$86+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Aug 5 — Aug 121
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 July 6, 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 July 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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.
Sat 8/158:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Sat 8/225:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/1![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:10 pm
JFK
- ORD
Nonstop3h 01m
JetBlue
Tue 8/46:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 7/5![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:40 pm
JFK
- ORD
Nonstop2h 55m
JetBlue
Thu 9/101:00 pm
ORD
- JFK
Nonstop2h 20m
JetBlue
Deal found 7/3![JetBlue logo]()
$193
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:05 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sat 8/85:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/2![JetBlue logo]()
$194
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 7/185:55 pm
LGA
- ORD
Nonstop3h 04m
Delta
Wed 7/227:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Deal found 7/1![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 7/1. 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 7/185:35 pm
LGA
- MDW
Nonstop2h 50m
Southwest
Wed 7/227:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Deal found 7/1![Southwest logo]()
$194
This JetBlue deal was found by Cheapflights users on 7/3. 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 8/206:55 am
JFK
- ORD
Nonstop2h 48m
JetBlue
Sat 8/225:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/3![JetBlue logo]()
$195
This Delta deal was found by Cheapflights users on 7/3. 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.
Thu 8/204:00 pm
LGA
- ORD
Nonstop3h 03m
Delta
Tue 8/256:00 am
ORD
- LGA
Nonstop2h 09m
Delta
Deal found 7/3![Delta logo]()
$195
This Southwest deal was found by Cheapflights users on 7/3. 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.
Wed 8/56:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Mon 8/105:15 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/3![Southwest logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Sun 7/197:05 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Tue 7/216:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Deal found 6/30![JetBlue logo]()
$196
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:16 am
LGA
- ORD
Nonstop2h 49m
American Airlines
Wed 8/198:25 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Deal found 7/3![American Airlines logo]()
$196
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/126:55 am
JFK
- ORD
Nonstop2h 48m
JetBlue
Thu 8/136:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 7/5![JetBlue logo]()
$197
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 July 6, 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 July 6, 2026.
This Delta deal was found by Cheapflights users on 7/3. 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 8/196:45 pm
LGA
- ORD
Nonstop3h 04m
Delta
Thu 8/202:25 pm
ORD
- LGA
Nonstop2h 22m
Delta
Deal found 7/3![Delta logo]()
$195
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/267:25 am
LGA
- MDW
Nonstop2h 20m
Southwest
Fri 8/287:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/5![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/3. 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 8/149:27 pm
LGA
- ORD
Nonstop2h 32m
United Airlines
Sun 8/167:00 am
ORD
- LGA
Nonstop2h 17m
United Airlines
Deal found 7/3![United Airlines logo]()
$207
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/48:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Tue 8/117:00 am
ORD
- JFK
1 stop6h 54m
JetBlue
Deal found 7/5![JetBlue logo]()
$266
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:46 am
JFK
- ORD
Nonstop2h 52m
Delta
Mon 10/56:00 am
ORD
- JFK
Nonstop2h 21m
Delta
Deal found 7/1![Delta logo]()
$203
This Southwest deal was found by Cheapflights users on 7/3. 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.
Tue 9/151:25 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 9/196:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/3![Southwest logo]()
$203
This United Airlines deal was found by Cheapflights users on 7/4. 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.
Wed 8/269:15 am
EWR
- ORD
Nonstop2h 43m
United Airlines
Sun 8/305:00 am
ORD
- EWR
Nonstop2h 14m
United Airlines
Deal found 7/4![United Airlines logo]()
$212
This KAYAK deal was found by Cheapflights users on 6/30. 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.
Tue 7/217:30 am
EWR
- ORD
1 stop5h 49m
American Airlines
Thu 7/235:07 am
ORD
- EWR
1 stop6h 30m
American Airlines
Deal found 6/30![American Airlines logo]()
$452
This Delta deal was found by Cheapflights users on 7/4. 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.
