This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
Want to see the latest flight deals as soon as they’re published? Follow The Points Guy on Facebook and Twitter, and subscribe to text message alerts from our deals feed, @tpg_alerts.
Airfare deals are typically only available on limited dates. We recommend you use Google Flights to find dates to fly, then book through an online travel agency such as Orbitz or Expedia, which allows you to cancel flights without penalty by 11pm Eastern Time within one day of booking. However, if you’re using The Platinum Card® from American Express, you’ll need to book directly with the airline or through the Amex Travel portal to get 5x MR points. Remember: Fares may disappear quickly, so book right away and take advantage of Orbitz or Expedia’s courtesy cancellation if you’re unable to get the time away from work or family
Great fares are currently available to a destination that’s usually quite expensive to get to. You can fly from Chicago (ORD) to San Jose, Costa Rica (SJO) from just $212 round-trip. Low fares are also up for grabs from Miami (MIA), Orlando (MCO), Houston (IAH), Atlanta (ATL), San Francisco (SFO) and Fort Lauderdale (FLL). You can find the dirt-cheap Chicago flights from January through March 2019 while deals for the other departure cities are scattered from November through May 2019.
Once you’re booked, check out Get Your Guide’s list of best activities in Costa Rica to maximize your time while on vacation. Consider staying at the Andaz Papagayo, a TPG favorite and great points hotel.
To search, head to Google Flights and enter your origin and destination cities. Scroll through the calendar function to find dates and prices that work for you. Then click through to the airline or online travel agency (OTA) to book the deal.
Airlines: United, JetBlue, American Airlines
Routes: ORD/MIA/MCO/IAH/ATL/SFO/FLL to SJO
Cost: $212+ round-trip
Travel Dates: November 2018 – March 2019
Pay With: The Platinum Card® from American Express (5x on airfare booked directly with the airline), Citi Premier Card, Chase Sapphire Reserve, American Express® Gold Card, or Chase Sapphire Preferred Card (2x on travel)
Here are a few examples of what you can book:
Chicago (ORD) to San José (SJO) for $212 round-trip on United:
Miami (MIA) to San José (SJO) for $240 round-trip on American Airlines:
Orlando (MCO) to San José (SJO) for $292 round-trip on JetBlue:
Houston (IAH) to San José (SJO) for $303 round-trip on American Airlines:
Atlanta (ATL) to San José (SJO) for $348 round-trip on JetBlue:
San Fransisco (SFO) to San José (SJO) for $335 round-trip on United:
Maximize Your Purchase
Don’t forget to use a credit card that earns additional points on airfare purchases, such as The Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Chase Sapphire Reserve, American Express® Gold Card, Citi Premier, or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this post for more on maximizing airfare purchases.
H/T: Scott’s Cheap Flights
Featured image by Matteo Colombo via Getty Images
Know before you go.
News and deals straight to your inbox every day.
LIMITED TIME OFFER: 70,000 Miles
TPG'S BONUS VALUATION: $980
CARD HIGHLIGHTS: 2x miles on AA purchases plus 2x miles at gas stations and at telecommunications merchants, cable and satellite providers and car rental merchants. Get your first checked bag free.
- Designed for businesses
- For a limited time: Earn 70,000 American Airlines AAdvantage® bonus miles after making $4,000 in purchases in first 4 months of account opening*
- First checked bag is free on domestic American Airlines itineraries to reduce travel costs and boost your bottom line*
- 25% savings on American Airlines inflight Wi-Fi when you use your card*
- Enjoy preferred boarding on American Airlines flights*
- Earn 2 AAdvantage® miles per $1 spent on eligible American Airlines purchases
- Earn 2 AAdvantage® miles per $1 spent on purchases at telecommunications merchants, cable and satellite providers, car rental merchants and at gas stations*
- Earn 1 AAdvantage® mile per $1 spent on other purchases*
- No Foreign Transaction Fees*
Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.
Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.
