$63+ Cheap flights from Connecticut to Illinois
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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Cheapest flights from Connecticut to IllinoisExplore the most affordable flight options available from Connecticut to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Connecticut to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:47 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Thu 6/116:10 am
ORD
- LGA
1 stop12h 42m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$151
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:59 am
LGA
- ORD
1 stop13h 16m
Spirit Airlines
Wed 6/31:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$152
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.
Wed 6/108:47 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Fri 6/197:07 pm
ORD
- LGA
1 stop13h 53m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$154
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.
Tue 6/28:47 pm
LGA
- ORD
Nonstop2h 38m
Multiple Airlines
Fri 6/51:29 pm
ORD
- LGA
1 stop6h 27m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$155
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.
Thu 5/2810:59 am
LGA
- ORD
1 stop13h 16m
Spirit Airlines
Fri 5/291:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$156
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:47 pm
LGA
- ORD
Nonstop2h 38m
Spirit Airlines
Fri 6/51:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$157
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Sat 6/136:00 am
ORD
- JFK
Nonstop2h 20m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$159
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Fri 5/151:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$159
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:00 pm
LGA
- ORD
1 stop10h 55m
Frontier
Fri 5/295:11 pm
ORD
- LGA
1 stop22h 00m
Frontier
Deal found 4/30![Frontier logo]()
$160
This flygcity.se 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Fri 6/196:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$161
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.
Thu 5/285:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Thu 6/412:54 pm
ORD
- EWR
Nonstop2h 05m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$163
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Thu 6/49:20 am
ORD
- LGA
1 stop8h 40m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$163
Best flights from Connecticut to IllinoisDiscover carefully curated flight deals from Connecticut to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Connecticut to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
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.
Sat 7/257:35 pm
JFK
- ORD
Nonstop3h 17m
Delta
Wed 8/56:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Deal found 4/30![Delta logo]()
$177
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.
Tue 9/17:05 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Wed 9/26:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 5/1![JetBlue logo]()
$177
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:10 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Mon 8/107:45 pm
ORD
- LGA
Nonstop2h 30m
United Airlines
Deal found 5/1![United Airlines logo]()
$177
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.
Sat 5/236:05 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Sun 5/245:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/1![Southwest logo]()
$197
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:30 pm
EWR
- ORD
1 stop7h 21m
American Airlines
Fri 7/318:09 pm
ORD
- EWR
Nonstop2h 21m
American Airlines
Deal found 4/30![American Airlines logo]()
$293
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 7/108:45 pm
LGA
- ORD
Nonstop2h 51m
Delta
Mon 7/1310:30 am
ORD
- LGA
Nonstop2h 18m
Delta
Deal found 5/1![Delta logo]()
$177
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.
Tue 6/98:59 pm
JFK
- ORD
Nonstop2h 59m
JetBlue
Wed 6/176:27 pm
ORD
- JFK
Nonstop2h 46m
JetBlue
Deal found 5/1![JetBlue logo]()
$187
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.
Wed 6/106:00 am
EWR
- ORD
Nonstop2h 42m
United Airlines
Tue 6/165:00 am
ORD
- EWR
Nonstop2h 13m
United Airlines
Deal found 4/29![United Airlines logo]()
$187
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 7/237:30 am
LGA
- ORD
Nonstop2h 36m
Delta
Sat 7/254:00 pm
ORD
- LGA
Nonstop2h 35m
Delta
Deal found 4/30![Delta 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.
Wed 5/206:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Sun 5/245:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/4![Southwest logo]()
$202
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:04 am
BDL
- ORD
1 stop7h 15m
Sun Country Air
Sat 7/116:19 pm
ORD
- BDL
1 stop15h 38m
Sun Country Air
Deal found 5/2![Sun Country Air logo]()
$425
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:12 pm
EWR
- ORD
Nonstop2h 48m
United Airlines
Sun 9/276:00 am
ORD
- EWR
Nonstop2h 12m
United Airlines
Deal found 5/1![United Airlines logo]()
$197
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.
Wed 5/277:35 pm
JFK
- ORD
Nonstop3h 01m
Delta
Sat 6/276:05 am
ORD
- JFK
Nonstop2h 21m
Delta
Deal found 5/1![Delta logo]()
$197
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:40 pm
EWR
- ORD
Nonstop2h 50m
United Airlines
Wed 6/36:00 am
ORD
- EWR
Nonstop2h 12m
United Airlines
Deal found 5/4![United Airlines logo]()
$197
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:55 pm
LGA
- MDW
Nonstop2h 45m
Southwest
Wed 5/202:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 4/30![Southwest logo]()
$217
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.
Tue 8/187:00 am
EWR
- ORD
1 stop6h 08m
Delta
Tue 8/251:35 pm
ORD
- EWR
1 stop4h 52m
Delta
Deal found 5/1![Delta logo]()
$197
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:25 pm
LGA
- ORD
Nonstop2h 47m
United Airlines
Tue 6/94:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Deal found 5/4![United Airlines logo]()
$197
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.
