$57+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Apr 9 — Apr 161
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 March 10, 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 March 10, 2026.
This Super.com deal was found by Cheapflights users on 3/8. 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.
Tue 3/2411:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Thu 3/267:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/8![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1710:29 pm
EWR
- MDW
1 stop21h 08m
Frontier
Tue 4/217:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/5![Frontier logo]()
$101
This Frontier deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/1311:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Sun 5/177:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/5![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 3/7. 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.
Thu 3/1911:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Tue 3/247:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/7![Frontier logo]()
$104
This Booking.com deal was found by Cheapflights users on 3/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 5/47:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/9![Frontier logo]()
$105
This Flightnetwork deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 5/47:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Sat 5/97:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/511:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 5/112:20 pm
MDW
- EWR
1 stop9h 56m
Frontier
Deal found 3/6![Frontier logo]()
$108
This Frontier deal was found by Cheapflights users on 3/9. 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.
Sat 4/1811:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 4/207:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/9![Frontier logo]()
$109
This eDestinos deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:29 pm
EWR
- MDW
1 stop22h 02m
Frontier
Mon 4/277:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Wed 4/85:39 pm
EWR
- MDW
1 stop5h 40m
Multiple Airlines
Tue 4/147:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/216:20 am
LGA
- MDW
1 stop14h 11m
Frontier
Tue 4/282:15 pm
MDW
- LGA
1 stop5h 44m
Frontier
Deal found 3/6![Frontier logo]()
$123
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 March 10, 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 March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:05 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 4/209:40 am
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 3/8![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
EWR
- MDW
1 stop3h 47m
Delta
Mon 4/205:21 pm
MDW
- EWR
1 stop5h 22m
Delta
Deal found 3/8![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/304:30 pm
LGA
- MDW
1 stop8h 10m
Southwest
Mon 5/49:40 am
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 3/5![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Wed 4/225:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/8![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1810:39 am
EWR
- MDW
1 stop6h 47m
Delta
Tue 4/216:00 am
MDW
- EWR
1 stop5h 22m
Delta
Deal found 3/5![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 5/45:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/8![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 4/166:00 am
EWR
- MDW
1 stop3h 47m
Delta
Mon 4/205:21 pm
MDW
- EWR
1 stop5h 22m
Delta
Deal found 3/8![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 3/8. 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 6/17:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 6/85:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/8![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/9. 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 3/247:00 am
EWR
- MDW
1 stop6h 02m
Delta
Fri 4/36:34 pm
MDW
- EWR
1 stop3h 28m
Delta
Deal found 3/9![Delta logo]()
$212
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/243:26 pm
EWR
- MDW
1 stop8h 02m
Delta
Sat 4/256:00 am
MDW
- EWR
1 stop7h 24m
Delta
Deal found 3/6![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 3/9. 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 5/27:15 am
LGA
- MDW
2 stops11h 00m
Southwest
Mon 5/47:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 3/9![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:38 am
EWR
- MDW
1 stop4h 04m
Delta
Sat 5/236:36 pm
MDW
- EWR
1 stop3h 42m
Delta
Deal found 3/9![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/153:40 pm
LGA
- MDW
Nonstop2h 35m
Southwest
Mon 5/185:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/6![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/286:00 am
EWR
- MDW
1 stop3h 47m
Delta
Sat 5/211:18 am
MDW
- EWR
1 stop5h 20m
Delta
Deal found 3/5![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/9. 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 4/86:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Wed 4/159:40 am
MDW
- LGA
2 stops8h 45m
Southwest
Deal found 3/9![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:15 am
EWR
- MDW
1 stop8h 04m
Delta
Sun 5/246:36 pm
MDW
- EWR
1 stop3h 42m
Delta
Deal found 3/9![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 3/7. 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.
