$127+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
PHX — MDW
Sep 3 — Sep 101
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 April or September, booked 89 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 August 4, 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 August 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/212:19 pm -
1 stop8h 28m
Sat 9/56:05 am -
2 stops19h 19m
Deal found 8/3![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:19 pm -
1 stop8h 28m
Mon 8/246:05 am -
2 stops30h 06m
Deal found 8/1![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/212:19 pm -
1 stop8h 28m
Tue 9/86:05 am -
2 stops15h 16m
Deal found 8/1![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/54:55 pm -
Nonstop3h 25m
Sun 9/67:00 am -
Nonstop3h 35m
Deal found 8/3![Southwest logo]()
$253
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Sat 8/156:24 am -
1 stop9h 02m
Sat 8/2211:45 am -
1 stop8h 46m
Deal found 8/2![Frontier logo]()
$257
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/54:55 pm -
Nonstop3h 25m
Fri 9/118:00 am -
1 stop5h 50m
Deal found 8/4![Southwest logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:19 pm -
1 stop8h 28m
Thu 8/279:26 pm -
2 stops36h 14m
Deal found 8/1![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2610:35 am -
1 stop4h 35m
Tue 9/110:10 am -
1 stop4h 55m
Deal found 7/30![Southwest logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am -
1 stop12h 31m
Sun 8/239:26 pm -
1 stop16h 46m
Deal found 7/31![Frontier logo]()
$265
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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 10/24:45 pm -
1 stop5h 50m
Mon 10/57:00 am -
1 stop6h 35m
Deal found 7/30![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/1011:05 pm -
1 stop8h 02m
Tue 9/151:19 pm -
1 stop7h 56m
Deal found 8/3![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 -
Nonstop3h 15m
Thu 9/245:55 pm -
1 stop6h 05m
Deal found 8/2![Southwest logo]()
$289
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2510:35 am -
1 stop4h 35m
Tue 9/110:10 am -
1 stop4h 50m
Deal found 8/2![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/2510:35 am -
1 stop4h 35m
Mon 8/318:00 am -
1 stop5h 50m
Deal found 8/1![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/195:45 am -
1 stop6h 20m
Tue 9/2210:10 am -
1 stop4h 50m
Deal found 8/4![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/191:25 pm -
1 stop5h 25m
Sat 9/2610:00 am -
2 stops6h 50m
Deal found 7/31![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/295:00 am -
2 stops7h 15m
Mon 8/318:00 am -
1 stop5h 50m
Deal found 8/1![Southwest logo]()
$312
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/34:55 pm -
1 stop5h 35m
Sun 9/67:35 am -
1 stop6h 00m
Deal found 7/31![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/174:00 pm -
1 stop5h 50m
Tue 9/2210:10 am -
1 stop4h 50m
Deal found 7/31![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/118:00 am -
1 stop4h 35m
Sun 9/138:00 am -
1 stop5h 05m
Deal found 8/1![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/1812:35 am -
Nonstop3h 15m
Thu 8/277:10 am -
Nonstop3h 35m
Deal found 8/3![Southwest logo]()
$360
Last-minute flights from Sky Harbor Intl to MidwayDiscover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Sky Harbor Intl to Midway. Data last updated August 4, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Sat 8/156:24 am -
1 stop9h 02m
Sat 8/2211:45 am -
1 stop8h 46m
Deal found 8/2![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am -
1 stop12h 31m
Sun 8/239:26 pm -
1 stop16h 46m
Deal found 7/31![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:19 pm -
1 stop8h 28m
Mon 8/246:05 am -
2 stops30h 06m
Deal found 8/1![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:19 pm -
1 stop8h 28m
Thu 8/279:26 pm -
2 stops36h 14m
Deal found 8/1![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 8/2610:35 am -
1 stop4h 35m
Tue 9/110:10 am -
1 stop4h 55m
Deal found 7/30![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/112:35 am -
Nonstop3h 15m
Sat 9/56:15 pm -
Nonstop3h 45m
Deal found 8/4![Southwest logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/212:19 pm -
1 stop8h 28m
Sat 9/56:05 am -
2 stops19h 19m
Deal found 8/3![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/212:19 pm -
1 stop8h 28m
Tue 9/86:05 am -
2 stops15h 16m
