$75+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Oct 18 — Oct 251
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 September 18, 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 September 18, 2026.
This eDestinos deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:17 pm -
Nonstop2h 22m
Mon 10/264:45 pm -
Nonstop2h 43m
Deal found 9/15![Avelo Airlines logo]()
$136
This Gotogate deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 pm -
Nonstop2h 32m
Wed 9/303:25 pm -
Nonstop2h 53m
Deal found 9/16![Avelo Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/77:35 am -
2 stops11h 55m
Mon 11/93:30 pm -
1 stop7h 30m
Deal found 9/14![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 12/111:45 am -
1 stop8h 10m
Sat 12/57:40 am -
1 stop7h 50m
Deal found 9/13![Southwest logo]()
$225
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:38 am -
1 stop6h 51m
Sat 10/241:00 pm -
1 stop7h 14m
Deal found 9/14![JetBlue logo]()
$229
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/302:25 pm -
1 stop5h 30m
Tue 11/38:45 am -
1 stop7h 45m
Deal found 9/14![Southwest logo]()
$230
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Thu 10/156:00 am -
Nonstop2h 12m
Fri 10/168:35 pm -
Nonstop2h 42m
Deal found 9/14![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/66:50 am -
1 stop8h 20m
Mon 11/96:45 am -
Nonstop2h 25m
Deal found 9/17![Southwest logo]()
$232
This KAYAK deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Fri 10/96:10 am -
Nonstop2h 20m
Wed 10/149:30 am -
Nonstop2h 54m
Deal found 9/17![JetBlue logo]()
$232
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/55:00 pm -
Nonstop2h 25m
Tue 10/62:59 pm -
1 stop4h 42m
Deal found 9/17![United Airlines logo]()
$233
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/116:10 am -
Nonstop2h 20m
Tue 10/139:30 am -
Nonstop2h 54m
Deal found 9/18![JetBlue logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:20 am -
1 stop8h 40m
Thu 10/156:29 am -
1 stop13h 02m
Deal found 9/17![Frontier logo]()
$234
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 September 18, 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 September 18, 2026.
This eDestinos deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:17 pm -
Nonstop2h 22m
Mon 10/264:45 pm -
Nonstop2h 43m
Deal found 9/15![Avelo Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/16:15 am -
Nonstop2h 12m
Tue 11/1011:20 am -
Nonstop2h 48m
Deal found 9/16![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/55:10 am -
Nonstop2h 05m
Wed 10/79:05 pm -
Nonstop2h 25m
Deal found 9/14![Southwest logo]()
$236
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
Nonstop2h 22m
Tue 10/271:26 pm -
1 stop7h 03m
Deal found 9/16![JetBlue logo]()
$248
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/42:00 pm -
Nonstop2h 15m
Sun 12/66:00 am -
Nonstop2h 46m
Deal found 9/17![United Airlines logo]()
$261
This eDestinos deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:17 pm -
Nonstop2h 22m
Mon 10/124:45 pm -
Nonstop2h 43m
Deal found 9/14![Avelo Airlines logo]()
$147
This Expedia deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/157:39 pm -
Nonstop2h 20m
Mon 10/194:45 pm -
Nonstop2h 43m
Deal found 9/13![Avelo Airlines logo]()
$150
This KAYAK deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Thu 12/1710:08 am -
Nonstop2h 28m
Thu 12/245:24 pm -
Nonstop3h 10m
Deal found 9/16![American Airlines logo]()
$348
This Expedia deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/167:17 pm -
Nonstop2h 22m
Mon 10/194:45 pm -
Nonstop2h 43m
Deal found 9/14![Avelo Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Wed 10/75:25 pm -
Nonstop2h 32m
Wed 10/212:40 pm -
Nonstop2h 53m
Deal found 9/13![Avelo Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/86:15 am -
Nonstop2h 12m
Sat 11/145:35 pm -
Nonstop2h 50m
Deal found 9/16![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 11/73:35 pm -
Nonstop2h 05m
Sat 11/217:55 pm -
Nonstop2h 30m
Deal found 9/14![Southwest logo]()
$236
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/67:17 pm -
Nonstop2h 22m
Sun 11/84:45 pm -
Nonstop2h 39m
Deal found 9/16![Avelo Airlines logo]()
$171
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:35 pm -
Nonstop2h 22m
Sun 10/187:17 am -
Nonstop2h 43m
Deal found 9/15![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 11/185:20 pm -
1 stop4h 15m
Fri 11/208:30 am -
Nonstop2h 35m
Deal found 9/15![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 12/106:00 pm -
Nonstop2h 37m
Sun 12/137:30 am -
Nonstop3h 00m
Deal found 9/15![Delta logo]()
$248
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/131:00 pm -
