United: Chicago – San Diego (and vice versa). $117 (Basic Economy) / $207 (Regular Economy). Roundtrip, including all Taxes

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.

American: Phoenix – Chicago (and vice versa). $129 (Basic Economy) / $277 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • September 27th – 30th
  • 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 early November or early December or early January 2026 for Tuesday, Wednesday and Saturday departures and returns. Availability is limited. Must purchase at least 14 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:

  • PHX – ORD (Chicago) –  PHX

Mileage:

  • Miles Flown: 2,872 miles or 4.5 cents per mile (Basic Economy) / 9.6 cents per mile (Regular Economy)
  • Loyalty Points: 1,145 points
  • Redeemable Miles: 1,145  miles

How to Buy:

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

American: San Francisco – Chicago (and vice versa). $129 (Basic Economy / $287 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • October 4th – 7th
  • 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 early November or early December or early January 2026 for Tuesday, Wednesday 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:

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

Routing:

  • SFO – ORD (Chicago) – SFO

Mileage:

  • Miles Flown: 3,680 miles or 3.5 cents per mile (Basic Economy) / 7.8 cents per mile (Regular Economy)
  • Loyalty Points: 1,192 points
  • Redeemable Miles: 1,192 miles

How to Buy:

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

Air Canada: Chicago – Auckland, New Zealand. $735 (Basic Economy) / $897 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • November 28th – December 5th
  • 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 on the outbound in late November. Availability is extremely limited. Must purchase at least 1 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: ac ac
      • Extension Codes: maxconnect 360
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on Google Flights and you will be presented with an option to upgrade to a regular economy fare.
    • Destination:  AKL
    • Return Advanced Routing Code:
      • Routing Codes: ac ac
      • Extension Codes: maxconnect 360
    • (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:

Routing:

  • ORD – YVR (Vancouver) – AKL (Auckland) – YVR – ORD

Stopover:

Mileage:

Air Canada is a member of the Star Alliance and United partner. Mileage earning with United is as follows:

  • Miles Flown: 17,628 miles or 4.2 cents per mile (Basic Economy) / 5.1 cents per mile (Regular Economy)
  • Redeemable Miles: 8,814 miles

How to Buy:

  • Book on  Google Flights with dates found on Matrix Airfare Search by ITA Software. Select “Book with Air Canada” to price
    • You must use the Google Flights redirect to price this. If you go to Air Canada directly, you will not receive this price.

United: Chicago – Managua, Nicaragua. $234 (Basic Economy) / $344 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • October 1st – 7th
  • 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 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:

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

Elite Qualifying Dollars:

Routing:

  • ORD – IAH (Houston) – MGA (Managua) – IAH – ORD

Stopover:

Mileage:

  • Miles Flown: 4,580 miles or 5.1 cents per mile (Basic Economy) / 7.5 cents per mile (Regular Economy)
  • Redeemable Miles: 1,000 miles

How to Buy:

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

Scandinavian Airlines: Chicago – Oslo, Norway. $408 (Basic Economy) / $508 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • November 19th – 26th
  • 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 November – early December or mid January 2026 – mid March 2026. A Sunday stay is required. Availability is limited. Must purchase at least 28 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: sk sk
      • Extension Codes: f bc=T ; maxconnect 360
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on Scandinavian and you will be presented with the option to upgrade to the regular economy fare.
    • Destination:  OSL
    • Return Advanced Routing Code:
      • Routing Codes: sk sk
      • Extension Codes: f bc=T ; maxconnect 360
    • (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:

Routing:

  • ORD – CPH (Copenhagen) – OSL (Oslo)  – CPH – ORD

Stopover:

Mileage:

Scandinavian Airlines is a member of the SkyTeam Alliance and Delta partner. Mileage earning with Delta is as follows:

  • Miles Flown: 9,154 miles or 4.4 cents per mile (Basic Economy) / 5.5 cents per mile (Regular Economy)
  • Medallion Qualifying Dollars: $457
  • Redeemable Miles: 915 miles

How to Buy:

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

Air Canada: Chicago – Sydney, Australia. $834 (Basic Economy) / $934 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • October 22nd – 29th
  • 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 October – early November or February 2026 – mid May 2026.  Availability is limited. Must purchase at least 14 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

Fare Class:

Routing:

  • ORD – YVR (Vancouver) – SYD (Sydney) – YVR – ORD

Stopover:

Mileage:

Air Canada is a member of the Star Alliance and United partner. Mileage earning with United is as follows:

  • Miles Flown: 19,044 miles or 4.4 cents per mile (Basic Economy) / 4.9 cents per mile (Regular Economy)
  • Redeemable Miles: 9,522 miles

How to Buy:

Delta: Chicago – Naples, Italy. $450 (Basic Economy) / $670 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • December 2nd – 9th
  • 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 November – early December for Sunday through Wednesday departures and Tuesday through Friday returns. A Sunday stay is required. Availability is limited. Must purchase at least 14 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: DL DL
      • Extension Codes: f .. VLX76OBA ; maxconnect 360
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on Delta and you will be presented with the option to upgrade to the regular economy fare.
    • Destination:  NAP
    • Return Advanced Routing Code:
      • Routing Codes: DL DL
      • Extension Codes: f .. VLX76OBA ; maxconnect 360
    • (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:

  • E (Basic Economy)
  • V (Regular Economy)

Elite Qualifying Dollars:

Routing:

  • ORD – CDG (Paris) – NAP (Naples) – CDG  – ORD

Stopover:

Mileage:

  • Miles Flown: 9,880 miles or 4.6 cents per mile (Basic Economy) / 6.8 cents per mile (Regular Economy)
  • Redeemable Miles: 2,625 miles

How to Buy:

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

Air Canada: Chicago – Manila, Philippines. $749. Roundtrip, including all Taxes

Sample Travel Date:

  • October 15th – 22nd
  • 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 October  – early November. Availability is limited. A Sunday stay is required. 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) – MNL (Manila)  – YVR – ORD

Stopover:

Mileage:

Air Canada is a member of the Star Alliance and United partner. Mileage earning with United is as follows:

  • Miles Flown: 16,626  miles or 4.5 cents per mile
  • Redeemable Miles: 8,313 miles

How to Buy:

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

United: Chicago – Athens, Greece. $474 (Basic Economy) / $674 (Regular Economy). Roundtrip, including all Taxes

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 from late October – early December for Sunday through Wednesday departures and Tuesday through Friday 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 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 an option to upgrade to a regular economy fare.
    • Destination:  ATH
    • 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 – YUL (Montreal)  – ATH (Athens) – YUL – ORD

Stopover:

Mileage:

  • Miles Flown: 10,970  miles or 4.3 cents per mile (Basic Economy) / 6.1 cents per mile (Regular Economy)
  • Redeemable Miles: 2,855 miles

How to Buy:

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