$128+ Cheap flights from Sky Harbor Intl (PHX) 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
PHX — MDW
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from Sky Harbor Intl 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.Cheapflights Tip: The best prices from Phoenix Sky Harbor Intl to Chicago Midway are usually found in September or April, booked 62 days in advance, depart on a Thursday or Saturday and return on a Thursday
Cheap flight deals from Sky Harbor Intl to Midway
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Best
Last-minute
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Cheapest flights from Sky Harbor Intl to MidwayExplore the most affordable flight options available from Sky Harbor Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
Explore the most affordable flight options available from Sky Harbor Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/215:45 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Tue 7/2812:20 pm
MDW
- PHX
1 stop4h 45m
Southwest
Deal found 6/16![Southwest logo]()
$251
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/259:50 pm
PHX
- MDW
1 stop11h 17m
Frontier
Wed 7/294:45 pm
MDW
- PHX
1 stop8h 14m
Frontier
Deal found 6/18![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/189:50 pm
PHX
- MDW
1 stop11h 17m
Frontier
Tue 7/215:46 pm
MDW
- PHX
1 stop7h 13m
Frontier
Deal found 6/16![Frontier logo]()
$254
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/84:25 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Tue 7/145:30 am
MDW
- PHX
1 stop6h 10m
Southwest
Deal found 6/15![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/512:35 am
PHX
- MDW
Nonstop3h 15m
Southwest
Wed 8/125:20 pm
MDW
- PHX
Nonstop3h 40m
Southwest
Deal found 6/15![Southwest logo]()
$257
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:23 pm
PHX
- MDW
1 stop8h 28m
Frontier
Tue 8/115:46 pm
MDW
- PHX
1 stop7h 34m
Frontier
Deal found 6/14![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/1711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Sat 7/2512:11 pm
MDW
- PHX
1 stop9h 26m
Frontier
Deal found 6/16![Frontier logo]()
$259
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/88:00 am
PHX
- MDW
1 stop4h 35m
Southwest
Wed 7/155:30 am
MDW
- PHX
1 stop6h 10m
Southwest
Deal found 6/16![Southwest logo]()
$260
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Tue 7/285:46 pm
MDW
- PHX
1 stop7h 13m
Frontier
Deal found 6/18![Frontier logo]()
$262
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:35 am
PHX
- MDW
1 stop5h 25m
Southwest
Mon 9/75:40 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/16![Southwest logo]()
$263
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Fri 7/2412:11 pm
MDW
- PHX
1 stop9h 33m
Frontier
Deal found 6/16![Frontier logo]()
$264
Best flights from Sky Harbor Intl to MidwayDiscover carefully curated flight deals from Sky Harbor Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
Discover carefully curated flight deals from Sky Harbor Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/215:45 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Tue 7/285:25 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/16![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:05 pm
PHX
- MDW
1 stop8h 12m
Delta
Mon 8/249:59 am
MDW
- PHX
1 stop8h 02m
Delta
Deal found 6/15![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:35 am
PHX
- MDW
Nonstop3h 15m
Southwest
Sat 8/85:40 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/14![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:35 am
PHX
- MDW
Nonstop3h 15m
Southwest
Mon 8/175:40 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/18![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/106:00 am
PHX
- MDW
Nonstop3h 20m
Southwest
Fri 8/146:15 pm
MDW
- PHX
Nonstop3h 40m
Southwest
Deal found 6/17![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:30 pm
PHX
- MDW
Nonstop3h 15m
Southwest
Sun 8/2310:40 am
MDW
- PHX
1 stop4h 55m
Southwest
Deal found 6/15![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/156:50 pm
PHX
- MDW
Nonstop3h 20m
Southwest
Sat 7/187:40 pm
MDW
- PHX
Nonstop3h 45m
Southwest
Deal found 6/17![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/155:45 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Sun 7/195:25 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/18![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:40 am
PHX
- MDW
1 stop4h 40m
Southwest
Sun 8/95:40 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/17![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:00 am
PHX
- MDW
1 stop4h 35m
Southwest
