$53+ Cheap flights from Chicago (CHI) to Connecticut
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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Connecticut with Cheapflights
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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 August 4, 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 August 4, 2026.
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/214:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$103
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.
Fri 10/27:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 10/54:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$107
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:10 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Wed 9/233:25 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$108
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.
Thu 9/176:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Thu 9/243:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/3![Avelo Airlines logo]()
$112
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/115:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 8/3![Avelo Airlines logo]()
$114
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 9/63:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$115
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.
Thu 11/57:37 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 11/85:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$117
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 9/63:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$118
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/43:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$119
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 9/176:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/214:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$123
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:37 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/115:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$124
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:00 am
ORD
- EWR
Nonstop2h 14m
Frontier
Wed 9/911:35 am
EWR
- ORD
1 stop7h 48m
Frontier
Deal found 8/2![Frontier logo]()
$195
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 August 4, 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 August 4, 2026.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:10 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Wed 9/233:25 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$108
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.
Tue 9/18:55 am
MDW
- LGA
1 stop5h 55m
Southwest
Tue 9/19:35 pm
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/31![Southwest logo]()
$217
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.
Tue 9/17:05 am
ORD
- LGA
Nonstop2h 14m
Delta
Wed 9/96:00 am
LGA
- ORD
Nonstop2h 29m
Delta
Deal found 7/31![Delta logo]()
$222
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/115:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 8/3![Avelo Airlines logo]()
$114
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:00 am
ORD
- LGA
Nonstop2h 15m
United Airlines
Sun 10/187:23 am
LGA
- ORD
Nonstop2h 37m
United Airlines
Deal found 7/30![United Airlines logo]()
$237
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Sun 8/307:09 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Deal found 8/3![JetBlue logo]()
$239
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.
Fri 10/307:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 11/24:45 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$117
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/43:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$119
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 10/97:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/115:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$124
This KAYAK deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:30 am
ORD
- JFK
1 stop7h 30m
American Airlines
Wed 9/162:58 pm
JFK
- ORD
Nonstop2h 48m
American Airlines
Deal found 7/30![American Airlines logo]()
$333
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.
Thu 10/87:37 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 10/115:10 pm
HVN
- ORD
Nonstop2h 42m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$124
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Sun 8/303:45 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$124
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:05 am
ORD
- LGA
Nonstop2h 14m
Delta
Sun 8/307:30 am
LGA
- ORD
Nonstop2h 36m
Delta
Deal found 8/2![Delta logo]()
$227
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.
Tue 9/297:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Mon 10/59:00 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 8/1![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
ORD
- EWR
Nonstop2h 13m
United Airlines
Sun 9/209:15 am
EWR
- ORD
Nonstop2h 42m
United Airlines
Deal found 7/30![United Airlines logo]()
$237
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.
Wed 9/27:00 am
ORD
- LGA
1 stop6h 59m
JetBlue
Tue 9/86:00 am
LGA
- ORD
1 stop8h 39m
JetBlue
Deal found 8/1![JetBlue logo]()
$242
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.
Tue 8/186:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Tue 8/257:33 am
JFK
- ORD
Nonstop2h 54m
Delta
Deal found 7/31![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/275:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 8/306:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/29![Southwest logo]()
$237
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.
Thu 9/35:00 am
ORD
- EWR
Nonstop2h 14m
United Airlines
Mon 9/711:00 pm
EWR
- ORD
Nonstop2h 28m
United Airlines
Deal found 8/2![United Airlines logo]()
$237
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 9/153:00 pm
ORD
- EWR
1 stop7h 06m
JetBlue
Fri 9/183:38 pm
EWR
- ORD
1 stop8h 30m
JetBlue
Deal found 8/1![JetBlue logo]()
$242
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:00 pm
ORD
- JFK
Nonstop2h 33m
Delta
Sun 8/307:33 am
JFK
- ORD
Nonstop2h 54m
Delta
Deal found 7/30![Delta logo]()
$228
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.
Thu 9/35:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Mon 9/76:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/31![Southwest logo]()
$242
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Thu 9/1012:59 pm
JFK
- ORD
1 stop7h 02m
JetBlue
Deal found 7/31![JetBlue logo]()
$242
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.
Thu 8/207:05 am
ORD
- LGA
Nonstop2h 14m
Delta
Tue 8/258:30 pm
LGA
- ORD
Nonstop2h 54m
Delta
Deal found 8/1![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/2411:00 am
ORD
- LGA
Nonstop2h 18m
United Airlines
Thu 8/273:29 pm
LGA
- ORD
Nonstop2h 45m
United Airlines
Deal found 7/29![United Airlines logo]()
$263
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 9/95:40 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Deal found 8/3![Southwest logo]()
$247
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Mon 8/316:14 am
JFK
- ORD
1 stop4h 57m
JetBlue
Deal found 7/31![JetBlue logo]()
$257
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.
