$99+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Sep 24 — Oct 11
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 August 25, 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 August 25, 2026.
This deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:30 pm -
1 stop6h 17m
Thu 10/17:46 am -
Nonstop2h 34m
Deal found 8/22![American Airlines logo]()
$221
This Justfly.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:55 am -
1 stop14h 07m
Mon 10/268:11 pm -
1 stop26h 52m
Deal found 8/23![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 8/25. 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.
Fri 10/161:45 pm -
1 stop11h 41m
Mon 10/199:00 am -
1 stop15h 02m
Deal found 8/25![Frontier logo]()
$224
This Traveloka deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:20 pm -
1 stop7h 02m
Wed 10/219:38 am -
1 stop6h 50m
Deal found 8/20![JetBlue logo]()
$225
This Expedia deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/2310:29 pm -
1 stop11h 51m
Sat 9/263:50 pm -
1 stop8h 11m
Deal found 8/24![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:30 am -
1 stop12h 38m
Tue 9/153:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$227
This Faresmojo deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:05 pm -
Nonstop2h 53m
Sun 9/136:00 am -
1 stop7h 07m
Deal found 8/23![JetBlue logo]()
$228
This Priceline deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:35 am -
1 stop8h 10m
Sun 11/110:26 am -
1 stop9h 53m
Deal found 8/24![Frontier logo]()
$228
This Flysmarter deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:10 am -
Nonstop2h 48m
Sat 10/33:00 pm -
1 stop7h 51m
Deal found 8/23![JetBlue logo]()
$229
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:30 pm -
1 stop12h 15m
Thu 9/2411:15 am -
1 stop12h 46m
Deal found 8/20![Frontier logo]()
$229
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/86:55 am -
Nonstop2h 47m
Tue 9/86:23 pm -
Nonstop2h 36m
Deal found 8/21![JetBlue logo]()
$230
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:30 am -
1 stop8h 15m
Mon 9/283:50 pm -
1 stop8h 11m
Deal found 8/21![Multiple Airlines logo]()
$230
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 August 25, 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 August 25, 2026.
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:35 am -
Nonstop2h 52m
Thu 10/16:00 am -
Nonstop2h 21m
Deal found 8/24![Delta logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/2010:00 am -
Nonstop2h 47m
Wed 10/211:00 pm -
Nonstop2h 20m
Deal found 8/20![JetBlue logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 11/47:15 am -
Nonstop2h 46m
Sun 11/85:00 am -
Nonstop2h 07m
Deal found 8/23![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/107:25 am -
Nonstop2h 20m
Mon 9/217:50 pm -
Nonstop2h 05m
Deal found 8/20![Southwest logo]()
$247
This KAYAK deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/175:00 am -
1 stop4h 52m
Fri 9/188:38 pm -
Nonstop2h 21m
Deal found 8/22![American Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:35 am -
Nonstop2h 52m
Mon 9/216:00 am -
Nonstop2h 21m
Deal found 8/23![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/216:10 am -
Nonstop2h 40m
Tue 9/228:10 pm -
Nonstop2h 25m
Deal found 8/24![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/73:25 pm -
Nonstop2h 20m
Wed 10/145:00 am -
Nonstop2h 05m
Deal found 8/23![Southwest logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/219:30 am -
Nonstop2h 54m
Sun 10/252:42 pm -
1 stop8h 10m
Deal found 8/24![JetBlue logo]()
$250
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:01 pm -
Nonstop2h 58m
Wed 9/166:00 am -
Nonstop2h 21m
Deal found 8/23![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
Nonstop2h 39m
Mon 9/287:45 pm -
Nonstop2h 25m
Deal found 8/23![United Airlines logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sun 9/136:00 am -
1 stop8h 45m
Tue 9/153:00 pm -
1 stop7h 09m
Deal found 8/22![JetBlue logo]()
$253
This Southwest deal was found by Cheapflights users on 8/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:00 pm -
1 stop5h 45m
Sun 9/205:25 am -
Nonstop2h 00m
Deal found 8/25![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/197:35 am -
Nonstop2h 52m
Tue 9/226:00 am -
Nonstop2h 21m
Deal found 8/22![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/289:27 pm -
Nonstop2h 32m
Wed 9/306:00 pm -
Nonstop2h 25m
