$109+ Cheap flights from Connecticut to Chicago (CHI)
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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Oct 5 — Oct 121
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Chicago 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Connecticut to Chicago
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Cheapest flights from Connecticut to ChicagoExplore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
Explore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 5, 2026.
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop13h 08m
Sat 9/266:00 am -
1 stop12h 44m
Deal found 9/2![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop12h 31m
Sat 9/266:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 9/2![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$222
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:45 pm -
1 stop11h 41m
Mon 10/268:11 pm -
1 stop26h 52m
Deal found 8/31![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 9/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:45 pm -
1 stop11h 41m
Mon 10/1910:26 am -
1 stop10h 02m
Deal found 9/1![Frontier logo]()
$229
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Wed 9/2311:35 am -
1 stop7h 48m
Tue 9/293:50 pm -
1 stop8h 11m
Deal found 8/31![Frontier logo]()
$230
This Orbitz deal was found by Cheapflights users on 9/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:35 am -
1 stop7h 48m
Mon 10/128:11 pm -
1 stop27h 51m
Deal found 9/2![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am -
1 stop13h 08m
Mon 10/510:26 am -
1 stop9h 33m
Deal found 9/2![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:30 pm -
1 stop10h 34m
Mon 9/283:50 pm -
1 stop8h 11m
Deal found 9/2![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop6h 36m
Tue 9/226:00 am -
1 stop12h 44m
Deal found 8/31![Frontier logo]()
$234
Best flights from Connecticut to ChicagoDiscover carefully curated flight deals from Connecticut to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
Discover carefully curated flight deals from Connecticut to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 5, 2026.
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
Nonstop2h 15m
Mon 9/287:50 pm -
Nonstop2h 05m
Deal found 9/3![Southwest logo]()
$243
This JetBlue deal was found by Cheapflights users on 9/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:15 pm -
Nonstop2h 55m
Wed 10/219:38 am -
1 stop6h 51m
Deal found 9/4![JetBlue logo]()
$256
This Delta deal was found by Cheapflights users on 9/2. 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.
Wed 9/307:35 am -
Nonstop2h 52m
Sat 10/36:00 pm -
Nonstop2h 43m
Deal found 9/2![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/247:23 am -
Nonstop2h 37m
Tue 9/295:00 pm -
Nonstop2h 25m
Deal found 8/31![United Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/45:55 am -
1 stop28h 59m
Wed 10/79:34 am -
1 stop14h 27m
Deal found 9/1![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:55 am -
Nonstop2h 30m
Sun 10/185:05 am -
Nonstop2h 05m
Deal found 9/3![Southwest logo]()
$243
This JetBlue deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/188:15 pm -
Nonstop2h 55m
Wed 10/2112:38 pm -
Nonstop2h 22m
Deal found 8/31![JetBlue logo]()
$267
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/18:50 am -
Nonstop2h 38m
Sun 10/47:00 am -
Nonstop2h 15m
Deal found 8/31![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/4. 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 9/234:25 pm -
Nonstop2h 44m
Wed 9/3011:00 am -
Nonstop2h 23m
Deal found 9/4![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 9/4. 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.
Fri 11/138:55 pm -
Nonstop2h 30m
Sun 11/155:00 am -
Nonstop2h 05m
Deal found 9/4![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/227:30 am -
Nonstop2h 57m
Mon 10/265:29 pm -
1 stop4h 38m
Deal found 8/31![Delta logo]()
$287
This JetBlue deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Fri 9/257:00 am -
1 stop7h 45m
Sat 9/263:00 pm -
1 stop7h 14m
Deal found 8/31![JetBlue logo]()
$289
This Southwest deal was found by Cheapflights users on 9/4. 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.
