$71+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Jul 18 — Jul 251
Round-trip
1 adult, Economy
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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 June 18, 2026.
Explore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2026.
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 6/17![Avelo Airlines logo]()
$141
This Super.com deal was found by Cheapflights users on 6/15. 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.
Mon 9/147:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/214:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$151
This Expedia deal was found by Cheapflights users on 6/16. 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 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
Mon 9/74:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 6/16![Avelo Airlines logo]()
$153
This CheapOair deal was found by Cheapflights users on 6/14. 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.
Fri 8/287:08 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Sun 8/303:45 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$155
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 8/34:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/12![Avelo Airlines logo]()
$168
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:27 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 8/244:30 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/17![Avelo Airlines logo]()
$171
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:13 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 8/174:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/17![Avelo Airlines logo]()
$173
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/134:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/12![Avelo Airlines logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 6/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:39 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Tue 8/253:30 pm
JFK
- ORD
Nonstop2h 50m
JetBlue
Deal found 6/15![JetBlue logo]()
$177
This flygcity.se deal was found by Cheapflights users on 6/15. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Mon 8/108:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/15![JetBlue logo]()
$178
This flygcity.se deal was found by Cheapflights users on 6/16. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 7/218:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/16![JetBlue logo]()
$179
This Flysmarter deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:40 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Wed 7/228:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/17![JetBlue logo]()
$181
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 June 18, 2026.
Discover carefully curated flight deals from Chicago to Connecticut that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 18, 2026.
This Super.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Sun 9/133:35 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 6/17![Avelo Airlines logo]()
$141
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:30 am
ORD
- LGA
Nonstop2h 16m
Delta
Tue 7/216:50 pm
LGA
- ORD
Nonstop3h 06m
Delta
Deal found 6/14![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Sat 8/227:35 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$187
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:11 am
ORD
- JFK
Nonstop2h 18m
JetBlue
Tue 8/188:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/14![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 6/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:00 am
ORD
- LGA
Nonstop2h 23m
United Airlines
Mon 9/289:10 am
LGA
- ORD
Nonstop2h 44m
United Airlines
Deal found 6/13![United Airlines logo]()
$197
This Mytrip deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:30 pm
ORD
- HVN
2 stops8h 18m
Multiple Airlines
Sun 9/133:35 pm
HVN
- ORD
Nonstop2h 43m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$269
This CheapOair deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:17 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Mon 9/144:30 pm
HVN
- ORD
Nonstop2h 43m
Avelo Airlines
Deal found 6/17![Avelo Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:10 pm
ORD
- JFK
Nonstop2h 35m
Delta
Mon 10/267:35 pm
JFK
- ORD
Nonstop2h 58m
Delta
Deal found 6/14![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sat 8/86:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Mon 8/106:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 6/15![Southwest logo]()
$195
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Tue 8/118:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/17![JetBlue logo]()
$196
This United Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/1412:00 pm
ORD
- LGA
Nonstop2h 23m
United Airlines
Fri 7/179:25 pm
LGA
- ORD
Nonstop2h 33m
United Airlines
Deal found 6/14![United Airlines logo]()
$197
This Expedia deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/64:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$183
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:20 pm
ORD
- LGA
Nonstop2h 24m
Delta
Thu 9/36:00 am
LGA
- ORD
Nonstop2h 29m
Delta
Deal found 6/14![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Sun 8/26:10 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/15![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Tue 7/286:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$197
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Sat 8/88:00 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Deal found 6/17![JetBlue logo]()
$197
This CheapOair deal was found by Cheapflights users on 6/14. 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.
