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Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $74

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 2/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Phoenix Sky Harbor Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:23 pm - 11:41 pm
PHX
-
MDW
3h 18mnonstop
Frontier Logo
3:21 pm - 6:28 pm
MDW
-
PHX
4h 07mnonstop
$82Frontier
Thu, Feb 26 - Sun, Mar 1
Frontier Logo
9:22 am - 2:49 pm
PHX
-
MDW
3h 27mnonstop
Frontier Logo
6:15 am - 8:12 am
MDW
-
PHX
3h 57mnonstop
$84Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
9:22 am - 2:49 pm
PHX
-
MDW
3h 27mnonstop
Frontier Logo
6:15 am - 8:12 am
MDW
-
PHX
3h 57mnonstop
$85Frontier
Thu, Apr 16 - Sun, Apr 19
Frontier Logo
7:23 pm - 11:41 pm
PHX
-
MDW
3h 18mnonstop
Frontier Logo
3:21 pm - 6:28 pm
MDW
-
PHX
4h 07mnonstop
$87Frontier
Fri, Feb 27 - Sun, Mar 1
Frontier Logo
7:23 pm - 11:41 pm
PHX
-
MDW
3h 18mnonstop
Frontier Logo
3:21 pm - 6:28 pm
MDW
-
PHX
4h 07mnonstop
$88Frontier
Fri, Feb 27 - Sun, Mar 1
Frontier Logo
5:24 pm - 10:45 pm
PHX
-
MDW
3h 21mnonstop
Frontier Logo
2:16 pm - 4:24 pm
MDW
-
PHX
4h 08mnonstop
$100Frontier
Sat, Mar 14 - Mon, Mar 16
Frontier Logo
11:59 pm - 2:26 pm
PHX
-
MDW
13h 27m
1 stop
Frontier Logo
3:29 pm - 6:36 pm
MDW
-
PHX
4h 07mnonstop
$102Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
7:36 pm - 11:54 pm
PHX
-
MDW
3h 18mnonstop
Frontier Logo
2:16 pm - 4:24 pm
MDW
-
PHX
4h 08mnonstop
$106Frontier
Mon, Mar 2 - Mon, Mar 9
Frontier Logo
9:22 am - 2:49 pm
PHX
-
MDW
3h 27mnonstop
Frontier Logo
6:15 am - 8:12 am
MDW
-
PHX
3h 57mnonstop
$108Frontier
Thu, Apr 23 - Sun, Apr 26
Frontier Logo
5:24 pm - 10:45 pm
PHX
-
MDW
3h 21mnonstop
Frontier Logo
2:16 pm - 4:24 pm
MDW
-
PHX
4h 08mnonstop
$109Frontier
Sat, Mar 14 - Mon, Mar 16

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
Feb 26
PHX7:23 pmPhoenix Sky Harbor Intl
3h 18m
MDW11:41 pmChicago Midway
Mar 1
MDW3:21 pmChicago Midway
4h 07m
PHX6:28 pmPhoenix Sky Harbor Intl
$82
Frontier
May 7
PHX9:22 amPhoenix Sky Harbor Intl
3h 27m
MDW2:49 pmChicago Midway
May 11
MDW6:15 amChicago Midway
3h 57m
PHX8:12 amPhoenix Sky Harbor Intl
$84
Frontier
Apr 16
PHX9:22 amPhoenix Sky Harbor Intl
3h 27m
MDW2:49 pmChicago Midway
Apr 19
MDW6:15 amChicago Midway
3h 57m
PHX8:12 amPhoenix Sky Harbor Intl
$85

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
Feb 14
PHX5:15 amPhoenix Sky Harbor Intl
3h 15m
MDW9:30 amChicago Midway
Feb 17
MDW5:15 pmChicago Midway
4h 00m
PHX8:15 pmPhoenix Sky Harbor Intl
$289
Southwest
Feb 14
PHX4:10 pmPhoenix Sky Harbor Intl
3h 10m
MDW8:20 pmChicago Midway
Feb 17
MDW11:20 amChicago Midway
5h 55m
1 stop
PHX4:15 pmPhoenix Sky Harbor Intl
$299
Southwest
Feb 15
PHX5:50 amPhoenix Sky Harbor Intl
3h 15m
MDW10:05 amChicago Midway
Feb 18
MDW8:10 amChicago Midway
6h 25m
1 stop
PHX1:35 pmPhoenix Sky Harbor Intl
$319

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 February 2, 2026.
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 2/26

7:23 pm-11:41 pm

Nonstop3h 18m

Chicago Midway

Sun 3/1

3:21 pm-6:28 pm

Nonstop4h 07m

$82

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 5/7

9:22 am-2:49 pm

Nonstop3h 27m

Chicago Midway

Mon 5/11

6:15 am-8:12 am

Nonstop3h 57m

$84

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 4/16

9:22 am-2:49 pm

Nonstop3h 27m

Chicago Midway

Sun 4/19

6:15 am-8:12 am

Nonstop3h 57m

$85

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 2/27

7:23 pm-11:41 pm

Nonstop3h 18m

Chicago Midway

Sun 3/1

3:21 pm-6:28 pm

Nonstop4h 07m

$87

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 2/27

7:23 pm-11:41 pm

Nonstop3h 18m

Chicago Midway

Sun 3/1

3:21 pm-6:28 pm

Nonstop4h 07m

$88

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 3/14

5:24 pm-10:45 pm

Nonstop3h 21m

Chicago Midway

Mon 3/16

2:16 pm-4:24 pm

Nonstop4h 08m

$100

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 2/26

11:59 pm-2:26 pm

1 stop13h 27m

Chicago Midway

Mon 3/2

3:29 pm-6:36 pm

Nonstop4h 07m

$102

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 3/2

7:36 pm-11:54 pm

Nonstop3h 18m

Chicago Midway

Mon 3/9

2:16 pm-4:24 pm

Nonstop4h 08m

$106

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 4/23

9:22 am-2:49 pm

Nonstop3h 27m

Chicago Midway

Sun 4/26

6:15 am-8:12 am

Nonstop3h 57m

$108

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Sat 3/14

5:24 pm-10:45 pm

Nonstop3h 21m

Chicago Midway

Mon 3/16

2:16 pm-4:24 pm

Nonstop4h 08m

$109

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $184. 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 $234.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport. The lowest ticket price found for a Thursday departure recently was $278. 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 $370.

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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $271 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $354. 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 $317 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 $201 on momondo.

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

There is only 1 cabin class 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 February 2026, prices for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights are approximately 86% 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

$129

Fastest flight time

3h 05m

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 $129. 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 $230.
The fastest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport takes 3h 05m
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 05m.

  • 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 $88Free CancellationRating
5.7
3,050 reviews
Search Frontier flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
9,226 reviews
Search United Airlines flights
SouthwestPriceFrom $206Free CancellationRating
8.0
4,272 reviews
Search Southwest flights

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

    Southwest operates around 48 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 $354, but momondo users have found Southwest deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport from as low as $206 round-trip. Southwest has been scored 8.0/10 in 4,272 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
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
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.

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