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Cheap flights from Phoenix Sky Harbor Intl Airport to Chicago from $123

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 10/12. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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.
Southwest Logo
7:35 pm - 11:45 pmPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
3h 10mnonstop
Southwest Logo
9:45 pm - 12:35 amMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
3h 50mnonstop
$238Southwest
Fri, Nov 6 - Mon, Nov 9
Southwest Logo
4:00 pm - 10:55 pmPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
4h 55m1 stop Denver Intl
Southwest Logo
10:00 am - 2:50 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
6h 50m2 stops Austin Bergstrom El Paso
$239Southwest
Wed, Sep 16 - Sat, Sep 19
Southwest Logo
8:10 am - 5:45 pmPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
7h 35m1 stop Omaha Eppley Airfield
Southwest Logo
10:00 am - 2:50 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
6h 50m2 stops Austin Bergstrom El Paso
$239Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
11:00 am - 5:45 pmPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
4h 45m1 stop Wichita Eisenhower National
Southwest Logo
12:05 pm - 3:05 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
5h 00m1 stop Kansas City
$240Southwest
Fri, Oct 2 - Tue, Oct 6
Frontier Logo
6:55 pm - 10:58 amPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
15h 03m2 stops Las Vegas Harry Reid Intl Atlanta Hartsfield-Jackson
Frontier Logo
1:12 pm - 8:18 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
8h 06m1 stop Dallas/Fort Worth
$242Frontier
Mon, Nov 2 - Mon, Nov 9
Frontier Logo
4:40 pm - 10:58 amPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
17h 18m2 stops Denver Intl Atlanta Hartsfield-Jackson
Frontier Logo
1:12 pm - 11:41 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
11h 29m1 stop Dallas/Fort Worth
$245Frontier
Tue, Nov 10 - Mon, Nov 16
Delta Logo
10:25 pm - 9:17 amPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
8h 52m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:27 pm - 8:18 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
7h 51m1 stop Detroit Metropolitan Wayne County
$245Delta
Fri, Oct 30 - Tue, Nov 3
Delta Logo
11:05 pm - 9:07 amPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
8h 02m1 stop Detroit Metropolitan Wayne County
Delta Logo
4:30 pm - 9:26 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
6h 56m1 stop Atlanta Hartsfield-Jackson
$245Delta
Tue, Sep 8 - Fri, Sep 11
Delta Logo
11:32 pm - 10:03 amPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
8h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 10:21 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
7h 06m1 stop Atlanta Hartsfield-Jackson
$245Delta
Tue, Oct 13 - Fri, Oct 30
Frontier Logo
7:22 pm - 12:17 pmPHX  Phoenix Sky Harbor Intl-MDW Chicago Midway
14h 55m1 stop Dallas/Fort Worth
Frontier Logo
6:15 am - 11:48 pmMDW  Chicago Midway-PHX Phoenix Sky Harbor Intl
19h 33m2 stops Atlanta Hartsfield-Jackson Denver Intl
$246Frontier
Mon, Oct 12 - Wed, Oct 14

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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
Nov 2
PHX6:55 pmPhoenix Sky Harbor Intl
15h 03m
2 stops
MDW10:58 amChicago Midway
Nov 9
MDW1:12 pmChicago Midway
8h 06m
1 stop
PHX8:18 pmPhoenix Sky Harbor Intl
$242
Frontier
Aug 28
PHX12:19 pmPhoenix Sky Harbor Intl
8h 28m
1 stop
MDW10:47 pmChicago Midway
Aug 29
MDW11:45 amChicago Midway
8h 46m
1 stop
PHX6:31 pmPhoenix Sky Harbor Intl
$248
Frontier
Sep 2
PHX12:19 pmPhoenix Sky Harbor Intl
8h 28m
1 stop
MDW10:47 pmChicago Midway
Sep 3
MDW9:26 pmChicago Midway
27h 34m
1 stop
PHX11:00 pmPhoenix Sky Harbor Intl
$249

