Deals

Flight Deal: From Chicago To Havana For Only $227

By DeAnna Taylor

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Hey Chicago, one of your favorite flight deals is back!

You can fly to Havana, Cuba via Copa Airlines for only $227 roundtrip.

This deal is valid for travel starting in early September and going through the end of the year. It is best to use Skyscanner to search for the lowest price available.

Americans traveling to Cuba will still need to take some extra steps before heading to the island. You will need to get a visa and fall under one of the 12 exceptions for travel to Cuba. You can check the State Department website to see a list of the exceptions before booking your ticket.

As you prepare for your trip, keep in mind that U.S. debit and credit cards do not typically work in Cuba. It is best to take cash and then convert it to local currency. Also, keep in mind that Cuba has a dual currency system. You will need to research both because they are both used throughout the area.

In addition to these points, WiFi is not easily accessible all around Cuba. You can purchase a WiFi card at local communications stores that will give you a specific amount of time to access the internet. Once you purchase this card, you will then need to connect in an area where WiFi is actually available. This is usually in hotels or in designated hotspot areas around Havana.


Since some of the date ranges for the deal are long, it gives you the perfect opportunity to city hop. It is very inexpensive to travel across Cuba, you just need to give yourself time. Two of the most popular options are Varadero, which is the beach or Vinales which is more mountainous.

Related: Traveler Story: Dear Cuba, You Had Me At Hello

Cuba is a country full of authentic beauty. Around every turn in Old Havana, you can find people dancing to the sounds of live bands playing in local bars and restaurants.

This deal is great for those living around the Chicago area. You may want to grab it soon because at this price, it won’t be around very long.

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DeAnna Taylor

DeAnna Taylor is a criminal defense Attorney turned travel blogger, author, and writer. While Charlotte, NC (her hometown) is her base, she's always somewhere on a plane. Catch her on IG: @brokeandabroadlife.

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