$104+ Cheap flights from Connecticut to Midway (MDW)
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Midway with Cheapflights
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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 July 27, 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 July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/24:10 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Wed 9/27:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/26![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Tue 9/88:55 am
MDW
- LGA
1 stop5h 55m
Southwest
Deal found 7/24![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:35 am
LGA
- MDW
Nonstop2h 20m
Southwest
Mon 9/147:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/24![Southwest logo]()
$218
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
EWR
- MDW
1 stop4h 59m
Delta
Wed 8/196:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Deal found 7/25![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:40 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sun 9/135:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:25 am
LGA
- MDW
Nonstop2h 20m
Southwest
Tue 9/157:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/24![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
LGA
- MDW
2 stops11h 40m
Southwest
Tue 9/12:45 pm
MDW
- LGA
1 stop6h 10m
Southwest
Deal found 7/24![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2012:00 pm
EWR
- MDW
1 stop5h 15m
Delta
Tue 8/256:05 am
MDW
- EWR
1 stop7h 09m
Delta
Deal found 7/26![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:20 am
LGA
- MDW
1 stop6h 45m
Southwest
Mon 8/245:50 pm
MDW
- LGA
1 stop4h 30m
Southwest
Deal found 7/24![Southwest logo]()
$238
This Frontier deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Mon 9/1412:03 pm
MDW
- EWR
1 stop11h 56m
Frontier
Deal found 7/24![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Wed 8/2611:50 am
MDW
- EWR
1 stop12h 13m
Frontier
Deal found 7/25![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:05 am
PVD
- MDW
2 stops8h 20m
Southwest
Tue 12/11:35 pm
MDW
- PVD
Nonstop2h 10m
Southwest
Deal found 7/24![Southwest logo]()
$240
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 July 27, 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 July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:45 pm
LGA
- MDW
1 stop5h 05m
Southwest
Tue 9/12:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/24![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
EWR
- MDW
1 stop4h 59m
Delta
Wed 8/196:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Deal found 7/25![Delta logo]()
$227
This Frontier deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Thu 9/311:50 am
MDW
- EWR
1 stop12h 13m
Frontier
Deal found 7/21![Frontier logo]()
$246
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/212:05 pm
LGA
- MDW
1 stop5h 45m
Southwest
Wed 9/27:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/26![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/218:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 8/226:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Mon 8/315:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:40 am
EWR
- MDW
1 stop4h 08m
Delta
Fri 10/165:21 pm
MDW
- EWR
1 stop5h 27m
Delta
Deal found 7/23![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Wed 9/210:10 am
MDW
- LGA
1 stop5h 45m
Southwest
Deal found 7/23![Southwest logo]()
$227
This Booking.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Sun 8/2311:50 am
MDW
- EWR
1 stop12h 13m
Frontier
Deal found 7/21![Frontier logo]()
$304
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:15 am
EWR
- MDW
1 stop5h 50m
Delta
Sat 10/179:59 am
MDW
- EWR
1 stop6h 52m
Delta
Deal found 7/24![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:35 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 9/127:50 am
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 7/22![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/265:21 pm
BDL
- MDW
1 stop6h 23m
Delta
Wed 9/306:05 am
MDW
- BDL
1 stop5h 55m
Delta
Deal found 7/26![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/52:40 pm
LGA
- MDW
1 stop5h 40m
Southwest
Tue 9/84:40 pm
MDW
- LGA
1 stop5h 35m
Southwest
Deal found 7/26![Southwest logo]()
$227
This Frontier deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1610:29 pm
EWR
- MDW
1 stop12h 22m
Frontier
Fri 8/2111:50 am
MDW
- EWR
1 stop12h 13m
Frontier
Deal found 7/21![Frontier logo]()
$347
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:24 pm
