$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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Dec 4 — Dec 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 November 4, 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 November 4, 2026.
This Expedia deal was found by Cheapflights users on 11/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:45 pm -
Nonstop2h 39m
Thu 11/197:13 pm -
Nonstop2h 23m
Deal found 11/2![Avelo Airlines logo]()
$214
This Flightnetwork deal was found by Cheapflights users on 11/2. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:35 pm -
Nonstop2h 53m
Thu 11/267:00 pm -
Nonstop2h 23m
Deal found 11/2![Avelo Airlines logo]()
$226
This Travelocity deal was found by Cheapflights users on 11/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 11/1![Avelo Airlines logo]()
$275
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/49:37 am -
2 stops16h 16m
Sun 12/67:07 pm -
Nonstop2h 23m
Deal found 10/31![Multiple Airlines logo]()
$293
This FlightHub deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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 10/31![Avelo Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/16:00 am -
1 stop6h 31m
Wed 12/26:20 pm -
Nonstop2h 20m
Deal found 11/3![United Airlines logo]()
$303
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 12/34:25 pm -
Nonstop2h 53m
Sat 12/58:30 am -
2 stops12h 40m
Deal found 10/31![Multiple Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 11/3. 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 12/46:25 pm -
Nonstop2h 30m
Mon 12/76:00 am -
1 stop4h 50m
Deal found 11/3![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:07 pm -
1 stop5h 24m
Thu 11/268:10 am -
Nonstop2h 10m
Deal found 11/2![American Airlines logo]()
$307
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop29h 32m
Mon 11/238:42 pm -
1 stop13h 49m
Deal found 10/31![Frontier logo]()
$308
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop25h 37m
Mon 11/235:40 am -
1 stop28h 51m
Deal found 10/31![Frontier logo]()
$308
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:56 pm -
1 stop13h 03m
Sun 12/65:35 am -
1 stop7h 14m
Deal found 11/3![Frontier logo]()
$309
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 November 4, 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 November 4, 2026.
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
Nonstop2h 43m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 11/3![Avelo Airlines logo]()
$214
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/16:00 am -
1 stop6h 31m
Wed 12/26:20 pm -
Nonstop2h 20m
Deal found 11/3![United Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 11/3. 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 12/117:25 am -
Nonstop2h 30m
Tue 12/151:20 pm -
2 stops7h 50m
Deal found 11/3![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/1811:31 am -
1 stop5h 45m
Wed 12/236:15 pm -
1 stop4h 18m
Deal found 10/31![Delta logo]()
$317
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:45 pm -
Nonstop2h 39m
Thu 11/1910:19 am -
2 stops25h 33m
Deal found 10/30![Multiple Airlines logo]()
$327
This Orbitz deal was found by Cheapflights users on 10/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/34:20 pm -
Nonstop2h 53m
Tue 1/57:03 pm -
Nonstop2h 23m
Deal found 10/30![Avelo Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 11/3. 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.
Thu 2/412:15 pm -
2 stops9h 30m
Wed 2/109:00 am -
Nonstop2h 10m
Deal found 11/3![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 10/30. 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 12/177:10 am -
1 stop5h 34m
Mon 12/217:00 am -
1 stop4h 06m
Deal found 10/30![Delta logo]()
$317
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Fri 12/116:02 am -
Nonstop2h 53m
Sun 12/1310:57 am -
Nonstop2h 18m
Deal found 11/3![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 11/2. 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.
