Category: Chicago

Sample Travel Date:

• September 3rd – 15th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel from late August – early September for Monday through Thursday departures and returns. Availability is extremely limited. Must purchase at least 3 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

Elite Qualifying Dollars:

Routing:

• ORD –   HND (Tokyo – Haneda) – CGK (Jakarta) – NRT (Tokyo – Narita) – ORD

Stopover:

Mileage:

• Miles Flown: 19,761 miles or 3.2 cents per mile
• Redeemable Miles: 2,590 miles

How to Buy:

• Book on United with dates found on Matrix Airfare Search by ITA Software.

Sample Travel Date:

• November 1st – 4th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel from September – early December or mid January 2026 – early February 2026. Availability is limited. Must purchase at least 3 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• Use Matrix Airfare Search by ITA Software and use the following search criteria:
  • Origin: ORD
  • Origin Advanced Routing Code:
    • Routing Codes: ua
    • Extension Codes:
      • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on United and you will be presented with an option to upgrade to a regular economy fare.
  • Destination:  SJU
  • Return Advanced Routing Code:
    • Routing Codes: ua
    • Extension Codes:
    • (Click on Advanced Routing Codes link to enable advanced routing code input)
    • Select “See calendar of lowest fares”
    • Length of stay “3-10” (This is just a sample, you can use any 7 day date range like 3-10, 7-14 etc)
• Beginner’s Guide on How to Use Matrix by ITA Software
• How to Read Airfare Rules and Use It to Your Advantage

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

• N (Basic Economy)
• G (Regular Economy)

Elite Qualifying Dollars:

Routing:

• ORD –  SJU (San Juan) – ORD

Mileage:

• Miles Flown: 4,146 miles
• Redeemable Miles: 1,390 miles

How to Buy:

• Book on United with dates found on Matrix Airfare Search by ITA Software.

Sample Travel Date:

• November 2nd – 6th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel from September – early December or January 2026 – early February 2026. Availability is limited. Must purchase at least 7 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

• B (Basic Economy)
• O (Regular Economy)

Routing:

• ORD – LAX (Los Angeles)  – LIH (Kauai) – LAX – ORD

Mileage:

• Miles Flown: 8,700 miles or 4.7 cents per mile (Basic Economy) / 6.3 cents per mile (Regular Economy)
• Loyalty Points: 2,372 points
• Redeemable Miles: 2,372 miles

How to Buy:

• Book on American with dates found on Matrix Airfare Search by ITA Software

Sample Travel Date:

• October 16th – 20th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until late October. Availability is limited. Must purchase at least 3 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

Routing:

• ORD – YVR (Vancouver) – ORD

Mileage:

• Miles Flown: 3,516 miles or 5.7 cents per mile
• Loyalty Points: 600 points
• Redeemable Miles: 600 miles

How to Buy:

• Book on American with dates found on Matrix Airfare Search by ITA Software

Sample Travel Date:

• November 20th – 27th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until late November for Monday through Thursday departures and returns. Availability is limited. Must purchase at least 3 days in advance of departure.

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

Routing:

• ORD – HKG (Hong Kong) – KHH (Kaohsiung)  – HKG – ORD

Stopover:

Mileage:

Cathay Pacific is an Alaska Air partner. Mileage earning with Alaska Air as follows:

• Miles Flown: 16,376 miles or 4.3 cents per mile
• Elite Qualifying Miles: 4,094 miles
• Redeemable Miles: 4,094 miles

Cathay Pacific is also an American partner. However, this fare earns ZERO miles with American.

How to Buy:

• Support us by using our Priceline link to book with dates found on Matrix Airfare Search by ITA Software.

Sample Travel Date:

• November 5th – 12th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until late November for Monday through Thursday departures and returns. Availability is limited. Must purchase at least 3 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• Use Matrix Airfare Search by ITA Software and use the following search criteria:
  • Origin: ORD
  • Origin Advanced Routing Code:
    • Routing Codes: ua ua
    • Extension Codes: maxconnect 300
      • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on United and you will be presented with the option to upgrade to the regular economy fare.
  • Destination:  TPE
  • Return Advanced Routing Code:
    • Routing Codes: ua ua
    • Extension Codes: maxconnect 300
  • (Click on Advanced Codes link to enable advanced routing code input)
  • Select “See calendar of lowest fares”
  • Duration “3-10” (This is just a sample, you can use any 7 day date range like 3-10, 7-14 etc)
• Beginner’s Guide on How to Use Matrix by ITA Software
• How to Read Airfare Rules and Use It to Your Advantage

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

Elite Qualifying Dollars:

Routing:

• ORD – SFO (San Francisco) – TPE (Taipei) – SFO – ORD

Stopover:

Mileage:

• Miles Flown: 16,586 miles or 4.0 cents per mile (Basic Economy) / 5.1 cents per mile (Regular Economy)
• Redeemable Miles: 3,670 miles

How to Buy:

• Book on United with dates found on ITA Software Matrix Airfare Search.

