$105+ Cheap flights from Wisconsin to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MDW
Nov 13 — Nov 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Wisconsin to Midway with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Wisconsin to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Wisconsin to MidwayExplore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
Explore the most affordable flight options available from Wisconsin to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:50 pm -
Nonstop0h 50m
Mon 11/99:15 pm -
Nonstop1h 00m
Deal found 10/9![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:15 pm -
Nonstop0h 55m
Thu 12/31:15 pm -
2 stops8h 10m
Deal found 10/13![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:05 pm -
1 stop5h 30m
Tue 11/1710:05 am -
1 stop5h 10m
Deal found 10/12![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 10/10. 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 11/76:15 am -
1 stop7h 15m
Sat 11/1410:25 am -
1 stop5h 45m
Deal found 10/10![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/284:45 pm -
Nonstop0h 50m
Thu 12/35:20 pm -
1 stop5h 00m
Deal found 10/11![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:50 pm -
Nonstop0h 50m
Sun 11/159:15 pm -
Nonstop1h 00m
Deal found 10/11![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:55 am -
Nonstop0h 50m
Sun 11/19:15 pm -
Nonstop0h 55m
Deal found 10/11![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:32 pm -
1 stop4h 07m
Tue 11/175:29 pm -
1 stop3h 58m
Deal found 10/11![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
1 stop5h 47m
Tue 11/101:31 pm -
1 stop4h 27m
Deal found 10/13![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:05 am -
1 stop5h 42m
Sat 10/315:31 pm -
1 stop4h 03m
Deal found 10/12![Delta logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sat 10/247:00 am -
1 stop24h 48m
Wed 10/286:42 pm -
2 stops27h 44m
Deal found 10/9![Multiple Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 10/10. 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 10/3112:30 pm -
1 stop4h 17m
Sun 11/110:12 am -
1 stop6h 29m
Deal found 10/10![Delta logo]()
$457
Best flights from Wisconsin to MidwayDiscover carefully curated flight deals from Wisconsin to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
Discover carefully curated flight deals from Wisconsin to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:50 am -
Nonstop1h 05m
Thu 12/39:10 pm -
Nonstop1h 05m
Deal found 10/12![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 10/10. 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 1/812:06 pm -
1 stop4h 44m
Mon 1/2512:30 pm -
1 stop4h 11m
Deal found 10/10![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:50 pm -
Nonstop0h 50m
Mon 11/99:15 pm -
Nonstop1h 00m
Deal found 10/11![Southwest logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sat 10/247:00 am -
1 stop24h 48m
Wed 10/286:42 pm -
2 stops27h 44m
Deal found 10/9![Multiple Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:30 am -
Nonstop1h 05m
Sat 11/146:15 pm -
Nonstop0h 55m
Deal found 10/14![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 10/10. 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 11/71:45 pm -
Nonstop0h 55m
Sat 11/1410:25 am -
1 stop5h 45m
Deal found 10/10![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:30 am -
1 stop4h 35m
Tue 11/179:10 pm -
Nonstop1h 05m
Deal found 10/12![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 10/10. 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 1/912:06 pm -
1 stop4h 44m
Tue 1/265:35 pm -
1 stop4h 00m
Deal found 10/10![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/126:30 am -
1 stop5h 21m
Tue 1/2612:30 pm -
1 stop4h 11m
Deal found 10/10![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/126:30 am -
1 stop5h 21m
Wed 1/271:00 pm -
1 stop3h 37m
Deal found 10/10![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:32 pm -
1 stop4h 07m
Tue 11/175:29 pm -
1 stop3h 58m
Deal found 10/11![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
1 stop5h 47m
Tue 11/101:31 pm -
1 stop4h 27m
Deal found 10/13![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:00 am -
1 stop5h 51m
Wed 11/1810:34 am -
1 stop5h 57m
Deal found 10/14![Delta logo]()
$329
This Mytrip deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:40 pm -
3 stops27h 07m
Sun 11/86:08 am -
3 stops31h 28m
Deal found 10/14![Multiple Airlines logo]()
$679
This Delta deal was found by Cheapflights users on 10/10. 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.
Sun 1/105:25 pm -
2 stops19h 08m
Sun 1/2412:30 pm -
1 stop4h 11m
Deal found 10/10![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 10/10. 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 1/115:25 pm -
2 stops19h 08m
Wed 1/271:00 pm -
1 stop3h 37m
Deal found 10/10![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:30 pm -
1 stop4h 17m
Sun 11/110:12 am -
1 stop6h 29m
Deal found 10/14![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:00 am -
1 stop5h 47m
Sun 11/110:12 am -
1 stop6h 29m
Deal found 10/13![Delta logo]()
$587
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2710:49 am -
1 stop5h 50m
Fri 12/410:24 am -
1 stop3h 46m
Deal found 10/13![Delta logo]()
$999
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/256:15 am -
1 stop5h 36m
Mon 3/19:55 am -
1 stop4h 00m
Deal found 10/10![Delta logo]()
$1,323
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop5h 47m
Sun 11/810:12 am -
1 stop3h 59m
Deal found 10/12![Delta logo]()
$1,323
This Delta deal was found by Cheapflights users on 10/10. 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 11/77:59 am -
1 stop3h 48m
Sat 11/1410:34 am -
1 stop3h 26m
Deal found 10/10![Delta logo]()
$1,323
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:32 am -
1 stop5h 27m
Sat 12/125:30 pm -
1 stop3h 59m
Deal found 10/13![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:59 am -
1 stop3h 48m
Wed 11/1812:30 pm -
1 stop6h 37m
Deal found 10/13![Delta logo]()
$1,343
This Delta deal was found by Cheapflights users on 10/10. 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.