Thu 9/106:00 am
LGA
- ORD
Nonstop2h 29m
Delta
Thu 9/176:00 am
ORD
- LGA
Nonstop2h 15m
Delta
Deal found 7/4![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 7/3. 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.
Fri 9/48:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Sun 9/68:45 am
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 7/3![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 7/4. 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 7/187:25 pm
LGA
- ORD
Nonstop2h 47m
United Airlines
Sat 7/256:12 pm
ORD
- LGA
1 stop4h 18m
United Airlines
Deal found 7/4![United Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 7/3. 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 7/228:45 pm
LGA
- ORD
Nonstop2h 51m
Delta
Thu 8/62:25 pm
ORD
- LGA
Nonstop2h 22m
Delta
Deal found 7/3![Delta logo]()
$210
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Mon 9/216:00 am
LGA
- ORD
1 stop4h 38m
United Airlines
Thu 9/2412:00 pm
ORD
- LGA
Nonstop2h 17m
United Airlines
Deal found 7/1![United Airlines logo]()
$213
This Southwest deal was found by Cheapflights users on 7/1. 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.
Wed 7/156:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 7/186:40 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 7/1![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/2. 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 8/218:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Sun 8/235:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/2![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:55 pm
LGA
- ORD
Nonstop3h 02m
Delta
Mon 8/248:12 pm
ORD
- LGA
Nonstop2h 32m
Delta
Deal found 7/2![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 7/148:25 pm
LGA
- ORD
Nonstop2h 47m
United Airlines
Sat 7/254:00 pm
ORD
- LGA
Nonstop2h 22m
United Airlines
Deal found 7/1![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 9/266:59 pm
EWR
- ORD
1 stop6h 00m
Delta
Wed 9/305:10 pm
ORD
- EWR
1 stop5h 05m
Delta
Deal found 7/5![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/3. 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.
Tue 7/286:30 am
LGA
- MDW
1 stop5h 15m
Southwest
Tue 7/287:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Deal found 7/3![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Mon 7/277:21 am
LGA
- ORD
Nonstop2h 39m
United Airlines
Mon 7/276:00 pm
ORD
- LGA
Nonstop2h 25m
United Airlines
Deal found 7/1![United Airlines logo]()
$254
This Southwest deal was found by Cheapflights users on 7/1. 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 8/85:50 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 8/105:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/1![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 7/1. 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 11/119:40 am
EWR
- ORD
1 stop3h 57m
Delta
Sun 11/156:00 am
ORD
- EWR
1 stop6h 27m
Delta
Deal found 7/1![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Tue 7/287:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Deal found 7/5![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/4. 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 7/289:25 pm
LGA
- ORD
Nonstop2h 33m
United Airlines
Sun 8/26:00 am
ORD
- LGA
Nonstop2h 11m
United Airlines
Deal found 7/4![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 7/4. 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.
Wed 8/126:00 am
EWR
- MDW
1 stop4h 59m
Delta
Sat 8/156:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Deal found 7/4![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 7/4. 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.
Sat 8/156:55 pm
EWR
- ORD
1 stop6h 02m
Delta
Sat 8/221:50 pm
ORD
- EWR
1 stop6h 04m
Delta
Deal found 7/4![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 7/4. 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 9/18:27 pm
LGA
- ORD
Nonstop2h 44m
United Airlines
Wed 9/26:00 am
ORD
- LGA
Nonstop2h 13m
United Airlines
Deal found 7/4![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 8/229:40 am
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 8/245:50 pm
MDW
- LGA
1 stop4h 30m
Southwest
Deal found 7/2![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/3. 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.
Fri 8/212:59 pm
JFK
- ORD
Nonstop3h 02m
Delta
Mon 8/246:00 am
ORD
- JFK
Nonstop2h 24m
Delta
Deal found 7/3![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 7/4. 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.