Fri 1/2212:20 pm -
2 stops7h 15m
Wed 1/278:45 am -
2 stops9h 30m
Deal found 11/2![Southwest logo]()
$327
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:45 pm -
Nonstop2h 43m
Fri 11/205:25 am -
2 stops16h 14m
Deal found 11/1![Multiple Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 11/1. 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 12/312:30 pm -
2 stops8h 15m
Mon 12/76:00 am -
1 stop7h 20m
Deal found 11/1![Southwest logo]()
$348
This United Airlines deal was found by Cheapflights users on 11/3. 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 11/259:37 am -
Nonstop2h 52m
Sat 11/287:25 am -
Nonstop2h 18m
Deal found 11/3![United Airlines logo]()
$384
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:30 am -
1 stop15h 59m
Sun 12/137:59 am -
2 stops28h 46m
Deal found 11/1![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 2/31:20 pm -
Nonstop2h 30m
Sun 2/77:35 am -
Nonstop2h 10m
Deal found 11/2![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 11/3. 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 3/36:00 am -
1 stop4h 45m
Thu 3/410:50 am -
Nonstop2h 11m
Deal found 11/3![United Airlines logo]()
$394
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/49:37 am -
2 stops16h 16m
Sun 12/67:59 am -
2 stops28h 46m
Deal found 10/31![Multiple Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 11/3. 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.
Thu 1/145:10 pm -
Nonstop2h 30m
Sun 1/179:00 am -
Nonstop2h 10m
Deal found 11/3![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/226:01 am -
Nonstop2h 59m
Wed 12/309:30 pm -
Nonstop2h 22m
Deal found 11/1![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 10/30. 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 12/46:25 pm -
Nonstop2h 30m
Sun 12/612:45 pm -
Nonstop2h 00m
Deal found 10/30![Southwest logo]()
$357
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 12/39:37 am -
3 stops14h 23m
Sat 12/510:00 am -
3 stops25h 41m
Deal found 10/31![Multiple Airlines logo]()
$435
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/156:00 am -
1 stop6h 33m
Fri 12/186:10 pm -
1 stop4h 36m
Deal found 11/3![United Airlines logo]()
$412
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:50 am -
1 stop10h 55m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 11/1![Multiple Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/186:44 pm -
Nonstop2h 56m
Tue 12/226:10 pm -
1 stop4h 36m
Deal found 10/31![United Airlines logo]()
$433
This Southwest deal was found by Cheapflights users on 11/3. 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.
Wed 3/39:25 am -
2 stops9h 10m
Thu 3/47:35 am -
Nonstop2h 10m
Deal found 11/3![Southwest logo]()
$399
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:15 am -
3 stops29h 22m
Sun 11/157:55 am -
2 stops32h 09m
Deal found 11/1![Multiple Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/1612:30 pm -
2 stops6h 55m
Sat 11/216:45 pm -
Nonstop2h 05m
Deal found 10/31![Southwest logo]()
$399
This United Airlines deal was found by Cheapflights users on 11/2. 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 11/186:00 am -
Nonstop2h 48m
Sat 11/217:25 am -
Nonstop2h 18m
Deal found 11/2![United Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Fri 11/206:00 am -
1 stop4h 44m
Sat 11/287:25 am -
Nonstop2h 18m
Deal found 11/1![United Airlines logo]()
$481
This United Airlines deal was found by Cheapflights users on 11/3. 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 11/186:00 am -
Nonstop2h 48m
Thu 11/198:50 am -
1 stop4h 12m
Deal found 11/3![United Airlines logo]()
$481
Last-minute flights from Connecticut to ChicagoDiscover last-minute flight deals from Connecticut to Chicago. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Chicago. Data last updated November 4, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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 10/31![Avelo Airlines logo]()
$302
This Travelocity deal was found by Cheapflights users on 11/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 11/1![Avelo Airlines logo]()
$275
This Expedia deal was found by Cheapflights users on 11/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:45 pm -
Nonstop2h 39m
Thu 11/197:13 pm -
Nonstop2h 23m
Deal found 11/2![Avelo Airlines logo]()
$214
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop29h 32m
Mon 11/238:42 pm -
1 stop13h 49m
Deal found 10/31![Frontier logo]()
$308
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:15 pm -
1 stop25h 37m
Mon 11/235:40 am -
1 stop28h 51m
Deal found 10/31![Frontier logo]()
$308
This Flightnetwork deal was found by Cheapflights users on 11/2. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:35 pm -
Nonstop2h 53m
Thu 11/267:00 pm -
Nonstop2h 23m
Deal found 11/2![Avelo Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:07 pm -
1 stop5h 24m
Thu 11/268:10 am -
Nonstop2h 10m
Deal found 11/2![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/16:00 am -
1 stop6h 31m
Wed 12/26:20 pm -
Nonstop2h 20m
Deal found 11/3![United Airlines logo]()
$303
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 12/34:25 pm -
Nonstop2h 53m
Sat 12/58:30 am -
2 stops12h 40m
Deal found 10/31![Multiple Airlines logo]()
$307
This Mytrip deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/49:37 am -
2 stops16h 16m
Sun 12/67:07 pm -
Nonstop2h 23m
Deal found 10/31![Multiple Airlines logo]()
$293
