$139+ Cheap flights from Hartford (BDL) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Sep 6 — Sep 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 October, 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 August 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:50 pm -
Nonstop2h 25m
Sun 9/68:45 am -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$277
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Wed 8/2612:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:52 pm -
Nonstop2h 57m
Sun 9/67:29 pm -
Nonstop2h 19m
Deal found 8/4![American Airlines logo]()
$278
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:25 am -
1 stop6h 22m
Wed 11/42:35 pm -
1 stop8h 20m
Deal found 8/5![JetBlue logo]()
$281
This Priceline deal was found by Cheapflights users on 8/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:31 pm -
1 stop8h 38m
Mon 12/76:15 am -
1 stop9h 21m
Deal found 8/7![Frontier logo]()
$282
This Super.com deal was found by Cheapflights users on 8/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:55 pm -
1 stop17h 21m
Sun 10/186:05 am -
1 stop12h 55m
Deal found 8/7![Frontier logo]()
$285
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 9/510:33 am -
1 stop7h 26m
Sun 9/63:00 pm -
Nonstop2h 20m
Deal found 8/2![United Airlines logo]()
$287
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:42 pm -
1 stop10h 45m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/5![Frontier logo]()
$288
This Travelocity deal was found by Cheapflights users on 8/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop4h 33m
Mon 10/53:00 pm -
1 stop7h 14m
Deal found 8/2![JetBlue logo]()
$289
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:16 pm -
1 stop8h 43m
Sun 10/116:05 am -
1 stop12h 55m
Deal found 8/6![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:07 pm -
1 stop7h 37m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$292
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:42 pm -
1 stop10h 45m
Sun 9/612:44 am -
1 stop11h 03m
Deal found 8/6![Frontier 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 August 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 August 7, 2026.
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:07 pm -
1 stop7h 37m
Mon 8/245:27 pm -
1 stop5h 53m
Deal found 8/5![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 8/4. 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 9/123:50 pm -
Nonstop2h 25m
Mon 9/141:10 pm -
Nonstop2h 05m
Deal found 8/4![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/6. 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 9/44:50 pm -
Nonstop2h 45m
Sat 9/511:06 am -
Nonstop2h 23m
Deal found 8/6![United Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
1 stop13h 06m
Sun 11/110:20 am -
2 stops23h 35m
Deal found 8/3![Multiple Airlines logo]()
$361
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am -
1 stop7h 45m
Sun 9/273:00 pm -
1 stop7h 14m
Deal found 8/4![JetBlue logo]()
$299
This Southwest deal was found by Cheapflights users on 8/6. 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.
Tue 9/155:55 pm -
Nonstop2h 20m
Wed 9/168:45 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$315
This JetBlue deal was found by Cheapflights users on 8/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:25 am -
1 stop4h 33m
Sun 9/133:00 pm -
1 stop7h 14m
Deal found 8/6![JetBlue logo]()
$311
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Fri 9/1112:12 pm -
Nonstop2h 45m
Sun 9/207:15 am -
Nonstop2h 19m
Deal found 8/2![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 8/4. 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 8/293:50 pm -
Nonstop2h 25m
Thu 9/38:45 am -
Nonstop2h 15m
Deal found 8/4![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 8/6. 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 8/293:50 pm -
Nonstop2h 25m
Mon 8/317:10 pm -
Nonstop2h 05m
Deal found 8/6![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Tue 9/154:50 pm -
Nonstop2h 45m
Fri 9/187:15 am -
Nonstop2h 19m
Deal found 8/4![United Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Wed 9/168:00 am -
1 stop28h 05m
Fri 9/185:05 pm -
1 stop16h 51m
Deal found 8/5![Multiple Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 8/2. 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 10/157:05 pm -
Nonstop2h 20m
Tue 10/201:10 pm -
Nonstop2h 05m
Deal found 8/2![Southwest logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:02 am -
2 stops9h 07m
Mon 8/246:56 pm -
1 stop18h 54m
Deal found 8/3![Multiple Airlines logo]()
$391
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:25 am -
1 stop4h 33m
Tue 10/63:00 pm -
1 stop7h 14m
Deal found 8/4![JetBlue logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 9/179:15 am -
Nonstop2h 46m
Sun 9/206:15 pm -
Nonstop2h 23m
Deal found 8/2![United Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 8/5. 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.