Mon 8/35:30 pm
LGA
- MDW
1 stop7h 40m
Southwest
Mon 8/105:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/4![Southwest logo]()
$252
Last-minute flights from Connecticut to IllinoisDiscover last-minute flight deals from Connecticut to Illinois. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Illinois. Data last updated July 6, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/1. 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.
Sat 7/185:55 pm
LGA
- ORD
Nonstop3h 04m
Delta
Wed 7/227:00 am
ORD
- LGA
Nonstop2h 14m
Delta
Deal found 7/1![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 7/1. 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 7/185:35 pm
LGA
- MDW
Nonstop2h 50m
Southwest
Wed 7/227:45 pm
MDW
- LGA
Nonstop2h 15m
Southwest
Deal found 7/1![Southwest logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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.
Sun 7/197:05 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Tue 7/216:30 pm
ORD
- JFK
Nonstop2h 36m
JetBlue
Deal found 6/30![JetBlue logo]()
$196
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:05 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Sat 8/85:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/2![JetBlue logo]()
$194
This Super.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:10 pm
JFK
- ORD
Nonstop3h 01m
JetBlue
Tue 8/46:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 7/5![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:59 am
JFK
- ORD
Nonstop2h 48m
JetBlue
Thu 8/66:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 7/3![JetBlue logo]()
$193
This Southwest deal was found by Cheapflights users on 7/3. 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.
Wed 8/56:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Thu 8/612:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/3![Southwest logo]()
$195
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” 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 8/126:55 am
JFK
- ORD
Nonstop2h 48m
JetBlue
Thu 8/136:00 am
ORD
- JFK
Nonstop2h 17m
JetBlue
Deal found 7/5![JetBlue logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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.
Sat 8/158:00 pm
JFK
- ORD
Nonstop2h 58m
JetBlue
Sat 8/225:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/1![JetBlue logo]()
$191
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:16 am
LGA
- ORD
Nonstop2h 49m
American Airlines
Wed 8/198:25 pm
ORD
- LGA
Nonstop2h 20m
American Airlines
Deal found 7/3![American Airlines logo]()
$196
This JetBlue deal was found by Cheapflights users on 7/3. 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 8/206:55 am
JFK
- ORD
Nonstop2h 48m
JetBlue
Sat 8/225:27 pm
ORD
- JFK
Nonstop2h 33m
JetBlue
Deal found 7/3![JetBlue logo]()
$195
This Delta deal was found by Cheapflights users on 7/3. 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.
Thu 8/204:00 pm
LGA
- ORD
Nonstop3h 03m
Delta
Sat 8/227:05 am
ORD
- LGA
Nonstop2h 14m
Delta
Deal found 7/3![Delta logo]()
$195
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 July 6, 2026.
Search for one-way flight options from Connecticut to Illinois. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:29 pm
EWR
- STL
1 stop19h 53m
Frontier
Deal found 7/2![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 8/1210:29 pm
EWR
- STL
1 stop20h 08m
Frontier
Deal found 6/30![Frontier logo]()
$87
This Trip.com deal was found by Cheapflights users on 7/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:55 am
EWR
- STL
1 stop12h 42m
Frontier
Deal found 7/3![Frontier logo]()
$95
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 9/1210:20 am
LGA
- ORD
1 stop5h 07m
United Airlines
Deal found 7/2![United Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 7/2. 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.
Tue 7/287:05 am
JFK
- ORD
Nonstop2h 45m
JetBlue
Deal found 7/2![JetBlue logo]()
$97
This Trip.com deal was found by Cheapflights users on 7/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:55 am
EWR
- STL
1 stop12h 27m
Frontier
Deal found 7/1![Frontier logo]()
$98
This Super.com deal was found by Cheapflights users on 7/1. 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.
