$107+ Cheap flights from Connecticut 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Nov 4 — Nov 111
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Chicago with Cheapflights
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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
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Cheapest flights from Connecticut to ChicagoExplore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
Explore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 5, 2026.
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/3![Avelo Airlines logo]()
$224
This CheapOair deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/295:15 pm -
Nonstop2h 39m
Thu 11/57:09 pm -
Nonstop2h 20m
Deal found 10/1![Avelo Airlines logo]()
$235
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:45 pm -
Nonstop2h 43m
Fri 10/237:17 pm -
Nonstop2h 22m
Deal found 10/4![Avelo Airlines logo]()
$236
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:45 pm -
Nonstop2h 39m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/1![Avelo Airlines logo]()
$240
This Super.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Thu 11/124:45 pm -
Nonstop2h 39m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 9/30![Avelo Airlines logo]()
$244
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:15 pm -
Nonstop2h 39m
Mon 10/197:17 pm -
Nonstop2h 22m
Deal found 9/30![Avelo Airlines logo]()
$269
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/124:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/4![Avelo Airlines logo]()
$277
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/3![Avelo Airlines logo]()
$294
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:26 pm -
1 stop13h 16m
Wed 11/252:59 pm -
1 stop8h 00m
Deal found 9/30![Multiple Airlines logo]()
$301
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.
Wed 12/24:00 pm -
2 stops7h 45m
Thu 12/31:15 pm -
2 stops5h 30m
Deal found 10/5![Southwest logo]()
$303
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Thu 10/293:00 pm -
Nonstop2h 18m
Deal found 9/30![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.
Wed 12/1612:25 pm -
1 stop7h 40m
Sat 12/196:45 pm -
Nonstop2h 00m
Deal found 10/5![Southwest logo]()
$304
Best flights from Connecticut to ChicagoDiscover carefully curated flight deals from Connecticut to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
Discover carefully curated flight deals from Connecticut to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 5, 2026.
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:45 pm -
Nonstop2h 43m
Fri 10/237:17 pm -
Nonstop2h 22m
Deal found 10/4![Avelo Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/310:37 am -
1 stop7h 23m
Mon 11/92:36 pm -
Nonstop2h 18m
Deal found 10/1![United Airlines logo]()
$303
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:40 pm -
Nonstop2h 53m
Tue 11/37:35 pm -
1 stop16h 18m
Deal found 10/4![Multiple Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/106:25 pm -
Nonstop2h 30m
Thu 11/126:30 am -
2 stops8h 40m
Deal found 9/30![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/129:43 am -
1 stop5h 16m
Sun 11/155:42 pm -
1 stop4h 54m
Deal found 9/30![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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
Fri 11/138:00 am -
Nonstop2h 10m
Deal found 10/1![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/115:02 pm -
Nonstop2h 48m
Fri 11/136:25 pm -
Nonstop2h 22m
Deal found 10/1![United Airlines logo]()
$313
This Booking.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Thu 11/124:45 pm -
Nonstop2h 39m
Mon 11/1610:26 am -
2 stops11h 33m
Deal found 9/30![Multiple Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 11/34:00 pm -
1 stop6h 25m
Mon 11/94:00 pm -
2 stops6h 50m
Deal found 10/1![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/287:55 am -
2 stops6h 45m
Deal found 9/30![Southwest logo]()
$327
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:45 pm -
Nonstop2h 43m
Fri 10/237:44 pm -
1 stop16h 26m
Deal found 10/4![Multiple Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/1![Delta logo]()
$412
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Sun 11/157:25 am -
Nonstop2h 18m
Deal found 9/30![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/235:50 pm -
1 stop5h 10m
Mon 10/268:55 pm -
1 stop10h 20m
Deal found 9/30![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/155:02 pm -
Nonstop2h 48m
Wed 11/186:04 am -
1 stop6h 58m
Deal found 9/30![United Airlines logo]()
$386
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:00 pm -
3 stops24h 51m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/3![Multiple Airlines logo]()
$390
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:30 am -
1 stop6h 09m
Tue 11/1711:19 am -
1 stop4h 07m
Deal found 10/2![Delta logo]()
$451
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 Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:55 pm -
2 stops20h 26m
Wed 10/215:25 pm -
Nonstop2h 32m
Deal found 10/2![Multiple Airlines logo]()
$407
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:05 pm -
1 stop5h 52m
Thu 10/296:30 am -
1 stop5h 23m
Deal found 10/2![Delta logo]()
$475
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.
Wed 12/29:35 am -
Nonstop2h 51m
Fri 12/42:15 pm -
Nonstop2h 18m
Deal found 10/3![United Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/225:50 am -
1 stop5h 10m
Mon 10/266:45 pm -
Nonstop2h 10m
Deal found 10/1![Southwest logo]()
$362
This Booking.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Fri 10/234:45 pm -
Nonstop2h 43m
Mon 10/268:04 am -
1 stop13h 25m
Deal found 9/30![Multiple Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:30 am -
1 stop6h 08m
Mon 11/305:05 pm -
1 stop5h 36m
Deal found 9/30![Delta logo]()
$486
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.
Sun 12/276:44 pm -
Nonstop2h 56m
Wed 12/306:10 pm -
1 stop4h 36m
Deal found 10/4![United Airlines logo]()
$443
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 11/512:55 pm -
Nonstop2h 30m
Sun 11/85:05 am -
1 stop6h 00m
Deal found 10/4![Southwest logo]()
$380
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.
