$61+ Cheap flights from Midway (MDW) to Connecticut
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
May 14 — May 211
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 April 14, 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 April 14, 2026.
This Frontier deal was found by Cheapflights users on 4/10. 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.
Tue 4/282:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Sat 5/211:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/10![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/302:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Mon 5/411:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/14![Frontier logo]()
$119
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/307:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Wed 5/65:55 am
EWR
- MDW
1 stop6h 14m
Frontier
Deal found 4/13![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 4/9. 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 4/217:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Thu 4/2311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/9![Frontier logo]()
$121
This Priceline deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sun 5/311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/13![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 4/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sun 4/2611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/12![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 4/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Thu 4/2311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/9![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Sat 5/27:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Tue 5/1210:29 pm
EWR
- MDW
1 stop13h 40m
Frontier
Deal found 4/10![Frontier logo]()
$125
This Trip.com deal was found by Cheapflights users on 4/11. 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.
Sat 4/187:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/11![Frontier logo]()
$126
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/13![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Mon 4/276:37 pm
EWR
- MDW
1 stop25h 54m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/267:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Fri 5/16:54 pm
EWR
- MDW
1 stop24h 43m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$129
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 April 14, 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 April 14, 2026.
This Southwest deal was found by Cheapflights users on 4/11. 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 5/125:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 5/128:55 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Deal found 4/11![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 5/211:18 am
MDW
- EWR
1 stop5h 20m
Delta
Mon 5/44:29 pm
EWR
- MDW
1 stop6h 59m
Delta
Deal found 4/10![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/205:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sun 5/248:30 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 4/14![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 4/9. 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 5/56:38 pm
MDW
- EWR
1 stop3h 25m
Delta
Thu 5/79:45 am
EWR
- MDW
1 stop3h 57m
Delta
Deal found 4/9![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 4/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:25 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Wed 5/206:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 4/12![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/9. 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.
Fri 5/85:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Sat 5/99:10 am
LGA
- MDW
1 stop6h 30m
Southwest
Deal found 4/9![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/266:36 pm
MDW
- EWR
1 stop13h 14m
Delta
Sat 5/306:15 am
EWR
- MDW
1 stop8h 04m
Delta
Deal found 4/13![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 4/9. 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 6/95:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Thu 6/116:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 4/9![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 4/9. 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 4/289:30 am
MDW
- LGA
Nonstop2h 05m
Southwest
Thu 4/308:55 am
LGA
- MDW
1 stop7h 00m
Southwest
Deal found 4/9![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 4/11. 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 6/109:17 am
MDW
- EWR
1 stop5h 42m
Delta
Sun 6/146:00 am
EWR
- MDW
1 stop5h 07m
Delta
Deal found 4/11![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 4/9. 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 4/256:10 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Tue 4/288:55 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Deal found 4/9![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/12. 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 4/259:27 am
MDW
- EWR
1 stop5h 32m
Delta
Tue 4/283:29 pm
EWR
- MDW
1 stop7h 59m
Delta
Deal found 4/12![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 4/10. 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 4/265:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 4/288:55 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Deal found 4/10![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/275:12 pm
MDW
- EWR
1 stop5h 52m
Delta
Fri 5/294:29 pm
EWR
- MDW
1 stop5h 40m
Delta
Deal found 4/13![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 4/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:30 am
MDW
- LGA
1 stop7h 30m
Southwest
Wed 5/131:25 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 4/12![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1610:45 am
MDW
- EWR
1 stop6h 09m
Delta
Tue 5/196:15 am
EWR
- MDW
1 stop8h 04m
Delta
Deal found 4/14![Delta logo]()
$272
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:22 pm
MDW
- EWR
1 stop5h 08m
Delta
Sun 5/246:00 am
EWR
- MDW
1 stop3h 43m
Delta
Deal found 4/13![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/305:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Tue 5/198:55 am
LGA
- MDW
1 stop7h 00m
Southwest
Deal found 4/13![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 5/25:21 pm
MDW
- EWR
1 stop5h 22m
Delta
Mon 5/113:28 pm
EWR
- MDW
1 stop6h 41m
Delta
Deal found 4/10![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 4/11. 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.
