$115+ Cheap flights from Midway (MDW) to Connecticut
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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Oct 12 — Oct 191
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Connecticut with Cheapflights
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Cheapest flights from Midway to ConnecticutExplore the most affordable flight options available from Midway to Connecticut. 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 Midway to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
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.
Tue 9/226:25 am -
1 stop8h 35m
Tue 9/296:15 am -
1 stop12h 31m
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.
Tue 9/296:25 am -
1 stop8h 35m
Wed 10/76:15 am -
1 stop12h 36m
Deal found 9/9![Frontier logo]()
$228
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.
Sat 10/317:25 am -
1 stop7h 36m
Thu 11/126:30 am -
1 stop12h 17m
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.
Sat 10/36:25 am -
1 stop8h 35m
Wed 10/76:15 am -
1 stop12h 36m
Deal found 9/10![Frontier logo]()
$235
This FlightHub deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop13h 41m
Mon 12/75:59 am -
1 stop8h 00m
Deal found 9/12![Frontier logo]()
$237
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.
Fri 11/208:42 pm -
1 stop23h 47m
Sun 11/2211:30 am -
1 stop9h 17m
Deal found 9/8![Frontier logo]()
$238
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am -
1 stop8h 35m
Wed 9/236:15 am -
1 stop12h 36m
Deal found 9/8![Frontier logo]()
$239
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:25 am -
1 stop7h 36m
Tue 11/175:30 pm -
1 stop7h 17m
Deal found 9/8![Frontier logo]()
$240
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.
Tue 9/226:25 am -
1 stop8h 35m
Sat 9/266:15 am -
1 stop12h 36m
Deal found 9/7![Frontier logo]()
$241
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.
Tue 9/226:25 am -
1 stop8h 35m
Fri 10/24:55 pm -
1 stop7h 49m
Deal found 9/7![Frontier logo]()
$242
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am -
1 stop8h 35m
Wed 9/306:15 am -
1 stop12h 36m
Deal found 9/8![Frontier logo]()
$243
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.
Sat 10/246:21 am -
1 stop8h 53m
Thu 10/299:29 am -
1 stop9h 18m
Deal found 9/10![Frontier logo]()
$244
Best flights from Midway to ConnecticutDiscover carefully curated flight deals from Midway to Connecticut 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 Midway to Connecticut 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.
Tue 10/137:25 pm -
Nonstop2h 10m
Sat 10/176:15 am -
Nonstop2h 30m
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.
Wed 10/286:04 am -
1 stop7h 08m
Thu 10/296:00 am -
1 stop6h 47m
Deal found 9/10![Delta logo]()
$287
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.
Tue 10/67:25 pm -
Nonstop2h 10m
Thu 10/158:55 am -
Nonstop2h 30m
Deal found 9/9![Southwest logo]()
$267
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 10/15:10 am -
Nonstop2h 05m
Mon 10/59:00 pm -
Nonstop2h 25m
Deal found 9/7![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 9/241:19 pm -
1 stop5h 11m
Sat 10/319:40 am -
1 stop4h 07m
Deal found 9/10![Delta logo]()
$306
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.
Sun 10/185:05 am -
Nonstop2h 05m
Fri 10/236:45 pm -
1 stop5h 25m
Deal found 9/10![Southwest logo]()
$277
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.
Tue 9/226:05 am -
1 stop5h 14m
Wed 9/236:00 am -
1 stop4h 07m
Deal found 9/7![Delta logo]()
$317
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.
Fri 10/165:50 pm -
1 stop4h 25m
Tue 10/204:35 pm -
1 stop6h 40m
Deal found 9/7![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.
Sat 10/246:04 am -
1 stop4h 57m
Tue 10/277:25 am -
1 stop5h 22m
Deal found 9/9![Delta logo]()
$317
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.
Sat 10/316:04 am -
1 stop4h 56m
Sat 10/315:30 pm -
1 stop6h 03m
Deal found 9/9![Delta logo]()
$317
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 9/261:45 pm -
1 stop7h 35m
Mon 10/59:00 pm -
Nonstop2h 25m
Deal found 9/9![Southwest logo]()
$292
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.
Wed 10/146:04 am -
1 stop5h 49m
Thu 10/155:23 am -
1 stop5h 09m
Deal found 9/8![Delta logo]()
$317
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.