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
Nov 6
PHX7:35 pmPhoenix Sky Harbor Intl
3h 10m
MDW11:45 pmChicago Midway
Nov 9
MDW9:45 pmChicago Midway
3h 50m
PHX12:35 amPhoenix Sky Harbor Intl
$238
Southwest
Sep 5
PHX8:10 amPhoenix Sky Harbor Intl
7h 35m
1 stop
MDW5:45 pmChicago Midway
Sep 12
MDW10:00 amChicago Midway
6h 50m
2 stops
PHX2:50 pmPhoenix Sky Harbor Intl
$239
Southwest
Sep 6
PHX9:25 amPhoenix Sky Harbor Intl
5h 45m
1 stop
MDW5:10 pmChicago Midway
Sep 14
MDW5:40 amChicago Midway
3h 35m
PHX7:15 amPhoenix Sky Harbor Intl
$240

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 14, 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

Cheapest round-trip
Quickest round-trip

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Fri 11/6

7:35 pm-11:45 pm

Nonstop3h 10m

Chicago Midway

Mon 11/9

9:45 pm-12:35 am

Nonstop3h 50m

$238

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Wed 9/16

4:00 pm-10:55 pm

1 stop4h 55m

Chicago Midway

Sat 9/19

10:00 am-2:50 pm

2 stops6h 50m

$239

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Sat 9/5

8:10 am-5:45 pm

1 stop7h 35m

Chicago Midway

Sat 9/12

10:00 am-2:50 pm

2 stops6h 50m

$239

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Fri 10/2

11:00 am-5:45 pm

1 stop4h 45m

Chicago Midway

Tue 10/6

12:05 pm-3:05 pm

1 stop5h 00m

$240

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Mon 11/2

6:55 pm-10:58 am

2 stops15h 03m

Chicago Midway

Mon 11/9

1:12 pm-8:18 pm

1 stop8h 06m

$242

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Tue 11/10

4:40 pm-10:58 am

2 stops17h 18m

Chicago Midway

Mon 11/16

1:12 pm-11:41 pm

1 stop11h 29m

$245

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Fri 10/30

10:25 pm-9:17 am

1 stop8h 52m

Chicago Midway

Tue 11/3

1:27 pm-8:18 pm

1 stop7h 51m

$245

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Tue 9/8

11:05 pm-9:07 am

1 stop8h 02m

Chicago Midway

Fri 9/11

4:30 pm-9:26 pm

1 stop6h 56m

$245

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Tue 10/13

11:32 pm-10:03 am

1 stop8h 31m

Chicago Midway

Fri 10/30

5:15 pm-10:21 pm

1 stop7h 06m

$245

PhoenixChicago

PHX Phoenix Sky Harbor Intl - MDW Chicago Midway

PHXMDW

Phoenix Sky Harbor Intl

Mon 10/12

7:22 pm-12:17 pm

1 stop14h 55m

Chicago Midway

Wed 10/14

6:15 am-11:48 pm

2 stops19h 33m

$246

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 typical price of a round-trip flight between Phoenix Sky Harbor Intl Airport and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $297 to $493.
The lowest price recently found on this route was $238.

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

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Phoenix Sky Harbor Intl Airport, with most prices found around $216. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Phoenix Sky Harbor Intl Airport during the month September is also very affordable. Most momondo users find prices during this month for around $244.

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 $319. 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 $453.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $304 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $403. 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 from Phoenix Sky Harbor Intl Airport 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 $353 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 $233 on momondo.

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

There is only 1 cabin class available to choose from on Phoenix Sky Harbor Intl Airport to Chicago Midway Airport 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 2026, prices for Phoenix Sky Harbor Intl Airport to Chicago Midway Airport flights are approximately 32% 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

$206

Fastest flight time

3h 10m

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 $206. 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 $319.
The fastest flight from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport takes 3h 10m
Direct flights go from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport

  • 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 10m.

  • 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 $73Free CancellationRating
5.6
2,695 reviews
Search Frontier flights
SouthwestPriceFrom $222Free CancellationRating
8.0
4,218 reviews
Search Southwest flights

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

    Southwest operates around 25 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 $386, but momondo users have found Southwest deals from Phoenix Sky Harbor Intl Airport to Chicago Midway Airport from as low as $222 round-trip. Southwest has been scored 8.0/10 in 4,218 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
Portage
Benton Harbor
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Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
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Porter
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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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