Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $88

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Phoenix Sky Harbor Intl Airport to Chicago departing on 11/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Phoenix Sky Harbor Intl Airport to Chicago (PHX-MDW)

Cheap round-trip flights

Frontier Logo
9:59 pm - 12:24 amPHX-MDW
24h 25m1 stop
Frontier Logo
7:50 am - 9:40 amMDW-PHX
3h 50mnonstop
$141Frontier
Find Deal
Thu, Oct 9 - Sun, Oct 12
Frontier Logo
7:16 pm - 12:45 amPHX-MDW
3h 29mnonstop
Frontier Logo
6:30 am - 12:51 pmMDW-PHX
8h 21m1 stop
$142Frontier
Find Deal
Sun, Aug 31 - Sun, Sep 7
Frontier Logo
10:39 am - 4:05 pmPHX-MDW
3h 26mnonstop
Frontier Logo
10:56 pm - 12:47 amMDW-PHX
3h 51mnonstop
$144Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
10:39 am - 4:05 pmPHX-MDW
3h 26mnonstop
Frontier Logo
7:50 am - 9:40 amMDW-PHX
3h 50mnonstop
$146Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
7:21 am - 12:24 amPHX-MDW
15h 03m1 stop
Frontier Logo
10:56 pm - 12:47 amMDW-PHX
3h 51mnonstop
$147Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 27
Frontier Logo
4:35 pm - 9:58 pmPHX-MDW
3h 23mnonstop
Frontier Logo
2:26 pm - 4:04 pmMDW-PHX
27h 38m1 stop
$148Frontier
Find Deal
Thu, Sep 11 - Fri, Sep 26
Frontier Logo
8:20 pm - 3:53 pmPHX-MDW
17h 33m1 stop
Frontier Logo
10:13 am - 7:10 pmMDW-PHX
10h 57m1 stop
$149Frontier
Find Deal
Thu, Sep 11 - Thu, Sep 18
Frontier Logo
4:35 pm - 9:58 pmPHX-MDW
3h 23mnonstop
Frontier Logo
6:24 pm - 11:29 pmMDW-PHX
7h 05m1 stop
$150Frontier
Find Deal
Thu, Oct 2 - Thu, Oct 9
Frontier Logo
8:37 am - 3:53 pmPHX-MDW
5h 16m1 stop
Frontier Logo
4:48 pm - 11:27 pmMDW-PHX
8h 39m1 stop
$151Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
10:39 am - 4:05 pmPHX-MDW
3h 26mnonstop
Frontier Logo
8:30 am - 10:23 amMDW-PHX
3h 53mnonstop
$152Frontier
Find Deal
Thu, Oct 9 - Thu, Oct 30

Southwest flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Our best Southwest deals on Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight tickets
Southwest
Aug 31
PHX6:55 pmPhoenix Sky Harbor Intl
3h 20m
MDW12:15 amChicago Midway
Sep 8
MDW5:25 pmChicago Midway
3h 45m
PHX7:10 pmPhoenix Sky Harbor Intl
$198
Find similar
Southwest
Aug 30
PHX1:10 pmPhoenix Sky Harbor Intl
3h 15m
MDW6:25 pmChicago Midway
Aug 31
MDW12:40 pmChicago Midway
3h 40m
PHX2:20 pmPhoenix Sky Harbor Intl
$257
Find similar
Southwest
Sep 1
PHX5:20 amPhoenix Sky Harbor Intl
3h 15m
MDW10:35 amChicago Midway
Sep 8
MDW5:25 pmChicago Midway
3h 45m
PHX7:10 pmPhoenix Sky Harbor Intl
$267
Find similar

Frontier flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Our best Frontier deals on Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight tickets
Frontier
Oct 9
PHX9:59 pmPhoenix Sky Harbor Intl
24h 25m
1 stop
MDW12:24 amChicago Midway
Oct 12
MDW7:50 amChicago Midway
3h 50m
PHX9:40 amPhoenix Sky Harbor Intl
$141
Find similar
Frontier
Aug 31
PHX7:16 pmPhoenix Sky Harbor Intl
3h 29m
MDW12:45 amChicago Midway
Sep 7
MDW6:30 amChicago Midway
8h 21m
1 stop
PHX12:51 pmPhoenix Sky Harbor Intl
$142
Find similar
Frontier
Oct 16
PHX10:39 amPhoenix Sky Harbor Intl
3h 26m
MDW4:05 pmChicago Midway
Oct 20
MDW10:56 pmChicago Midway
3h 51m
PHX12:47 amPhoenix Sky Harbor Intl
$144
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 18, 2025.
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