Deal found 8/21![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/216:00 am -
Nonstop2h 15m
Tue 9/226:00 am -
1 stop6h 50m
Deal found 8/24![Southwest logo]()
$257
This JetBlue deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/71:00 pm -
1 stop7h 03m
Wed 10/142:55 pm -
1 stop8h 00m
Deal found 8/23![JetBlue logo]()
$270
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/107:30 am -
Nonstop2h 57m
Thu 11/1210:30 am -
Nonstop2h 16m
Deal found 8/24![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/268:15 am -
Nonstop2h 46m
Thu 10/293:00 pm -
Nonstop2h 19m
Deal found 8/24![United Airlines logo]()
$247
This Alaska Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:29 pm -
2 stops31h 30m
Wed 10/147:02 am -
2 stops14h 57m
Deal found 8/20![Alaska Airlines logo]()
$682
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/136:35 pm -
1 stop5h 05m
Mon 11/167:05 pm -
Nonstop2h 05m
Deal found 8/24![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/256:50 pm -
Nonstop2h 41m
Mon 9/288:15 pm -
Nonstop2h 24m
Deal found 8/23![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/228:27 pm -
Nonstop2h 44m
Sun 9/277:00 am -
Nonstop2h 17m
Deal found 8/24![United Airlines logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/108:10 am -
Nonstop2h 48m
Sun 9/137:00 am -
Nonstop2h 27m
Deal found 8/20![JetBlue logo]()
$279
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/1512:05 pm -
1 stop5h 45m
Wed 9/165:45 pm -
Nonstop2h 10m
Deal found 8/24![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 1/274:00 pm -
1 stop6h 50m
Mon 2/18:05 pm -
Nonstop2h 05m
Deal found 8/22![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/168:00 am -
Nonstop2h 44m
Mon 9/215:00 am -
Nonstop2h 14m
Deal found 8/21![United Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
1 stop4h 07m
Sat 10/36:40 pm -
1 stop3h 35m
Deal found 8/22![Delta logo]()
$267
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sun 9/65:07 pm -
1 stop7h 37m
Thu 9/103:00 pm -
1 stop7h 14m
Deal found 8/22![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/117:00 am -
2 stops11h 05m
Fri 11/135:15 pm -
Nonstop2h 05m
Deal found 8/24![Southwest logo]()
$262
Last-minute flights from Connecticut to IllinoisDiscover last-minute flight deals from Connecticut to Illinois. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Illinois. Data last updated August 25, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:30 am -
1 stop12h 38m
Tue 9/153:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$227
This Super.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/86:55 am -
Nonstop2h 47m
Tue 9/86:23 pm -
Nonstop2h 36m
Deal found 8/21![JetBlue logo]()
$230
This Flysmarter deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:50 am -
1 stop7h 55m
Sun 9/136:00 am -
1 stop7h 07m
Deal found 8/20![JetBlue logo]()
$232
This Faresmojo deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:05 pm -
Nonstop2h 53m
Sun 9/136:00 am -
1 stop7h 07m
Deal found 8/23![JetBlue logo]()
$228
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:30 pm -
1 stop12h 15m
Thu 9/2411:15 am -
1 stop12h 46m
Deal found 8/20![Frontier logo]()
$229
This Flysmarter deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:45 am -
1 stop8h 00m
Sun 9/206:00 am -
1 stop7h 07m
Deal found 8/24![JetBlue logo]()
$231
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:30 am -
1 stop8h 15m
Mon 9/283:50 pm -
1 stop8h 11m
Deal found 8/21![Multiple Airlines logo]()
$230
This Expedia deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/216:30 am -
1 stop8h 15m
Thu 9/243:50 pm -
1 stop8h 11m
Deal found 8/21![Multiple Airlines logo]()
$231
This Expedia deal was found by Cheapflights users on 8/25. 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.
Wed 9/2310:29 pm -
1 stop11h 51m
Sat 9/263:50 pm -
1 stop8h 11m
Deal found 8/25![Frontier logo]()
$226
This deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:30 pm -
1 stop6h 17m
Thu 10/17:46 am -
Nonstop2h 34m
Deal found 8/22![American Airlines logo]()
$221
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:29 pm -
1 stop11h 51m
Wed 9/303:50 pm -
1 stop8h 11m
Deal found 8/23![Frontier logo]()
$228
This Flysmarter deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:10 am -
Nonstop2h 48m
Sat 10/33:00 pm -
1 stop7h 51m
Deal found 8/23![JetBlue logo]()
$229
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 August 25, 2026.