Mon 3/309:55 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Mon 4/65:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/7![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/259:43 am
EWR
- MDW
1 stop3h 46m
Delta
Mon 3/306:34 pm
MDW
- EWR
1 stop3h 28m
Delta
Deal found 3/9![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/287:20 am
LGA
- MDW
Nonstop2h 40m
Southwest
Tue 3/315:10 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 3/8![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:43 am
EWR
- MDW
1 stop3h 46m
Delta
Mon 4/136:38 pm
MDW
- EWR
1 stop3h 25m
Delta
Deal found 3/9![Delta logo]()
$276
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/152:55 pm
JFK
- MDW
1 stop8h 33m
Delta
Tue 4/215:21 pm
MDW
- JFK
1 stop6h 27m
Delta
Deal found 3/5![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/511:45 am
JFK
- MDW
1 stop5h 41m
Delta
Tue 5/1212:51 pm
MDW
- JFK
1 stop5h 49m
Delta
Deal found 3/5![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/16:50 am
PVD
- MDW
Nonstop2h 30m
Southwest
Mon 5/46:45 pm
MDW
- PVD
Nonstop2h 15m
Southwest
Deal found 3/6![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 3/8. 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 5/139:00 am
JFK
- MDW
1 stop8h 12m
Delta
Sat 5/165:10 pm
MDW
- JFK
1 stop6h 56m
Delta
Deal found 3/8![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/57:00 pm
PVD
- MDW
Nonstop2h 30m
Southwest
Mon 6/86:10 pm
MDW
- PVD
Nonstop2h 15m
Southwest
Deal found 3/6![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 3/9. 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.
Mon 5/42:05 pm
BDL
- MDW
1 stop7h 15m
Southwest
Tue 5/57:40 am
MDW
- BDL
Nonstop2h 00m
Southwest
Deal found 3/9![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 3/7. 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 3/2412:27 pm
JFK
- MDW
1 stop5h 55m
Delta
Tue 3/3112:47 pm
MDW
- JFK
1 stop5h 33m
Delta
Deal found 3/7![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/265:35 am
PVD
- MDW
1 stop4h 10m
Southwest
Wed 4/297:40 am
MDW
- PVD
Nonstop2h 10m
Southwest
Deal found 3/5![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 3/8. 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.
Fri 4/172:55 pm
JFK
- MDW
1 stop8h 33m
Delta
Wed 4/2212:52 pm
MDW
- JFK
1 stop6h 38m
Delta
Deal found 3/8![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/25:34 am
PVD
- MDW
1 stop7h 28m
Delta
Mon 4/66:34 pm
MDW
- PVD
1 stop3h 45m
Delta
Deal found 3/6![Delta logo]()
$319
Last-minute flights from Connecticut to MidwayDiscover last-minute flight deals from Connecticut to Midway. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Midway. Data last updated March 10, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/1711:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Thu 3/197:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/5![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 3/7. 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.
Thu 3/1911:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Tue 3/247:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/7![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 3/8. 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.
Tue 3/2411:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Thu 3/267:30 am
MDW
- EWR
Nonstop2h 00m
Frontier
Deal found 3/8![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Wed 4/85:39 pm
EWR
- MDW
1 stop5h 40m
Multiple Airlines
Tue 4/147:30 am
MDW
- EWR
Nonstop2h 08m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1710:29 pm
EWR
- MDW
1 stop21h 08m
Frontier
Tue 4/217:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/5![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1711:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Wed 4/227:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/5![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 3/9. 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.
Sat 4/1811:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 4/207:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/9![Frontier logo]()
$109
This eDestinos deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:29 pm
EWR
- MDW
1 stop22h 02m
Frontier
Mon 4/277:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/216:20 am
LGA
- MDW
1 stop14h 11m
Frontier
Tue 4/282:15 pm
MDW
- LGA
1 stop5h 44m
Frontier
Deal found 3/6![Frontier logo]()
$123
This Frontier deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/2911:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Fri 5/12:15 pm
MDW
- EWR
1 stop10h 01m
Frontier
Deal found 3/6![Frontier logo]()
$108
This Flightnetwork deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Mon 5/47:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$106
This deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Sat 5/27:30 am
MDW
- EWR
Nonstop2h 08m
Frontier
Deal found 3/6![Frontier logo]()
$107
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 March 10, 2026.
