$100 Cheap Flights from Phoenix (PHX) to Chicago (MDW)

View $100 flight on Wed, May 21, 2025Opens in a new window

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key
Find available prices by choosing your travel dates.

Cheap Flights from Phoenix to Chicago (PHX-MDW)

Prices were available within the past 7 days and start at $100 for one-way flights and $172 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, May 10 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, May 10 from Phoenix to Chicago, returning Sun, May 25, priced at $172 found 4 days ago
Frontier Airlines
Sun, May 11 - Thu, May 29
PHX
Phoenix
MDW
Chicago
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 11 from Phoenix to Chicago, returning Thu, May 29, priced at $176 found 4 days ago
Frontier Airlines
Sun, May 11 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, May 11 from Phoenix to Chicago, returning Sun, May 25, priced at $186 found 2 days ago
Frontier Airlines
Sat, May 24 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Phoenix to Chicago, returning Sun, May 25, priced at $190 found 3 hours ago
Southwest Airlines
Sat, May 10 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, May 10 from Phoenix to Chicago, returning Sun, May 25, priced at $192 found 4 days ago
Frontier Airlines
Sun, May 18 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 18 from Phoenix to Chicago, returning Sun, May 25, priced at $193 found 1 day ago
Frontier Airlines
Sun, May 18 - Sun, May 25
PHX
Phoenix
MDW
Chicago
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, May 18 from Phoenix to Chicago, returning Sun, May 25, priced at $195 found 3 days ago
Frontier Airlines
Tue, May 27 - Thu, Jun 5
PHX
Phoenix
MDW
Chicago
$198 Roundtrip, found 1 hour ago
$198
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, May 27 from Phoenix to Chicago, returning Thu, Jun 5, priced at $198 found 1 hour ago
Southwest Airlines
Wed, May 14 - Sat, May 17
PHX
Phoenix
MDW
Chicago
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, May 14 from Phoenix to Chicago, returning Sat, May 17, priced at $199 found 4 days ago
Delta
Wed, May 21 - Sat, May 31
PHX
Phoenix
MDW
Chicago
$222 Roundtrip, found 3 hours ago
$222
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, May 21 from Phoenix to Chicago, returning Sat, May 31, priced at $222 found 3 hours ago
Flights from Phoenix (PHX) to Chicago (MDW)
Origin airport
Sky Harbor Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$158
Distance
1441 mi

Phoenix to Chicago Flights

The cheapest times to fly from Phoenix to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Phoenix to Chicago are during the month of May. You can find some of the cheapest flights from Phoenix to Chicago with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Phoenix to Chicago

Sunday is one of the best days to book for cheap flights from Phoenix to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Phoenix to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Phoenix to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $100 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Phoenix to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Phoenix to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How long does it take to fly from Phoenix Sky Harbor Intl. Airport to Chicago Airport?
Book a fare with Frontier Airlines and you’ll be cruising the skies for around 3 hours and 22 minutes. This well-known airline has a direct flight that departs at 4:22PM from Phoenix Sky Harbor Intl. Airport and lands at Midway Airport at 9:44PM. Expedia has some amazing flight deals, so take a peek at what’s available on this route today.
Is it cheaper to buy a plane ticket from Phoenix Sky Harbor Intl. Airport to Chicago Airport last minute?
When it’s time to book your flights, it’s better to be prepared. While you may be able to score a deal on a PHX to Chicago Airport flight at the last minute, prices usually don’t get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days in advance. For international journeys it’s three to four months.
What airports do you fly into for Chicago from Phoenix?
Midway Intl. Airport (MDW), O’Hare Intl. Airport (ORD) and Lewis University Airport (LOT) are your options when connecting from Phoenix to Chicago. Around 9 mi southwest of the center of Chicago, Midway Intl. Airport (MDW) is the city’s major hub. Keep in mind things such as flight arrival and departure times and the distance to your hotel before settling on an airport. Wrigley Field and Millennium Park are a couple of amazing attractions to add to your must-see list when you get to your destination.
What are the most popular departure times for flights from Phoenix Sky Harbor Intl. Airport to Midway Airport?
Between 3:00 PM - 4:00 PM is when you’ll find the largest number of Frontier Airlines flights jetting off from PHX to Midway Airport. Our recommendation? Book a trip that departs earlier in the day. With air traffic yet to build up around airports, your odds of traveling on a delay-free flight are better.
Can I change the date of my flight from Sky Harbor Intl. Airport (PHX) to Midway Airport?
You can quickly make changes to your Sky Harbor Intl. Airport (PHX) to Chicago Airport ticket by logging in to the Expedia Trips portal. Before making any amendments, review the rules and restrictions in your itinerary to learn what you’re able to do and whether fees apply. Some carriers have a change fee per person, on top of any difference in ticket prices. But if you booked in the last 24 hours, you may be able to cancel for free and arrange new flights. You can also swing by our Customer Service portal for further details and to chat with our Virtual Agent.

Explore a world of travel with Expedia

*Available to One Key members.