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C$67 Cheap Flights from Phoenix Sky Harbor (PHX) to Chicago Midway (MDW)

Compare Phoenix Sky Harbor to Chicago Midway flight deals

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Flight deals from Phoenix Sky Harbor Airport to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Phoenix Sky Harbor Airport to Chicago Midway Airport? If you want to travel next month, return fares start from C$112. Find the lowest prices on one-way and return tickets right here.
Chicago.C$66 per passenger.Departing Thu., Apr. 30.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Phoenix Sky Harbor on Thu., Apr. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$66, select.
Chicago.C$107 per passenger.Departing Tue., May 19.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Phoenix Sky Harbor on Tue., May 19, arriving in Chicago Midway.Price includes taxes and charges.From C$107, select.
Chicago.C$114 per passenger.Departing Tue., May 12.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Tue., May 12, arriving in Chicago Midway.Price includes taxes and charges.From C$114, select.
Chicago.C$142 per passenger.Departing Sun., Jun. 7.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Phoenix Sky Harbor on Sun., Jun. 7, arriving in Chicago Midway.Price includes taxes and charges.From C$142, select.
Chicago.C$172 per passenger.Departing Fri., Aug. 14.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Phoenix Sky Harbor on Fri., Aug. 14, arriving in Chicago Midway.Price includes taxes and charges.From C$172, select.
Chicago.C$172 per passenger.Departing Sat., Jul. 11.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Phoenix Sky Harbor on Sat., Jul. 11, arriving in Chicago Midway.Price includes taxes and charges.From C$172, select.
Chicago.C$176 per passenger.Departing Sat., Aug. 1.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Sat., Aug. 1, arriving in Chicago Midway.Price includes taxes and charges.From C$176, select.
Chicago.C$176 per passenger.Departing Wed., Jun. 3.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Wed., Jun. 3, arriving in Chicago Midway.Price includes taxes and charges.From C$176, select.
Chicago.C$176 per passenger.Departing Sat., Jul. 11.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Sat., Jul. 11, arriving in Chicago Midway.Price includes taxes and charges.From C$176, select.
Chicago.C$177 per passenger.Departing Wed., Sep. 23.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Wed., Sep. 23, arriving in Chicago Midway.Price includes taxes and charges.From C$177, select.
Chicago.C$189 per passenger.Departing Tue., Oct. 27.One-way flight with Delta.Outbound indirect flight with Delta, departs from Phoenix Sky Harbor on Tue., Oct. 27, arriving in Chicago Midway.Price includes taxes and charges.From C$189, select.
Chicago.C$192 per passenger.Departing Mon., Mar. 30.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Phoenix Sky Harbor on Mon., Mar. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$192, select.
Chicago.C$219 per passenger.Departing Tue., Oct. 27.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Phoenix Sky Harbor on Tue., Oct. 27, arriving in Chicago Midway.Price includes taxes and charges.From C$219, select.
Chicago.C$232 per passenger.Departing Mon., Jan. 4.One-way flight with Delta.Outbound indirect flight with Delta, departs from Phoenix Sky Harbor on Mon., Jan. 4, arriving in Chicago Midway.Price includes taxes and charges.From C$232, select.
Chicago.C$370 per passenger.Departing Mon., Feb. 15.One-way flight with Delta.Outbound indirect flight with Delta, departs from Phoenix Sky Harbor on Mon., Feb. 15, arriving in Chicago Midway.Price includes taxes and charges.From C$370, select.

Find the cheapest month to fly from Phoenix Sky Harbor to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Phoenix Sky Harbor to Chicago Midway flights are currently cheapest in April.
Mar.
from C$192
Apr.
from C$66
May
from C$107
Jun.
from C$142
Jul.
from C$172
Aug.
from C$172
Sep.
from C$177
Oct.
from C$189
Nov.
Find prices
Dec.
Find prices
Jan.
from C$232
Feb.
from C$370

Which airlines fly from Phoenix Sky Harbor to Chicago Midway?