BDL
- MDW
1 stop6h 12m
Delta
Wed 9/26:05 am
MDW
- BDL
1 stop5h 43m
Delta
Deal found 7/23![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:00 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Wed 10/218:15 am
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/24![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am
EWR
- MDW
1 stop6h 45m
Delta
Fri 9/181:00 pm
MDW
- EWR
1 stop6h 57m
Delta
Deal found 7/25![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Tue 9/158:40 am
MDW
- LGA
2 stops7h 25m
Southwest
Deal found 7/25![Southwest logo]()
$233
This Booking.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:35 pm
EWR
- MDW
1 stop7h 57m
Frontier
Sun 8/1611:06 am
MDW
- EWR
1 stop9h 22m
Frontier
Deal found 7/21![Frontier logo]()
$379
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:40 pm
JFK
- MDW
1 stop7h 56m
Delta
Tue 8/255:10 pm
MDW
- JFK
1 stop7h 04m
Delta
Deal found 7/21![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
LGA
- MDW
2 stops11h 40m
Southwest
Mon 8/315:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/25![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am
BDL
- MDW
1 stop6h 50m
Delta
Mon 10/195:15 pm
MDW
- BDL
1 stop5h 44m
Delta
Deal found 7/25![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:00 pm
LGA
- MDW
1 stop5h 45m
Southwest
Sun 8/165:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/23![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:25 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sun 9/62:45 pm
MDW
- LGA
1 stop7h 15m
Southwest
Deal found 7/23![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2210:00 am
BDL
- MDW
1 stop6h 38m
Delta
Thu 8/276:42 pm
MDW
- BDL
1 stop4h 09m
Delta
Deal found 7/26![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:20 pm
PVD
- MDW
1 stop7h 20m
Southwest
Tue 10/138:10 am
MDW
- PVD
1 stop6h 45m
Southwest
Deal found 7/25![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:40 pm
JFK
- MDW
1 stop5h 56m
Delta
Thu 8/279:24 am
MDW
- JFK
1 stop7h 24m
Delta
Deal found 7/22![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:23 pm
PVD
- MDW
1 stop6h 13m
Delta
Wed 8/195:10 pm
MDW
- PVD
1 stop5h 49m
Delta
Deal found 7/23![Delta logo]()
$332
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:10 pm
PVD
- MDW
Nonstop2h 25m
Southwest
Mon 8/248:05 am
MDW
- PVD
Nonstop2h 25m
Southwest
Deal found 7/25![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:43 pm
PVD
- MDW
1 stop6h 50m
Delta
Sat 8/226:42 pm
MDW
- PVD
1 stop4h 09m
Delta
Deal found 7/25![Delta logo]()
$337
Last-minute flights from Connecticut to MidwayDiscover last-minute flight deals from Connecticut to Midway. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Midway. Data last updated July 27, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
EWR
- MDW
1 stop4h 59m
Delta
Wed 8/196:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Deal found 7/25![Delta logo]()
$227
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Wed 8/2611:50 am
MDW
- EWR
1 stop12h 13m
Frontier
Deal found 7/25![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Sun 8/235:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/24![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2012:00 pm
EWR
- MDW
1 stop5h 15m
Delta
Tue 8/256:05 am
MDW
- EWR
1 stop7h 09m
Delta
Deal found 7/26![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Sat 8/226:00 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/24![Southwest logo]()
$218
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/228:20 am
LGA
- MDW
1 stop6h 45m
Southwest
Sun 8/235:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:20 am
LGA
- MDW
1 stop6h 45m
Southwest
Sun 8/305:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:20 am
LGA
- MDW
1 stop6h 45m
Southwest
Mon 8/245:50 pm
MDW
- LGA
1 stop4h 30m
Southwest
Deal found 7/24![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Tue 9/17:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/24![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:40 am
LGA
- MDW
Nonstop2h 25m
Southwest
Sun 8/305:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/24![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
LGA
- MDW
2 stops11h 40m
Southwest
Tue 9/15:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 7/24![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:40 am
LGA
- MDW
Nonstop2h 25m
Southwest
Tue 9/85:10 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$227
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 July 27, 2026.
