$79+ Cheap flights from Connecticut to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 October 30, 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 October 30, 2026.
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Mon 11/94:45 pm -
Nonstop2h 43m
Fri 11/137:17 pm -
Nonstop2h 22m
Deal found 10/25![Avelo Airlines logo]()
$157
This Expedia deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:35 pm -
Nonstop2h 53m
Tue 12/17:03 pm -
Nonstop2h 23m
Deal found 10/27![Avelo Airlines logo]()
$158
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/25![Avelo Airlines logo]()
$179
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/94:45 pm -
Nonstop2h 43m
Fri 11/1310:19 am -
2 stops11h 40m
Deal found 10/25![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/124:45 pm -
Nonstop2h 39m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 10/25![Avelo Airlines logo]()
$207
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:45 pm -
Nonstop2h 39m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/26![Avelo Airlines logo]()
$209
This Expedia deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 10/28![Avelo Airlines logo]()
$214
This Travelocity deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/14:10 pm -
Nonstop2h 53m
Thu 12/37:07 pm -
Nonstop2h 23m
Deal found 10/28![Avelo Airlines logo]()
$216
This Orbitz deal was found by Cheapflights users on 10/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Sun 11/227:13 pm -
Nonstop2h 23m
Deal found 10/29![Avelo Airlines logo]()
$225
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:15 pm -
Nonstop2h 53m
Thu 12/310:37 pm -
1 stop12h 48m
Deal found 10/26![Multiple Airlines logo]()
$234
This Southwest deal was found by Cheapflights users on 10/29. 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.
Fri 12/112:30 pm -
2 stops6h 40m
Tue 12/151:20 pm -
2 stops7h 50m
Deal found 10/29![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:07 pm -
1 stop5h 24m
Thu 11/268:10 am -
Nonstop2h 10m
Deal found 10/30![American Airlines logo]()
$307
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 October 30, 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 October 30, 2026.
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Mon 11/94:45 pm -
Nonstop2h 43m
Fri 11/137:17 pm -
Nonstop2h 22m
Deal found 10/25![Avelo Airlines logo]()
$157
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:50 am -
2 stops27h 33m
Thu 11/197:13 pm -
Nonstop2h 23m
Deal found 10/25![Multiple Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/175:10 pm -
Nonstop2h 30m
Thu 2/257:10 pm -
Nonstop2h 00m
Deal found 10/26![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/46:00 am -
1 stop6h 33m
Sun 12/66:20 pm -
Nonstop2h 20m
Deal found 10/28![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 10/29. 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 1/67:05 am -
1 stop5h 59m
Fri 1/86:40 pm -
1 stop4h 01m
Deal found 10/29![Delta logo]()
$333
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 11/126:26 pm -
1 stop6h 33m
Mon 11/162:34 pm -
2 stops8h 07m
Deal found 10/28![American Airlines logo]()
$394
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/124:45 pm -
Nonstop2h 39m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 10/25![Avelo Airlines logo]()
$207
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:40 am -
3 stops28h 04m
Tue 12/17:03 pm -
Nonstop2h 23m
Deal found 10/27![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/46:25 pm -
Nonstop2h 30m
Sun 12/68:00 am -
Nonstop2h 10m
Deal found 10/26![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 1/131:09 pm -
1 stop5h 51m
Sat 1/166:00 am -
1 stop5h 51m
Deal found 10/26![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/312:30 pm -
2 stops6h 55m
Sun 12/65:00 am -
1 stop6h 20m
Deal found 10/28![Southwest logo]()
$330
This United Airlines deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/2112:40 pm -
Nonstop2h 52m
Mon 11/307:25 am -
Nonstop2h 18m
Deal found 10/27![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/215:33 pm -
1 stop7h 21m
Tue 12/16:20 am -
1 stop6h 43m
Deal found 10/26![Delta logo]()
$333
This Mytrip deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:50 am -
2 stops31h 47m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 10/28![Multiple Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Sun 12/66:00 am -
1 stop6h 33m
Fri 12/116:20 pm -
Nonstop2h 20m
Deal found 10/25![United Airlines logo]()
$376
This Mytrip deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:15 am -
2 stops22h 31m
Tue 11/179:51 am -
2 stops35h 03m
Deal found 10/27![Multiple Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:09 am -
1 stop7h 49m
Tue 11/175:00 am -
1 stop5h 25m
Deal found 10/29![American Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/196:00 am -
1 stop6h 59m
Sun 11/226:44 pm -
1 stop3h 57m
Deal found 10/26![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 10/29. 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.
