Cheap Flights: Chicago to San Jose, Costa Rica $197-$221 r/t – COPA

[06/16/2020 @ 07:05 PM CT] Book this fare on: Priceline, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets.

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COPA has round-trip flights from Chicago (ORD) to San Jose, Costa Rica (SJO) for $221 with a connection. Flights November to April. Weekends available.

Note: Some small OTAs on Skyscanner have this for $197. If you plan on booking there, beware of any site that charges a fee to cancel a ticket within the 24-hour “free” period. Use unknown booking sites at your own risk.

Change fees are waived on flights purchased before July 31. Airline waiver policy [Link]. Carry-on bag is allowed for free. Seat fees can be avoided by accepting the randomly assigned seat at the gate.

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All Example Dates: (Skyscanner) Nov 22 – Nov 24 / Nov 22 – Nov 25 / Nov 22 – Nov 26 / Nov 22 – Nov 27 / Nov 23 – Nov 25 / Nov 23 – Nov 26 / Nov 23 – Nov 27 / Nov 24 – Nov 26 / Nov 24 – Nov 27 / Nov 24 – Dec 01 / Nov 25 – Nov 27 / Nov 25 – Dec 02 / Nov 26 – Dec 01 / Nov 26 – Dec 03 / Nov 27 – Dec 01 / Nov 27 – Dec 02 / Nov 27 – Dec 04 / Nov 28 – Dec 01 / Nov 28 – Dec 02 / Nov 28 – Dec 03 / Nov 28 – Dec 05 / Nov 29 – Dec 01 / Nov 29 – Dec 02 / Nov 29 – Dec 03 / Nov 29 – Dec 04 / Nov 29 – Dec 06 / Nov 30 – Dec 02 / Nov 30 – Dec 03 / Nov 30 – Dec 04 / Nov 30 – Dec 05 / Nov 30 – Dec 07 / Dec 01 – Dec 03 / Dec 01 – Dec 04 / Dec 01 – Dec 05 / Dec 01 – Dec 06 / Dec 01 – Dec 08 / Dec 02 – Dec 04 / Dec 02 – Dec 05 / Dec 02 – Dec 06 / Dec 02 – Dec 07 / Dec 02 – Dec 09 / Dec 03 – Dec 05 / Dec 03 – Dec 06 / Dec 03 – Dec 07 / Dec 03 – Dec 08 / Dec 03 – Dec 10 / Dec 04 – Dec 06 / Dec 04 – Dec 07 / Dec 04 – Dec 08 / Dec 04 – Dec 09 / Dec 04 – Dec 11 / Dec 05 – Dec 07 / Dec 05 – Dec 08 / Dec 05 – Dec 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26 / Apr 22 – Apr 27 / Apr 22 – Apr 29 / Apr 23 – Apr 25 / Apr 23 – Apr 26 / Apr 23 – Apr 27 / Apr 23 – Apr 28 / Apr 23 – Apr 30 / Apr 24 – Apr 26 / Apr 24 – Apr 27 / Apr 24 – Apr 28 / Apr 24 – Apr 29 / Apr 25 – Apr 27 / Apr 25 – Apr 28 / Apr 25 – Apr 29 / Apr 25 – Apr 30 / Apr 26 – Apr 28 / Apr 26 – Apr 29 / Apr 26 – Apr 30 / Apr 27 – Apr 29 / Apr 27 – Apr 30 / Apr 28 – Apr 30 / Other dates: There are more dates available than the ones we list here, experiment on your own.

Weekend Dates: (Skyscanner) Dec 04 – Dec 06 / Dec 04 – Dec 07 / Jan 22 – Jan 24 / Jan 22 – Jan 25 / Jan 29 – Jan 31 / Jan 29 – Feb 01 / Feb 05 – Feb 07 / Feb 05 – Feb 08 / Feb 26 – Feb 28 / Feb 26 – Mar 01 / Mar 05 – Mar 07 / Mar 05 – Mar 08 / Mar 12 – Mar 14 / Mar 12 – Mar 15 / Mar 19 – Mar 21 / Mar 19 – Mar 22 / Apr 09 – Apr 11 / Apr 09 – Apr 12 / Apr 16 – Apr 18 / Apr 16 – Apr 19 / Apr 23 – Apr 25 / Apr 23 – Apr 26 / Other dates: There are more dates available than the ones we list here, experiment on your own.

Extended Weekend Dates: (Skyscanner) Nov 26 – Dec 01 / Nov 27 – Dec 01 / Nov 27 – Dec 02 / Nov 28 – Dec 01 / Dec 03 – Dec 06 / Dec 03 – Dec 07 / Dec 03 – Dec 08 / Dec 04 – Dec 08 / Dec 04 – Dec 09 / Dec 05 – Dec 07 / Dec 05 – Dec 08 / Dec 10 – Dec 13 / Dec 10 – Dec 14 / Dec 10 – Dec 15 / Jan 21 – Jan 24 / Jan 21 – Jan 25 / Jan 21 – Jan 26 / Jan 22 – Jan 26 / Jan 22 – Jan 27 / Jan 23 – Jan 25 / Jan 23 – Jan 26 / Jan 28 – Jan 31 / Jan 28 – Feb 01 / Jan 28 – Feb 02 / Jan 29 – Feb 02 / Jan 29 – Feb 03 / Jan 30 – Feb 01 / Jan 30 – Feb 02 / Feb 04 – Feb 07 / Feb 04 – Feb 08 / Feb 04 – Feb 09 / Feb 05 – Feb 09 / Feb 06 – Feb 08 / Feb 06 – Feb 09 / Feb 25 – Feb 28 / Feb 25 – Mar 01 / Feb 25 – Mar 02 / Feb 26 – Mar 02 / Feb 26 – Mar 03 / Feb 27 – Mar 01 / Feb 27 – Mar 02 / Mar 04 – Mar 07 / Mar 04 – Mar 08 / Mar 04 – Mar 09 / Mar 05 – Mar 09 / Mar 05 – Mar 10 / Mar 06 – Mar 08 / Mar 06 – Mar 09 / Mar 11 – Mar 14 / Mar 11 – Mar 15 / Mar 11 – Mar 16 / Mar 12 – Mar 16 / Mar 12 – Mar 17 / Mar 13 – Mar 15 / Mar 13 – Mar 16 / Mar 18 – Mar 21 / Mar 18 – Mar 22 / Mar 18 – Mar 23 / Mar 19 – Mar 23 / Mar 19 – Mar 24 / Mar 20 – Mar 22 / Mar 20 – