$78+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Jun 10 — Jun 171
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Midway with Cheapflights
1. Tell us where you want to go
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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 May 11, 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 May 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Mon 8/1710:00 pm
LGA
- MDW
1 stop14h 12m
Frontier
Wed 8/1912:04 pm
MDW
- LGA
1 stop10h 23m
Frontier
Deal found 5/6![Frontier logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Mon 6/110:00 pm
LGA
- MDW
1 stop14h 12m
Frontier
Sat 6/611:59 am
MDW
- LGA
1 stop6h 30m
Frontier
Deal found 5/6![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/41:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
- JFK
1 stop22h 55m
Frontier
Deal found 5/6![Frontier logo]()
$175
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 6/276:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 5/8![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Tue 6/96:00 am
MDW
- JFK
1 stop28h 59m
Frontier
Deal found 5/7![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:29 pm
EWR
- MDW
1 stop13h 43m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 5/9![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 5/10. 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.
Fri 7/109:30 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Wed 7/157:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 5/10![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/205:55 am
EWR
- MDW
1 stop6h 17m
Frontier
Wed 9/212:04 pm
MDW
- EWR
1 stop8h 25m
Frontier
Deal found 5/6![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Thu 5/2810:29 pm
EWR
- MDW
1 stop13h 40m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 5/8![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Tue 6/912:27 pm
MDW
- JFK
1 stop22h 32m
Frontier
Deal found 5/7![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 7/166:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Mon 7/201:00 pm
MDW
- LGA
1 stop4h 55m
Southwest
Deal found 5/8![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Sat 5/306:29 am
LGA
- MDW
1 stop16h 33m
Frontier
Tue 6/212:27 pm
MDW
- LGA
1 stop7h 29m
Frontier
Deal found 5/6![Frontier logo]()
$188
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 May 11, 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 May 11, 2026.
This Southwest deal was found by Cheapflights users on 5/6. 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.
Sat 6/206:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Wed 6/245:50 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 5/6![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 5/10. 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.
Fri 6/126:00 am
EWR
- MDW
1 stop5h 09m
Delta
Sat 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Deal found 5/10![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 5/10. 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.
Fri 7/109:30 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Wed 7/157:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 5/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/6. 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.
Tue 6/166:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Tue 6/305:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/6![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 5/6. 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.
Tue 6/26:00 am
EWR
- MDW
1 stop3h 43m
Delta
Tue 6/26:36 pm
MDW
- EWR
1 stop3h 42m
Delta
Deal found 5/6![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 5/10. 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.
Fri 7/1712:00 pm
LGA
- MDW
1 stop8h 35m
Southwest
Mon 7/201:00 pm
MDW
- LGA
1 stop4h 55m
Southwest
Deal found 5/10![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 5/6. 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.
Wed 9/98:30 am
EWR
- MDW
1 stop7h 57m
Delta
Wed 9/161:00 pm
MDW
- EWR
1 stop5h 27m
Delta
Deal found 5/6![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:55 am
LGA
- MDW
1 stop7h 00m
Southwest
Fri 5/2910:15 am
MDW
- LGA
1 stop5h 35m
Southwest
Deal found 5/8![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 5/9. 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 6/53:28 pm
EWR
- MDW
1 stop6h 41m
Delta
Fri 6/125:11 pm
MDW
- EWR
1 stop6h 46m
Delta
Deal found 5/9![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
LGA
- MDW
Nonstop2h 25m
Southwest
Sat 6/66:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 5/8![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
EWR
- MDW
1 stop4h 08m
Delta
Thu 7/301:18 pm
MDW
- EWR
1 stop5h 12m
Delta
Deal found 5/8![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 5/7. 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 6/166:00 am
EWR
- MDW
1 stop5h 09m
Delta
Sat 6/209:17 am
MDW
- EWR
1 stop5h 42m
Delta
Deal found 5/7![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 5/6. 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 6/199:30 pm
LGA
- MDW
Nonstop2h 25m
Southwest
Tue 6/235:10 pm
MDW
- LGA
1 stop5h 10m
Southwest
Deal found 5/6![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 5/7. 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.
