$104+ Cheap flights from Chicago (CHI) to Connecticut
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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Dec 5 — Dec 121
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Connecticut 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
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Cheapest flights from Chicago to ConnecticutExplore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
Explore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 5, 2026.
This CheapOair deal was found by Cheapflights users on 11/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:07 pm -
Nonstop2h 23m
Thu 1/74:35 pm -
Nonstop2h 53m
Deal found 11/5![Avelo Airlines logo]()
$172
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:07 pm -
Nonstop2h 23m
Thu 12/104:25 pm -
Nonstop2h 53m
Deal found 11/3![Avelo Airlines logo]()
$199
This Expedia deal was found by Cheapflights users on 11/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:03 pm -
Nonstop2h 23m
Thu 12/34:25 pm -
Nonstop2h 53m
Deal found 11/4![Avelo Airlines logo]()
$204
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.
Fri 11/137:17 pm -
Nonstop2h 22m
Sun 11/154:45 pm -
Nonstop2h 39m
Deal found 11/1![Avelo Airlines logo]()
$214
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:17 pm -
Nonstop2h 22m
Sun 12/64:25 pm -
Nonstop2h 53m
Deal found 11/3![Avelo Airlines logo]()
$218
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.
Thu 11/127:09 pm -
Nonstop2h 20m
Mon 11/164:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$222
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.
Fri 11/137:17 pm -
Nonstop2h 22m
Mon 11/164:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$224
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.
Thu 11/197:13 pm -
Nonstop2h 23m
Sun 11/224:35 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$225
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.
Thu 12/177:13 pm -
Nonstop2h 23m
Thu 12/244:15 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$237
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.
Thu 11/267:00 pm -
Nonstop2h 23m
Tue 12/14:10 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$239
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 11/97:17 pm -
Nonstop2h 22m
Fri 11/134:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$247
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.
Tue 12/812:45 pm -
2 stops8h 25m
Sat 12/123:15 pm -
1 stop5h 25m
Deal found 11/1![Southwest logo]()
$322
Best flights from Chicago to ConnecticutDiscover carefully curated flight deals from Chicago to Connecticut that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
Discover carefully curated flight deals from Chicago to Connecticut that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 5, 2026.
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.
Thu 12/107:07 pm -
Nonstop2h 23m
Sun 1/104:35 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$172
This Booking.com deal was found by Cheapflights users on 11/4. 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.
Tue 12/17:03 pm -
Nonstop2h 23m
Thu 12/39:37 am -
2 stops12h 57m
Deal found 11/4![Multiple Airlines logo]()
$286
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.
Sat 12/198:55 pm -
1 stop9h 50m
Sat 1/911:40 am -
2 stops6h 35m
Deal found 10/31![Southwest logo]()
$328
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:55 pm -
1 stop4h 38m
Sat 12/265:30 am -
1 stop5h 19m
Deal found 11/3![Delta logo]()
$384
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.
Sun 12/279:30 pm -
Nonstop2h 22m
Fri 1/16:44 pm -
Nonstop2h 56m
Deal found 11/1![United Airlines logo]()
$384
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.
Thu 12/37:07 pm -
Nonstop2h 23m
Thu 12/104:25 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$204
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:03 pm -
Nonstop2h 23m
Thu 12/34:25 pm -
Nonstop2h 53m
Deal found 11/3![Avelo Airlines logo]()
$213
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 11/137:17 pm -
Nonstop2h 22m
Sun 11/154:45 pm -
Nonstop2h 39m
Deal found 11/3![Avelo Airlines logo]()
$214
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:09 pm -
Nonstop2h 20m
Sun 11/154:45 pm -
Nonstop2h 39m
Deal found 10/31![Avelo Airlines logo]()
$224
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.
Sun 12/207:13 pm -
Nonstop2h 23m
Fri 12/259:45 am -
1 stop7h 05m
Deal found 10/31![Multiple Airlines logo]()
$316
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.
Sat 12/198:55 pm -
1 stop9h 50m
Fri 1/812:20 pm -
2 stops9h 55m
Deal found 10/31![Southwest logo]()
$328
This Mytrip deal was found by Cheapflights users on 11/4. 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 12/25:35 am -
1 stop7h 25m
Thu 12/34:25 pm -
Nonstop2h 53m
Deal found 11/4![Multiple Airlines logo]()
$326
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.
Thu 12/109:37 am -
1 stop5h 45m
Sat 1/25:30 am -
1 stop4h 19m
Deal found 10/31![Delta logo]()
$384
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.