Sun 8/305:40 am
MDW
- PHX
Nonstop3h 35m
Southwest
Deal found 6/15![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:35 am
PHX
- MDW
Nonstop3h 15m
Southwest
Sun 9/208:00 am
MDW
- PHX
1 stop5h 05m
Southwest
Deal found 6/18![Southwest logo]()
$333
Last-minute flights from Sky Harbor Intl to MidwayDiscover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated June 19, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/46:24 am
PHX
- MDW
1 stop6h 51m
Frontier
Sat 7/1812:11 pm
MDW
- PHX
1 stop9h 26m
Frontier
Deal found 6/18![Frontier logo]()
$257
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/84:25 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Tue 7/145:30 am
MDW
- PHX
1 stop6h 10m
Southwest
Deal found 6/15![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/88:00 am
PHX
- MDW
1 stop4h 35m
Southwest
Wed 7/155:30 am
MDW
- PHX
1 stop6h 10m
Southwest
Deal found 6/16![Southwest logo]()
$260
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Wed 7/2212:11 pm
MDW
- PHX
1 stop9h 33m
Frontier
Deal found 6/16![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Fri 7/1711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Sat 7/2512:11 pm
MDW
- PHX
1 stop9h 26m
Frontier
Deal found 6/16![Frontier logo]()
$259
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Fri 7/2412:11 pm
MDW
- PHX
1 stop9h 33m
Frontier
Deal found 6/16![Frontier logo]()
$264
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/189:50 pm
PHX
- MDW
1 stop11h 17m
Frontier
Tue 7/215:46 pm
MDW
- PHX
1 stop7h 13m
Frontier
Deal found 6/16![Frontier logo]()
$254
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/215:45 pm
PHX
- MDW
Nonstop3h 25m
Southwest
Tue 7/2812:20 pm
MDW
- PHX
1 stop4h 45m
Southwest
Deal found 6/16![Southwest logo]()
$251
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/259:50 pm
PHX
- MDW
1 stop11h 17m
Frontier
Wed 7/294:45 pm
MDW
- PHX
1 stop8h 14m
Frontier
Deal found 6/18![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Tue 7/285:46 pm
MDW
- PHX
1 stop7h 13m
Frontier
Deal found 6/18![Frontier logo]()
$262
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/281:15 pm
PHX
- MDW
1 stop7h 00m
Delta
Wed 7/296:00 am
MDW
- PHX
1 stop8h 03m
Delta
Deal found 6/18![Delta logo]()
$265
One-way flights from Sky Harbor Intl to MidwaySearch for one-way flight options from Sky Harbor Intl to Midway. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
Search for one-way flight options from Sky Harbor Intl to Midway. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/148:00 am
PHX
- MDW
1 stop4h 35m
Southwest
Deal found 6/16![Southwest logo]()
$128
This Frontier deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Fri 8/1411:23 pm
PHX
- MDW
1 stop8h 28m
Frontier
Deal found 6/19![Frontier logo]()
$129
This Booking.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/116:24 am
PHX
- MDW
1 stop9h 02m
Frontier
Deal found 6/19![Frontier logo]()
$130
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/214:50 pm
PHX
- MDW
1 stop5h 20m
Southwest
Deal found 6/19![Southwest logo]()
$133
This Priceline deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Sat 7/46:24 am
PHX
- MDW
1 stop6h 51m
Frontier
Deal found 6/17![Frontier logo]()
$134
This Expedia deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Sun 8/166:24 am
PHX
- MDW
1 stop12h 08m
Frontier
Deal found 6/19![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/166:24 am
PHX
- MDW
1 stop12h 08m
Frontier
Deal found 6/16![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/1410:44 pm
PHX
- MDW
1 stop10h 14m
Frontier
Deal found 6/19![Frontier logo]()
$137
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:50 pm
PHX
- MDW
Nonstop3h 20m
Southwest
Deal found 6/17![Southwest logo]()
$138
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Fri 7/2411:23 pm
PHX
- MDW
1 stop9h 44m
Frontier
Deal found 6/18![Frontier logo]()
$139
This Priceline deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Sat 8/16:24 am
PHX
- MDW
1 stop9h 02m
Frontier
Deal found 6/17![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:24 am
PHX
- MDW
1 stop12h 08m
Frontier
Deal found 6/17![Frontier logo]()
$141
Find flight deals from Sky Harbor Intl to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Sky Harbor Intl (PHX) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Southwest) |
One-way from | $128 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $345 |
Good round-trip deal | $355 or less |
Good one-way deal | $194 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Sky Harbor Intl 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 June 19, 2026.
