$54+ Cheap flights from Connecticut to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Connecticut to Chicago
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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 August 6, 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 August 6, 2026.
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:35 pm -
Nonstop2h 43m
Mon 10/57:17 pm -
Nonstop2h 22m
Deal found 8/2![Avelo Airlines logo]()
$107
This Trip.com deal was found by Cheapflights users on 8/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:45 pm -
Nonstop2h 53m
Wed 9/26:10 pm -
Nonstop2h 32m
Deal found 8/1![Avelo Airlines logo]()
$112
This Trip.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:25 pm -
Nonstop2h 53m
Fri 9/47:17 pm -
Nonstop2h 22m
Deal found 8/3![Avelo Airlines logo]()
$117
This Expedia deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/63:35 pm -
Nonstop2h 43m
Thu 9/106:07 pm -
Nonstop2h 22m
Deal found 8/5![Avelo Airlines logo]()
$118
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:30 pm -
Nonstop2h 43m
Thu 9/176:07 pm -
Nonstop2h 22m
Deal found 8/3![Avelo Airlines logo]()
$122
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Fri 10/234:45 pm -
Nonstop2h 43m
Sun 10/257:37 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$123
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Wed 9/93:25 pm -
Nonstop2h 53m
Fri 9/117:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$124
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:35 pm -
Nonstop2h 43m
Sun 10/46:07 pm -
Nonstop2h 22m
Deal found 8/5![Avelo Airlines logo]()
$129
This CheapOair deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:35 pm -
Nonstop2h 43m
Mon 9/147:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$136
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:45 pm -
Nonstop2h 53m
Fri 8/287:08 pm -
Nonstop2h 31m
Deal found 8/1![Avelo Airlines logo]()
$140
This CheapOair deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:45 pm -
Nonstop2h 43m
Sun 10/187:37 pm -
Nonstop2h 22m
Deal found 8/5![Avelo Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 8/227:35 pm -
Nonstop3h 17m
Tue 8/2510:07 am -
Nonstop2h 23m
Deal found 7/31![Delta logo]()
$207
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 August 6, 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 August 6, 2026.
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:35 pm -
Nonstop2h 43m
Sun 10/46:07 pm -
Nonstop2h 22m
Deal found 8/4![Avelo Airlines logo]()
$107
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:30 am -
Nonstop2h 36m
Wed 9/25:40 pm -
Nonstop2h 27m
Deal found 8/3![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:29 pm -
Nonstop2h 44m
Wed 9/27:00 am -
Nonstop2h 17m
Deal found 8/5![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:50 pm -
Nonstop2h 25m
Wed 9/25:10 am -
Nonstop2h 00m
Deal found 8/4![Southwest logo]()
$227
This Super.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:35 pm -
Nonstop2h 43m
Mon 10/57:17 pm -
Nonstop2h 22m
Deal found 8/5![Avelo Airlines logo]()
$117
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:45 am -
1 stop8h 00m
Tue 9/227:05 am -
Nonstop2h 28m
Deal found 8/1![JetBlue logo]()
$240
This Frontier deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:55 am -
1 stop6h 00m
Mon 9/711:50 am -
1 stop12h 13m
Deal found 8/5![Frontier logo]()
$255
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Fri 10/234:45 pm -
Nonstop2h 43m
Sun 10/257:37 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$123
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:30 pm -
Nonstop2h 43m
Sun 9/276:07 pm -
Nonstop2h 22m
Deal found 8/2![Avelo Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:48 am -
1 stop7h 13m
Mon 8/317:35 pm -
Nonstop2h 19m
Deal found 7/31![American Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Fri 9/44:30 pm -
Nonstop2h 43m
Mon 9/147:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$124
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
Nonstop2h 43m
Sun 11/157:37 pm -
Nonstop2h 22m
Deal found 8/2![Avelo Airlines logo]()
$124
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:25 pm -
Nonstop2h 53m
Fri 9/117:17 pm -
Nonstop2h 22m
Deal found 8/2![Avelo Airlines logo]()
$124
This Delta deal was found by Cheapflights users on 7/31. 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.