Search for one-way flight options from Connecticut to Illinois. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Trip.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Wed 10/2811:35 am -
1 stop7h 05m
Deal found 8/24![Frontier logo]()
$99
This Trip.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Wed 10/2111:35 am -
1 stop7h 05m
Deal found 8/24![Frontier logo]()
$103
This Trip.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Wed 11/1811:35 am -
1 stop7h 05m
Deal found 8/22![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/2210:29 pm -
1 stop15h 41m
Deal found 8/23![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:35 am -
1 stop7h 10m
Deal found 8/20![Frontier logo]()
$106
This Trip.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/2011:35 am -
1 stop7h 56m
Deal found 8/20![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Sat 11/711:35 am -
1 stop7h 12m
Deal found 8/20![Frontier logo]()
$107
This FlightHub deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Sun 11/111:35 am -
1 stop8h 10m
Deal found 8/20![Frontier logo]()
$107
This Jetabroad deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:35 am -
1 stop7h 16m
Deal found 8/22![Frontier logo]()
$108
This Jetabroad deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3011:35 am -
1 stop7h 48m
Deal found 8/22![Frontier logo]()
$108
This Kissandfly.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:35 am -
1 stop7h 11m
Deal found 8/20![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/135:55 am -
1 stop18h 04m
Deal found 8/20![Frontier logo]()
$109
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 August 25, 2026.
Round-trip from | $221 |
|---|---|
One-way from | $99 (Trip.com) |
Popular in | July |
Cheapest in | January |
Average price | $387 |
Good round-trip deal | $142 or less |
Good one-way deal | $59 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 August 25, 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 New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Wed 9/30
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Thu 10/1
6:00 am-9:21 am
Nonstop2h 21m
$247
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Tue 10/20
10:00 am-11:47 am
Nonstop2h 47m
Chicago O'Hare Intl
Wed 10/21
1:00 pm-4:20 pm
Nonstop2h 20m
$247
NewarkChicago
EWR Newark - ORD Chicago O'Hare Intl
EWRORD
Newark
Wed 11/4
7:15 am-9:01 am
Nonstop2h 46m
Chicago O'Hare Intl
Sun 11/8
5:00 am-8:07 am
Nonstop2h 07m
$247
Quickest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 9/10
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Mon 9/21
7:50 pm-10:55 pm
Nonstop2h 05m
$247
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Wed 9/16
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Mon 9/21
6:00 am-9:21 am
Nonstop2h 21m
$247
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Mon 9/21
6:10 am-7:50 am
Nonstop2h 40m
Chicago O'Hare Intl
Tue 9/22
8:10 pm-11:35 pm
Nonstop2h 25m
$247
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 10/7
3:25 pm-4:45 pm
Nonstop2h 20m
Chicago Midway
Wed 10/14
5:00 am-8:05 am
Nonstop2h 05m
$247
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Tue 9/15
3:01 pm-4:59 pm
Nonstop2h 58m
Chicago O'Hare Intl
Wed 9/16
6:00 am-9:21 am
Nonstop2h 21m
$247
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Thu 9/24
6:00 am-7:39 am
Nonstop2h 39m
Chicago O'Hare Intl
Mon 9/28
7:45 pm-11:10 pm
Nonstop2h 25m
$247
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Sat 9/19
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 9/22
6:00 am-9:21 am
Nonstop2h 21m
$247
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
EWR-ORD
LGA-MDW
LGA-ORD
JFK-STL
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
EWR-ORD
LGA-MDW
LGA-ORD
What is the cheapest month to book a flight from Connecticut to Illinois?
Currently, January is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $330). Flying from Connecticut to Illinois in July is currently the most expensive (average of $466). 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 August 25, 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 27% 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 August 25, 2026.
The most flights from USCT to USIL are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
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 $329 and $477 in September.The cheapest round-trip price found within the last 5 days was $279 on Multiple Airlines (Sep 8-Sep 12).
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 August 22, 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 August 25, 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.
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Avelo Airlines
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
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 August 25, 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$206 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$113 | Average$215 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$228 | Average$511 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$241 | Average$473 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$279 | Average$426 | FlexibilityNo cancel fee | On-time63% |