Fri 7/106:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/134:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$188
This Sun Country Air deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:31 pm
ORD
- PVD
1 stop14h 50m
Sun Country Air
Mon 7/2011:18 am
PVD
- ORD
1 stop26h 04m
Sun Country Air
Deal found 6/17![Sun Country Air logo]()
$475
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Wed 7/222:28 pm
LGA
- ORD
Nonstop2h 46m
United Airlines
Deal found 6/17![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:10 pm
ORD
- JFK
Nonstop2h 35m
Delta
Mon 10/1910:50 am
JFK
- ORD
Nonstop2h 46m
Delta
Deal found 6/13![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Sat 7/116:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$202
This JetBlue deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Wed 8/58:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/16![JetBlue logo]()
$207
This Expedia deal was found by Cheapflights users on 6/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Fri 7/314:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/16![Avelo Airlines logo]()
$195
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:30 am
ORD
- EWR
1 stop5h 48m
Delta
Sat 9/54:53 pm
EWR
- ORD
1 stop4h 37m
Delta
Deal found 6/14![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 7/151:35 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 6/13![Southwest logo]()
$212
This CheapOair deal was found by Cheapflights users on 6/14. 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.
Fri 7/316:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Sun 8/23:30 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:26 am
ORD
- HVN
1 stop8h 48m
Multiple Airlines
Mon 9/216:24 pm
HVN
- ORD
2 stops18h 38m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 6/16. 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 8/208:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Fri 8/216:00 am
LGA
- ORD
1 stop4h 38m
United Airlines
Deal found 6/16![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Mon 10/127:30 am
LGA
- ORD
Nonstop2h 42m
Delta
Deal found 6/17![Delta logo]()
$210
This JetBlue deal was found by Cheapflights users on 6/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Sun 7/57:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Deal found 6/15![JetBlue logo]()
$237
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated June 18, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/13. 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.
Sat 6/275:22 pm
ORD
- JFK
Nonstop2h 38m
JetBlue
Sat 7/42:29 pm
JFK
- ORD
Nonstop2h 47m
JetBlue
Deal found 6/13![JetBlue logo]()
$197
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:05 am
ORD
- LGA
Nonstop2h 20m
Delta
Sat 7/42:50 pm
LGA
- ORD
Nonstop3h 00m
Delta
Deal found 6/13![Delta logo]()
$202
This American Airlines deal was found by Cheapflights users on 6/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:37 pm
ORD
- EWR
Nonstop2h 23m
American Airlines
Sat 7/45:21 pm
EWR
- ORD
Nonstop3h 02m
American Airlines
Deal found 6/13![American Airlines logo]()
$202
This Expedia deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/64:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$183
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Wed 7/810:55 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/17![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 6/16. 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.
Wed 7/87:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Tue 7/146:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/16![Southwest logo]()
$197
This Super.com deal was found by Cheapflights users on 6/15. 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 7/96:13 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 7/134:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$192
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 7/134:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/12![Avelo Airlines logo]()
$174
This Southwest deal was found by Cheapflights users on 6/14. 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.
Tue 7/145:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 8/49:35 pm
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 6/14![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sat 7/256:40 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Mon 8/318:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$195
This Super.com deal was found by Cheapflights users on 6/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Mon 8/34:10 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/12![Avelo Airlines logo]()
$168
This CheapOair deal was found by Cheapflights users on 6/14. 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.
Fri 7/316:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Sun 8/23:30 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$198
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 June 18, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This Super.com deal was found by Cheapflights users on 6/14. 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.
Thu 9/36:07 pm
ORD
- HVN
Nonstop2h 22m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$71
This Super.com deal was found by Cheapflights users on 6/14. 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 7/36:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Deal found 6/14![Avelo Airlines logo]()
$72
This CheapOair deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:27 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$81
This JetBlue deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:22 pm
ORD
- PVD
1 stop4h 58m
JetBlue
Deal found 6/13![JetBlue logo]()
$85
This Super.com deal was found by Cheapflights users on 6/15. 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.
Fri 7/106:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Deal found 6/15![Avelo Airlines logo]()
$87
This Expedia deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:48 pm
ORD
- HVN
Nonstop2h 31m
Avelo Airlines
Deal found 6/17![Avelo Airlines logo]()
$88
This Faresmojo deal was found by Cheapflights users on 6/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:00 pm
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 6/13![JetBlue logo]()
$90
This Super.com deal was found by Cheapflights users on 6/13. 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.
