlines logo]()
$455
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:50 am -
2 stops10h 05m
Sun 11/17:50 am -
2 stops7h 20m
Deal found 10/7![Southwest logo]()
$419
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:00 am -
1 stop6h 32m
Mon 1/2510:51 am -
Nonstop2h 23m
Deal found 10/3![United Airlines logo]()
$461
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:35 am -
Nonstop2h 51m
Mon 12/72:15 pm -
Nonstop2h 18m
Deal found 10/5![United Airlines logo]()
$541
Last-minute flights from Hartford to ChicagoDiscover last-minute flight deals from Hartford to Chicago. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute flight deals from Hartford to Chicago. Data last updated October 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:35 am -
2 stops9h 50m
Mon 11/98:15 pm -
1 stop10h 40m
Deal found 10/5![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:25 pm -
Nonstop2h 20m
Wed 10/284:45 pm -
1 stop4h 35m
Deal found 10/7![Southwest logo]()
$300
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:37 am -
1 stop7h 23m
Thu 11/57:25 am -
Nonstop2h 18m
Deal found 10/7![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:50 am -
2 stops8h 00m
Mon 11/98:15 pm -
1 stop10h 40m
Deal found 10/5![Southwest logo]()
$302
This Southwest deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:40 pm -
Nonstop2h 25m
Mon 11/98:00 am -
Nonstop2h 10m
Deal found 10/5![Southwest logo]()
$305
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:37 pm -
Nonstop2h 52m
Tue 11/101:30 pm -
1 stop4h 12m
Deal found 10/7![United Airlines logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:02 pm -
Nonstop2h 48m
Thu 11/126:07 pm -
1 stop4h 52m
Deal found 10/6![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:37 am -
1 stop7h 23m
Tue 11/1711:00 am -
Nonstop2h 18m
Deal found 10/7![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1710:37 am -
1 stop7h 23m
Sun 11/2210:25 am -
1 stop7h 17m
Deal found 10/7![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:10 pm -
Nonstop2h 55m
Sat 11/218:10 am -
Nonstop2h 10m
Deal found 10/5![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:25 pm -
1 stop7h 40m
Sun 11/228:00 am -
Nonstop2h 10m
Deal found 10/6![Southwest logo]()
$304
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:18 pm -
1 stop8h 16m
Tue 11/248:10 am -
Nonstop2h 10m
Deal found 10/5![American Airlines logo]()
$304
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 October 7, 2026.
Search for one-way flight options from Hartford to Chicago. Find affordable one-way fares based on user searches. Data last updated October 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:00 am -
2 stops37h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$152
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:35 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:05 am -
2 stops29h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:05 am -
2 stops17h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:39 pm -
2 stops42h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/712:36 pm -
2 stops12h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/113:13 pm -
3 stops21h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:00 am -
3 stops42h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:39 pm -
2 stops30h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:13 pm -
3 stops21h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:15 am -
3 stops30h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$161
This Southwest deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:25 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$162
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 October 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (American Airlines) |
One-way from | $152 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $402 |
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 October 7, 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 - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 12/18
7:20 am-8:50 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$165
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 11/6
6:00 am-7:51 am
Nonstop2h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 12/19
5:20 am-8:50 am
1 stop4h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 12/18
6:00 am-12:04 pm
1 stop7h 04m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Sat 11/7
5:02 pm-6:50 pm
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Wed 11/4
5:02 pm-6:50 pm
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 1/8
9:26 am-11:25 am
Nonstop2h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 3/25
1:12 pm-7:42 pm
1 stop7h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sun 2/28
1:12 pm-7:42 pm
1 stop7h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Wed 12/2
8:40 am-2:40 pm
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$216
Showing 1-10 of 43 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 October.
| 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-ORD
BDL-MDW
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-ORD
BDL-MDW
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 $361). 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 October 7, 2026.
It’s typically best to fly out from Hartford to Chicago at noon. Doing so could potentially save you 17% 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 October 7, 2026.
The most flights from BDL to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 $342 and $489 in November.The cheapest round-trip price found within the last 5 days was $299 on American Airlines (Nov 19-Nov 21).
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 October 3, 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. Sunday 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 October 7, 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.
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
7.9
Comfort
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 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
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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 October 7, 2026.
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Hartford and Chicago flights
Browse other Hartford and Chicago flight options. Last updated on October 7, 2026.
Popular flight searches
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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 October 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$297 | Average$436 | FlexibilityNo cancel fee | On-time63% |