Mon 11/232:36 pm -
Nonstop2h 18m
Thu 12/36:00 am -
1 stop4h 37m
Deal found 11/3![United Airlines logo]()
$394
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.
Sat 12/196:45 pm -
Nonstop2h 05m
Sun 1/103:35 pm -
1 stop6h 10m
Deal found 11/1![Southwest logo]()
$367
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.
Thu 12/107:07 pm -
Nonstop2h 23m
Sun 1/34:20 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$286
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:55 am -
1 stop13h 34m
Sun 11/154:45 pm -
Nonstop2h 39m
Deal found 11/3![Multiple Airlines logo]()
$357
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.
Thu 12/108:45 am -
1 stop4h 25m
Sun 1/39:16 am -
Nonstop2h 59m
Deal found 11/2![United Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 11/5. 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.
Wed 11/186:00 am -
1 stop5h 23m
Thu 1/75:12 pm -
1 stop6h 05m
Deal found 11/5![Delta logo]()
$409
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.
Sun 12/203:05 pm -
2 stops7h 50m
Mon 1/113:35 pm -
1 stop6h 10m
Deal found 11/1![Southwest logo]()
$382
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 12/26:20 pm -
Nonstop2h 20m
Sat 12/56:00 am -
1 stop6h 33m
Deal found 11/3![United Airlines logo]()
$403
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.
Sat 12/268:55 pm -
1 stop9h 50m
Thu 12/315:40 am -
1 stop4h 20m
Deal found 11/1![Southwest logo]()
$389
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 11/252:56 pm -
Nonstop2h 18m
Thu 11/2610:37 am -
1 stop5h 02m
Deal found 11/2![United Airlines logo]()
$407
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.
Thu 12/106:20 pm -
Nonstop2h 05m
Sun 1/37:25 pm -
Nonstop2h 25m
Deal found 11/2![Southwest logo]()
$430
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.
Sun 11/228:50 am -
1 stop4h 12m
Mon 11/309:37 am -
Nonstop2h 52m
Deal found 11/1![United Airlines logo]()
$454
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 11/2411:00 am -
Nonstop2h 18m
Fri 11/279:37 am -
Nonstop2h 52m
Deal found 11/1![United Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:00 am -
Nonstop2h 16m
Fri 11/277:54 pm -
1 stop5h 07m
Deal found 11/4![United Airlines logo]()
$467
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 11/276:25 pm -
Nonstop2h 22m
Sun 11/298:40 pm -
Nonstop2h 48m
Deal found 11/1![United Airlines logo]()
$471
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated November 5, 2026 and is based on user searches.
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 11/97:17 pm -
Nonstop2h 22m
Fri 11/134:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$247
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.
Thu 11/127:09 pm -
Nonstop2h 20m
Mon 11/164:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$222
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.
Fri 11/137:17 pm -
Nonstop2h 22m
Sun 11/154:45 pm -
Nonstop2h 39m
Deal found 11/1![Avelo Airlines logo]()
$214
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.
Fri 11/137:17 pm -
Nonstop2h 22m
Mon 11/164:45 pm -
Nonstop2h 43m
Deal found 11/2![Avelo Airlines logo]()
$224
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:17 pm -
Nonstop2h 22m
Sun 12/64:25 pm -
Nonstop2h 53m
Deal found 11/3![Avelo Airlines logo]()
$218
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.
Thu 11/197:13 pm -
Nonstop2h 23m
Sun 11/224:35 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$225
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.
Thu 11/267:00 pm -
Nonstop2h 23m
Tue 12/14:10 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$239
This Expedia deal was found by Cheapflights users on 11/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:03 pm -
Nonstop2h 23m
Thu 12/34:25 pm -
Nonstop2h 53m
Deal found 11/4![Avelo Airlines logo]()
$204
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:07 pm -
Nonstop2h 23m
Thu 12/104:25 pm -
Nonstop2h 53m
Deal found 11/3![Avelo Airlines logo]()
$199
This CheapOair deal was found by Cheapflights users on 11/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/67:07 pm -
Nonstop2h 23m
Thu 1/74:35 pm -
Nonstop2h 53m
Deal found 11/5![Avelo Airlines logo]()
$172
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.
Tue 12/812:45 pm -
2 stops8h 25m
Sat 12/123:15 pm -
1 stop5h 25m
Deal found 11/1![Southwest logo]()
$322
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.
Thu 12/177:13 pm -
Nonstop2h 23m
Thu 12/244:15 pm -
Nonstop2h 53m
Deal found 11/2![Avelo Airlines logo]()
$237
One-way flights from Chicago to ConnecticutSearch for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:09 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Avelo Airlines logo]()
$107
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 12/17:03 pm -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Avelo Airlines logo]()
$110
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.