Price

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/9

9:59 pm-12:24 am

1 stop24h 25m

Chicago Midway

Sun 10/12

7:50 am-9:40 am

Nonstop3h 50m

$141

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sun 8/31

7:16 pm-12:45 am

Nonstop3h 29m

Chicago Midway

Sun 9/7

6:30 am-12:51 pm

1 stop8h 21m

$142

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/16

10:39 am-4:05 pm

Nonstop3h 26m

Chicago Midway

Mon 10/20

10:56 pm-12:47 am

Nonstop3h 51m

$144

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/16

10:39 am-4:05 pm

Nonstop3h 26m

Chicago Midway

Sun 10/19

7:50 am-9:40 am

Nonstop3h 50m

$146

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 10/10

7:21 am-12:24 am

1 stop15h 03m

Chicago Midway

Mon 10/27

10:56 pm-12:47 am

Nonstop3h 51m

$147

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 9/11

4:35 pm-9:58 pm

Nonstop3h 23m

Chicago Midway

Fri 9/26

2:26 pm-4:04 pm

1 stop27h 38m

$148

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 9/11

8:20 pm-3:53 pm

1 stop17h 33m

Chicago Midway

Thu 9/18

10:13 am-7:10 pm

1 stop10h 57m

$149

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/2

4:35 pm-9:58 pm

Nonstop3h 23m

Chicago Midway

Thu 10/9

6:24 pm-11:29 pm

1 stop7h 05m

$150

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 9/5

8:37 am-3:53 pm

1 stop5h 16m

Chicago Midway

Mon 9/8

4:48 pm-11:27 pm

1 stop8h 39m

$151

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 10/9

10:39 am-4:05 pm

Nonstop3h 26m

Chicago Midway

Thu 10/30

8:30 am-10:23 am

Nonstop3h 53m

$152

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport, with most prices found around $168. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Phoenix Sky Harbor Intl Airport during the month October is also very affordable. Most momondo users find prices during this month for around $220.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport. The lowest ticket price found for a Tuesday departure recently was $280. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Phoenix Sky Harbor Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $397.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $341. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Phoenix Sky Harbor Intl to Chicago Midway flight route?

Fly from Phoenix Sky Harbor Intl to Chicago Midway for the best Phoenix Sky Harbor Intl - Chicago Midway flight prices

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $291 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport for as low as $197 on momondo.

What cabin class options are available on Phoenix Sky Harbor Intl to Chicago Midway flights?

There are 1 cabin classes available to choose from on Phoenix Sky Harbor Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Phoenix Sky Harbor Intl Airport to Chicago Midway Airport.

How have Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flight prices changed over time?

As of August 2025, prices for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights are approximately 59% more expensive when compared to flights at the same time last year.

When to book flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Phoenix Sky Harbor Intl Airport to Chicago Midway Airport (PHX to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Best Price Found

$88

Fastest flight time

3h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport in the past 72 hours is $88. The best round-trip flight deal from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport found on momondo in the last 72 hours is $141.
The fastest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport takes 3h 15m
Direct flights go from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport every day.
Search flight deals

  • How far is Phoenix Sky Harbor Intl to Chicago Midway by plane?

    Phoenix Sky Harbor Intl and Chicago Midway are 1440.0 mi apart from one another. In terms of flight time, this usually takes a little over 3h 23m.

  • When did momondo last update prices for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

    Prices for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

  • What is the most popular airline from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport?

Best airlines flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

Compare and see reviews for airlines that fly from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $102Free CancellationRating
5.8
3,212 reviews
Search Frontier flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
8,925 reviews
Search United Airlines flights
SouthwestPriceFrom $199Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

  • Southwest Flights From Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

    Southwest operates around 49 flights from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $340, but momondo users have found Southwest deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport from as low as $199 round-trip. Southwest has been scored 8.0/10 in 4,246 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Phoenix to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Phoenix to Chicago for you.

Can I find flights from Phoenix to Chicago with flexible booking policies on momondo?

All flight searches from Phoenix to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Phoenix to Chicago?

Once you have performed a search for Phoenix to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Phoenix to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Phoenix are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 8/23
Sat 8/30
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago