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Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $78

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 11/21. 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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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
6:00 am - 7:42 pmPHX-MDW
12h 42m1 stop
Frontier Logo
6:15 am - 3:18 pmMDW-PHX
10h 03m1 stop
$134Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
4:58 pm - 10:17 pmPHX-MDW
28h 19m1 stop
Frontier Logo
4:00 pm - 11:29 pmMDW-PHX
8h 29m1 stop
$136Frontier
Find Deal
Mon, Nov 24 - Thu, Nov 27
Frontier Logo
10:06 pm - 11:30 amPHX-MDW
12h 24m1 stop
Frontier Logo
5:47 pm - 11:11 pmMDW-PHX
30h 24m1 stop
$137Frontier
Find Deal
Wed, Nov 19 - Mon, Nov 24
Frontier Logo
6:15 am - 2:04 pmPHX-MDW
6h 49m1 stop
Frontier Logo
3:52 pm - 12:42 amMDW-PHX
9h 50m1 stop
$138Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15
Frontier Logo
10:29 am - 2:52 pmPHX-MDW
3h 23mnonstop
Frontier Logo
7:24 pm - 10:29 pmMDW-PHX
4h 05mnonstop
$140Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
4:58 pm - 10:12 pmPHX-MDW
28h 14m1 stop
Frontier Logo
5:30 pm - 11:11 pmMDW-PHX
30h 41m1 stop
$141Frontier
Find Deal
Fri, Nov 21 - Wed, Nov 26
Frontier Logo
5:50 pm - 9:28 pmPHX-MDW
26h 38m1 stop
Frontier Logo
2:01 pm - 12:31 amMDW-PHX
11h 30m1 stop
$142Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
5:35 am - 5:01 pmPHX-MDW
10h 26m1 stop
Frontier Logo
3:31 pm - 12:32 amMDW-PHX
10h 01m1 stop
$143Frontier
Find Deal
Mon, Nov 17 - Mon, Nov 24
Southwest Logo
5:25 am - 12:30 pmPHX-MDW
6h 05m2 stops
Southwest Logo
7:30 pm - 10:20 pmMDW-PHX
3h 50mnonstop
$180Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 6
Southwest Logo
6:40 pm - 10:55 pmPHX-MDW
3h 15mnonstop
Southwest Logo
5:15 pm - 10:40 pmMDW-PHX
6h 25m1 stop
$181Southwest
Find Deal
Thu, Dec 25 - Wed, Dec 31

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
Dec 5
PHX6:00 amPhoenix Sky Harbor Intl
12h 42m
1 stop
MDW7:42 pmChicago Midway
Dec 8
MDW6:15 amChicago Midway
10h 03m
1 stop
PHX3:18 pmPhoenix Sky Harbor Intl
$134
Find similar
Frontier
Nov 24
PHX4:58 pmPhoenix Sky Harbor Intl
28h 19m
1 stop
MDW10:17 pmChicago Midway
Nov 27
MDW4:00 pmChicago Midway
8h 29m
1 stop
PHX11:29 pmPhoenix Sky Harbor Intl
$136
Find similar
Frontier
Nov 19
PHX10:06 pmPhoenix Sky Harbor Intl
12h 24m
1 stop
MDW11:30 amChicago Midway
Nov 24
MDW5:47 pmChicago Midway
30h 24m
1 stop
PHX11:11 pmPhoenix Sky Harbor Intl
$137
Find similar

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
Dec 3
PHX5:25 amPhoenix Sky Harbor Intl
6h 05m
2 stops
MDW12:30 pmChicago Midway
Dec 6
MDW7:30 pmChicago Midway
3h 50m
PHX10:20 pmPhoenix Sky Harbor Intl
$180
Find similar
Southwest
Dec 25
PHX6:40 pmPhoenix Sky Harbor Intl
3h 15m
MDW10:55 pmChicago Midway
Dec 31
MDW5:15 pmChicago Midway
6h 25m
1 stop
PHX10:40 pmPhoenix Sky Harbor Intl
$181
Find similar
Southwest
Jan 14
PHX10:30 amPhoenix Sky Harbor Intl
3h 15m
MDW2:45 pmChicago Midway
Jan 18
MDW5:05 amChicago Midway
4h 10m
PHX8:15 amPhoenix Sky Harbor Intl
$187
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 November 4, 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

Fri 12/5

6:00 am-7:42 pm

1 stop12h 42m

Chicago Midway

Mon 12/8

6:15 am-3:18 pm

1 stop10h 03m

$134

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 11/24

4:58 pm-10:17 pm

1 stop28h 19m

Chicago Midway

Thu 11/27

4:00 pm-11:29 pm

1 stop8h 29m

$136

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 11/19

10:06 pm-11:30 am

1 stop12h 24m

Chicago Midway

Mon 11/24

5:47 pm-11:11 pm

1 stop30h 24m

$137

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 12/11

6:15 am-2:04 pm

1 stop6h 49m

Chicago Midway

Mon 12/15

3:52 pm-12:42 am

1 stop9h 50m

$138

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 12/5

10:29 am-2:52 pm

Nonstop3h 23m

Chicago Midway

Sun 12/7

7:24 pm-10:29 pm

Nonstop4h 05m

$140

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Fri 11/21

4:58 pm-10:12 pm

1 stop28h 14m

Chicago Midway

Wed 11/26

5:30 pm-11:11 pm

1 stop30h 41m

$141

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 12/4

5:50 pm-9:28 pm

1 stop26h 38m

Chicago Midway

Sun 12/7

2:01 pm-12:31 am

1 stop11h 30m

$142

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Mon 11/17

5:35 am-5:01 pm

1 stop10h 26m

Chicago Midway

Mon 11/24

3:31 pm-12:32 am

1 stop10h 01m

$143

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Wed 12/3

5:25 am-12:30 pm

2 stops6h 05m

Chicago Midway

Sat 12/6

7:30 pm-10:20 pm

Nonstop3h 50m

$180

PhoenixChicago

PHX - MDW

PHXMDW

Phoenix Sky Harbor Intl

Thu 12/25

6:40 pm-10:55 pm

Nonstop3h 15m

Chicago Midway

Wed 12/31

5:15 pm-10:40 pm

1 stop6h 25m

$181

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 $229.

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 $283. 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 $273 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $356. 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 $289 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 $220 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 November 2025, prices for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights are approximately 167% 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

$128

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 $128. 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 $218.
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 15m.

  • 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 $109Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights
SouthwestPriceFrom $206Free CancellationRating
8.0
4,237 reviews
Search Southwest flights

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

    Southwest operates around 23 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 $348, 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 4,237 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
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.

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