Fri 10/169:00 pm -
Nonstop2h 25m
Mon 10/265:10 pm -
Nonstop2h 05m
Deal found 9/4![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 10/229:10 am -
Nonstop2h 43m
Sat 10/247:52 pm -
Nonstop2h 23m
Deal found 9/4![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 9/1. 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 10/157:30 am -
Nonstop2h 57m
Sun 10/186:10 am -
Nonstop2h 17m
Deal found 9/1![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/309:35 pm -
Nonstop2h 20m
Wed 10/77:25 pm -
Nonstop2h 10m
Deal found 8/31![Southwest logo]()
$267
This JetBlue deal was found by Cheapflights users on 9/2. 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.
Wed 9/167:00 am -
1 stop7h 45m
Sat 9/193:00 pm -
1 stop7h 14m
Deal found 9/2![JetBlue logo]()
$315
This Delta deal was found by Cheapflights users on 9/1. 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 11/56:00 am -
1 stop4h 32m
Mon 11/96:44 pm -
1 stop3h 31m
Deal found 9/1![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 11/128:30 pm -
Nonstop2h 48m
Sat 11/147:00 am -
Nonstop2h 08m
Deal found 9/4![United Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/1111:35 am -
2 stops22h 05m
Mon 11/1610:38 am -
1 stop12h 25m
Deal found 9/3![Multiple Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/247:25 am -
Nonstop2h 20m
Tue 9/291:55 pm -
1 stop7h 35m
Deal found 8/31![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/2. 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.
Tue 11/176:00 am -
1 stop5h 24m
Tue 11/176:44 pm -
1 stop3h 31m
Deal found 9/2![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 9/4. 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 11/144:20 pm -
Nonstop2h 51m
Fri 11/201:00 pm -
Nonstop2h 15m
Deal found 9/4![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 pm -
1 stop5h 25m
Wed 10/2812:55 pm -
Nonstop2h 05m
Deal found 9/1![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:30 am -
1 stop8h 15m
Tue 10/63:00 pm -
1 stop7h 35m
Deal found 9/4![JetBlue logo]()
$337
This Delta deal was found by Cheapflights users on 9/1. 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 10/315:30 pm -
1 stop6h 03m
Mon 11/26:44 pm -
1 stop3h 32m
Deal found 9/1![Delta logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Tue 10/610:29 pm -
2 stops35h 21m
Mon 11/210:44 am -
1 stop12h 19m
Deal found 9/2![Multiple Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:03 pm -
Nonstop2h 45m
Tue 10/66:15 pm -
Nonstop2h 22m
Deal found 9/1![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 9/1. 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 9/236:55 am -
1 stop7h 35m
Sat 9/2612:10 pm -
Nonstop2h 10m
Deal found 9/1![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/126:00 am -
1 stop5h 24m
Mon 11/161:31 pm -
1 stop4h 52m
Deal found 8/31![Delta logo]()
$287
Last-minute flights from Connecticut to ChicagoDiscover last-minute flight deals from Connecticut to Chicago. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Chicago. Data last updated September 5, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 9/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:35 am -
1 stop7h 48m
Mon 10/128:11 pm -
1 stop27h 51m
Deal found 9/2![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop6h 36m
Tue 9/226:00 am -
1 stop12h 44m
Deal found 8/31![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:30 pm -
1 stop10h 34m
Mon 9/283:50 pm -
1 stop8h 11m
Deal found 9/2![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop13h 08m
Sat 9/266:00 am -
1 stop12h 44m
Deal found 9/2![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:15 am -
1 stop12h 31m
Sat 9/266:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop6h 36m
Wed 9/306:20 am -
1 stop8h 40m
Deal found 9/2![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Wed 9/2311:35 am -
1 stop7h 48m
Tue 9/293:50 pm -
1 stop8h 11m
Deal found 8/31![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am -
1 stop13h 08m
Mon 10/510:26 am -
1 stop9h 33m
Deal found 9/2![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/2![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 9/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:45 pm -
1 stop11h 41m
Mon 10/1910:26 am -
1 stop10h 02m
Deal found 9/1![Frontier logo]()
$229
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:45 pm -
1 stop11h 41m
Mon 10/268:11 pm -
1 stop26h 52m
Deal found 8/31![Frontier logo]()
$228
One-way flights from Connecticut to ChicagoSearch for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
Search for one-way flight options from Connecticut to Chicago. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This Flightnetwork deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:15 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/1611:35 am -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/301:00 pm -
1 stop7h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![JetBlue logo]()
$110
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/1611:35 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 9/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:35 am -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$111
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:00 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 9/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 9/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:35 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$111
This Expedia deal was found by Cheapflights users on 9/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:15 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:00 pm -
1 stop6h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$112
This Booking.com deal was found by Cheapflights users on 9/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:00 pm -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$112
This Frontier deal was found by Cheapflights users on 9/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$112
Find flight deals from Connecticut to Chicago
Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated September 5, 2026.