Tue 7/216:00 am
JFK
- ORD
1 stop5h 06m
JetBlue
Fri 7/246:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 4/30![JetBlue logo]()
$245
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.
Mon 5/187:15 am
LGA
- ORD
1 stop6h 35m
Southwest
Sat 5/232:05 pm
ORD
- LGA
1 stop7h 10m
Southwest
Deal found 5/3![Southwest logo]()
$237
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.
Tue 7/711:47 am
EWR
- ORD
1 stop6h 12m
Delta
Sat 7/255:18 pm
ORD
- EWR
1 stop5h 07m
Delta
Deal found 4/29![Delta logo]()
$197
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:30 pm
LGA
- ORD
Nonstop2h 52m
United Airlines
Wed 5/275:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Deal found 5/4![United Airlines logo]()
$202
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.
Mon 6/298:55 am
LGA
- MDW
1 stop5h 50m
Southwest
Tue 7/77:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 5/2![Southwest logo]()
$237
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.
Mon 6/293:00 pm
JFK
- ORD
Nonstop3h 11m
Delta
Tue 7/146:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Deal found 4/29![Delta logo]()
$207
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:10 am
LGA
- ORD
Nonstop2h 46m
United Airlines
Thu 6/48:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Deal found 5/2![United Airlines logo]()
$214
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:55 am
LGA
- MDW
1 stop5h 50m
Southwest
Thu 6/115:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 4/29![Southwest logo]()
$237
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.
Mon 5/256:00 am
PVD
- ORD
1 stop4h 54m
JetBlue
Sat 5/303:11 pm
ORD
- PVD
1 stop7h 48m
JetBlue
Deal found 5/3![JetBlue logo]()
$289
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 6/46:00 am
PVD
- ORD
1 stop4h 54m
JetBlue
Tue 6/93:27 pm
ORD
- PVD
1 stop7h 31m
JetBlue
Deal found 5/3![JetBlue logo]()
$289
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:00 am
LGA
- ORD
Nonstop2h 30m
United Airlines
Mon 7/68:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Deal found 5/1![United Airlines logo]()
$220
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
EWR
- ORD
1 stop5h 16m
Delta
Sun 5/249:25 am
ORD
- EWR
1 stop5h 34m
Delta
Deal found 5/4![Delta logo]()
$222
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:10 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Wed 8/54:40 pm
MDW
- LGA
1 stop5h 35m
Southwest
Deal found 4/30![Southwest logo]()
$247
Last-minute flights from Connecticut to IllinoisDiscover last-minute flight deals from Connecticut to Illinois. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Illinois. Data last updated May 5, 2026 and is based on user searches.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:29 pm
LGA
- ORD
Nonstop2h 42m
Spirit Airlines
Fri 5/151:49 pm
ORD
- LGA
Nonstop2h 11m
Spirit Airlines
Deal found 4/29![Spirit Airlines logo]()
$159
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:29 pm
LGA
- ORD
Nonstop2h 42m
Multiple Airlines
Fri 5/151:59 pm
ORD
- LGA
1 stop8h 15m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$164
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:29 pm
EWR
- ORD
1 stop10h 26m
Frontier
Wed 6/31:29 pm
ORD
- EWR
1 stop7h 00m
Frontier
Deal found 5/4![Frontier logo]()
$167
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Sat 6/136:00 am
ORD
- JFK
Nonstop2h 20m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$159
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:00 pm
JFK
- ORD
1 stop7h 41m
Multiple Airlines
Thu 5/283:27 pm
ORD
- JFK
Nonstop2h 32m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$164
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.
Thu 5/285:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Thu 6/412:54 pm
ORD
- EWR
Nonstop2h 05m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$163
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Thu 6/117:33 pm
ORD
- EWR
1 stop12h 26m
Spirit Airlines
Deal found 4/30![Spirit Airlines logo]()
$166
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.
Mon 6/110:29 pm
EWR
- MDW
1 stop13h 43m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop8h 25m
Frontier
Deal found 5/1![Frontier logo]()
$167
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.
Mon 6/85:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Fri 6/195:06 pm
ORD
- EWR
Nonstop2h 22m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$168
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.
Tue 6/910:29 pm
EWR
- ORD
1 stop10h 34m
Multiple Airlines
Mon 6/1512:54 pm
ORD
- EWR
Nonstop2h 05m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$165
This flygcity.se 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Fri 6/196:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$161
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:00 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sun 6/286:00 am
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 5/3![JetBlue logo]()
$168
One-way flights from Connecticut to IllinoisSearch for one-way flight options from Connecticut to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Connecticut to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:29 pm
EWR
- STL
1 stop11h 26m
Frontier
Deal found 5/4![Frontier logo]()
$63
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:29 pm
EWR
- STL
1 stop11h 26m
Frontier
Deal found 5/4![Frontier logo]()
$65
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:29 pm
EWR
- STL
1 stop20h 04m
Frontier
Deal found 5/4![Frontier logo]()
$71
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 5/2710:29 pm
EWR
- ORD
1 stop10h 26m
Frontier
Deal found 4/30![Frontier logo]()
$73
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.
