After having received a number of requests to discuss starting points other than New York or Los Angeles, I’ve decided to feature some of the best value destinations this winter starting from Chicago. As we all know, Chicago is the third largest city in the United States, and its O’Hare Airport is one of the busiest in the world, with some great bargains available to even lesser-known destinations.
Cheap flights to Chicago into the sunshine
While many cheapskates and wise travelers are headed to Europe this time of year, when airfares are very low to go along with extremely cheap hotel rates and zero attraction queues, most people realistically want to head somewhere sunny instead. New York can get cold during the winter, but Chicago is colder and it stays that way longer so you can’t fault anyone for thinking about a beach vacation.
Fortunately, there are many great options that are weirdly cheap at the moment. If you want to mix some culture with decent temperatures you can fly from Chicago to Mexico City for only $250 round-trip, but it’s really not beach weather there in December so we’ll go a bit further.
Cancun is just over at the edge of the Mediterranean and you can fly there for only $300 round-trip in the coming months. For only $330 round-trip you can fly from Chicago to Montego Bay, Jamaica, which is the main airport serving several different beach resort areas on that part of the island.
Bargain hunters will find that Aruba is a good choice, with flights starting at $370 round-trip, and a nice selection of affordable beach hotels there.
What about Central America?
I’m glad you asked. For only $390 round-trip you can fly from Chicago to Guatemala City, which is a short ride to the touristy and wonderful colonial city of Antigua, and also a short van ride to a few new beach resorts with very affordable hotels.
There’s also Liberia, Costa Rica, with flights from $430 round-trip from Chicago. You are obviously paying more to get there, but the hotels are quite a bit cheaper so if you are staying at least 4 nights it’s very likely that you’ll come out saving money and you’ll be in a more exotic and interesting place as well. The northern Pacific coast is filled with little resort towns loaded with cheap all-inclusive hotels, and you are also a few hours’ ride away from the Arenal volcano or the adventure tourism that Costa Rica is known for.
Going a bit further to save even more money you could fly to Cartagena, Colombia for $540. Not many people realize that it’s also right on the Caribbean, and it’s emerged as one of the best sunshine holiday destinations in the world for those who like to stretch their travel funds. If you are going for at least a week you’ll likely find that the cheap hotels on the beach make up for the increased cost in getting there.