Tue 6/165:45 pm
LGA
- MDW
1 stop5h 50m
Southwest
Sat 6/2012:50 pm
MDW
- LGA
2 stops9h 35m
Southwest
Deal found 5/7![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 5/9. 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 8/57:05 am
EWR
- MDW
1 stop5h 46m
Delta
Sun 8/91:27 pm
MDW
- EWR
1 stop4h 58m
Delta
Deal found 5/9![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/9. 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 7/243:40 pm
LGA
- MDW
1 stop6h 40m
Southwest
Sun 7/265:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/9![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/8. 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 6/259:39 am
EWR
- MDW
1 stop4h 07m
Delta
Sat 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Deal found 5/8![Delta logo]()
$267
This Delta deal was found by Cheapflights users on 5/10. 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 8/19:55 am
EWR
- MDW
1 stop3h 43m
Delta
Sat 8/86:42 pm
MDW
- EWR
1 stop3h 43m
Delta
Deal found 5/10![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sat 7/410:05 am
LGA
- MDW
1 stop5h 20m
Southwest
Sun 7/55:20 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/10![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 5/10. 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 6/138:30 am
EWR
- MDW
1 stop8h 10m
Delta
Tue 6/165:11 pm
MDW
- EWR
1 stop5h 57m
Delta
Deal found 5/10![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 5/8. 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 8/318:55 pm
LGA
- MDW
Nonstop2h 20m
Southwest
Wed 9/25:10 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/8![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 5/10. 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.
Fri 6/126:00 am
JFK
- MDW
1 stop5h 09m
Delta
Sat 6/274:25 pm
MDW
- JFK
1 stop5h 39m
Delta
Deal found 5/10![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 5/6. 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.
Wed 8/55:55 pm
PVD
- MDW
Nonstop2h 30m
Southwest
Tue 8/118:40 am
MDW
- PVD
2 stops7h 25m
Southwest
Deal found 5/6![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:20 am
JFK
- MDW
1 stop6h 22m
Delta
Fri 6/55:08 pm
MDW
- JFK
1 stop5h 15m
Delta
Deal found 5/10![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 5/6. 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.
Tue 7/214:20 pm
PVD
- MDW
2 stops7h 50m
Southwest
Wed 7/229:25 am
MDW
- PVD
Nonstop2h 15m
Southwest
Deal found 5/6![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 5/10. 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 7/186:00 am
JFK
- MDW
1 stop5h 05m
Delta
Wed 7/2212:41 pm
MDW
- JFK
1 stop7h 48m
Delta
Deal found 5/10![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 5/10. 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.
Mon 6/2210:31 am
EWR
- MDW
1 stop6h 45m
Delta
Tue 6/309:17 am
MDW
- EWR
1 stop5h 42m
Delta
Deal found 5/10![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 5/10. 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.
Mon 6/16:15 pm
PVD
- MDW
1 stop5h 05m
Southwest
Wed 6/36:05 am
MDW
- PVD
1 stop5h 05m
Southwest
Deal found 5/10![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 5/8. 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 6/246:00 am
EWR
- MDW
1 stop4h 14m
Delta
Sat 6/279:54 am
MDW
- EWR
1 stop6h 01m
Delta
Deal found 5/8![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 5/7. 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.
Wed 6/177:00 am
PVD
- MDW
Nonstop2h 25m
Southwest
Sun 6/2111:10 am
MDW
- PVD
1 stop6h 30m
Southwest
Deal found 5/7![Southwest logo]()
$343
Last-minute flights from Connecticut to MidwayDiscover last-minute flight deals from Connecticut to Midway. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Midway. Data last updated May 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Thu 5/2810:29 pm
EWR
- MDW
1 stop13h 40m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 5/8![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Fri 5/2910:29 pm
EWR
- MDW
1 stop13h 35m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 5/6![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Sat 5/306:29 am
LGA
- MDW
1 stop16h 33m
Frontier
Tue 6/212:27 pm
MDW
- LGA
1 stop7h 29m
Frontier
Deal found 5/6![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Mon 6/110:00 pm
LGA
- MDW
1 stop14h 12m
Frontier
Sat 6/611:59 am
MDW
- LGA
1 stop6h 30m
Frontier
Deal found 5/6![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:29 pm
EWR
- MDW
1 stop13h 43m
Frontier
Wed 6/312:04 pm
MDW
- EWR
1 stop12h 14m
Frontier
Deal found 5/9![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Tue 6/912:27 pm
MDW
- JFK
1 stop22h 32m
Frontier
Deal found 5/7![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Tue 6/96:00 am
MDW
- JFK
1 stop28h 59m
Frontier
Deal found 5/7![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 6/41:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Mon 6/812:04 pm
MDW
- JFK
1 stop22h 55m
Frontier
Deal found 5/6![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 5/6. 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 6/96:25 am
LGA
- MDW
1 stop5h 47m
Frontier
Wed 6/1712:04 pm
MDW
- LGA
1 stop10h 10m
Frontier
Deal found 5/6![Frontier logo]()
$190
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:25 am
LGA
- MDW
Nonstop2h 25m
Southwest
Fri 6/197:45 pm
MDW
- LGA
Nonstop2h 10m
Southwest
Deal found 5/8![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1611:05 am
LGA
- MDW
1 stop7h 00m
Southwest
Wed 6/245:15 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 5/8![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sat 6/276:40 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 5/8![Southwest logo]()
$177
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 May 11, 2026.