Wed 12/26:00 am -
1 stop6h 33m
Sun 12/68:52 am -
1 stop4h 18m
Deal found 10/2![United Airlines logo]()
$448
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 12/2412:30 pm -
2 stops8h 55m
Sun 12/279:05 pm -
1 stop9h 40m
Deal found 10/4![Southwest logo]()
$423
Last-minute flights from Connecticut to ChicagoDiscover last-minute flight deals from Connecticut to Chicago. Data last updated October 5, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Chicago. Data last updated October 5, 2026 and is based on user searches.
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/124:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/4![Avelo Airlines logo]()
$277
This Expedia deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:15 pm -
Nonstop2h 39m
Mon 10/197:17 pm -
Nonstop2h 22m
Deal found 9/30![Avelo Airlines logo]()
$269
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:45 pm -
Nonstop2h 43m
Fri 10/237:17 pm -
Nonstop2h 22m
Deal found 10/4![Avelo Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/226:00 am -
1 stop4h 38m
Sat 10/242:30 pm -
Nonstop2h 23m
Deal found 9/30![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Thu 10/293:00 pm -
Nonstop2h 18m
Deal found 9/30![United Airlines logo]()
$303
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:40 pm -
Nonstop2h 53m
Tue 11/37:35 pm -
1 stop16h 18m
Deal found 10/4![Multiple Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 10/286:50 pm -
Nonstop2h 20m
Wed 11/46:00 am -
1 stop7h 20m
Deal found 9/30![Southwest logo]()
$307
This CheapOair deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/295:15 pm -
Nonstop2h 39m
Thu 11/57:09 pm -
Nonstop2h 20m
Deal found 10/1![Avelo Airlines logo]()
$235
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/3![Avelo Airlines logo]()
$224
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/3![Avelo Airlines logo]()
$294
This Expedia deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:45 pm -
Nonstop2h 39m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/1![Avelo Airlines logo]()
$240
This Super.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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.
Thu 11/124:45 pm -
Nonstop2h 39m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 9/30![Avelo Airlines logo]()
$244
One-way flights from Connecticut to ChicagoSearch for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
Search for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated October 5, 2026.
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:15 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Avelo Airlines logo]()
$107
This Super.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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.
Thu 10/295:15 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Avelo Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/96:44 pm -
2 stops43h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/612:30 pm -
2 stops28h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$139
This Super.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/64:45 pm -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Avelo Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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.
Thu 10/225:15 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Avelo Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/163:13 pm -
3 stops33h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![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 United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/263:13 pm -
3 stops33h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$155
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:35 pm -
Nonstop2h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Avelo Airlines logo]()
$157
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 12/312:30 pm -
2 stops8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Southwest logo]()
$158
Find flight deals from Connecticut to Chicago
Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated October 5, 2026.
Round-trip from | $224 (Super.com) |
|---|---|
One-way from | $107 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $402 |
Good round-trip deal | $195 or less |
Good one-way deal | $97 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut 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 5, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 11/1
5:15 pm-6:54 pm
Nonstop2h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$107
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Mon 10/26
4:45 pm-6:28 pm
Nonstop2h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Thu 10/22
5:15 pm-6:54 pm
Nonstop2h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 10/16
4:45 pm-6:28 pm
Nonstop2h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$150
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 11/26
5:35 am-11:55 am
1 stop7h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$153
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 2/28
7:54 pm-11:23 pm
2 stops28h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 10/16
6:24 pm-6:31 pm
2 stops25h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Thu 11/19
4:35 pm-6:28 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 10/31
6:00 am-10:37 am
1 stop5h 37m
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
6:00 am-11:54 am
1 stop6h 54m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Connecticut with our price prediction graph.
HVN-ORD
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 Connecticut to Chicago
USCT-CHI
HVN-ORD
BDL-ORD
BDL-MDW
What is the cheapest month to book a flight from Connecticut to Chicago?
Currently, January is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $360). Flying from Connecticut to Chicago in July is currently the most expensive (average of $467). 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 CT to CHI?
Find hourly flight availability from Connecticut 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 5, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 30% on flights from Connecticut to Chicago by exploring options for tickets at noon.
Weekly flight availability from Connecticut to Chicago
Explore weekly flight availability from Connecticut 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 5, 2026.
The most flights from USCT to CHI are scheduled on a Friday (23 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Connecticut to Chicago?
Airfare is below average for this route at the moment.
Connecticut to Chicago flights typically cost between $342 and $489 in November.The cheapest round-trip price found within the last 5 days was $301 on Multiple Airlines (Nov 23-Nov 25).
How far ahead should I book a flight from Connecticut to Chicago?
The best time to book flights from Connecticut to Chicago is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Connecticut to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on October 3, 2026.
Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Connecticut 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
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Alternative routes for Connecticut 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 October 5, 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 Connecticut to Chicago by cabin class
Find flights from Connecticut to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Connecticut and Chicago flights
Browse other Connecticut and Chicago flight options. Last updated on October 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Chicago flights
Consider these flights traveling from Connecticut to Chicago.
Top 6 airlines flying from Connecticut to Chicago
Discover the top 6 airlines that operate flights from Connecticut 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$216 | FlexibilityNo cancel fee | On-timeN/A | |
| 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% |