Thu 10/17:05 pm -
Nonstop2h 20m
Mon 10/55:00 am -
1 stop5h 50m
Deal found 8/5![Southwest logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sun 8/237:02 am -
2 stops9h 07m
Mon 8/246:56 pm -
1 stop18h 54m
Deal found 8/5![Multiple Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 8/3. 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.
Sun 9/136:00 am -
Nonstop2h 46m
Mon 9/148:42 am -
1 stop4h 23m
Deal found 8/3![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/41:40 pm -
Nonstop2h 15m
Sat 9/57:50 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$328
This United Airlines deal was found by Cheapflights users on 8/6. 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 9/1112:12 pm -
Nonstop2h 45m
Sat 9/127:15 am -
Nonstop2h 19m
Deal found 8/6![United Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:55 pm -
1 stop12h 07m
Mon 10/126:13 pm -
1 stop19h 48m
Deal found 8/3![Multiple Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 8/4. 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.
Mon 9/281:40 pm -
Nonstop2h 15m
Wed 9/308:55 am -
2 stops7h 30m
Deal found 8/4![Southwest logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:16 pm -
1 stop18h 36m
Thu 9/173:53 pm -
2 stops21h 00m
Deal found 8/4![Multiple Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 9/13:05 pm -
1 stop4h 40m
Sat 9/59:20 am -
2 stops9h 15m
Deal found 8/2![Southwest logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 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
Mon 9/284:50 pm -
2 stops23h 18m
Deal found 8/4![Multiple Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:40 pm -
2 stops7h 45m
Sun 9/68:45 am -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:00 am -
1 stop13h 08m
Mon 11/167:03 pm -
1 stop18h 58m
Deal found 8/3![Multiple Airlines logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 10/97:00 am -
1 stop13h 12m
Mon 10/1210:39 am -
2 stops29h 29m
Deal found 8/5![Multiple Airlines logo]()
$487
Last-minute flights from Hartford to ChicagoDiscover last-minute flight deals from Hartford to Chicago. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Hartford to Chicago. Data last updated August 7, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:07 pm -
1 stop7h 37m
Thu 8/205:27 pm -
1 stop5h 53m
Deal found 8/4![JetBlue logo]()
$295
This Justfly.com deal was found by Cheapflights users on 8/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:07 pm -
1 stop7h 37m
Sat 8/295:27 pm -
1 stop5h 53m
Deal found 8/2![JetBlue logo]()
$289
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Wed 8/2612:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$277
This Justfly.com deal was found by Cheapflights users on 8/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:07 pm -
1 stop7h 37m
Fri 8/282:35 pm -
1 stop8h 23m
Deal found 8/5![JetBlue logo]()
$281
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:07 pm -
1 stop7h 37m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/6![Multiple Airlines logo]()
$292
This Priceline deal was found by Cheapflights users on 8/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:42 pm -
1 stop10h 45m
Sat 8/2912:44 am -
1 stop11h 03m
Deal found 8/5![Frontier logo]()
$288
This Priceline deal was found by Cheapflights users on 8/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:42 pm -
1 stop10h 45m
Sun 9/612:44 am -
1 stop11h 03m
Deal found 8/6![Frontier logo]()
$293
This Southwest deal was found by Cheapflights users on 8/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:50 pm -
Nonstop2h 25m
Sun 9/68:45 am -
Nonstop2h 15m
Deal found 8/3![Southwest logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:52 pm -
Nonstop2h 57m
Sun 9/67:29 pm -
Nonstop2h 19m
Deal found 8/4![American Airlines logo]()
$278
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Sat 9/510:33 am -
1 stop7h 26m
Sun 9/63:00 pm -
Nonstop2h 20m
Deal found 8/2![United Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 9/511:44 am -
Nonstop2h 45m
Mon 9/76:15 pm -
Nonstop2h 23m
Deal found 8/7![United Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 8/7. 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.
Fri 9/116:20 pm -
Nonstop2h 20m
Sat 9/127:50 am -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$296
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 August 7, 2026.
