$58+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Jun 3 — Jun 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 May 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 May 4, 2026.
This Jettzy deal was found by Cheapflights users on 5/1. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 6/154:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 5/1![Avelo Airlines logo]()
$114
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 6/84:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 4/29![Avelo Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Wed 6/178:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Mon 6/88:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Mon 6/18:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$127
This CheapOair deal was found by Cheapflights users on 4/30. 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 6/57:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 6/73:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 4/30![Avelo Airlines logo]()
$127
This Booking.com deal was found by Cheapflights users on 5/1. 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 6/41:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Tue 6/98:47 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Tue 6/98:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$129
This CheapOair deal was found by Cheapflights users on 4/30. 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 6/127:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 6/154:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 4/30![Avelo Airlines logo]()
$129
This Expedia deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Wed 5/206:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Multiple Airlines
Thu 5/2810:00 pm
LGA
- ORD
1 stop10h 55m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$137
This Gotogate deal was found by Cheapflights users on 4/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:59 pm
ORD
- EWR
Nonstop2h 07m
Spirit Airlines
Mon 6/15:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$138
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 May 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 May 4, 2026.
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Mon 6/84:20 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 4/29![Avelo Airlines logo]()
$140
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/16:30 pm
ORD
- LGA
Nonstop2h 29m
United Airlines
Tue 7/71:25 pm
LGA
- ORD
Nonstop2h 37m
United Airlines
Deal found 4/30![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
ORD
- LGA
Nonstop2h 12m
Delta
Wed 6/248:45 pm
LGA
- ORD
Nonstop2h 49m
Delta
Deal found 5/3![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 5/3. 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.
Thu 7/25:15 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Sun 7/56:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/3![Southwest logo]()
$177
This Spirit deal was found by Cheapflights users on 5/2. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:10 am
ORD
- LGA
1 stop9h 38m
Spirit Airlines
Mon 7/66:09 pm
LGA
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 5/2![Spirit Airlines logo]()
$207
This JetBlue deal was found by Cheapflights users on 5/1. 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.
Sat 5/168:34 am
ORD
- JFK
Nonstop2h 25m
JetBlue
Mon 5/186:00 am
JFK
- ORD
Nonstop2h 44m
JetBlue
Deal found 5/1![JetBlue logo]()
$217
This Super.com deal was found by Cheapflights users on 5/2. 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 6/127:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 6/143:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 5/2![Avelo Airlines logo]()
$141
This Trip.com deal was found by Cheapflights users on 5/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:35 pm
ORD
- HVN
Nonstop2h 32m
Multiple Airlines
Sat 6/62:50 pm
HVN
- ORD
1 stop9h 23m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$284
This Super.com deal was found by Cheapflights users on 5/2. 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 6/57:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 6/73:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 5/2![Avelo Airlines logo]()
$141
This KAYAK deal was found by Cheapflights users on 5/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:10 am
ORD
- JFK
1 stop5h 19m
American Airlines
Wed 6/38:29 am
JFK
- ORD
1 stop7h 45m
American Airlines
Deal found 5/1![American Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 7/303:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Mon 8/39:25 pm
LGA
- ORD
Nonstop2h 33m
United Airlines
Deal found 4/29![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 5/1. 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 5/297:10 pm
ORD
- LGA
Nonstop2h 22m
Delta
Sun 5/315:10 pm
LGA
- ORD
Nonstop2h 59m
Delta
Deal found 5/1![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 7/307:10 am
ORD
- EWR
Nonstop2h 20m
United Airlines
Sat 8/18:04 pm
EWR
- ORD
Nonstop2h 50m
United Airlines
Deal found 4/30![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:10 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Wed 5/2710:55 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/4![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 4/30. 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.
Fri 5/296:31 pm
ORD
- JFK
Nonstop2h 29m
Delta
Wed 6/310:30 am
JFK
- ORD
Nonstop2h 46m
Delta
Deal found 4/30![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/17:10 am
ORD
- EWR
Nonstop2h 20m
United Airlines
Tue 7/78:04 pm
EWR
- ORD
Nonstop2h 50m
United Airlines
Deal found 4/30![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/3. 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.