Deal found 8/1![Frontier logo]()
$251
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/53:00 pm -
Nonstop3h 15m
Fri 9/117:10 am -
Nonstop3h 35m
Deal found 8/4![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/58:10 am -
1 stop7h 35m
Sun 9/67:00 am -
Nonstop3h 35m
Deal found 8/3![Southwest logo]()
$263
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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/54:55 pm -
Nonstop3h 25m
Deal found 8/3![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/104:00 pm -
1 stop5h 50m
Deal found 7/30![Southwest logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:56 pm -
2 stops18h 55m
Deal found 7/30![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/168:39 pm -
2 stops13h 20m
Deal found 7/31![Frontier logo]()
$136
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/3011:57 am -
1 stop8h 36m
Deal found 8/3![Delta logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” 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 9/106:25 am -
2 stops15h 19m
Deal found 7/30![Frontier logo]()
$138
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/23:50 pm -
Nonstop3h 15m
Deal found 7/31![Southwest logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/308:30 am -
2 stops25h 29m
Deal found 8/1![Frontier logo]()
$143
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/2510:35 am -
1 stop4h 35m
Deal found 7/31![Southwest logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:40 pm -
2 stops21h 13m
Deal found 8/2![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:30 pm -
2 stops34h 25m
Deal found 7/31![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/12:04 pm -
2 stops18h 51m
Deal found 8/3![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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $245 (Kiwi.com) |
One-way from | $127 (Southwest) |
Popular in | January |
Cheapest in | April |
Average price | $335 |
Good round-trip deal | $344 or less |
Good one-way deal | $215 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 August 4, 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
Fri 10/2
4:45 pm-12:35 am
1 stop5h 50m
Chicago Midway
Mon 10/5
7:00 am-11:35 am
1 stop6h 35m
$289
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Wed 9/16
12:35 am-5:50 am
Nonstop3h 15m
Chicago Midway
Thu 9/24
5:55 pm-10:00 pm
1 stop6h 05m
$289
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Tue 8/25
10:35 am-5:10 pm
1 stop4h 35m
Chicago Midway
Tue 9/1
10:10 am-1:00 pm
1 stop4h 50m
$290
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Tue 8/25
10:35 am-5:10 pm
1 stop4h 35m
Chicago Midway
Mon 8/31
8:00 am-11:50 am
1 stop5h 50m
$290
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Sat 9/19
5:45 am-2:05 pm
1 stop6h 20m
Chicago Midway
Tue 9/22
10:10 am-1:00 pm
1 stop4h 50m
$294
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 9/10
11:05 pm-9:07 am
1 stop8h 02m
Chicago Midway
Tue 9/15
1:19 pm-7:15 pm
1 stop7h 56m
$299
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Sat 9/19
1:25 pm-8:50 pm
1 stop5h 25m
Chicago Midway
Sat 9/26
10:00 am-2:50 pm
2 stops6h 50m
$300
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Sat 8/29
5:00 am-2:15 pm
2 stops7h 15m
Chicago Midway
Mon 8/31
8:00 am-11:50 am
1 stop5h 50m
$312
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 9/3
4:55 pm-12:30 am
1 stop5h 35m
Chicago Midway
Sun 9/6
7:35 am-11:35 am
1 stop6h 00m
$320
PhoenixChicago
PHX - MDW
PHXMDW
Phoenix Sky Harbor Intl
Thu 9/17
4:00 pm-11:50 pm
1 stop5h 50m
Chicago Midway
Tue 9/22
10:10 am-1:00 pm
1 stop4h 50m
$334
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 August.
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 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
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 August 4, 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 August 1, 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 August 4, 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.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
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
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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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$73 | Average$187 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$222 | Average$387 | FlexibilityNo cancel fee | On-time63% |