Round-trip from | $221 (Frontier) |
|---|---|
One-way from | $109 (Flightnetwork) |
Popular in | July |
Cheapest in | January |
Average price | $370 |
Good round-trip deal | $149 or less |
Good one-way deal | $59 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut to Chicago 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 September 5, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago 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
Sat 9/26
10:40 am-12:25 pm
Nonstop2h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Mon 10/5
8:05 pm-10:00 pm
Nonstop2h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Sat 10/24
1:25 pm-3:09 pm
Nonstop2h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
Quickest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 10/14
3:25 pm-4:45 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
JFK New York John F Kennedy Intl - ORD Chicago O'Hare Intl
JFKORD
New York John F Kennedy Intl
Tue 9/22
8:10 am-9:58 am
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - ORD Chicago O'Hare Intl
LGAORD
New York LaGuardia
Tue 9/29
6:00 am-7:29 am
Nonstop2h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Tue 10/6
5:55 pm-7:25 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
ProvidenceChicago
PVD Providence-TFGreen - ORD Chicago O'Hare Intl
PVDORD
Providence-TFGreen
Wed 10/21
6:40 am-11:24 am
1 stop5h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Wed 10/7
7:25 am-8:45 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Sat 10/24
9:25 am-10:55 am
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Connecticut with our price prediction graph.
LGA-ORD
EWR-MDW
JFK-ORD
EWR-ORD
JFK-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 Chicago
USCT-CHI
LGA-ORD
EWR-MDW
JFK-ORD
EWR-ORD
What is the cheapest month to book a flight from Connecticut to Chicago?
Currently, January is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $344). Flying from Connecticut to Chicago in July is currently the most expensive (average of $467). 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 CHI?
Find hourly flight availability from Connecticut to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 5, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 28% on flights from Connecticut to Chicago by exploring options for tickets at noon.
Weekly flight availability from Connecticut to Chicago
Explore weekly flight availability from Connecticut to Chicago. 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 September 5, 2026.
The most flights from USCT to CHI are scheduled on a Wednesday (24 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (12 on average).
How much does it cost to fly round-trip from Connecticut to Chicago?
Airfare is below average for this route at the moment.
Connecticut to Chicago flights typically cost between $296 and $429 in December.The cheapest round-trip price found within the last 5 days was $279 on Frontier (Dec 12-Dec 14).
How far ahead should I book a flight from Connecticut to Chicago?
The best time to book flights from Connecticut to Chicago 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 Chicago?
Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
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Alternative routes for Connecticut to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 5, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Connecticut to Chicago by cabin class
Find flights from Connecticut to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Connecticut and Chicago flights
Browse other Connecticut and Chicago flight options. Last updated on September 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Chicago flights
Consider these flights traveling from Connecticut to Chicago.
Top 6 airlines flying from Connecticut to Chicago
Discover the top 6 airlines that operate flights from Connecticut to Chicago. 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 September 5, 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$245 | Average$407 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$441 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$293 | Average$428 | FlexibilityNo cancel fee | On-time63% |