Search for one-way flight options from Hartford to Chicago. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/5. 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 9/53:50 pm -
Nonstop2h 25m
Deal found 8/5![Southwest logo]()
$139
This American Airlines deal was found by Cheapflights users on 8/5. 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 9/55:41 pm -
Nonstop3h 09m
Deal found 8/5![American Airlines logo]()
$139
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:07 pm -
1 stop7h 37m
Deal found 8/3![JetBlue logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 10/53:16 pm -
2 stops28h 07m
Deal found 8/7![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 11/98:55 pm -
1 stop27h 55m
Deal found 8/7![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am -
2 stops34h 20m
Deal found 8/4![Multiple Airlines logo]()
$143
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:55 pm -
1 stop12h 26m
Deal found 8/7![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am -
2 stops30h 50m
Deal found 8/3![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:16 pm -
1 stop19h 16m
Deal found 8/4![Multiple Airlines logo]()
$148
This JetBlue deal was found by Cheapflights users on 8/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:07 pm -
1 stop7h 37m
Deal found 8/7![JetBlue logo]()
$148
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/51:09 pm -
1 stop4h 50m
Deal found 8/5![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:00 am -
2 stops34h 20m
Deal found 8/3![Multiple Airlines logo]()
$149
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 August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (Southwest) |
One-way from | $139 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $377 |
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 2,558,603 searches. Data last updated August 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 - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 8/21
5:07 pm-11:44 pm
1 stop7h 37m
Chicago O'Hare Intl
Mon 8/24
5:27 pm-12:20 am
1 stop5h 53m
$295
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Wed 9/23
7:00 am-1:45 pm
1 stop7h 45m
Chicago O'Hare Intl
Sun 9/27
3:00 pm-11:14 pm
1 stop7h 14m
$299
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 9/11
6:25 am-9:58 am
1 stop4h 33m
Chicago O'Hare Intl
Sun 9/13
3:00 pm-11:14 pm
1 stop7h 14m
$311
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 9/12
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Mon 9/14
1:10 pm-4:15 pm
Nonstop2h 05m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Tue 9/15
5:55 pm-7:15 pm
Nonstop2h 20m
Chicago Midway
Wed 9/16
8:45 am-12:00 pm
Nonstop2h 15m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 8/29
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Thu 9/3
8:45 am-12:00 pm
Nonstop2h 15m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 8/29
3:50 pm-5:15 pm
Nonstop2h 25m
Chicago Midway
Mon 8/31
7:10 pm-10:15 pm
Nonstop2h 05m
$315
Quickest round-trip
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 10/15
7:05 pm-8:25 pm
Nonstop2h 20m
Chicago Midway
Tue 10/20
1:10 pm-4:15 pm
Nonstop2h 05m
$315
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 10/1
7:05 pm-8:25 pm
Nonstop2h 20m
Chicago Midway
Mon 10/5
5:00 am-11:50 am
1 stop5h 50m
$325
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 9/4
4:50 pm-6:35 pm
Nonstop2h 45m
Chicago O'Hare Intl
Sat 9/5
11:06 am-2:29 pm
Nonstop2h 23m
$328
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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
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-ORD
BDL-MDW
BDL-RFD
What is the cheapest month to book a flight from Hartford to Chicago?
Currently, September is the cheapest month in which you can book a flight from Hartford to Chicago (average of $341). Flying from Hartford to Chicago in July is currently the most expensive (average of $468). 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 August 7, 2026.
It’s typically best to fly out from Hartford to Chicago in the evening. Doing so could potentially save you 19% on the flight price compared to flying at noon, 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 August 7, 2026.
The most flights from BDL to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 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 $333 and $448 in September.The cheapest round-trip price found within the last 5 days was $277 on Southwest (Sep 5-Sep 6).
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 August 1, 2026.
Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing 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 August 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.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from 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 August 7, 2026.
Complete your trip
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Hartford and Chicago flights
Browse other Hartford and Chicago flight options. Last updated on August 7, 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 2,558,603 searches. Data last updated August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$439 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$428 | FlexibilityNo cancel fee | On-time63% |