Sat 5/22:15 pm
MDW
- LGA
1 stop6h 55m
Southwest
Sun 5/35:30 pm
LGA
- MDW
1 stop6h 35m
Southwest
Deal found 4/11![Southwest logo]()
$240
This Southwest deal was found by Cheapflights users on 4/10. 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 5/175:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Mon 5/186:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 4/10![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 4/9. 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.
Fri 5/156:36 pm
MDW
- EWR
1 stop3h 42m
Delta
Tue 5/199:45 am
EWR
- MDW
1 stop3h 57m
Delta
Deal found 4/9![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/71:22 pm
MDW
- JFK
1 stop4h 07m
Delta
Mon 5/113:55 pm
JFK
- MDW
1 stop6h 14m
Delta
Deal found 4/13![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 4/11. 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 5/197:40 am
MDW
- PVD
Nonstop2h 10m
Southwest
Tue 5/266:25 pm
PVD
- MDW
1 stop5h 10m
Southwest
Deal found 4/11![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 4/10. 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.
Tue 6/212:53 pm
MDW
- JFK
1 stop7h 34m
Delta
Wed 6/37:20 am
JFK
- MDW
1 stop6h 22m
Delta
Deal found 4/10![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/51:24 pm
MDW
- JFK
1 stop4h 21m
Delta
Wed 5/612:59 pm
JFK
- MDW
1 stop5h 59m
Delta
Deal found 4/14![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/9. 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.
Mon 5/41:24 pm
MDW
- JFK
1 stop5h 01m
Delta
Fri 5/83:55 pm
JFK
- MDW
1 stop6h 31m
Delta
Deal found 4/9![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/245:40 am
MDW
- PVD
1 stop3h 50m
Southwest
Wed 6/246:30 pm
PVD
- MDW
Nonstop2h 25m
Southwest
Deal found 4/13![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:22 pm
MDW
- JFK
1 stop4h 07m
Delta
Thu 6/412:59 pm
JFK
- MDW
1 stop6h 34m
Delta
Deal found 4/13![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 5/25:21 pm
MDW
- JFK
1 stop6h 27m
Delta
Mon 5/113:55 pm
JFK
- MDW
1 stop6h 14m
Delta
Deal found 4/10![Delta logo]()
$297
Last-minute flights from Midway to ConnecticutDiscover last-minute flight deals from Midway to Connecticut. Data last updated April 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Connecticut. Data last updated April 14, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 4/11. 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.
Sat 4/187:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/11![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 4/9. 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 4/217:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Thu 4/2311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/9![Frontier logo]()
$121
This Trip.com deal was found by Cheapflights users on 4/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Thu 4/2311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/9![Frontier logo]()
$124
This Super.com deal was found by Cheapflights users on 4/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sun 4/2611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/12![Frontier logo]()
$123
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/13![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Thu 4/237:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Mon 4/276:37 pm
EWR
- MDW
1 stop25h 54m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/267:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Fri 5/16:54 pm
EWR
- MDW
1 stop24h 43m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$129
This Frontier deal was found by Cheapflights users on 4/10. 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.
Tue 4/282:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Sat 5/211:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/10![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/302:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Mon 5/411:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/14![Frontier logo]()
$119
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/307:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Wed 5/65:55 am
EWR
- MDW
1 stop6h 14m
Frontier
Deal found 4/13![Frontier logo]()
$120
This Priceline deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Sun 5/311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 4/13![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Sat 5/27:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Mon 5/410:29 pm
EWR
- MDW
1 stop13h 40m
Frontier
Deal found 4/10![Frontier logo]()
$125
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 April 14, 2026.
Search for one-way flight options from Midway to Connecticut. Find affordable one-way fares based on user searches. Data last updated April 14, 2026.