Fri 2/126:55 pm -
Nonstop2h 25m
Sun 2/141:25 pm -
Nonstop2h 05m
Deal found 10/29![Southwest logo]()
$357
This KAYAK deal was found by Cheapflights users on 10/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:37 am -
Nonstop2h 52m
Fri 11/207:25 am -
Nonstop2h 18m
Deal found 10/29![United Airlines logo]()
$377
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/94:00 pm -
2 stops24h 31m
Fri 11/1310:19 am -
2 stops11h 40m
Deal found 10/25![Multiple Airlines logo]()
$363
This KAYAK deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 11/195:30 am -
1 stop6h 09m
Fri 11/203:47 pm -
1 stop6h 49m
Deal found 10/28![Delta logo]()
$366
This Southwest deal was found by Cheapflights users on 10/29. 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.
Fri 2/53:30 pm -
1 stop5h 45m
Sun 2/710:10 am -
2 stops7h 05m
Deal found 10/29![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/196:00 am -
2 stops8h 04m
Mon 11/238:50 am -
1 stop4h 12m
Deal found 10/29![United Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 3/256:21 am -
1 stop6h 19m
Sat 3/276:56 pm -
1 stop4h 22m
Deal found 10/28![American Airlines logo]()
$479
This Mytrip deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/49:37 am -
2 stops9h 26m
Sun 12/610:37 pm -
1 stop12h 48m
Deal found 10/28![Multiple Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/155:30 am -
1 stop5h 16m
Wed 11/256:44 pm -
1 stop3h 57m
Deal found 10/29![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/126:55 pm -
Nonstop2h 25m
Mon 2/158:10 am -
2 stops9h 05m
Deal found 10/26![Southwest logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 2/25:07 pm -
1 stop5h 37m
Sat 2/62:26 pm -
1 stop6h 11m
Deal found 10/28![United Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Thu 11/1912:10 pm -
1 stop7h 20m
Wed 12/211:58 am -
1 stop4h 36m
Deal found 10/28![American Airlines logo]()
$489
Last-minute flights from Connecticut to IllinoisDiscover last-minute flight deals from Connecticut to Illinois. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Illinois. Data last updated October 30, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:45 pm -
Nonstop2h 39m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/26![Avelo Airlines logo]()
$209
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:45 pm -
Nonstop2h 43m
Mon 11/97:17 pm -
Nonstop2h 22m
Deal found 10/25![Avelo Airlines logo]()
$179
This Expedia deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Mon 11/94:45 pm -
Nonstop2h 43m
Fri 11/137:17 pm -
Nonstop2h 22m
Deal found 10/25![Avelo Airlines logo]()
$157
This Mytrip deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/94:45 pm -
Nonstop2h 43m
Fri 11/1310:19 am -
2 stops11h 40m
Deal found 10/25![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/124:45 pm -
Nonstop2h 39m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 10/25![Avelo Airlines logo]()
$207
This Expedia deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Mon 11/167:17 pm -
Nonstop2h 22m
Deal found 10/28![Avelo Airlines logo]()
$214
This Orbitz deal was found by Cheapflights users on 10/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:45 pm -
Nonstop2h 39m
Sun 11/227:13 pm -
Nonstop2h 23m
Deal found 10/29![Avelo Airlines logo]()
$225
This Travelocity deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
Nonstop2h 43m
Sun 11/157:09 pm -
Nonstop2h 20m
Deal found 10/27![Avelo Airlines logo]()
$247
This Expedia deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/194:35 pm -
Nonstop2h 53m
Tue 12/17:03 pm -
Nonstop2h 23m
Deal found 10/27![Avelo Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/232:30 pm -
2 stops9h 15m
Fri 11/275:30 am -
2 stops9h 40m
Deal found 10/26![Southwest logo]()
$307
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:07 pm -
1 stop5h 24m
Thu 11/268:10 am -
Nonstop2h 10m
Deal found 10/30![American Airlines logo]()
$307
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/264:15 pm -
Nonstop2h 53m
Thu 12/310:37 pm -
1 stop12h 48m
Deal found 10/26![Multiple Airlines logo]()
$234
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 October 30, 2026.