Wed 10/2110:10 am -
2 stops7h 55m
Thu 10/224:20 pm -
1 stop6h 40m
Deal found 9/9![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am -
1 stop5h 14m
Sat 10/36:00 am -
1 stop4h 07m
Deal found 9/12![Delta logo]()
$322
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 9/285:10 pm -
Nonstop2h 05m
Wed 9/308:50 am -
1 stop7h 35m
Deal found 9/8![Southwest logo]()
$296
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.
Sat 9/261:19 pm -
1 stop5h 50m
Thu 10/16:00 am -
1 stop4h 07m
Deal found 9/9![Delta logo]()
$325
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.
Mon 10/55:10 am -
Nonstop2h 05m
Wed 10/712:00 pm -
1 stop6h 10m
Deal found 9/11![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/261:19 pm -
1 stop5h 50m
Sat 10/37:15 am -
1 stop6h 24m
Deal found 9/12![Delta logo]()
$332
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 9/247:50 pm -
Nonstop2h 05m
Sat 10/311:45 pm -
Nonstop2h 20m
Deal found 9/10![Southwest logo]()
$312
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 10/296:44 pm -
1 stop3h 48m
Mon 11/25:35 pm -
1 stop5h 58m
Deal found 9/10![Delta logo]()
$337
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.
Thu 10/15:10 am -
Nonstop2h 05m
Sun 10/46:05 am -
1 stop7h 05m
Deal found 9/9![Southwest logo]()
$312
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/236:05 am -
1 stop5h 14m
Wed 9/309:48 am -
1 stop3h 51m
Deal found 9/12![Delta logo]()
$341
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 10/97:35 pm -
Nonstop2h 10m
Fri 10/169:00 pm -
Nonstop2h 25m
Deal found 9/11![Southwest logo]()
$322
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.
Sat 9/269:29 am -
1 stop5h 30m
Tue 9/299:48 am -
1 stop3h 51m
Deal found 9/7![Delta logo]()
$342
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 10/18:55 pm -
1 stop10h 15m
Sat 10/318:55 am -
1 stop5h 45m
Deal found 9/10![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/166:05 am -
1 stop7h 06m
Wed 9/236:00 am -
1 stop4h 07m
Deal found 9/12![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.
Tue 10/201:00 pm -
1 stop3h 45m
Fri 10/237:05 pm -
Nonstop2h 20m
Deal found 9/9![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 9/166:05 am -
1 stop6h 13m
Mon 9/211:00 pm -
1 stop6h 33m
Deal found 9/12![Delta logo]()
$345
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/1211:27 am -
1 stop5h 02m
Sun 11/156:00 am -
1 stop5h 24m
Deal found 9/12![Delta logo]()
$347
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 11/188:20 am -
1 stop8h 25m
Sat 11/216:50 pm -
Nonstop2h 25m
Deal found 9/8![Southwest logo]()
$354
Last-minute flights from Midway to ConnecticutDiscover last-minute flight deals from Midway to Connecticut. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Connecticut. Data last updated September 12, 2026 and is based on user searches.
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.
Tue 9/226:25 am -
1 stop8h 35m
Tue 9/296:15 am -
1 stop12h 31m
Deal found 9/7![Frontier logo]()
$222
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am -
1 stop8h 35m
Wed 9/236:15 am -
1 stop12h 36m
Deal found 9/8![Frontier logo]()
$239
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.
Tue 9/226:25 am -
1 stop8h 35m
Tue 10/66:15 am -
1 stop12h 31m
Deal found 9/7![Frontier logo]()
$240
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.
Tue 9/226:25 am -
1 stop8h 35m
Sat 9/266:15 am -
1 stop12h 36m
Deal found 9/7![Frontier logo]()
$241
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.
Tue 9/226:25 am -
1 stop8h 35m
Fri 10/24:55 pm -
1 stop7h 49m
Deal found 9/7![Frontier logo]()
$242
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:25 am -
1 stop8h 35m
Wed 9/306:15 am -
1 stop12h 36m
Deal found 9/8![Frontier logo]()
$243
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 9/296:25 am -
1 stop8h 35m
Wed 10/76:15 am -
1 stop12h 36m
Deal found 9/9![Frontier logo]()
$228
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.