Sat 7/412:00 pm
MDW
- LGA
2 stops9h 55m
Southwest
Mon 7/68:55 am
LGA
- MDW
1 stop5h 50m
Southwest
Deal found 5/3![Southwest logo]()
$202
This Spirit deal was found by Cheapflights users on 5/1. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:05 am
ORD
- EWR
1 stop11h 42m
Spirit Airlines
Thu 5/282:50 pm
EWR
- ORD
1 stop8h 24m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 5/2. 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.
Fri 6/58:20 pm
ORD
- LGA
Nonstop2h 24m
Delta
Tue 6/96:00 am
LGA
- ORD
Nonstop2h 41m
Delta
Deal found 5/2![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Fri 5/296:00 am
ORD
- EWR
Nonstop2h 12m
United Airlines
Fri 6/129:40 pm
EWR
- ORD
Nonstop2h 50m
United Airlines
Deal found 5/3![United Airlines logo]()
$182
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Mon 7/66:00 am
JFK
- ORD
1 stop5h 06m
JetBlue
Deal found 4/30![JetBlue logo]()
$250
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 5/313:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 4/29![Avelo Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 5/2. 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.
Thu 6/1812:50 pm
MDW
- EWR
1 stop6h 54m
Delta
Mon 6/2210:31 am
EWR
- MDW
1 stop6h 45m
Delta
Deal found 5/2![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Mon 6/227:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/2![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 6/103:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Sun 6/146:10 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Deal found 4/30![United Airlines logo]()
$187
This JetBlue deal was found by Cheapflights users on 5/3. 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.
Thu 5/213:40 pm
ORD
- PVD
1 stop7h 19m
JetBlue
Tue 5/266:00 am
PVD
- ORD
1 stop4h 54m
JetBlue
Deal found 5/3![JetBlue logo]()
$256
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:18 pm
MDW
- EWR
1 stop5h 12m
Delta
Tue 8/46:00 am
EWR
- MDW
1 stop5h 03m
Delta
Deal found 4/29![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/1. 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.
Fri 7/32:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Mon 7/69:30 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/1![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Thu 5/285:00 am
ORD
- EWR
Nonstop2h 13m
United Airlines
Tue 6/27:59 am
EWR
- ORD
Nonstop2h 44m
United Airlines
Deal found 5/3![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/115:11 pm
MDW
- EWR
1 stop6h 46m
Delta
Sun 6/146:00 am
EWR
- MDW
1 stop4h 14m
Delta
Deal found 4/30![Delta logo]()
$197
Last-minute flights from Chicago to ConnecticutDiscover last-minute flight deals from Chicago to Connecticut. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Connecticut. Data last updated May 4, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Wed 5/206:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Mon 6/88:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Mon 6/18:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Multiple Airlines
Thu 5/2810:00 pm
LGA
- ORD
1 stop10h 55m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$137
This Orbitz deal was found by Cheapflights users on 4/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Fri 5/296:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:49 pm
ORD
- LGA
Nonstop2h 11m
Multiple Airlines
Tue 6/26:29 am
LGA
- ORD
1 stop14h 00m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:05 am
ORD
- LGA
1 stop9h 53m
Spirit Airlines
Mon 6/18:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:59 pm
ORD
- EWR
Nonstop2h 07m
Spirit Airlines
Mon 6/15:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Fri 6/58:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:33 pm
ORD
- LGA
1 stop13h 27m
Spirit Airlines
Mon 6/18:42 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$149
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:59 pm
ORD
- EWR
Nonstop2h 07m
Spirit Airlines
Fri 6/54:59 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Sun 6/73:50 pm
HVN
- ORD
Nonstop2h 53m
Avelo Airlines
Deal found 5/1![Avelo Airlines logo]()
$149
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 May 4, 2026.