Search for one-way flight options from Connecticut to Midway. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Trip.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/1911:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Deal found 3/6![Frontier logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/1611:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/6![Frontier logo]()
$58
This Priceline deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/2011:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/5![Frontier logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:25 pm
LGA
- MDW
1 stop12h 01m
Frontier
Deal found 3/6![Frontier logo]()
$59
This Trip.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/1211:30 am
JFK
- MDW
1 stop9h 01m
Frontier
Deal found 3/6![Frontier logo]()
$60
This Trip.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/126:00 am
LGA
- MDW
1 stop14h 31m
Frontier
Deal found 3/6![Frontier logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/911:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/10![Frontier logo]()
$61
This Orbitz deal was found by Cheapflights users on 3/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:30 am
EWR
- MDW
Nonstop2h 30m
Frontier
Deal found 3/7![Frontier logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/1511:30 am
EWR
- MDW
Nonstop2h 32m
Frontier
Deal found 3/5![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:00 pm
JFK
- MDW
1 stop7h 31m
Frontier
Deal found 3/8![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/56:00 am
LGA
- MDW
1 stop14h 31m
Frontier
Deal found 3/6![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1310:29 pm
EWR
- MDW
1 stop22h 02m
Frontier
Deal found 3/5![Frontier logo]()
$65
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 March 10, 2026.
Round-trip from | $100 (Super.com) |
|---|---|
One-way from | $57 (Trip.com) |
Popular in | March |
Cheapest in | January |
Average price | $413 |
Good round-trip deal | $426 or less |
Good one-way deal | $213 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 March 10, 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
Sat 4/18
6:05 pm-7:30 pm
Nonstop2h 25m
Chicago Midway
Mon 4/20
9:40 am-12:45 pm
Nonstop2h 05m
$162
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Thu 4/30
4:30 pm-11:40 pm
1 stop8h 10m
Chicago Midway
Mon 5/4
9:40 am-12:45 pm
Nonstop2h 05m
$167
Quickest round-trip
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 4/17
6:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Wed 4/22
5:15 am-8:15 am
Nonstop2h 00m
$177
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 5/1
6:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Mon 5/4
5:15 am-8:15 am
Nonstop2h 00m
$177
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Mon 6/1
7:25 am-8:50 am
Nonstop2h 25m
Chicago Midway
Mon 6/8
5:20 am-8:20 am
Nonstop2h 00m
$177
NewarkChicago
EWR - MDW
EWRMDW
Newark
Sat 4/18
6:00 am-8:47 am
1 stop3h 47m
Chicago Midway
Mon 4/20
5:21 pm-11:43 pm
1 stop5h 22m
$197
NewarkChicago
EWR - MDW
EWRMDW
Newark
Sat 4/18
10:39 am-4:26 pm
1 stop6h 47m
Chicago Midway
Tue 4/21
6:00 am-12:22 pm
1 stop5h 22m
$197
NewarkChicago
EWR - MDW
EWRMDW
Newark
Thu 4/16
6:00 am-8:47 am
1 stop3h 47m
Chicago Midway
Mon 4/20
5:21 pm-11:43 pm
1 stop5h 22m
$197
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Sat 5/2
7:15 am-5:15 pm
2 stops11h 00m
Chicago Midway
Mon 5/4
7:50 pm-10:55 pm
Nonstop2h 05m
$197
NewarkChicago
EWR - MDW
EWRMDW
Newark
Tue 3/24
7:00 am-12:02 pm
1 stop6h 02m
Chicago Midway
Fri 4/3
6:34 pm-11:02 pm
1 stop3h 28m
$212
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
JFK-MDW
BDL-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
JFK-MDW
What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?
Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $137). Flying from Connecticut to Chicago Midway Airport in February is currently the most expensive (average of $414). 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 March 10, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 33% on flights from Connecticut to Chicago Midway Airport by exploring options for tickets at noon.
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 March 10, 2026.
Connecticut and Midway flights
Browse other Connecticut and Midway flight options. Last updated on March 10, 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$176 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$382 | FlexibilityNo cancel fee | On-time63% |