Sun 8/237:33 am -
Nonstop2h 54m
Tue 8/256:00 am -
Nonstop2h 24m
Deal found 7/31![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am -
Nonstop2h 15m
Tue 9/88:55 am -
1 stop5h 55m
Deal found 8/2![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:25 pm -
Nonstop2h 44m
Mon 8/317:00 am -
Nonstop2h 17m
Deal found 8/2![United Airlines logo]()
$237
This CheapOair deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:35 pm -
Nonstop2h 43m
Mon 9/147:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$137
This JetBlue deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:40 pm -
Nonstop2h 55m
Sat 9/55:27 pm -
Nonstop2h 33m
Deal found 8/5![JetBlue logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/1. 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 8/281:25 pm -
Nonstop2h 44m
Sun 8/309:00 am -
Nonstop2h 23m
Deal found 8/1![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:30 am -
Nonstop2h 36m
Wed 9/97:00 am -
Nonstop2h 15m
Deal found 8/1![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 8/1. 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.
Mon 9/146:00 am -
Nonstop2h 15m
Mon 9/147:50 pm -
Nonstop2h 05m
Deal found 8/1![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:30 am -
1 stop8h 15m
Sat 9/123:00 pm -
1 stop7h 35m
Deal found 8/4![JetBlue logo]()
$247
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/154:15 pm -
Nonstop2h 49m
Tue 9/229:30 am -
Nonstop2h 19m
Deal found 8/1![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 10/59:27 pm -
Nonstop2h 32m
Fri 10/97:45 pm -
Nonstop2h 25m
Deal found 7/31![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 7/31. 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.
Fri 9/258:55 pm -
Nonstop2h 25m
Mon 9/285:10 pm -
Nonstop2h 05m
Deal found 7/31![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:00 pm -
1 stop8h 08m
Fri 9/253:00 pm -
1 stop7h 09m
Deal found 8/4![JetBlue logo]()
$253
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:45 pm -
Nonstop2h 53m
Sun 9/66:07 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$160
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:50 pm -
Nonstop2h 30m
Sun 9/65:25 am -
Nonstop2h 00m
Deal found 8/5![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:35 pm -
Nonstop3h 17m
Sun 8/236:00 am -
Nonstop2h 24m
Deal found 8/1![Delta logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:30 am -
1 stop5h 48m
Sat 10/108:29 am -
1 stop5h 20m
Deal found 7/31![American Airlines logo]()
$335
Last-minute flights from Connecticut to ChicagoDiscover last-minute flight deals from Connecticut to Chicago. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Chicago. Data last updated August 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 8/227:35 pm -
Nonstop3h 17m
Wed 8/266:00 am -
Nonstop2h 24m
Deal found 7/31![Delta logo]()
$207
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:40 pm -
Nonstop2h 55m
Sat 8/296:00 am -
Nonstop2h 17m
Deal found 7/31![JetBlue logo]()
$205
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:45 pm -
Nonstop2h 53m
Fri 8/287:08 pm -
Nonstop2h 31m
Deal found 8/1![Avelo Airlines logo]()
$140
This CheapOair deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/273:45 pm -
Nonstop2h 53m
Thu 9/36:07 pm -
Nonstop2h 22m
Deal found 8/5![Avelo Airlines logo]()
$158
This Trip.com deal was found by Cheapflights users on 8/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:45 pm -
Nonstop2h 53m
Wed 9/26:10 pm -
Nonstop2h 32m
Deal found 8/1![Avelo Airlines logo]()
$112
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:45 pm -
Nonstop2h 53m
Sun 9/66:07 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$160
This Trip.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:25 pm -
Nonstop2h 53m
Fri 9/47:17 pm -
Nonstop2h 22m
Deal found 8/3![Avelo Airlines logo]()
$117
This Trip.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:30 pm -
Nonstop2h 43m
Sun 9/66:07 pm -
Nonstop2h 22m
Deal found 8/3![Avelo Airlines logo]()
$152
This CheapOair deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:35 pm -
Nonstop2h 43m
Mon 9/147:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$136
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Fri 9/114:30 pm -
Nonstop2h 43m
Mon 9/147:17 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$123
This Expedia deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:30 pm -
Nonstop2h 43m
Thu 9/176:07 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$118
This FlightHub deal was found by Cheapflights users on 8/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:30 pm -
Nonstop2h 43m
Sun 9/276:07 pm -
Nonstop2h 22m
Deal found 8/1![Avelo Airlines logo]()
$124
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 August 6, 2026.