This Trip.com deal was found by Cheapflights users on 4/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/9![Frontier logo]()
$61
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/11![Frontier logo]()
$62
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 4/257:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/14![Frontier logo]()
$63
This Super.com deal was found by Cheapflights users on 4/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/10![Frontier logo]()
$68
This Super.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/512:24 pm
MDW
- LGA
1 stop7h 32m
Frontier
Deal found 4/14![Frontier logo]()
$69
This Super.com deal was found by Cheapflights users on 4/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/12![Frontier logo]()
$69
This Expedia deal was found by Cheapflights users on 4/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- EWR
1 stop8h 25m
Frontier
Deal found 4/12![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/9. 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.
Thu 4/306:00 am
MDW
- BDL
1 stop7h 49m
Frontier
Deal found 4/9![Frontier logo]()
$70
This Mytrip deal was found by Cheapflights users on 4/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- LGA
1 stop7h 52m
Frontier
Deal found 4/9![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- EWR
1 stop18h 16m
Frontier
Deal found 4/12![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Mon 5/47:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 4/13![Frontier logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:41 am
MDW
- LGA
1 stop30h 30m
Frontier
Deal found 4/12![Frontier logo]()
$73
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 April 14, 2026.
Round-trip from | $118 (Frontier) |
|---|---|
One-way from | $61 (Trip.com) |
Popular in | April |
Cheapest in | August |
Average price | $509 |
Good round-trip deal | $474 or less |
Good one-way deal | $216 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 2,558,603 searches. Data last updated April 14, 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
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 5/12
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Tue 5/12
8:55 pm-10:30 pm
Nonstop2h 35m
$187
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Wed 5/20
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Sun 5/24
8:30 am-9:55 am
Nonstop2h 25m
$187
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Wed 5/13
7:25 pm-10:30 pm
Nonstop2h 05m
New York LaGuardia
Wed 5/20
6:00 am-7:25 am
Nonstop2h 25m
$192
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Fri 5/8
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Sat 5/9
9:10 am-2:40 pm
1 stop6h 30m
$197
Quickest round-trip
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 6/9
5:15 am-8:15 am
Nonstop2h 00m
New York LaGuardia
Thu 6/11
6:00 am-7:20 am
Nonstop2h 20m
$202
ChicagoNewark
MDW - EWR
MDWEWR
Chicago Midway
Sat 5/2
11:18 am-5:38 pm
1 stop5h 20m
Newark
Mon 5/4
4:29 pm-10:28 pm
1 stop6h 59m
$207
ChicagoNewark
MDW - EWR
MDWEWR
Chicago Midway
Tue 5/5
6:38 pm-11:03 pm
1 stop3h 25m
Newark
Thu 5/7
9:45 am-12:42 pm
1 stop3h 57m
$207
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Tue 4/28
9:30 am-12:35 pm
Nonstop2h 05m
New York LaGuardia
Thu 4/30
8:55 am-2:55 pm
1 stop7h 00m
$212
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sat 4/25
6:10 pm-9:15 pm
Nonstop2h 05m
New York LaGuardia
Tue 4/28
8:55 pm-10:30 pm
Nonstop2h 35m
$217
ChicagoNew York
MDW - LGA
MDWLGA
Chicago Midway
Sun 4/26
5:20 am-8:20 am
Nonstop2h 00m
New York LaGuardia
Tue 4/28
8:55 pm-10:30 pm
Nonstop2h 35m
$217
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-EWR
MDW-LGA
MDW-JFK
MDW-PVD
MDW-BDL
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-EWR
MDW-LGA
MDW-JFK
MDW-PVD
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 April 14, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 38% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the morning.
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 April 11, 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. Tuesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago Midway Airport to Connecticut?
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 April 14, 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.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
Complete your trip to Connecticut by adding a car rental and/or hotel reservation to your travel itinerary.
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 April 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated April 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$373 | FlexibilityNo cancel fee | On-time63% |