Search for one-way flight options from Connecticut to Illinois. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Travelocity deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
Nonstop2h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Avelo Airlines logo]()
$79
This Super.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/154:45 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Avelo Airlines logo]()
$85
This Travelocity deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:20 pm -
Nonstop2h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Avelo Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 12/512:05 pm -
2 stops6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$144
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/176:01 am -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$144
This Expedia deal was found by Cheapflights users on 10/29. 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.
Sun 11/228:28 pm -
1 stop26h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$146
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/2012:55 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Southwest logo]()
$149
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/209:37 am -
Nonstop2h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$149
This Trip.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Sun 11/2212:26 pm -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/157:05 am -
2 stops15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$150
This CheapOair deal was found by Cheapflights users on 10/29. 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.
Sun 1/1010:45 am -
1 stop15h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$151
This Trip.com deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Sun 12/62:44 pm -
1 stop27h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$153
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 October 30, 2026.
Round-trip from | $157 (Expedia) |
|---|---|
One-way from | $79 (Travelocity) |
Popular in | July |
Cheapest in | January |
Average price | $424 |
Good round-trip deal | $255 or less |
Good one-way deal | $161 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 7,457,451 searches. Data last updated October 30, 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 HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 11/15
4:45 pm-6:24 pm
Nonstop2h 39m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Sun 12/20
4:20 pm-6:13 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Thu 12/24
4:15 pm-6:08 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
New HavenChicago
HVN Tweed-New Haven - ORD Chicago O'Hare Intl
HVNORD
Tweed-New Haven
Tue 12/22
4:20 pm-6:13 pm
Nonstop2h 53m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 11/20
12:55 pm-2:25 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Wed 11/25
7:03 am-9:05 am
Nonstop3h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
Quickest round-trip
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Wed 11/25
7:25 pm-8:50 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$149
HartfordChicago
BDL Hartford Bradley Intl - ORD Chicago O'Hare Intl
BDLORD
Hartford Bradley Intl
Fri 2/19
9:29 am-11:25 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 12/18
7:25 pm-8:50 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
HartfordChicago
BDL Hartford Bradley Intl - MDW Chicago Midway
BDLMDW
Hartford Bradley Intl
Fri 2/19
12:30 pm-1:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
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.
HVN-ORD
BDL-MDW
BDL-ORD
BDL-BMI
BDL-CMI
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
HVN-ORD
BDL-MDW
BDL-ORD
BDL-BMI
What is the cheapest month to book a flight from Connecticut to Illinois?
Currently, December is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $371). Flying from Connecticut to Illinois in July is currently the most expensive (average of $465). 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 October 30, 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 at noon could potentially save you up to 28% on airfare.
How much does it cost to fly round-trip from Connecticut to Illinois?
Airfare is below average for this route at the moment.
Connecticut to Illinois flights typically cost between $352 and $541 in November.The cheapest round-trip price found within the last 5 days was $309 on JetBlue (Nov 16-Nov 18).
How far ahead should I book a flight from Connecticut to Illinois?
The best time to book flights from Connecticut to Illinois is 84 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 October 24, 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.
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 October 30, 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.
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Avelo Airlines
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
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.
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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 October 30, 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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$269 | Average$513 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$272 | Average$482 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$297 | Average$439 | FlexibilityNo cancel fee | On-time63% |