$52+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Apr 16 — Apr 231
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 March 17, 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 March 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/282:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Sat 5/22:38 pm
LGA
- ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Wed 4/17:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Thu 4/166:15 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$90
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Thu 5/76:15 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Sat 4/116:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 3/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Wed 4/86:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$99
This Super.com deal was found by Cheapflights users on 3/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Tue 4/76:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
Fri 4/36:01 pm
ORD
- EWR
Nonstop2h 08m
Spirit Airlines
Thu 4/910:54 pm
EWR
- ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Mon 3/306:01 pm
ORD
- EWR
Nonstop2h 08m
Spirit Airlines
Fri 4/1010:54 pm
EWR
- ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:33 am
ORD
- LGA
Nonstop2h 10m
Spirit Airlines
Sat 4/252:38 pm
LGA
- ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$102
This Frontier deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/147:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Fri 4/1711:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/12![Frontier logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Fri 4/106:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Thu 4/1611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/15![Frontier logo]()
$103
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 March 17, 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 March 17, 2026.
This Expedia deal was found by Cheapflights users on 3/14. 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.
Thu 4/236:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 4/274:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/14![Avelo Airlines logo]()
$143
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/305:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 5/36:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 3/12![Southwest logo]()
$197
This Mytrip deal was found by Cheapflights users on 3/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:07 pm
ORD
- HVN
Nonstop2h 32m
Multiple Airlines
Mon 4/2711:05 am
HVN
- ORD
3 stops24h 18m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$212
This JetBlue deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/199:41 am
ORD
- JFK
1 stop7h 42m
JetBlue
Sun 5/248:00 am
JFK
- ORD
Nonstop2h 53m
JetBlue
Deal found 3/11![JetBlue logo]()
$212
This Delta deal was found by Cheapflights users on 3/16. 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.
Sat 5/25:50 pm
ORD
- LGA
Nonstop2h 09m
Delta
Mon 5/48:25 pm
LGA
- ORD
Nonstop2h 50m
Delta
Deal found 3/16![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Fri 5/86:00 am
ORD
- EWR
Nonstop2h 12m
United Airlines
Tue 5/127:52 pm
EWR
- ORD
Nonstop2h 48m
United Airlines
Deal found 3/16![United Airlines logo]()
$217
This Spirit deal was found by Cheapflights users on 3/16. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:10 pm
ORD
- EWR
1 stop13h 59m
Spirit Airlines
Fri 4/36:00 am
EWR
- ORD
1 stop12h 15m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$270
This CheapOair deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 5/36:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 5/44:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/12![Avelo Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/247:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 4/263:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/12![Avelo Airlines logo]()
$161
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 4/149:30 am
MDW
- LGA
Nonstop2h 05m
Southwest
Tue 4/218:55 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Deal found 3/16![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/38:20 pm
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 4/78:55 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Deal found 3/12![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/36:34 pm
MDW
- EWR
1 stop3h 28m
Delta
Tue 4/79:43 am
EWR
- MDW
1 stop3h 46m
Delta
Deal found 3/12![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 3/14. 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.
Thu 9/39:35 pm
ORD
- EWR
Nonstop2h 22m
United Airlines
Mon 9/77:00 am
EWR
- ORD
Nonstop2h 43m
United Airlines
Deal found 3/14![United Airlines logo]()
$217
This JetBlue deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/107:45 am
ORD
- JFK
Nonstop2h 34m
JetBlue
Wed 4/156:00 am
JFK
- ORD
Nonstop2h 41m
JetBlue
Deal found 3/12![JetBlue logo]()
$221
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/138:10 am
ORD
- EWR
1 stop5h 13m
Delta
Wed 5/209:38 am
EWR
- ORD
1 stop4h 23m
Delta
Deal found 3/11![Delta logo]()
$217
This CheapOair deal was found by Cheapflights users on 3/14. 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.