Use the filters below to find and compare flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Tue 7/21
5:45 pm-11:10 pm
Nonstop3h 25m
Chicago Midway
Tue 7/28
5:25 am-7:00 am
Nonstop3h 35m
$260
Quickest round-trip
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Wed 8/5
12:35 am-5:50 am
Nonstop3h 15m
Chicago Midway
Sat 8/8
5:40 am-7:15 am
Nonstop3h 35m
$269
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 8/20
11:05 pm-9:17 am
1 stop8h 12m
Chicago Midway
Mon 8/24
9:59 am-4:01 pm
1 stop8h 02m
$289
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 8/13
12:35 am-5:50 am
Nonstop3h 15m
Chicago Midway
Mon 8/17
5:40 am-7:15 am
Nonstop3h 35m
$293
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Mon 8/10
6:00 am-11:20 am
Nonstop3h 20m
Chicago Midway
Fri 8/14
6:15 pm-7:55 pm
Nonstop3h 40m
$293
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 8/20
1:30 pm-6:45 pm
Nonstop3h 15m
Chicago Midway
Sun 8/23
10:40 am-1:35 pm
1 stop4h 55m
$299
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Wed 7/15
6:50 pm-12:10 am
Nonstop3h 20m
Chicago Midway
Sat 7/18
7:40 pm-9:25 pm
Nonstop3h 45m
$311
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Wed 7/15
5:45 pm-11:10 pm
Nonstop3h 25m
Chicago Midway
Sun 7/19
5:25 am-7:00 am
Nonstop3h 35m
$321
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Fri 8/7
10:40 am-5:20 pm
1 stop4h 40m
Chicago Midway
Sun 8/9
5:40 am-7:15 am
Nonstop3h 35m
$323
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Fri 8/28
8:00 am-2:35 pm
1 stop4h 35m
Chicago Midway
Sun 8/30
5:40 am-7:15 am
Nonstop3h 35m
$323
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Sky Harbor Intl to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sky Harbor Intl to Midway in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Phoenix Sky Harbor Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Sky Harbor Intl to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Sky Harbor Intl with our price prediction graph.
PHX-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 Phoenix Sky Harbor Intl Airport to Chicago Midway Airport
Prices
Airlines
How far ahead should I book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?
Booking 61 days in advance of your planned departure date is, on average, the best time to get cheap flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $195). Flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of $497). 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 PHX to MDW?
Find hourly flight availability from Sky Harbor Intl 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 June 19, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 24% on flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Sky Harbor Intl to Midway. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight should consider departing on Thursday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Phoenix Sky Harbor Intl Airport to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 19, 2026.
Read reviews from past customers who have flown Southwest and Frontier from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Sky Harbor Intl 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
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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 June 19, 2026.
Sky Harbor Intl and Midway flights
Browse other Sky Harbor Intl and Midway flight options. Last updated on June 19, 2026.
Other flights from Sky Harbor Intl
Browse through other flights departing from Sky Harbor Intl. Flights are based on user searches made on Cheapflights and were last updated on June 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Sky Harbor Intl to Midway
Discover the top 2 airlines that operate flights from Sky Harbor Intl 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 June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$195 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$207 | Average$363 | FlexibilityNo cancel fee | On-time63% |