$112+ Cheap flights from Connecticut to Midway (MDW)
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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Oct 12 — Oct 191
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Midway 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 MidwayExplore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
Explore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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
Tue 9/296:25 am -
1 stop8h 35m
Deal found 9/7![Frontier logo]()
$222
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/226:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:15 am -
1 stop12h 31m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/286:30 am -
1 stop12h 17m
Sat 10/317:25 am -
1 stop12h 21m
Deal found 9/10![Frontier logo]()
$235
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 9/296:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Fri 12/1111:55 am -
1 stop8h 07m
Sun 12/132:04 pm -
1 stop10h 08m
Deal found 9/9![Frontier logo]()
$238
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/7![Frontier logo]()
$240
This Expedia deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Sat 9/266:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/8![Frontier logo]()
$241
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Thu 9/246:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$242
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/2211:30 am -
1 stop9h 17m
Mon 11/308:42 pm -
1 stop13h 06m
Deal found 9/10![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 -
1 stop20h 22m
Sat 10/106:21 am -
1 stop14h 07m
Deal found 9/10![Frontier logo]()
$244
Best flights from Connecticut to MidwayDiscover carefully curated flight deals from Connecticut to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 2026.
Discover carefully curated flight deals from Connecticut to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 2026.
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/73:30 pm -
Nonstop2h 40m
Sun 11/88:15 am -
Nonstop2h 10m
Deal found 9/8![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:00 am -
1 stop4h 07m
Sat 10/36:40 pm -
1 stop3h 35m
Deal found 9/10![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/288:30 am -
1 stop9h 15m
Mon 11/27:15 pm -
Nonstop2h 05m
Deal found 9/8![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/66:00 am -
1 stop4h 32m
Tue 10/66:44 pm -
1 stop3h 32m
Deal found 9/8![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/239:00 pm -
Nonstop2h 25m
Fri 10/302:25 pm -
1 stop5h 30m
Deal found 9/8![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/286:00 am -
1 stop4h 32m
Sat 10/316:44 pm -
1 stop3h 32m
Deal found 9/11![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/295:10 am -
Nonstop2h 00m
Deal found 9/7![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:00 am -
1 stop4h 07m
Sat 10/31:19 pm -
1 stop5h 50m
Deal found 9/10![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/54:25 pm -
1 stop7h 15m
Mon 11/95:20 am -
1 stop7h 00m
Deal found 9/10![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/136:00 am -
Nonstop2h 30m
Tue 10/205:00 am -
Nonstop2h 05m
Deal found 9/11![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/307:15 am -
1 stop6h 24m
Sat 10/34:30 pm -
1 stop7h 29m
Deal found 9/7![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/206:45 am -
Nonstop2h 25m
Sun 11/225:00 am -
Nonstop2h 05m
Deal found 9/11![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/1012:59 pm -
1 stop6h 05m
Thu 11/1211:27 am -
1 stop7h 53m
Deal found 9/9![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/306:55 am -
1 stop7h 35m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 9/10![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2812:59 pm -
1 stop6h 01m
Sun 11/16:44 pm -
1 stop3h 32m
Deal found 9/9![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/29:00 pm -
Nonstop2h 20m
Sun 10/45:05 am -
Nonstop2h 05m
Deal found 9/11![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/16:00 am -
1 stop4h 07m
Mon 10/55:06 pm -
1 stop6h 54m
Deal found 9/11![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:30 am -
Nonstop2h 35m
Mon 11/168:10 am -
1 stop6h 50m
Deal found 9/9![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/269:48 am -
1 stop3h 51m
Wed 9/301:19 pm -
1 stop5h 11m
Deal found 9/8![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/277:10 am -
1 stop6h 37m
Wed 10/286:04 am -
1 stop4h 56m
Deal found 9/11![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 1/257:25 am -
Nonstop2h 40m
Wed 1/278:25 am -
1 stop5h 40m
Deal found 9/8![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/234:20 pm -
1 stop6h 40m
Mon 10/265:50 pm -
1 stop4h 25m
Deal found 9/11![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/176:00 am -
1 stop4h 32m
Tue 10/2012:49 pm -
1 stop7h 04m
Deal found 9/11![Delta logo]()
$341
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/267:00 am -
2 stops10h 10m
Wed 9/307:15 am -
1 stop7h 35m
Deal found 9/8![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/221:00 pm -
1 stop6h 33m
Thu 9/249:29 am -
1 stop7h 01m
Deal found 9/11![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/227:15 am -
1 stop6h 24m
Wed 9/239:29 am -
1 stop7h 01m
Deal found 9/11![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/35:40 am -
1 stop6h 00m
Mon 10/57:50 am -
Nonstop2h 15m
Deal found 9/9![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/911:44 am -
1 stop5h 34m
Fri 11/136:44 pm -
1 stop3h 31m
Deal found 9/11![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/173:35 pm -
1 stop4h 20m
Thu 11/196:15 pm -
Nonstop2h 10m
Deal found 9/10![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/156:00 am -
1 stop4h 42m
Mon 11/166:44 pm -
1 stop3h 31m
Deal found 9/9![Delta logo]()
$350
Last-minute flights from Connecticut to MidwayDiscover last-minute flight deals from Connecticut to Midway. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Midway. Data last updated September 12, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/226:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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
Tue 9/296:25 am -
1 stop8h 35m
Deal found 9/7![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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