Search for one-way flight options from Connecticut to Midway. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
This Trip.com deal was found by Cheapflights users on 5/9. 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 6/35:55 am
EWR
- MDW
1 stop17h 07m
Frontier
Deal found 5/9![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Fri 5/2910:29 pm
EWR
- MDW
1 stop13h 35m
Frontier
Deal found 5/6![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 5/10. 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.
Wed 6/105:58 am
EWR
- MDW
1 stop6h 11m
Frontier
Deal found 5/10![Frontier logo]()
$87
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
LGA
- MDW
Nonstop2h 20m
Southwest
Deal found 5/8![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2610:29 pm
EWR
- MDW
1 stop13h 40m
Frontier
Deal found 5/10![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:00 pm
JFK
- MDW
1 stop23h 12m
Frontier
Deal found 5/7![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:49 pm
LGA
- MDW
1 stop17h 20m
Frontier
Deal found 5/10![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:29 am
LGA
- MDW
1 stop16h 33m
Frontier
Deal found 5/7![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:55 am
EWR
- MDW
1 stop6h 17m
Frontier
Deal found 5/10![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:00 pm
JFK
- MDW
1 stop10h 02m
Frontier
Deal found 5/10![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Mon 6/110:00 pm
LGA
- MDW
1 stop14h 12m
Frontier
Deal found 5/6![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 5/8. 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.
Sun 5/248:30 am
LGA
- MDW
Nonstop2h 25m
Southwest
Deal found 5/8![Southwest logo]()
$94
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 May 11, 2026.
Round-trip from | $169 (Kiwi.com) |
|---|---|
One-way from | $78 (Trip.com) |
Popular in | May |
Cheapest in | January |
Average price | $427 |
Good round-trip deal | $413 or less |
Good one-way deal | $253 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 May 11, 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 6/20
6:00 am-7:20 am
Nonstop2h 20m
Chicago Midway
Wed 6/24
5:50 pm-8:55 pm
Nonstop2h 05m
$177
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 7/10
9:30 pm-10:55 pm
Nonstop2h 25m
Chicago Midway
Wed 7/15
7:45 pm-10:55 pm
Nonstop2h 10m
$182
Quickest round-trip
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 6/16
6:00 am-7:20 am
Nonstop2h 20m
Chicago Midway
Tue 6/30
5:15 am-8:15 am
Nonstop2h 00m
$192
NewarkChicago
EWR - MDW
EWRMDW
Newark
Fri 6/12
6:00 am-10:09 am
1 stop5h 09m
Chicago Midway
Sat 6/27
9:54 am-4:55 pm
1 stop6h 01m
$202
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 7/17
12:00 pm-7:35 pm
1 stop8h 35m
Chicago Midway
Mon 7/20
1:00 pm-6:55 pm
1 stop4h 55m
$207
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 5/27
8:55 am-2:55 pm
1 stop7h 00m
Chicago Midway
Fri 5/29
10:15 am-4:50 pm
1 stop5h 35m
$207
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Wed 6/3
6:00 am-7:25 am
Nonstop2h 25m
Chicago Midway
Sat 6/6
6:40 pm-9:45 pm
Nonstop2h 05m
$212
NewarkChicago
EWR - MDW
EWRMDW
Newark
Tue 6/2
6:00 am-8:43 am
1 stop3h 43m
Chicago Midway
Tue 6/2
6:36 pm-11:18 pm
1 stop3h 42m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Fri 6/19
9:30 pm-10:55 pm
Nonstop2h 25m
Chicago Midway
Tue 6/23
5:10 pm-11:20 pm
1 stop5h 10m
$227
New YorkChicago
LGA - MDW
LGAMDW
New York LaGuardia
Tue 6/16
5:45 pm-10:35 pm
1 stop5h 50m
Chicago Midway
Sat 6/20
12:50 pm-11:25 pm
2 stops9h 35m
$232
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Connecticut with our price prediction graph.
LGA-MDW
EWR-MDW
JFK-MDW
PVD-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
JFK-MDW
PVD-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 $413). 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 May 11, 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.
How much does it cost to fly round-trip from Connecticut to Chicago Midway Airport?
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
Hammond
Porter
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 May 11, 2026.
Connecticut and Midway flights
Browse other Connecticut and Midway flight options. Last updated on May 11, 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 May 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$176 | Average$292 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$402 | FlexibilityNo cancel fee | On-time63% |