Sat 7/45:22 pm
ORD
- JFK
Nonstop2h 38m
JetBlue
Deal found 6/13![JetBlue logo]()
$91
This Flysmarter deal was found by Cheapflights users on 6/13. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:41 am
ORD
- JFK
Nonstop2h 19m
JetBlue
Deal found 6/13![JetBlue logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 6/17![JetBlue logo]()
$93
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:05 pm
ORD
- LGA
Nonstop2h 29m
Delta
Deal found 6/15![Delta logo]()
$94
This Southwest deal was found by Cheapflights users on 6/15. 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 7/217:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Deal found 6/15![Southwest logo]()
$94
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 June 18, 2026.
Round-trip from | $141 (Super.com) |
|---|---|
One-way from | $71 (Super.com) |
Popular in | April |
Cheapest in | August |
Average price | $433 |
Good round-trip deal | $149 or less |
Good one-way deal | $70 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 June 18, 2026.
Use the filters below to find and compare flights from Chicago to Connecticut that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 9/11
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Sun 9/13
3:35 pm-5:18 pm
Nonstop2h 43m
$141
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 9/11
7:17 pm-10:39 pm
Nonstop2h 22m
Tweed-New Haven
Mon 9/14
4:30 pm-6:13 pm
Nonstop2h 43m
$155
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 7/3
6:48 pm-10:19 pm
Nonstop2h 31m
Tweed-New Haven
Mon 7/6
4:10 pm-6:03 pm
Nonstop2h 53m
$183
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Tue 7/21
9:30 am-12:46 pm
Nonstop2h 16m
New York LaGuardia
Tue 7/21
6:50 pm-8:56 pm
Nonstop3h 06m
$187
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Wed 8/19
5:45 pm-8:55 pm
Nonstop2h 10m
New York LaGuardia
Sat 8/22
7:35 am-8:55 am
Nonstop2h 20m
$187
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Sat 8/15
10:11 am-1:29 pm
Nonstop2h 18m
New York John F Kennedy Intl
Tue 8/18
8:00 pm-9:55 pm
Nonstop2h 55m
$187
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 7/10
6:48 pm-10:19 pm
Nonstop2h 31m
Tweed-New Haven
Mon 7/13
4:10 pm-6:03 pm
Nonstop2h 53m
$188
ChicagoNew York
ORD - JFK
ORDJFK
Chicago O'Hare Intl
Sat 10/24
6:10 pm-9:45 pm
Nonstop2h 35m
New York John F Kennedy Intl
Mon 10/26
7:35 pm-9:33 pm
Nonstop2h 58m
$192
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 8/8
6:00 am-9:00 am
Nonstop2h 00m
New York LaGuardia
Mon 8/10
6:00 am-7:15 am
Nonstop2h 15m
$195
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 7/24
6:48 pm-10:19 pm
Nonstop2h 31m
Tweed-New Haven
Fri 7/31
4:10 pm-6:03 pm
Nonstop2h 53m
$195
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-PVD
ORD-JFK
ORD-LGA
MDW-LGA
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-PVD
ORD-JFK
ORD-LGA
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 $158). 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 June 18, 2026.
It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Chicago to Connecticut
Explore weekly flight availability from Chicago to Connecticut. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 18, 2026.
The most flights from CHI to USCT are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Chicago to Connecticut?
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 66 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 June 13, 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. Monday 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 June 18, 2026.
Get a feel of what it's like to fly with Southwest,Avelo Airlines, andUnited Airlines from Chicago to Connecticut by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Avelo Airlines
Food
7.0
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Overall
7.9
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Connecticut flights
Consider these flights traveling from Chicago to Connecticut.
Top 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$145 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$185 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$201 | Average$431 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$373 | FlexibilityNo cancel fee | On-time63% |