Phoenix Sky Harbor to Chicago Midway: Alternative routes

Compare routes from Phoenix Sky Harbor to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Chicago Midway

14km from central Chicago
ClosestCheapest
from C$66
Search flights

Chicago O'Hare International

25km from central Chicago
from C$103
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from C$178
Search flights

Phoenix to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$66
Cheapest month to flyApril
Average flight time3 hrs, 17 mins
Most popular airlineSouthwest Airlines
Average flights per week38

Finding cheap flights from Phoenix Sky Harbor to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Phoenix Sky Harbor to Chicago Midway is C$112. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 17 minutes is the average flight time from Phoenix Sky Harbor to Chicago Midway.
Southwest Airlines, Frontier Airlines and Volaris fly direct from Phoenix Sky Harbor to Chicago Midway.
As of March 2026, there are 38 flights per week flying from Phoenix Sky Harbor to Chicago Midway.
The cheapest month to fly from Phoenix Sky Harbor to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Phoenix Sky Harbor Airport to Chicago Midway Airport on Thursday, April 23, 2026.
Yes – the average flight time is 3 hours and 17 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Phoenix Sky Harbor International Airport (PHX) to Chicago Midway International Airport (MDW): what you need to know

  • A direct flight from Phoenix Sky Harbor International Airport to Chicago Midway International Airport takes an average of 3 hours 21 minutes. The timezone in Chicago is UTC-5, making it 2 hours ahead of Phoenix.

  • For the earliest departure, take the 05:00 flight from Phoenix Sky Harbor International Airport to Chicago Midway International Airport. If you'd like to go later, the latest flight departs at 22:55. With 46 flights each week from PHX to MDW, you can pick the one that works best for you.

  • Longer lines at security and check-in are likely if you're heading away during high season, so give yourself some extra breathing room. A good rule of thumb for peak periods? Get there up to four hours early for international flights and at least two hours for domestic departures.

  • We make it a cinch to get a flight with a stopover. To see all the options for flights from Phoenix Sky Harbor International Airport to Chicago Midway International Airport, uncheck 'Direct flights only.' Then, choose a flight offering a stop long enough to tour the city of your choice. Popular stopovers between PHX and MDW are:

    • Eppley Airfield

    • Denver International Airport

    • Albuquerque International Sunport

How to find the cheapest flights from Phoenix Sky Harbor International Airport (PHX) to Chicago Midway International Airport (MDW)

  • C$67 is currently the lowest price for a one-way ticket from Phoenix Sky Harbor International Airport to Chicago Midway International Airport. Return flights start from C$112. These fares may change depending on availability and demand.

  • Score cheap flight tickets from PHX to MDW by booking at least 9 months ahead. Based on our research, that's the sweet spot for finding a bargain.

  • Organize your trip for May. That's the cheapest month for flight tickets from Phoenix Sky Harbor International Airport to Chicago Midway International Airport. If you're flexible with your travel dates, use the 'Whole month' tool to see the lowest price across every month.

  • Log into your online account or use the app to set up a Price Alert. We'll get in touch right away if there's a better deal on this route. It's simple to do, and it'll save you the hassle of checking for cheap flight tickets from PHX to MDW every day.

  • Tailor your flights using filters. Pick your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Phoenix Sky Harbor International Airport to Chicago Midway International Airport.

Handy information about Phoenix Sky Harbor International Airport (PHX)

Arriving at Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Chicago Midway International Airport to the center of Chicago is around 21 minutes in a car. It's approximately 19 kilometres away. Find out what options are available, such as car rentals, cabs or ride-sharing.

  • It takes roughly 46 minutes if you're using public transport.

When to fly to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from Phoenix Sky Harbor International Airport to Chicago Midway International Airport. To steer clear of the crowds, visit Chicago in May.

  • When booking your flight from Phoenix Sky Harbor International Airport to Chicago Midway International Airport, think about the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • If you'd rather travel in cooler conditions, search for a cheap ticket from PHX to MDW in January. Average temperatures are between -12ºC and 3ºC then.

More about Chicago

Complete your Chicago trip with hotels and a car rental

  • Comparing flights is not the only thing we're good at. Once you've booked your cheap ticket to Chicago Midway International Airport, check out our car rental deals that'll give you the flexibility and freedom to see the sights at your own pace. Next, take a look at our exclusive rates for hotels to find the perfect Chicago stay.

Plan the rest of your trip from Phoenix to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.