Thu 4/236:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 4/263:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 3/14![Avelo Airlines logo]()
$200
This JetBlue deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/158:31 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Sun 4/196:00 am
JFK
- ORD
Nonstop2h 41m
JetBlue
Deal found 3/12![JetBlue logo]()
$221
This Southwest deal was found by Cheapflights users on 3/14. 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 5/15:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Fri 5/86:35 pm
LGA
- MDW
1 stop5h 15m
Southwest
Deal found 3/14![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Thu 6/256:00 am
ORD
- EWR
Nonstop2h 12m
United Airlines
Thu 6/259:40 pm
EWR
- ORD
Nonstop2h 50m
United Airlines
Deal found 3/16![United Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 6/171:35 pm
ORD
- EWR
1 stop4h 52m
Delta
Sat 7/116:00 am
EWR
- ORD
1 stop4h 24m
Delta
Deal found 3/11![Delta logo]()
$217
This Mytrip deal was found by Cheapflights users on 3/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 pm
ORD
- HVN
Nonstop2h 34m
Multiple Airlines
Thu 4/168:00 am
HVN
- ORD
3 stops17h 24m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 5/129:50 am
MDW
- LGA
1 stop5h 10m
Southwest
Wed 5/206:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 3/15![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 5/146:00 am
ORD
- LGA
Nonstop2h 13m
United Airlines
Sun 5/177:10 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Deal found 3/12![United Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 3/15. 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 4/97:00 am
ORD
- JFK
Nonstop2h 25m
Delta
Fri 4/107:59 pm
JFK
- ORD
Nonstop2h 59m
Delta
Deal found 3/15![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/159:40 am
MDW
- LGA
2 stops8h 45m
Southwest
Fri 4/176:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 3/12![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/1110:10 pm
ORD
- EWR
Nonstop2h 20m
United Airlines
Sat 4/189:50 pm
EWR
- ORD
Nonstop2h 47m
United Airlines
Deal found 3/12![United Airlines logo]()
$237
This JetBlue deal was found by Cheapflights users on 3/16. 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.
Fri 5/18:31 am
ORD
- JFK
Nonstop2h 18m
JetBlue
Fri 5/84:45 pm
JFK
- ORD
1 stop5h 51m
JetBlue
Deal found 3/16![JetBlue logo]()
$261
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/166:00 pm
ORD
- HVN
Nonstop2h 34m
Avelo Airlines
Sun 4/193:20 pm
HVN
- ORD
Nonstop2h 45m
Avelo Airlines
Deal found 3/11![Avelo Airlines logo]()
$239
This Mytrip deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/85:05 am
ORD
- HVN
1 stop15h 59m
Multiple Airlines
Thu 4/91:20 pm
HVN
- ORD
2 stops10h 57m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 5/27:25 am
MDW
- LGA
2 stops8h 50m
Southwest
Mon 5/49:45 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 3/16![Southwest logo]()
$212
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated March 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated March 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Mon 3/306:01 pm
ORD
- EWR
Nonstop2h 08m
Spirit Airlines
Fri 4/1010:54 pm
EWR
- ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Wed 4/17:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Thu 4/166:15 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$90
This Super.com deal was found by Cheapflights users on 3/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Tue 4/76:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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.
Fri 4/36:01 pm
ORD
- EWR
Nonstop2h 08m
Spirit Airlines
Thu 4/910:54 pm
EWR
- ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$100
This Super.com deal was found by Cheapflights users on 3/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Wed 4/86:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Fri 4/106:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Sat 4/116:30 am
LGA
- ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/147:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Fri 4/1711:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/12![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Thu 4/1611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/15![Frontier logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1810:33 am
ORD
- LGA
Nonstop2h 10m
Spirit Airlines
Sat 4/252:38 pm
LGA
- ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/282:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Sat 5/22:38 pm
LGA
- ORD
Nonstop2h 36m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$88
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Thu 5/76:15 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$93
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 March 17, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$52
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Thu 4/96:00 pm
ORD
- HVN
Nonstop2h 34m
Avelo Airlines
Deal found 3/12![Avelo Airlines logo]()
$52
This CheapOair deal was found by Cheapflights users on 3/13. 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 4/172:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$55
This Super.com deal was found by Cheapflights users on 3/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:05 pm
ORD
- JFK
Nonstop2h 24m
Frontier
Deal found 3/13![Frontier logo]()
$56
This Super.com deal was found by Cheapflights users on 3/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$57
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Mon 5/1811:28 am
ORD
- EWR
1 stop5h 31m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$57
This Mytrip deal was found by Cheapflights users on 3/16. 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.
