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 | $163 (CheapOair) |
One-way from | $86 (Priceline) |
Popular in | March |
Cheapest in | January |
Average price | $252 |
Good round-trip deal | $180 or less |
Good one-way deal | $111 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 1/7
1:55 pm-4:50 pm
Nonstop3h 55m
Phoenix Sky Harbor Intl
Sun 1/11
6:05 pm-10:20 pm
Nonstop3h 15m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 12/10
5:15 pm-8:05 pm
Nonstop3h 50m
Phoenix Sky Harbor Intl
Tue 12/16
4:05 pm-10:35 pm
1 stop5h 30m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 1/24
7:50 pm-10:45 pm
Nonstop3h 55m
Phoenix Sky Harbor Intl
Sat 1/31
10:20 pm-5:05 am
1 stop5h 45m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Tue 1/6
7:50 pm-10:45 pm
Nonstop3h 55m
Phoenix Sky Harbor Intl
Tue 1/13
12:05 pm-7:05 pm
2 stops6h 00m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Mon 11/24
1:15 pm-7:17 pm
1 stop7h 02m
Phoenix Sky Harbor Intl
Wed 11/26
12:59 am-9:01 am
1 stop7h 02m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 12/24
5:59 pm-12:03 am
1 stop7h 04m
Phoenix Sky Harbor Intl
Wed 12/31
1:08 am-11:06 am
1 stop8h 58m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 12/17
5:29 pm-12:16 am
1 stop7h 47m
Phoenix Sky Harbor Intl
Wed 12/24
11:50 pm-8:49 am
1 stop7h 59m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Wed 12/24
5:59 pm-12:03 am
1 stop7h 04m
Phoenix Sky Harbor Intl
Wed 12/31
11:50 pm-8:49 am
1 stop7h 59m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 12/13
1:50 pm-9:23 pm
1 stop8h 33m
Phoenix Sky Harbor Intl
Mon 12/15
12:59 am-9:19 am
1 stop7h 20m
ChicagoPhoenix
MDW - PHX
MDWPHX
Chicago Midway
Sat 1/31
4:30 pm-11:48 pm
1 stop8h 18m
Phoenix Sky Harbor Intl
Wed 2/4
11:59 pm-8:54 am
1 stop7h 55m
| 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 Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 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 82 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 $104). 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 17% 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 130 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 13% of flights being delayed.
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Food
Crew
Overall
Boarding
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$220 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$213 | Average$369 | FlexibilityNo cancel fee | On-time63% |