Sun 10/256:00 am -
1 stop5h 47m
Thu 10/295:31 pm -
1 stop3h 24m
Deal found 10/10![Delta logo]()
$1,359
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop5h 47m
Wed 10/2810:12 am -
1 stop3h 59m
Deal found 10/12![Delta logo]()
$1,383
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:59 am -
1 stop3h 48m
Thu 12/249:30 am -
1 stop6h 44m
Deal found 10/11![Delta logo]()
$1,399
Last-minute flights from Wisconsin to MidwayDiscover last-minute flight deals from Wisconsin to Midway. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Midway. Data last updated October 14, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:05 am -
1 stop5h 42m
Sat 10/315:31 pm -
1 stop4h 03m
Deal found 10/12![Delta logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Sat 10/247:00 am -
1 stop24h 48m
Wed 10/286:42 pm -
2 stops27h 44m
Deal found 10/9![Multiple Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:55 am -
Nonstop0h 50m
Sun 11/19:15 pm -
Nonstop0h 55m
Deal found 10/11![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 10/10. 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 10/3112:30 pm -
1 stop4h 17m
Sun 11/110:12 am -
1 stop6h 29m
Deal found 10/10![Delta logo]()
$457
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
1 stop5h 47m
Tue 11/101:31 pm -
1 stop4h 27m
Deal found 10/13![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:50 pm -
Nonstop0h 50m
Mon 11/99:15 pm -
Nonstop1h 00m
Deal found 10/9![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 10/10. 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 11/76:15 am -
1 stop7h 15m
Sat 11/1410:25 am -
1 stop5h 45m
Deal found 10/10![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/84:50 pm -
Nonstop0h 50m
Sun 11/159:15 pm -
Nonstop1h 00m
Deal found 10/11![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:05 pm -
1 stop5h 30m
Tue 11/1710:05 am -
1 stop5h 10m
Deal found 10/12![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:32 pm -
1 stop4h 07m
Tue 11/175:29 pm -
1 stop3h 58m
Deal found 10/11![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:15 pm -
Nonstop0h 55m
Thu 12/31:15 pm -
2 stops8h 10m
Deal found 10/13![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/284:45 pm -
Nonstop0h 50m
Thu 12/35:20 pm -
1 stop5h 00m
Deal found 10/11![Southwest logo]()
$239
One-way flights from Wisconsin to MidwaySearch for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
Search for one-way flight options from Wisconsin to Midway. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Southwest deal was found by Cheapflights users on 10/10. 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.
Tue 11/106:20 am -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:15 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$120
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:45 am -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:40 am -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Southwest logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Mon 12/75:24 pm -
2 stops18h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:11 pm -
2 stops38h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$160
This Mytrip deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
2 stops18h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$199
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:59 pm -
1 stop16h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:37 pm -
2 stops16h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:00 am -
1 stop26h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Allegiant Air logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:51 am -
2 stops25h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$241
This Trip.com deal was found by Cheapflights users on 10/9. 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.
Thu 12/106:10 pm -
1 stop26h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Multiple Airlines logo]()
$244
Find flight deals from Wisconsin to Midway
Keep the following information in mind while searching for Wisconsin to Midway flight deals. Data was last updated October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Southwest) |
One-way from | $105 (Southwest) |
Good round-trip deal | $384 or less |
Good one-way deal | $183 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin 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 7,457,451 searches. Data last updated October 14, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Wed 12/2
6:20 am-7:20 am
Nonstop1h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Tue 11/10
11:30 am-4:05 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Mon 11/9
7:55 am-2:10 pm
1 stop6h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Wed 11/25
7:55 am-12:15 pm
1 stop4h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sun 12/13
7:55 am-11:40 am
1 stop3h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Fri 11/13
5:35 pm-8:50 am
1 stop15h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 11/26
5:50 am-6:55 am
Nonstop1h 05m
Chicago Midway
Thu 12/3
9:10 pm-10:15 pm
Nonstop1h 05m
$209
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 11/5
4:50 pm-5:40 pm
Nonstop0h 50m
Chicago Midway
Mon 11/9
9:15 pm-10:15 pm
Nonstop1h 00m
$209
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 11/12
5:30 am-6:35 am
Nonstop1h 05m
Chicago Midway
Sat 11/14
6:15 pm-7:10 pm
Nonstop0h 55m
$209
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sat 11/7
1:45 pm-2:40 pm
Nonstop0h 55m
Chicago Midway
Sat 11/14
10:25 am-4:10 pm
1 stop5h 45m
$219
Showing 1-10 of 54 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Wisconsin with our price prediction graph.
MKE-MDW
ATW-MDW
MSN-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 Wisconsin to Chicago Midway Airport
USWI-MDW
MKE-MDW
ATW-MDW
MSN-MDW
What is the cheapest time of day to fly from WI to MDW?
Find hourly flight availability from Wisconsin 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 October 14, 2026.
When flying from Wisconsin to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
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.
Alternative routes
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Popular flights
Top destinations