Search for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This Super.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:30 pm -
Nonstop2h 43m
Deal found 8/4![Avelo Airlines logo]()
$54
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:35 pm -
Nonstop2h 43m
Deal found 8/3![Avelo Airlines logo]()
$56
This Expedia deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:30 pm -
Nonstop2h 53m
Deal found 8/4![Avelo Airlines logo]()
$59
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:45 pm -
Nonstop2h 53m
Deal found 8/2![Avelo Airlines logo]()
$65
This CheapOair deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm -
Nonstop2h 53m
Deal found 8/2![Avelo Airlines logo]()
$78
This CheapOair deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:10 pm -
Nonstop2h 53m
Deal found 8/4![Avelo Airlines logo]()
$80
This CheapOair deal was found by Cheapflights users on 7/31. 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 8/203:45 pm -
Nonstop2h 53m
Deal found 7/31![Avelo Airlines logo]()
$89
This CheapOair deal was found by Cheapflights users on 7/31. 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.
Fri 8/144:10 pm -
Nonstop2h 53m
Deal found 7/31![Avelo Airlines logo]()
$95
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:35 pm -
Nonstop3h 17m
Deal found 8/1![Delta logo]()
$104
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 9/55:00 pm -
Nonstop3h 13m
Deal found 7/31![Delta logo]()
$104
This Southwest deal was found by Cheapflights users on 8/1. 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 8/295:50 pm -
Nonstop2h 25m
Deal found 8/1![Southwest logo]()
$104
This Booking.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:30 am -
1 stop12h 38m
Deal found 8/3![Frontier logo]()
$105
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 August 6, 2026.
Round-trip from | $107 (Super.com) |
|---|---|
One-way from | $54 (Super.com) |
Popular in | July |
Cheapest in | January |
Average price | $377 |
Good round-trip deal | $178 or less |
Good one-way deal | $109 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 2,558,603 searches. Data last updated August 6, 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
Thu 10/1
3:35 pm-5:18 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 10/4
6:07 pm-9:29 pm
Nonstop2h 22m
$107
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Thu 10/1
3:35 pm-5:18 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 10/5
7:17 pm-10:39 pm
Nonstop2h 22m
$117
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 10/23
4:45 pm-6:28 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 10/25
7:37 pm-10:59 pm
Nonstop2h 22m
$123
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 9/25
4:30 pm-6:13 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 9/27
6:07 pm-9:29 pm
Nonstop2h 22m
$123
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 9/4
4:30 pm-6:13 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 9/14
7:17 pm-10:39 pm
Nonstop2h 22m
$124
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Fri 11/13
4:45 pm-6:28 pm
Nonstop2h 43m
Chicago O'Hare Intl
Sun 11/15
7:37 pm-10:59 pm
Nonstop2h 22m
$124
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Wed 9/9
3:25 pm-5:18 pm
Nonstop2h 53m
Chicago O'Hare Intl
Fri 9/11
7:17 pm-10:39 pm
Nonstop2h 22m
$124
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Thu 9/10
3:35 pm-5:18 pm
Nonstop2h 43m
Chicago O'Hare Intl
Mon 9/14
7:17 pm-10:39 pm
Nonstop2h 22m
$137
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 8/30
3:45 pm-5:38 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sun 9/6
6:07 pm-9:29 pm
Nonstop2h 22m
$160
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Wed 9/2
7:30 am-9:06 am
Nonstop2h 36m
Chicago O'Hare Intl
Wed 9/2
5:40 pm-9:07 pm
Nonstop2h 27m
$217
Showing 1-10 of 60 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
JFK-ORD
LGA-ORD
LGA-MDW
EWR-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
JFK-ORD
LGA-ORD
LGA-MDW
What is the cheapest month to book a flight from Connecticut to Chicago?
Currently, January is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $330). Flying from Connecticut to Chicago in July is currently the most expensive (average of $462). 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 August 6, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 22% on flights from Connecticut to Chicago by exploring options for tickets in the afternoon.
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 August 6, 2026.
The most flights from USCT to CHI are scheduled on a Wednesday (23 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Connecticut to Chicago?
Airfare is below average for this route at the moment.
Connecticut to Chicago flights typically cost between $333 and $448 in September.The cheapest round-trip price found within the last 5 days was $277 on Southwest (Sep 5-Sep 6).
How far ahead should I book a flight from Connecticut to Chicago?
The best time to book flights from Connecticut to Chicago is 84 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Connecticut to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 August 6, 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 August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Chicago flights
Consider these flights traveling from Connecticut to Chicago.
Top 6 airlines flying from Connecticut to Chicago
Discover the top 6 airlines that operate flights from Connecticut to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$439 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$428 | FlexibilityNo cancel fee | On-time63% |