Search for one-way flight options from Connecticut to Midway. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$104
This Trip.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
EWR
- MDW
1 stop4h 07m
Delta
Deal found 7/22![Delta logo]()
$113
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:10 pm
PVD
- MDW
Nonstop2h 25m
Southwest
Deal found 7/24![Southwest logo]()
$113
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
EWR
- MDW
1 stop4h 59m
Delta
Deal found 7/25![Delta logo]()
$114
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/22![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
LGA
- MDW
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$115
This Super.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Deal found 7/23![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
LGA
- MDW
2 stops11h 40m
Southwest
Deal found 7/24![Southwest logo]()
$119
This Frontier deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/611:35 am
EWR
- MDW
1 stop7h 11m
Frontier
Deal found 7/26![Frontier logo]()
$120
This Frontier deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:35 am
EWR
- MDW
1 stop7h 16m
Frontier
Deal found 7/25![Frontier logo]()
$121
This Trip.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:55 am
EWR
- MDW
1 stop6h 00m
Frontier
Deal found 7/23![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/145:59 am
EWR
- MDW
1 stop5h 59m
Frontier
Deal found 7/26![Frontier logo]()
$123
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 July 27, 2026.
Round-trip from | $207 (Southwest) |
|---|---|
One-way from | $104 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $451 |
Good round-trip deal | $391 or less |
Good one-way deal | $239 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 2,558,603 searches. Data last updated July 27, 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 - MDW
LGAMDW
New York LaGuardia
Tue 8/25
5:45 pm-9:50 pm
1 stop5h 05m
Chicago Midway
Tue 9/1
2:40 pm-5:45 pm
Nonstop2h 05m
$217
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 9/2
12:05 pm-4:50 pm
1 stop5h 45m
Chicago Midway
Wed 9/2
7:05 pm-10:10 pm
Nonstop2h 05m
$217
Quickest round-trip
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 8/21
8:55 pm-10:15 pm
Nonstop2h 20m
Chicago Midway
Sat 8/22
6:00 am-9:00 am
Nonstop2h 00m
$218
NewarkChicago
EWR - MDW
EWRMDW
Newark
Wed 8/19
6:00 am-9:59 am
1 stop4h 59m
Chicago Midway
Wed 8/19
6:42 pm-11:25 pm
1 stop3h 43m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 8/28
8:55 pm-10:15 pm
Nonstop2h 20m
Chicago Midway
Mon 8/31
5:00 am-8:00 am
Nonstop2h 00m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sun 8/30
6:00 am-7:15 am
Nonstop2h 15m
Chicago Midway
Wed 9/2
10:10 am-4:55 pm
1 stop5h 45m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 9/5
7:35 am-8:55 am
Nonstop2h 20m
Chicago Midway
Sat 9/12
7:50 am-11:00 am
Nonstop2h 10m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 9/5
2:40 pm-7:20 pm
1 stop5h 40m
Chicago Midway
Tue 9/8
4:40 pm-11:15 pm
1 stop5h 35m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 10/15
9:00 pm-10:20 pm
Nonstop2h 20m
Chicago Midway
Wed 10/21
8:15 am-11:20 am
Nonstop2h 05m
$229
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 9/8
6:00 am-7:15 am
Nonstop2h 15m
Chicago Midway
Tue 9/15
8:40 am-5:05 pm
2 stops7h 25m
$233
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
PVD-MDW
BDL-MDW
JFK-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Connecticut to Chicago Midway Airport
USCT-MDW
LGA-MDW
EWR-MDW
PVD-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 July 27, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 34% on flights from Connecticut to Chicago Midway Airport by exploring options for tickets at noon.
Weekly flight availability from Connecticut to Chicago Midway Airport
Explore weekly flight availability from Connecticut to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 27, 2026.
The most flights from USCT to MDW are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Connecticut to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Connecticut to Chicago Midway Airport flights typically cost between $292 and $462 in October.The cheapest round-trip price found within the last 5 days was $282 on Southwest (Oct 30-Nov 2).
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
Lansing
Merrillville
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
See prices for flight routes from nearby airports that may be better suited for you.
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 July 27, 2026.
Connecticut and Midway flights
Browse other Connecticut and Midway flight options. Last updated on July 27, 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 2 airlines flying from Connecticut to Midway
Discover the top 2 airlines 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 2,558,603 searches. Data last updated July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$176 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$260 | Average$420 | FlexibilityNo cancel fee | On-time63% |