Sat 10/36:25 am -
1 stop8h 35m
Wed 10/76:15 am -
1 stop12h 36m
Deal found 9/10![Frontier logo]()
$235
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 10/66:25 am -
1 stop13h 59m
Tue 10/2010:29 pm -
1 stop26h 14m
Deal found 9/10![Frontier logo]()
$246
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 10/66:25 am -
1 stop8h 35m
Wed 10/144:59 pm -
1 stop7h 44m
Deal found 9/9![Frontier logo]()
$247
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.
Sat 10/246:21 am -
1 stop8h 53m
Thu 10/299:29 am -
1 stop9h 18m
Deal found 9/10![Frontier logo]()
$244
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.
Sat 10/317:25 am -
1 stop7h 36m
Thu 11/126:30 am -
1 stop12h 17m
Deal found 9/10![Frontier logo]()
$234
One-way flights from Midway to ConnecticutSearch for one-way flight options from Midway to Connecticut. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
Search for one-way flight options from Midway to Connecticut. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
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 9/226:25 am -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$115
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:25 am -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![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 9/296:25 am -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$117
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.
Sat 10/36:25 am -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$123
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.
Sat 12/55:20 pm -
1 stop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$123
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:21 am -
1 stop8h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$125
This iWofly 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:07 pm -
1 stop13h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$126
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.
Wed 11/116:16 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$127
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:25 am -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$128
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:50 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$129
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:07 pm -
1 stop13h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$129
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.
Fri 11/208:42 pm -
1 stop23h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$130
Find flight deals from Midway to Connecticut
Keep the following information in mind while searching for Midway to Connecticut flight deals. Data was last updated September 12, 2026.
Round-trip from | $222 (Expedia) |
|---|---|
One-way from | $115 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $315 |
Good round-trip deal | $317 or less |
Good one-way deal | $243 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Connecticut 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 Chicago Midway Airport to Connecticut that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Wed 12/9
1:55 pm-5:00 pm
Nonstop2h 05m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Thu 11/5
8:15 am-11:25 am
Nonstop2h 10m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Wed 10/28
3:10 pm-6:15 pm
Nonstop2h 05m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Sun 10/4
5:05 am-8:10 am
Nonstop2h 05m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoNewark
MDW Chicago Midway - EWR Newark
MDWEWR
Chicago Midway
Tue 10/27
6:44 pm-11:16 pm
1 stop3h 32m
Newark
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoNewark
MDW Chicago Midway - EWR Newark
MDWEWR
Chicago Midway
Tue 10/13
6:44 pm-11:16 pm
1 stop3h 32m
Newark
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoNewark
MDW Chicago Midway - EWR Newark
MDWEWR
Chicago Midway
Mon 11/2
6:44 pm-11:16 pm
1 stop3h 32m
Newark
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Mon 10/5
5:10 am-8:15 am
Nonstop2h 05m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Thu 11/19
5:00 am-8:05 am
Nonstop2h 05m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoNew York
MDW Chicago Midway - LGA New York LaGuardia
MDWLGA
Chicago Midway
Tue 10/27
2:40 pm-5:50 pm
Nonstop2h 10m
New York LaGuardia
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Connecticut
Have a flexible travel schedule? Discover the best time to fly to Connecticut from Midway with our price prediction graph.
MDW-LGA
MDW-EWR
MDW-JFK
MDW-BDL
MDW-PVD
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 Chicago Midway Airport to Connecticut
MDW-USCT
MDW-LGA
MDW-EWR
MDW-JFK
MDW-BDL
What is the cheapest time of day to fly from MDW to CT?
Find hourly flight availability from Midway to Connecticut. 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 at noon, when flights are generally more expensive, you can save up to 46% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Connecticut?
Use this chart to determine the cheapest time to fly round-trip from Midway to Connecticut. Price data was last updated on September 12, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Connecticut flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Connecticut
Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated September 12, 2026.
Read reviews from past customers who have flown Southwest from Chicago Midway Airport to Connecticut. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Midway to Connecticut. 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 Midway to Connecticut
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Complete your trip
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Search flights from Midway to Connecticut by cabin class
Find flights from Midway to Connecticut, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Connecticut flights
Browse other Midway and Connecticut flight options. Last updated on September 12, 2026.
Popular flight searches
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Midway to Connecticut flights
Consider these flights traveling from Midway to Connecticut.
Top airline flying from Midway to Connecticut
Discover the top airline that operate flights from Midway to Connecticut. 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$248 | Average$423 | FlexibilityNo cancel fee | On-time63% |