Delta: Chicago – Bengaluru, India. $845 (Basic Economy) / $995 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • September 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 September – early October. A Sunday stay is required. 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: DL DL
      • Extension Codes: f .. VLN00LBC ; 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:  BLR
    • Return Advanced Routing Code:
      • Routing Codes: DL DL
      • Extension Codes: f .. VLN00LBC ; 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) – BLR (Bengaluru) – CDG  – ORD

Stopover:

Mileage:

  • Miles Flown: 18,038 miles or 4.7 cents per mile (Basic Economy) / 5.5 cents per mile (Regular Economy)
  • Redeemable Miles: 4,130 miles

How to Buy:

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

American: Chicago – San Juan, Puerto Rico. $307 (Basic Economy) / $397 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • May 4th – 8th
  • 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 April – early May. Availability is extremely 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 – SJU (San Juan) – ORD

Mileage:

  • Miles Flown: 4,146 miles
  • Loyalty Points: 1,200 points
  • Redeemable Miles: 1,200 miles

How to Buy:

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

Delta: Chicago – Tulum, Mexico. $327 (Basic Economy) / $447 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • April 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 mid April – early May 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: DL DL
      • Extension Codes: maxconnect 300
        • 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:  TQO
    • Return Advanced Routing Code:
      • Routing Codes: DL DL
      • 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:

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

Elite Qualifying Dollars:

Routing:

  • ORD – ATL (Atlanta) – TQO (Tulum) – ATL – ORD

Stopover:

Mileage:

  • Miles Flown: 3,112 miles
  • Redeemable Miles: 1,250 miles

How to Buy:

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

American: Chicago – Maui, Hawaii (and vice versa). $470 (Basic Economy) / $620 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • April 23rd – 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 from mid January 2026 – April 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
  • Use Matrix Airfare Search by ITA Software and use the following search criteria:
    • Origin: ORD
    • Origin Advanced Routing Code:
      • Routing Codes: aa aa
      • Extension Codes: maxconnect 300
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on American and you will be presented with an option to upgrade to a regular economy fare.
    • Destination:  OGG
    • Return Advanced Routing Code:
      • Routing Codes: aa aa
      • Extension Codes: maxconnect 300
      • (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:

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

Routing:

  • ORD – LAX (Los Angeles) – OGG (Maui) – LAX – ORD

Mileage:

  • Miles Flown: 8,442 miles or 5.6 cents per mile (Basic Economy) / 7.3 cents per mile (Regular Economy)
  • Loyalty Points: 2,643 points
  • Redeemable Miles: 2,643 miles

How to Buy:

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

American: Chicago – Guatemala City, Guatemala. $342 (Basic Economy) / $424 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • October 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 from late August – October or late January 2027 – early February 2027. 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 ITA Software Matrix Airfare Search and use the following search criteria:
    • Origin: ORD
    • Origin Advanced Routing Code:
      • Routing Codes: aa+
      • Extension Codes: maxconnect 240
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on American and you will be presented with an option to upgrade to a regular economy fare.
    • Destination:  GUA
    • Return Advanced Routing Code:
      • Routing Codes: aa+
      • 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:

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

Routing:

  • ORD – DFW (Dallas) – GUA (Guatemala City) – DFW – ORD

Stopover:

Mileage:

  • Miles Flown: 4,260 miles
  • Loyalty Points: 1,510 points
  • Redeemable Miles: 1,510 miles

How to Buy:

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

Korean Air: Chicago – Ho Chi Minh City, Vietnam. $906. Roundtrip, including all Taxes

Sample Travel Date:

  • November 3rd – 10th
  • 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 or late October – November or January 2027 – mid February 2027 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 – ICN (Seoul) – SGN (Ho Chi Minh City) – ICN – ORD

Stopover:

Mileage:

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

  • Miles Flown: 17,492 miles or 5.2 cents per mile
  • Medallion Qualifying Dollars: $874
  • Redeemable Miles: 4,373 miles