This Southwest deal was found by Cheapflights users on 11/3. 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 12/46:25 pm -
Nonstop2h 30m
Mon 12/76:00 am -
1 stop4h 50m
Deal found 11/3![Southwest logo]()
$307
This Frontier deal was found by Cheapflights users on 11/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:56 pm -
1 stop13h 03m
Sun 12/65:35 am -
1 stop7h 14m
Deal found 11/3![Frontier logo]()
$309
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 November 4, 2026.
Search for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Expedia deal was found by Cheapflights users on 11/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:45 pm -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Avelo Airlines logo]()
$107
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/294:20 pm -
Nonstop2h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Avelo Airlines logo]()
$113
This Jetabroad deal was found by Cheapflights users on 11/3. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/224:35 pm -
Nonstop2h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Avelo Airlines logo]()
$118
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:29 pm -
1 stop25h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$145
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:26 pm -
1 stop13h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$146
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1512:00 pm -
1 stop12h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![JetBlue logo]()
$147
This Southwest deal was found by Cheapflights users on 11/3. 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.
Thu 12/176:40 pm -
Nonstop2h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$149
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:10 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 11/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:45 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Avelo Airlines logo]()
$150
This Trip.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1010:45 am -
1 stop9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$150
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:01 am -
Nonstop3h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$150
This Super.com deal was found by Cheapflights users on 10/30. 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.
Tue 12/224:20 pm -
Nonstop2h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Avelo Airlines logo]()
$151
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 November 4, 2026.
Round-trip from | $214 (Expedia) |
|---|---|
One-way from | $107 (Expedia) |
Popular in | July |
Cheapest in | January |
Average price | $402 |
Good round-trip deal | $189 or less |
Good one-way deal | $161 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 November 4, 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
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Mon 11/16
4:45 pm-6:28 pm
Nonstop2h 43m
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
Sun 11/22
4:35 pm-6:28 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$118
Quickest round-trip
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 1/15
12:30 pm-1:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 12/18
6:44 pm-8:40 pm
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Sat 1/23
7:30 am-9:00 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 12/3
7:45 am-9:15 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Tue 12/1
5:17 am-10:59 am
1 stop6h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Tue 11/24
7:10 am-2:55 pm
1 stop8h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$159
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Thu 12/17
12:45 pm-8:05 pm
2 stops8h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 11/22
6:34 pm-11:34 pm
2 stops30h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$191
Showing 1-10 of 57 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-MDW
BDL-ORD
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-MDW
BDL-ORD
What is the cheapest month to book a flight from Connecticut to Chicago?
Currently, December is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $371). 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 November 4, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 28% 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 November 4, 2026.
The most flights from USCT to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Saturday, 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 $356 and $564 in December.The cheapest round-trip price found within the last 5 days was $303 on United Airlines (Dec 1-Dec 2).
How far ahead should I book a flight from Connecticut to Chicago?
The best time to book flights from Connecticut to Chicago is 55 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 31, 2026.
Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Tuesday mornings 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
Merrillville
Lansing
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 November 4, 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 November 4, 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 5 airlines flying from Connecticut to Chicago
Discover the top 5 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$275 | Average$415 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$287 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$488 | FlexibilityNo cancel fee | On-time63% |