Mon 6/84:59 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$74
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 6/35:55 am
EWR
- MDW
1 stop17h 07m
Frontier
Deal found 4/30![Frontier logo]()
$75
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:01 pm
EWR
- ORD
Nonstop2h 37m
Spirit Airlines
Deal found 5/1![Spirit Airlines logo]()
$75
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:29 pm
EWR
- MDW
1 stop24h 33m
Frontier
Deal found 5/4![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.
Sat 5/3011:30 am
EWR
- ORD
1 stop12h 43m
Frontier
Deal found 4/30![Frontier logo]()
$77
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:55 am
EWR
- MDW
1 stop17h 07m
Frontier
Deal found 5/4![Frontier logo]()
$78
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:55 am
EWR
- ORD
1 stop14h 34m
Frontier
Deal found 5/4![Frontier logo]()
$78
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.
Fri 5/2910:29 pm
EWR
- MDW
1 stop24h 33m
Frontier
Deal found 5/3![Frontier logo]()
$79
Find flight deals from Connecticut to Illinois
Keep the following information in mind while searching for Connecticut to Illinois flight deals. Data was last updated May 5, 2026.
Round-trip from | $151 (Flightnetwork) |
|---|---|
One-way from | $63 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $410 |
Good round-trip deal | $142 or less |
Good one-way deal | $132 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut to Illinois 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 5, 2026.
Use the filters below to find and compare flights from Connecticut to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Sat 7/25
7:35 pm-9:52 pm
Nonstop3h 17m
Chicago O'Hare Intl
Wed 8/5
6:00 am-9:24 am
Nonstop2h 24m
$177
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 9/1
7:05 am-8:48 am
Nonstop2h 43m
Chicago O'Hare Intl
Wed 9/2
6:00 am-9:17 am
Nonstop2h 17m
$177
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 8/6
6:10 am-7:49 am
Nonstop2h 39m
Chicago O'Hare Intl
Mon 8/10
7:45 pm-11:15 pm
Nonstop2h 30m
$177
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Fri 7/10
8:45 pm-10:36 pm
Nonstop2h 51m
Chicago O'Hare Intl
Mon 7/13
10:30 am-1:48 pm
Nonstop2h 18m
$177
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 7/23
7:30 am-9:06 am
Nonstop2h 36m
Chicago O'Hare Intl
Sat 7/25
4:00 pm-7:35 pm
Nonstop2h 35m
$177
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Tue 6/9
8:59 pm-10:58 pm
Nonstop2h 59m
Chicago O'Hare Intl
Wed 6/17
6:27 pm-10:13 pm
Nonstop2h 46m
$187
NewarkChicago
EWR - ORD
EWRORD
Newark
Wed 6/10
6:00 am-7:42 am
Nonstop2h 42m
Chicago O'Hare Intl
Tue 6/16
5:00 am-8:13 am
Nonstop2h 13m
$187
Quickest round-trip
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 5/23
6:05 pm-7:30 pm
Nonstop2h 25m
Chicago Midway
Sun 5/24
5:20 am-8:20 am
Nonstop2h 00m
$197
NewarkChicago
EWR - ORD
EWRORD
Newark
Fri 9/25
7:12 pm-9:00 pm
Nonstop2h 48m
Chicago O'Hare Intl
Sun 9/27
6:00 am-9:12 am
Nonstop2h 12m
$197
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 5/27
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sat 6/27
6:05 am-9:26 am
Nonstop2h 21m
$197
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Connecticut with our price prediction graph.
JFK-ORD
LGA-ORD
LGA-MDW
EWR-ORD
BDL-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Connecticut to Illinois
USCT-USIL
JFK-ORD
LGA-ORD
LGA-MDW
EWR-ORD
How far ahead should I book a flight from Connecticut to Illinois?
The best time to book flights from Connecticut to Illinois is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Connecticut to Illinois?
Currently, September is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $51). Flying from Connecticut to Illinois in July is currently the most expensive (average of $157). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CT to IL?
Find hourly flight availability from Connecticut to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
One of the essential ways to save on airfare from Connecticut to Illinois is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.
What is the cheapest day to fly from Connecticut to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Connecticut to Illinois. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Connecticut to Illinois flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Connecticut to Illinois
Explore weekly flight availability from Connecticut to Illinois. 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 5, 2026.
The most flights from USCT to USIL are scheduled on a Monday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Connecticut to Illinois?
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated May 5, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAvelo Airlines from Connecticut to Illinois by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Avelo Airlines
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Illinois. 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
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Alternative routes for Connecticut to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Connecticut to Illinois by cabin class
Find flights from Connecticut to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Connecticut and Illinois flights
Browse other Connecticut and Illinois flight options. Last updated on May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Connecticut after your stay in Illinois
Connecticut to Illinois flights
Consider these flights traveling from Connecticut to Illinois.
Top 5 airlines flying from Connecticut to Illinois
Discover the top 5 airlines that operate flights from Connecticut to Illinois. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$188 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$157 | Average$351 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$176 | Average$287 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$396 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$217 | Average$403 | FlexibilityNo cancel fee | On-time69% |