Thu 9/246:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$242
This Expedia deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Sat 9/266:15 am -
1 stop12h 36m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/8![Frontier logo]()
$241
This FlightHub deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Tue 9/296:15 am -
1 stop12h 31m
Wed 9/306:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$237
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/9![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/306:15 am -
1 stop12h 36m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/7![Frontier logo]()
$240
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:15 am -
1 stop12h 31m
Sat 10/36:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$234
This Orbitz deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/16:15 am -
1 stop12h 31m
Wed 10/76:25 am -
1 stop8h 35m
Deal found 9/10![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 -
1 stop20h 22m
Sat 10/106:21 am -
1 stop14h 07m
Deal found 9/10![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/1310:29 pm -
1 stop26h 14m
Sun 10/186:40 pm -
1 stop14h 53m
Deal found 9/10![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/286:30 am -
1 stop12h 17m
Sat 10/317:25 am -
1 stop12h 21m
Deal found 9/10![Frontier logo]()
$235
One-way flights from Connecticut to MidwaySearch for one-way flight options from Connecticut to Midway. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
Search for one-way flight options from Connecticut to Midway. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
This Flightnetwork deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/2311:35 am -
1 stop7h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$112
This Mytrip deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Tue 9/221:00 pm -
1 stop5h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/1811:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$113
This Mytrip deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/2911:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$114
This Super.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/226:15 am -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$115
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/296:15 am -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$117
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Sat 10/31:00 pm -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/236:15 am -
1 stop12h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
This Trip.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/411:35 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$118
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/204:59 pm -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$119
Find flight deals from Connecticut to Midway
Keep the following information in mind while searching for Connecticut to Midway flight deals. Data was last updated September 12, 2026.
Round-trip from | $222 (Frontier) |
|---|---|
One-way from | $112 (Flightnetwork) |
Popular in | July |
Cheapest in | January |
Average price | $370 |
Good round-trip deal | $398 or less |
Good one-way deal | $211 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut to Midway 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 12, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkChicago
LGA New York LaGuardia - MDW Chicago Midway
LGAMDW
New York LaGuardia
Thu 11/5
5:55 pm-7:30 pm
Nonstop2h 35m
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
Tue 1/12
8:30 am-10:10 am
Nonstop2h 40m
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
Thu 10/15
8:55 am-10:25 am
Nonstop2h 30m
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
Wed 12/9
10:00 am-11:40 am
Nonstop2h 40m
Chicago Midway
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
Tue 10/27
3:25 pm-4:45 pm
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 1/30
3:20 pm-5:00 pm
Nonstop2h 40m
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
Thu 10/1
7:15 am-8:35 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$134
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Tue 10/20
9:40 am-12:47 pm
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Sat 11/21
12:55 pm-6:04 pm
1 stop6h 09m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
NewarkChicago
EWR Newark - MDW Chicago Midway
EWRMDW
Newark
Tue 1/5
9:40 am-12:33 pm
1 stop3h 53m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Connecticut with our price prediction graph.
LGA-MDW
EWR-MDW
JFK-MDW
BDL-MDW
PVD-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 Midway Airport
USCT-MDW
LGA-MDW
EWR-MDW
JFK-MDW
BDL-MDW
What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $176). Flying from Connecticut to Chicago Midway Airport in April is currently the most expensive (average of $892). 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 MDW?
Find hourly flight availability from Connecticut to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 12, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 36% on flights from Connecticut to Chicago Midway Airport by exploring options for tickets at noon.
How much does it cost to fly round-trip from Connecticut to Chicago Midway Airport?
Airfare is typical for this route at the moment.
Connecticut to Chicago Midway Airport flights typically cost between $264 and $413 in October.The cheapest round-trip price found within the last 5 days was $297 on Southwest (Oct 3-Oct 5).
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Connecticut to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Connecticut to Midway by cabin class
Find flights from Connecticut to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 12, 2026.
Connecticut and Midway flights
Browse other Connecticut and Midway flight options. Last updated on September 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Midway flights
Consider these flights traveling from Connecticut to Midway.
Top airline flying from Connecticut to Midway
Discover the top airline that operate flights from Connecticut to Midway. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$293 | Average$428 | FlexibilityNo cancel fee | On-time63% |