Fri 11/137:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Avelo Airlines logo]()
$114
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Avelo Airlines logo]()
$139
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.
Sun 12/207:13 pm -
Nonstop2h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Avelo Airlines logo]()
$141
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/177:28 pm -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Avelo Airlines logo]()
$149
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 11/252:56 pm -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 11/4. 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.
Wed 11/257:10 pm -
Nonstop2h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$149
This Jetabroad deal was found by Cheapflights users on 11/5. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/189:51 am -
1 stop27h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Frontier logo]()
$150
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.
Sun 2/78:47 pm -
1 stop14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/47:08 pm -
2 stops27h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$153
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:02 pm -
2 stops29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$153
Find flight deals from Chicago to Connecticut
Keep the following information in mind while searching for Chicago to Connecticut flight deals. Data was last updated November 5, 2026.
Round-trip from | $172 (CheapOair) |
|---|---|
One-way from | $107 (Travelocity) |
Popular in | April |
Cheapest in | January |
Average price | $463 |
Good round-trip deal | $166 or less |
Good one-way deal | $174 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Connecticut 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 5, 2026.
Use the filters below to find and compare flights from Chicago to Connecticut that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Sun 2/7
7:28 pm-10:46 pm
Nonstop2h 18m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$104
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Thu 11/12
7:09 pm-10:29 pm
Nonstop2h 20m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$107
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Tue 12/1
7:03 pm-10:26 pm
Nonstop2h 23m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$110
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Sun 12/6
7:07 pm-10:30 pm
Nonstop2h 23m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$110
ChicagoHartford
ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl
ORDBDL
Chicago O'Hare Intl
Sat 12/5
6:20 pm-9:40 pm
Nonstop2h 20m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoHartford
ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl
ORDBDL
Chicago O'Hare Intl
Mon 11/23
8:10 am-11:20 am
Nonstop2h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Sat 12/5
8:05 am-11:15 am
Nonstop2h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoHartford
ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl
ORDBDL
Chicago O'Hare Intl
Wed 11/25
2:56 pm-6:14 pm
Nonstop2h 18m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Wed 11/25
7:10 pm-10:20 pm
Nonstop2h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
ChicagoHartford
MDW Chicago Midway - BDL Hartford Bradley Intl
MDWBDL
Chicago Midway
Wed 12/30
7:10 pm-10:20 pm
Nonstop2h 10m
Hartford Bradley Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$149
Showing 1-10 of 56 resultsSorted by cheapest first
Best time to book a flight from Chicago to Connecticut
Have a flexible travel schedule? Discover the best time to fly to Connecticut from Chicago with our price prediction graph.
ORD-HVN
MDW-BDL
ORD-BDL
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 Chicago to Connecticut
CHI-USCT
ORD-HVN
MDW-BDL
ORD-BDL
What is the cheapest month to book a flight from Chicago to Connecticut?
Currently, December is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $358). Flying from Chicago to Connecticut in July is currently the most expensive (average of $503). 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 CHI to CT?
Find hourly flight availability from Chicago to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2026.
It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Chicago to Connecticut
Explore weekly flight availability from Chicago to Connecticut. 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 5, 2026.
The most flights from CHI to USCT are scheduled on a Wednesday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to Connecticut?
Airfare is below average for this route at the moment.
Chicago to Connecticut flights typically cost between $360 and $539 in December.The cheapest round-trip price found within the last 5 days was $322 on Southwest (Dec 8-Dec 12).
How far ahead should I book a flight from Chicago to Connecticut?
The price you pay for your flight from Chicago to Connecticut may vary depending on when you book. For the best chance of a lower fare, look to book 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Connecticut?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Connecticut. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Chicago to Connecticut flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Connecticut
Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated November 5, 2026.
Get a feel of what it's like to fly with Southwest,Avelo Airlines, andUnited Airlines from Chicago to Connecticut by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Avelo Airlines
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Connecticut. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Connecticut
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Connecticut by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Connecticut by cabin class
Find flights from Chicago to Connecticut, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Connecticut flights
Browse other Chicago and Connecticut flight options. Last updated on November 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Connecticut flights
Consider these flights traveling from Chicago to Connecticut.
Top 4 airlines flying from Chicago to Connecticut
Discover the top 4 airlines that operate flights from Chicago to Connecticut. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$150 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$403 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$252 | Average$449 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$277 | Average$508 | FlexibilityNo cancel fee | On-time69% |