Fri 10/232:29 pm
ORD
- LGA
Nonstop2h 20m
Delta
Sun 10/256:59 am
LGA
- ORD
Nonstop2h 36m
Delta
Deal found 8/1![Delta logo]()
$237
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:00 am
ORD
- LGA
Nonstop2h 23m
United Airlines
Wed 8/126:00 am
LGA
- ORD
1 stop4h 38m
United Airlines
Deal found 8/3![United Airlines logo]()
$267
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 9/185:50 pm
MDW
- LGA
1 stop4h 30m
Southwest
Sun 9/206:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/31![Southwest logo]()
$247
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated August 4, 2026 and is based on user searches.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 8/244:30 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$130
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.
Sat 8/226:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Wed 8/263:40 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 7/31![JetBlue logo]()
$195
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Sun 8/303:45 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$124
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 8/314:30 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$127
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Fri 9/114:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$128
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORD
- EWR
Nonstop2h 07m
Frontier
Tue 9/11:35 pm
EWR
- ORD
1 stop7h 40m
Frontier
Deal found 8/3![Frontier logo]()
$197
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:00 am
ORD
- EWR
Nonstop2h 14m
Frontier
Wed 9/911:35 am
EWR
- ORD
1 stop7h 48m
Frontier
Deal found 8/2![Frontier logo]()
$195
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 9/36:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 9/63:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$112
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 9/63:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$118
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/214:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$103
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:10 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Wed 9/233:25 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 8/2![Avelo Airlines logo]()
$108
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 9/176:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/214:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$123
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 August 4, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$53
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 10/46:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Deal found 8/3![Avelo Airlines logo]()
$54
This Super.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Deal found 7/29![Avelo Airlines logo]()
$55
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.
Thu 9/36:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Deal found 8/3![Avelo Airlines logo]()
$56
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:07 pm
ORD
- HVN
Nonstop2h 23m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$58
This Booking.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:10 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$59
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.
Wed 9/26:10 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 7/31![Avelo Airlines logo]()
$65
This Travelocity deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Deal found 7/30![Avelo Airlines logo]()
$72
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 8/276:27 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 8/1![Avelo Airlines logo]()
$78
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Deal found 7/31![JetBlue logo]()
$99
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:03 pm
MDW
- EWR
1 stop11h 56m
Frontier
Deal found 7/30![Frontier logo]()
$101
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:20 am
ORD
- EWR
1 stop11h 08m
Frontier
Deal found 7/30![Frontier logo]()
$101
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 August 4, 2026.
Round-trip from | $103 (Flightnetwork) |
|---|---|
One-way from | $53 (eDestinos) |
Popular in | April |
Cheapest in | September |
Average price | $318 |
Good round-trip deal | $127 or less |
Good one-way deal | $88 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 2,558,603 searches. Data last updated August 4, 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 - HVN
ORDHVN
Chicago O'Hare Intl
Wed 9/16
6:10 pm-9:42 pm
Nonstop2h 32m
Tweed-New Haven
Wed 9/23
3:25 pm-5:18 pm
Nonstop2h 53m
$108
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Sun 10/4
6:07 pm-9:29 pm
Nonstop2h 22m
Tweed-New Haven
Sun 10/11
5:10 pm-6:52 pm
Nonstop2h 42m
$114
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 10/30
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Mon 11/2
4:45 pm-6:28 pm
Nonstop2h 43m
$117
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Thu 10/1
6:07 pm-9:29 pm
Nonstop2h 22m
Tweed-New Haven
Sun 10/4
3:35 pm-5:18 pm
Nonstop2h 43m
$119
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 10/9
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Sun 10/11
5:10 pm-6:52 pm
Nonstop2h 42m
$124
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Thu 10/8
7:37 pm-10:59 pm
Nonstop2h 22m
Tweed-New Haven
Sun 10/11
5:10 pm-6:52 pm
Nonstop2h 42m
$124
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 8/28
7:08 pm-10:39 pm
Nonstop2h 31m
Tweed-New Haven
Sun 8/30
3:45 pm-5:38 pm
Nonstop2h 53m
$124
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 9/1
8:55 am-3:50 pm
1 stop5h 55m
New York LaGuardia
Tue 9/1
9:35 pm-10:50 pm
Nonstop2h 15m
$217
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Tue 9/1
7:05 am-10:19 am
Nonstop2h 14m
New York LaGuardia
Wed 9/9
6:00 am-7:29 am
Nonstop2h 29m
$222
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Sat 8/29
7:05 am-10:19 am
Nonstop2h 14m
New York LaGuardia
Sun 8/30
7:30 am-9:06 am
Nonstop2h 36m
$227
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-PVD
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
ORD-LGA
MDW-LGA
ORD-PVD
What is the cheapest month to book a flight from Chicago to Connecticut?
Currently, September is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $282). Flying from Chicago to Connecticut in July is currently the most expensive (average of $473). 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 August 4, 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 August 4, 2026.
The most flights from CHI to USCT are scheduled on a Monday (22 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (11 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 $242 and $433 in August.The cheapest round-trip price found within the last 5 days was $277 on United Airlines (Aug 24-Aug 31).
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 August 1, 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. Friday 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 August 4, 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.
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Avelo Airlines
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
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
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 August 4, 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 5 airlines flying from Chicago to Connecticut
Discover the top 5 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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$149 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$204 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$403 | FlexibilityNo cancel fee | On-time63% |