$128+ Cheap flights from Sky Harbor Intl (PHX) 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PHX — MDW
Oct 17 — Oct 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 April or October, booked 57 days in advance, depart on a Thursday or Friday and return on a Thursday
Cheap flight deals from Sky Harbor Intl to Midway
Cheapest
Best
Last-minute
One-way
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 10/194:45 pm -
1 stop5h 55m
Mon 10/267:15 pm -
Nonstop3h 45m
Deal found 9/16![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 9/16. 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.
Fri 10/234:45 pm -
1 stop5h 55m
Tue 10/276:55 am -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 9/14. 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 11/181:35 am -
Nonstop3h 10m
Tue 12/16:05 am -
1 stop6h 10m
Deal found 9/14![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 9/15. 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 10/157:55 pm -
Nonstop3h 20m
Thu 10/226:00 pm -
1 stop5h 20m
Deal found 9/15![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/96:55 pm -
Nonstop3h 20m
Wed 10/146:05 am -
1 stop6h 10m
Deal found 9/14![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/208:20 am -
1 stop5h 40m
Thu 10/2210:55 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$247
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:01 am -
1 stop7h 34m
Mon 10/191:12 pm -
1 stop11h 47m
Deal found 9/15![Frontier logo]()
$248
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/224:45 pm -
1 stop5h 55m
Sat 10/243:00 pm -
1 stop5h 35m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/17. 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 10/246:55 pm -
Nonstop3h 20m
Fri 10/3011:20 am -
Nonstop3h 45m
Deal found 9/17![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/136:35 pm -
Nonstop3h 20m
Tue 10/208:45 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$254
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/166:55 pm -
Nonstop3h 20m
Wed 10/214:45 pm -
1 stop5h 40m
Deal found 9/15![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 11/301:35 am -
Nonstop3h 10m
Sat 12/56:25 pm -
Nonstop3h 55m
Deal found 9/16![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 9/17. 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 11/301:35 am -
Nonstop3h 10m
Tue 12/18:50 pm -
Nonstop3h 50m
Deal found 9/17![Southwest logo]()
$266
This Southwest deal was found by Cheapflights users on 9/16. 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 10/215:25 pm -
Nonstop3h 20m
Sun 11/19:45 pm -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 9/16. 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.
Fri 10/234:45 pm -
1 stop5h 55m
Mon 10/266:05 am -
1 stop5h 35m
Deal found 9/16![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 9/15. 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 10/1511:00 am -
1 stop4h 45m
Thu 10/226:00 pm -
1 stop5h 20m
Deal found 9/15![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sun 11/225:45 am -
Nonstop3h 10m
Fri 11/275:10 am -
Nonstop3h 55m
Deal found 9/16![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 2/135:20 pm -
1 stop5h 35m
Tue 2/1610:25 am -
1 stop5h 15m
Deal found 9/12![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 9/16. 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 10/75:25 pm -
Nonstop3h 20m
Wed 10/1412:05 pm -
1 stop5h 00m
Deal found 9/16![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sat 11/211:35 am -
Nonstop3h 10m
Sun 12/69:45 pm -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 9/15. 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 10/224:45 pm -
1 stop5h 55m
Mon 10/263:55 pm -
2 stops8h 05m
Deal found 9/15![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 9/16. 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.
Fri 10/97:55 pm -
Nonstop3h 20m
Wed 10/148:45 pm -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$373
Last-minute flights from Sky Harbor Intl to MidwayDiscover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated September 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/96:55 pm -
Nonstop3h 20m
Wed 10/146:05 am -
1 stop6h 10m
Deal found 9/14![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/136:35 pm -
Nonstop3h 20m
Tue 10/208:45 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 9/15. 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 10/157:55 pm -
Nonstop3h 20m
Thu 10/226:00 pm -
1 stop5h 20m
Deal found 9/15![Southwest logo]()
$245
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:01 am -
1 stop7h 34m
Mon 10/191:12 pm -
1 stop11h 47m
Deal found 9/15![Frontier logo]()
$248
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 10/194:45 pm -
1 stop5h 55m
Mon 10/267:15 pm -
Nonstop3h 45m
Deal found 9/16![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/208:20 am -
1 stop5h 40m
Thu 10/2210:55 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$247
This Southwest deal was found by Cheapflights users on 9/16. 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.
Thu 10/224:45 pm -
1 stop5h 55m
Sat 10/243:00 pm -
1 stop5h 35m
Deal found 9/16![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 9/16. 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.
Fri 10/234:45 pm -
1 stop5h 55m
Tue 10/276:55 am -
Nonstop3h 50m
Deal found 9/16![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 9/17. 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 10/246:55 pm -
Nonstop3h 20m
Fri 10/3011:20 am -
Nonstop3h 45m
Deal found 9/17![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/2611:32 pm -
1 stop8h 31m
Mon 11/21:27 pm -
1 stop7h 51m
Deal found 9/15![Delta logo]()
$255
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 September 17, 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 September 17, 2026.
This Southwest deal was found by Cheapflights users on 9/16. 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.
Sun 11/1512:50 am -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 9/15. 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 10/97:55 pm -
Nonstop3h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Southwest logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
2 stops15h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$136
This Southwest deal was found by Cheapflights users on 9/16. 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.
Mon 10/194:45 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$138
This Southwest deal was found by Cheapflights users on 9/14. 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 10/224:45 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$139
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:01 am -
1 stop7h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 11/179:59 pm -
2 stops18h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 11/103:46 pm -
2 stops25h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$142
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:04 pm -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:20 am -
2 stops36h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 9/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:14 pm -
1 stop19h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$148
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Delta) |
One-way from | $128 (Delta) |
Popular in | January |
Cheapest in | April |
Average price | $357 |
Good round-trip deal | $328 or less |
Good one-way deal | $230 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 7,457,451 searches. Data last updated September 17, 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 Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Mon 10/19
6:55 pm-12:15 am
Nonstop3h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Fri 1/15
5:25 pm-9:40 pm
Nonstop3h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
Quickest round-trip
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Mon 10/5
12:35 am-5:45 am
Nonstop3h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Thu 10/29
3:45 pm-9:00 pm
Nonstop3h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Mon 10/5
6:55 pm-12:15 am
Nonstop3h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Fri 10/30
4:55 pm-12:50 am
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Fri 11/13
3:00 pm-10:54 pm
1 stop6h 54m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Fri 10/16
7:05 am-4:47 pm
1 stop7h 42m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Thu 12/17
7:25 am-4:50 pm
1 stop8h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
PhoenixChicago
PHX Phoenix Sky Harbor Intl - MDW Chicago Midway
PHXMDW
Phoenix Sky Harbor Intl
Sat 3/13
11:10 pm-7:45 am
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
Showing 1-10 of 23 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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 56 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, April is the cheapest month in which you can book a flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (average of $216). 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 September 17, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 23% 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 September 12, 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. Sunday mornings 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 September 17, 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
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
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
Other flights from Sky Harbor Intl
Popular flights
Alternative routes for Sky Harbor Intl 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 Sky Harbor Intl to Midway by cabin class
Find flights from Sky Harbor Intl 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 September 17, 2026.
Sky Harbor Intl and Midway flights
Browse other Sky Harbor Intl and Midway flight options. Last updated on September 17, 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 September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$214 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$239 | Average$395 | FlexibilityNo cancel fee | On-time63% |