Search for one-way flight options from Chicago to Connecticut. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Super.com deal was found by Cheapflights users on 4/29. 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 6/17:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 4/29![Avelo Airlines logo]()
$58
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Mon 6/87:07 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/1![Avelo Airlines logo]()
$70
This Super.com deal was found by Cheapflights users on 5/2. 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 6/46:35 pm
ORD
- HVN
Nonstop2h 32m
Avelo Airlines
Deal found 5/2![Avelo Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/101:29 pm
ORD
- EWR
1 stop7h 00m
Frontier
Deal found 5/1![Frontier logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:59 pm
ORD
- EWR
Nonstop2h 07m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 4/29![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/31:29 pm
ORD
- EWR
1 stop7h 00m
Frontier
Deal found 4/30![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
MDW
- LGA
1 stop16h 14m
Frontier
Deal found 5/3![Frontier logo]()
$77
This Jettzy deal was found by Cheapflights users on 5/1. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:59 pm
ORD
- EWR
Nonstop2h 07m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:29 pm
ORD
- LGA
1 stop8h 45m
Frontier
Deal found 5/3![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- LGA
1 stop13h 58m
Frontier
Deal found 5/1![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:57 pm
ORD
- LGA
Nonstop2h 17m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$83
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 May 4, 2026.
Round-trip from | $114 (Jettzy) |
|---|---|
One-way from | $58 (Super.com) |
Popular in | April |
Cheapest in | August |
Average price | $375 |
Good round-trip deal | $106 or less |
Good one-way deal | $100 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 May 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
Thu 6/4
6:35 pm-10:07 pm
Nonstop2h 32m
Tweed-New Haven
Mon 6/8
4:20 pm-6:13 pm
Nonstop2h 53m
$140
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 6/12
7:07 pm-10:39 pm
Nonstop2h 32m
Tweed-New Haven
Sun 6/14
3:50 pm-5:43 pm
Nonstop2h 53m
$141
ChicagoNew Haven
ORD - HVN
ORDHVN
Chicago O'Hare Intl
Fri 6/5
7:07 pm-10:39 pm
Nonstop2h 32m
Tweed-New Haven
Sun 6/7
3:50 pm-5:43 pm
Nonstop2h 53m
$141
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Wed 7/1
6:30 pm-9:59 pm
Nonstop2h 29m
New York LaGuardia
Tue 7/7
1:25 pm-3:02 pm
Nonstop2h 37m
$177
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Wed 6/17
6:00 am-9:12 am
Nonstop2h 12m
New York LaGuardia
Wed 6/24
8:45 pm-10:34 pm
Nonstop2h 49m
$177
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Thu 7/2
5:15 pm-8:20 pm
Nonstop2h 05m
New York LaGuardia
Sun 7/5
6:00 am-7:20 am
Nonstop2h 20m
$177
ChicagoNew York
ORD - LGA
ORDLGA
Chicago O'Hare Intl
Thu 7/30
3:00 pm-6:22 pm
Nonstop2h 22m
New York LaGuardia
Mon 8/3
9:25 pm-10:58 pm
Nonstop2h 33m
$177
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Thu 7/30
7:10 am-10:30 am
Nonstop2h 20m
Newark
Sat 8/1
8:04 pm-9:54 pm
Nonstop2h 50m
$177
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Wed 7/1
7:10 am-10:30 am
Nonstop2h 20m
Newark
Tue 7/7
8:04 pm-9:54 pm
Nonstop2h 50m
$177
ChicagoNewark
ORD - EWR
ORDEWR
Chicago O'Hare Intl
Fri 5/29
6:00 am-9:12 am
Nonstop2h 12m
Newark
Fri 6/12
9:40 pm-11:30 pm
Nonstop2h 50m
$182
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-EWR
MDW-EWR
MDW-LGA
ORD-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-EWR
MDW-EWR
MDW-LGA
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 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 May 4, 2026.
It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 25% 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 May 2, 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 May 4, 2026.
The most flights from CHI to USCT are scheduled on a Monday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 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 May 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.
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Avelo Airlines
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$141 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$109 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$388 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$416 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$337 | FlexibilityNo cancel fee | On-time63% |