Sat 4/47:31 pm
ORD
- LGA
Nonstop2h 05m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$58
This Super.com deal was found by Cheapflights users on 3/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/15![Frontier logo]()
$58
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/32:09 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$59
This Trip.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/12![Frontier logo]()
$59
This CheapOair deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/247:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 3/11![Avelo Airlines logo]()
$59
This Trip.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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.
Tue 3/247:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/12![Frontier logo]()
$60
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 March 17, 2026.
Round-trip from | $88 (Cheapflightsfares) |
|---|---|
One-way from | $52 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $453 |
Good round-trip deal | $142 or less |
Good one-way deal | $130 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 March 17, 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
Thu 4/23
6:35 pm-10:07 pm
Nonstop2h 32m
Tweed-New Haven
Mon 4/27
4:20 pm-6:13 pm
Nonstop2h 53m
$143
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Sun 5/3
6:35 pm-10:07 pm
Nonstop2h 32m
Tweed-New Haven
Mon 5/4
4:20 pm-6:13 pm
Nonstop2h 53m
$159
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 4/24
7:07 pm-10:39 pm
Nonstop2h 32m
Tweed-New Haven
Sun 4/26
3:50 pm-5:43 pm
Nonstop2h 53m
$161
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Thu 4/30
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Sun 5/3
6:00 am-7:25 am
Nonstop2h 25m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 4/14
9:30 am-12:35 pm
Nonstop2h 05m
New York LaGuardia
Tue 4/21
8:55 pm-10:30 pm
Nonstop2h 35m
$197
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Fri 4/3
8:20 pm-11:20 pm
Nonstop2h 00m
New York LaGuardia
Tue 4/7
8:55 pm-10:30 pm
Nonstop2h 35m
$197
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Thu 4/23
6:35 pm-10:07 pm
Nonstop2h 32m
Tweed-New Haven
Sun 4/26
3:50 pm-5:43 pm
Nonstop2h 53m
$200
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Fri 5/1
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Fri 5/8
6:35 pm-10:50 pm
1 stop5h 15m
$207
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 5/12
9:50 am-4:00 pm
1 stop5h 10m
New York LaGuardia
Wed 5/20
6:00 am-7:25 am
Nonstop2h 25m
$207
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 4/24
7:07 pm-10:39 pm
Nonstop2h 32m
Tweed-New Haven
Mon 4/27
11:05 am-10:23 am
3 stops24h 18m
$212
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-LGA
ORD-EWR
MDW-EWR
ORD-HVN
ORD-JFK
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-LGA
ORD-EWR
MDW-EWR
ORD-HVN
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 $23). Flying from Chicago to Connecticut in March is currently the most expensive (average of $314). 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 March 17, 2026.
It’s typically best to fly out from Chicago to Connecticut in the evening. Doing so could potentially save you 24% on the flight price compared to flying at noon, which is usually more expensive.
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 March 14, 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. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 17, 2026.
The most flights from CHI to USCT are scheduled on a Monday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Chicago to Connecticut?
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 March 17, 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Avelo Airlines
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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.
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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 March 17, 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 2,558,603 searches. Data last updated March 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$138 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$373 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$412 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$373 | FlexibilityNo cancel fee | On-time63% |