Go from frozen tundra to frozen margaritas with flights to Mexico beach cities. Nonstop flights from Chicago to Cabo and Cancun are available for $355-$369 roundtrip, including tax. These fares are $100 off regular prices and save even more in peak season.

Fly.com Fare Calendars:

Roundtrip flights from Chicago, including tax, to:

Note: Nonstop flights are available on United Airlines. Some travel dates offer cheaper 1-stop fares on Aeromexico.


  • $100 OFF regular pricing

Travel Dates:

  • Cabo: Through May 4
  • Cancun: April 17 – May 26 (March dates available for $369)

Sample Screenshots:

Chicago to Cabo: Fly.com Results

Chicago to Cabo: Fly.com Results

Chicago to Cabo: United Booking Page

Chicago to Cabo: United Booking Page

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Featured Image: Sunny Lover’s Beach in Cabo San Lucas, Mexico from Simple Tourist Boat (Shutterstock.com)

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