How to Buy:

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

Delta: Chicago – New Delhi, India. $700 (Basic Economy) / $850 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • September 10th – 17th
  • 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 in September or late January 2027. A Sunday stay is required. 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: DL DL
      • Extension Codes: 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:  DEL
    • Return Advanced Routing Code:
      • Routing Codes: DL DL
      • 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:

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

Elite Qualifying Dollars:

Routing:

  • ORD – CDG (Paris) – DEL (New Delhi) – AMS (Amsterdam)  – ORD

Stopover:

Mileage:

  • Miles Flown: 16,322 miles or 4.3 cents per mile (Basic Economy) / 5.2 cents per mile (Regular Economy)
  • Redeemable Miles: 3,440 miles

How to Buy:

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

Chicago to Cartagena, Colombia for only $333 roundtrip

Cheap flights from Chicago to Cartagena, Colombia for only $333 roundtrip with Copa Airlines.

 

DEPART:
Chicago, USA

 

ARRIVE:
Cartagena, Colombia

 

RETURN:
Chicago, USA

 

DATES:
Availability from April to November 2026 (excluding summer)

Example dates:

9th-16th Apr
10th-17th Apr
13th-20th Apr
14th-21st Apr
15th-22nd Apr
16th-23rd Apr
22nd-29th Apr
28th Apr – 5th May
29th Apr – 6th May
30th Apr – 7th May
4th-11th May
5th-12th May
11th-18th May
12th-19th May
13th-20th May
19th-26th May
16th-23rd Sep
23rd-30th Sep
27th Sep – 4th Oct
21st-28th Oct
28th Oct – 4th Nov
31st Oct – 7th Nov
1st-8th Nov
3rd-10th Nov
4th-11th Nov
7th-14th Nov
8th-15th Nov
11th-18th Nov

and more…

 

STOPS:
Panama City

 

AIRLINES:
Copa Airlines

 

 

Non-stop from Chicago to Portland, Oregon (& vice versa) for only $195 roundtrip

Non-stop flights from Chicago to Portland, Oregon for only $195 roundtrip with American Airlines.

Also works in reverse.

 

DEPART:
Chicago, USA

 

ARRIVE:
Portland, USA

 

RETURN:
Chicago, USA

 

DATES:
Availability from April to June 2026

Example dates:

 

Chicago – Portland
5th-12th May
12th-19th May
20th-27th May
27th May – 3rd Jun
2nd-9th Jun

 

Portland – Chicago
22nd-29th Apr
5th-12th May
6th-13th May
12th-19th May
26th May – 2nd Jun
27th May – 3rd Jun
2nd-9th Jun
3rd-10th Jun

and more…

 

STOPS:

 

AIRLINES:
American Airlines

 

 

American: Chicago – Portland, Oregon (and vice versa). $195 (Basic Economy) / $295 (Regular Economy). Roundtrip, including all Taxes

Sample Travel Date:

  • May 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 April – early June for Tuesday and Wednesday departures and returns. Availability is limited. Must purchase at least 14 days in advance of departure and by March 26th (TODAY)
  • 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: aa
      • Extension Codes:
        • This is instructing Matrix Airfare Search by ITA Software to search for the Basic Economy fare. Use those dates on American and you will be presented with an option to upgrade to a regular economy fare.
    • Destination:  PDX
      • This works both ways, so PDX can be the Origin and ORD can be the Destination
    • Return Advanced Routing Code:
      • Routing Codes: aa
      • Extension Codes:
    • (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:

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

Routing:

  • ORD –  PDX (Portland) – ORD

Mileage:

  • Miles Flown: 3,466 miles or 5.6 cents per mile (Basic Economy) / 8.5 cents per mile (Regular Economy)
  • Loyalty Points: 1,227 points
  • Redeemable Miles: 1,227 miles

How to Buy:

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