1 stop7h 29m
Sun 11/156:40 am -
1 stop6h 19m
Deal found 9/13![JetBlue logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/109:35 pm -
Nonstop2h 22m
Wed 10/149:10 am -
Nonstop2h 43m
Deal found 9/16![United Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/33:10 pm -
1 stop6h 45m
Sun 11/86:45 am -
Nonstop2h 25m
Deal found 9/13![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
Tue 10/276:04 am -
1 stop7h 08m
Sun 11/16:00 am -
1 stop5h 47m
Deal found 9/15![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 -
Nonstop2h 10m
Tue 10/278:30 pm -
Nonstop2h 48m
Deal found 9/15![United Airlines logo]()
$276
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/237:17 pm -
Nonstop2h 22m
Sun 10/255:15 pm -
Nonstop2h 39m
Deal found 9/13![Avelo Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:35 pm -
Nonstop2h 10m
Thu 10/224:20 pm -
1 stop6h 40m
Deal found 9/17![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Tue 12/12:39 pm -
Nonstop2h 21m
Fri 12/411:25 am -
Nonstop2h 44m
Deal found 9/17![Delta logo]()
$271
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:00 pm -
1 stop7h 14m
Sat 10/36:25 am -
1 stop4h 33m
Deal found 9/14![JetBlue logo]()
$335
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:06 pm -
1 stop4h 53m
Tue 10/207:40 pm -
1 stop4h 52m
Deal found 9/14![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/307:35 pm -
Nonstop2h 10m
Fri 11/63:05 pm -
Nonstop2h 40m
Deal found 9/15![Southwest logo]()
$261
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
Thu 10/157:39 pm -
Nonstop2h 20m
Sun 10/185:15 pm -
Nonstop2h 39m
Deal found 9/13![Avelo Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/226:10 am -
Nonstop2h 17m
Tue 10/277:30 am -
Nonstop2h 57m
Deal found 9/16![Delta logo]()
$274
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:00 pm -
1 stop7h 14m
Tue 10/66:25 am -
1 stop4h 34m
Deal found 9/18![JetBlue logo]()
$336
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated September 18, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 pm -
Nonstop2h 32m
Wed 9/303:25 pm -
Nonstop2h 53m
Deal found 9/16![Avelo Airlines logo]()
$151
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/55:00 pm -
Nonstop2h 25m
Tue 10/62:59 pm -
1 stop4h 42m
Deal found 9/17![United Airlines logo]()
$233
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/610:10 am -
2 stops7h 55m
Wed 10/712:00 pm -
1 stop6h 10m
Deal found 9/17![Southwest logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:20 am -
1 stop8h 40m
Thu 10/156:29 am -
1 stop13h 02m
Deal found 9/17![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/66:25 am -
1 stop8h 35m
Tue 10/204:59 pm -
1 stop7h 44m
Deal found 9/16![Frontier logo]()
$234
This KAYAK deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Fri 10/96:10 am -
Nonstop2h 20m
Wed 10/149:30 am -
Nonstop2h 54m
Deal found 9/17![JetBlue logo]()
$232
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/116:10 am -
Nonstop2h 20m
Tue 10/139:30 am -
Nonstop2h 54m
Deal found 9/18![JetBlue logo]()
$233
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Thu 10/156:00 am -
Nonstop2h 12m
Fri 10/168:35 pm -
Nonstop2h 42m
Deal found 9/14![Delta logo]()
$232
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/195:10 am -
Nonstop2h 05m
Fri 10/234:20 pm -
1 stop6h 40m
Deal found 9/16![Southwest logo]()
$232
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:38 am -
1 stop6h 51m
Sat 10/241:00 pm -
1 stop7h 14m
Deal found 9/14![JetBlue logo]()
$229
This eDestinos deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:17 pm -
Nonstop2h 22m
Mon 10/264:45 pm -
Nonstop2h 43m
Deal found 9/15![Avelo Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 10/302:25 pm -
1 stop5h 30m
Wed 11/410:30 am -
1 stop10h 25m
Deal found 9/14![Southwest logo]()
$230
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 September 18, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/27:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Avelo Airlines logo]()
$75
This CheapOair deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Avelo Airlines logo]()
$80
This CheapOair deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
Wed 9/306:10 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Avelo Airlines logo]()
$82
This Booking.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 9/257:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Avelo Airlines logo]()
$85
This Expedia deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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 10/197:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Avelo Airlines logo]()