Thu 8/277:00 am
JFK
- ORD
Nonstop2h 46m
JetBlue
Deal found 7/1![JetBlue logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:29 pm
EWR
- STL
1 stop11h 28m
Frontier
Deal found 7/2![Frontier logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 8/107:09 am
JFK
- ORD
Nonstop2h 43m
JetBlue
Deal found 7/1![JetBlue logo]()
$101
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:05 am
LGA
- ORD
Nonstop2h 49m
American Airlines
Deal found 7/3![American Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Wed 8/510:29 pm
EWR
- STL
1 stop20h 08m
Frontier
Deal found 7/3![Frontier logo]()
$101
This Delta deal was found by Cheapflights users on 7/3. 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.
Thu 10/157:35 pm
JFK
- ORD
Nonstop3h 08m
Delta
Deal found 7/3![Delta logo]()
$102
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 July 6, 2026.
Round-trip from | $192 (Super.com) |
|---|---|
One-way from | $86 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $433 |
Good round-trip deal | $271 or less |
Good one-way deal | $74 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 July 6, 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
LGA - ORD
LGAORD
New York LaGuardia
Wed 8/19
6:45 pm-8:49 pm
Nonstop3h 04m
Chicago O'Hare Intl
Thu 8/20
2:25 pm-5:47 pm
Nonstop2h 22m
$195
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 8/26
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Fri 8/28
7:50 pm-10:55 pm
Nonstop2h 05m
$197
New YorkChicago
JFK - ORD
JFKORD
New York John F Kennedy Intl
Thu 10/1
7:46 am-9:38 am
Nonstop2h 52m
Chicago O'Hare Intl
Mon 10/5
6:00 am-9:21 am
Nonstop2h 21m
$203
Quickest round-trip
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/15
1:25 pm-2:45 pm
Nonstop2h 20m
Chicago Midway
Sat 9/19
6:00 am-9:00 am
Nonstop2h 00m
$203
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Fri 8/14
9:27 pm-10:59 pm
Nonstop2h 32m
Chicago O'Hare Intl
Sun 8/16
7:00 am-10:17 am
Nonstop2h 17m
$207
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Thu 9/10
6:00 am-7:29 am
Nonstop2h 29m
Chicago O'Hare Intl
Thu 9/17
6:00 am-9:15 am
Nonstop2h 15m
$207
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 9/4
8:55 pm-10:15 pm
Nonstop2h 20m
Chicago Midway
Sun 9/6
8:45 am-11:55 am
Nonstop2h 10m
$207
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Wed 7/22
8:45 pm-10:36 pm
Nonstop2h 51m
Chicago O'Hare Intl
Thu 8/6
2:25 pm-5:47 pm
Nonstop2h 22m
$210
NewarkChicago
EWR - ORD
EWRORD
Newark
Wed 8/26
9:15 am-10:58 am
Nonstop2h 43m
Chicago O'Hare Intl
Sun 8/30
5:00 am-8:14 am
Nonstop2h 14m
$212
New YorkChicago
LGA - ORD
LGAORD
New York LaGuardia
Sat 7/18
7:25 pm-9:12 pm
Nonstop2h 47m
Chicago O'Hare Intl
Sat 7/25
6:12 pm-11:30 pm
1 stop4h 18m
$212
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
EWR-MDW
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
What is the cheapest month to book a flight from Connecticut to Illinois?
Currently, November is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $55). Flying from Connecticut to Illinois in June is currently the most expensive (average of $161). 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 July 6, 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 22% on airfare.
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 July 6, 2026.
The most flights from USCT to USIL are scheduled on a Monday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).
How much does it cost to fly round-trip from Connecticut to Illinois?
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 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 July 4, 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. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 6, 2026.
Get a feel of what it's like to fly with Southwest,Avelo Airlines, andUnited 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Avelo Airlines
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 July 6, 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 6 airlines flying from Connecticut to Illinois
Discover the top 6 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 July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$471 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$199 | Average$412 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$225 | Average$431 | FlexibilityNo cancel fee | On-time69% |