Enjoy free snacks and non-alcoholic beverages, plus a complimentary drink on special occasions.
Southwest offers free messaging and high-speed Wi-Fi for a fee on flights.

Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $111 (Kiwi.com) |
One-way from | $63 (Trip.com) |
Popular in | December |
Cheapest in | January |
Average price | $378 |
Good round-trip deal | $190 or less |
Good one-way deal | $123 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 1/24
7:50 pm-10:45 pm
Nonstop3h 55m
Phoenix Sky Harbor Intl
Sat 1/31
11:05 am-3:20 pm
Nonstop3h 15m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Tue 1/13
7:50 pm-10:45 pm
Nonstop3h 55m
Phoenix Sky Harbor Intl
Wed 1/21
8:50 am-1:10 pm
Nonstop3h 20m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 2/21
2:05 pm-7:00 pm
1 stop5h 55m
Phoenix Sky Harbor Intl
Sat 2/28
5:15 am-9:30 am
Nonstop3h 15m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 1/21
5:05 am-8:15 am
Nonstop4h 10m
Phoenix Sky Harbor Intl
Fri 1/23
6:35 pm-10:50 pm
Nonstop3h 15m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 2/18
8:10 am-1:35 pm
1 stop6h 25m
Phoenix Sky Harbor Intl
Sat 2/21
5:15 am-9:30 am
Nonstop3h 15m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 2/21
4:13 pm-10:16 pm
1 stop7h 03m
Phoenix Sky Harbor Intl
Tue 2/24
11:59 pm-8:54 am
1 stop7h 55m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Tue 1/13
1:49 pm-9:02 pm
1 stop8h 13m
Phoenix Sky Harbor Intl
Sat 1/17
11:59 pm-8:52 am
1 stop7h 53m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 2/18
7:20 pm-12:11 am
1 stop5h 51m
Phoenix Sky Harbor Intl
Tue 2/24
11:50 pm-9:54 am
1 stop9h 04m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Tue 1/13
1:49 pm-9:02 pm
1 stop8h 13m
Phoenix Sky Harbor Intl
Sun 1/18
11:59 pm-8:52 am
1 stop7h 53m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Tue 1/13
1:49 pm-9:02 pm
1 stop8h 13m
Phoenix Sky Harbor Intl
Wed 1/21
11:53 pm-9:53 am
1 stop9h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
The best time to book flights from Chicago Midway Airport to Phoenix Sky Harbor Intl Airport is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Phoenix Sky Harbor Intl Airport (average of $80). Flying from Chicago Midway Airport to Phoenix Sky Harbor Intl Airport in June is currently the most expensive (average of $176). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Phoenix Sky Harbor Intl Airport at noon. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the afternoon.
Travelers seeking maximum savings on their Chicago Midway Airport to Phoenix Sky Harbor Intl Airport flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
About 14% of weekly flights between Chicago and Phoenix have experienced delays in the past year, with the average delay time being 128 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Thursday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 14% of flights being delayed.
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Entertainment
Boarding
Overall
Crew
Comfort
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$209 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$210 | Average$364 | FlexibilityNo cancel fee | On-time63% |