Sample Travel Date:

• November 6th – 13th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until late November for Monday through Thursday departures and returns. A Sunday stay is required. Availability is limited. Must purchase at least 3 days in advance of departure.

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• Use Matrix Airfare Search by ITA Software and use the following search criteria:
  • Origin: ORD
  • Origin Advanced Routing Code:
    • Routing Codes: ua ua
    • Extension Codes: maxconnect 240
      • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare.  Use those dates on United and you will be provided with an option to upgrade to the regular economy fare
  • Destination:  SIN
  • Return Advanced Routing Code:
    • Routing Codes: ua ua
    • Extension Codes: maxconnect 240
  • (Click on Advanced Codes link to enable advanced routing code input)
  • Select “See calendar of lowest fares”
  • Duration “3-10” (This is just a sample, you can use any 7 day date range like 3-10, 7-14 etc)
• Beginner’s Guide on How to Use Matrix by ITA Software
• How to Read Airfare Rules and Use It to Your Advantage

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

Elite Qualifying Dollars:

Routing:

• ORD – SFO (San Francisco) – SIN (Singapore) – SFO – ORD

Stopover:

Mileage:

• Miles Flown: 20,550 miles or 3.2 cents per mile (Basic Economy) / 4.1 cents per mile (Regular Economy)
• Redeemable Miles: 3,590 miles

How to Buy:

• Book on United with dates found on Matrix Airfare Search by ITA Software.

Sample Travel Date:

• November 1st – 4th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until late December or January 2026 for Monday, Tuesday, Wednesday, Thursday and Saturday departures and returns. Availability is limited. Must purchase at least 7 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• Use Matrix Airfare Search by ITA Software and use the following search criteria:
  • Origin: ORD
  • Origin Advanced Routing Code:
    • Routing Codes: ua
    • Extension Codes:
      • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on United and you will be presented with an option to upgrade to a regular economy fare.
  • Destination:  LAS
    • This works both ways, so LAS can be the Origin and ORD can be the Destination
  • Return Advanced Routing Code:
    • Routing Codes: ua
    • Extension Codes:
    • (Click on Advanced Routing Codes link to enable advanced routing code input)
    • Select “See calendar of lowest fares”
    • Length of stay “3-10” (This is just a sample, you can use any 7 day date range like 3-10, 7-14 etc)
• Beginner’s Guide on How to Use Matrix by ITA Software
• How to Read Airfare Rules and Use It to Your Advantage

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

• N (Basic Economy)
• G (Regular Economy)

Elite Qualifying Dollars:

Routing:

• ORD – LAS (Las Vegas) – ORD

Mileage:

• Miles Flown: 3,020 miles or 4.8 cents per mile (Basic Economy) / 7.7 cents per mile (Regular Economy)
• Redeemable Miles: 950 miles

How to Buy:

• Book on United with dates found on Matrix Airfare Search by ITA Software.

Sample Travel Date:

• November 1st – 4th

• This is just ONE SAMPLE travel date, for more availability, please follow the “Fare Availability” and “How to Search for Availability” instructions below

Fare Availability:

• Valid for travel until  mid December or January 2026 for Monday, Tuesday, Wednesday, Thursday and Saturday departures and returns. Availability is limited. Must purchase at least 7 days in advance of departure

• Please note that while this fare is valid at time of posting, if this post is more than two days old, the fare is likely gone.

How to Search for Availability:

• This is just to search for availability. To buy your tickets, scroll down to “How to Buy” section of this post

• The Matrix Airfare Search by ITA Software search page should be like below when all values are inputted

• You cannot buy tickets using Matrix Airfare Search by ITA Software. To buy, follow our instructions in the “How to Buy” section below.

Fare Class:

• N (Basic Economy)
• G (Regular Economy)

Elite Qualifying Dollars:

Routing:

• ORD – SAN (San Diego) – ORD

Mileage:

• Miles Flown: 3,438 miles or 3.4 cents per mile (Basic Economy) / 6.0 cents per mile (Regular Economy)
• Redeemable Miles: 820 miles
  

How to Buy:

• Book on United with dates found on Matrix Airfare Search by ITA Software.