$88
This Expedia deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Avelo Airlines logo]()
$93
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/167:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Avelo Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:04 am -
2 stops26h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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.
Wed 9/236:10 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Avelo Airlines logo]()
$104
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 11/17:39 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Avelo Airlines logo]()
$106
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/157:39 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Avelo Airlines logo]()
$109
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” 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 10/97:17 pm -
Nonstop2h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Avelo Airlines logo]()
$118
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 September 18, 2026.
Round-trip from | $135 (eDestinos) |
|---|---|
One-way from | $75 (Expedia) |
Popular in | April |
Cheapest in | January |
Average price | $315 |
Good round-trip deal | $117 or less |
Good one-way deal | $91 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 September 18, 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
Fri 10/16
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$75
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Wed 9/30
6:10 pm-9:42 pm
Nonstop2h 32m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$82
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Mon 11/2
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$106
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Sun 11/1
7:39 pm-10:59 pm
Nonstop2h 20m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$106
ChicagoNew Haven
ORD Chicago O'Hare Intl - HVN Tweed-New Haven
ORDHVN
Chicago O'Hare Intl
Fri 9/25
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
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
$126
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Fri 11/27
6:50 am-4:10 pm
1 stop8h 20m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
ChicagoNew York
ORD Chicago O'Hare Intl - LGA New York LaGuardia
ORDLGA
Chicago O'Hare Intl
Mon 12/14
7:00 am-10:20 am
Nonstop2h 20m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoNew York
ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl
ORDJFK
Chicago O'Hare Intl
Tue 10/13
6:10 am-9:27 am
Nonstop2h 17m
New York John F Kennedy Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
ChicagoNew York
ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl
ORDJFK
Chicago O'Hare Intl
Fri 11/6
6:00 pm-9:40 pm
Nonstop2h 40m
New York John F Kennedy Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
Showing 1-10 of 60 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
ORD-LGA
MDW-LGA
ORD-JFK
ORD-EWR
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
ORD-LGA
MDW-LGA
ORD-JFK
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 $319). 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 September 18, 2026.
It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 21% 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 September 18, 2026.
The most flights from CHI to USCT are scheduled on a Wednesday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago to Connecticut?
Airfare is typical for this route at the moment.
Chicago to Connecticut flights typically cost between $277 and $391 in December.The cheapest round-trip price found within the last 5 days was $277 on United Airlines (Dec 16-Jan 18).
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 September 12, 2026.
Travelers seeking maximum savings on their Chicago to Connecticut flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing 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 September 18, 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.
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Avelo Airlines
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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
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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 September 18, 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 September 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$145 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$472 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$403 | FlexibilityNo cancel fee | On-time63% |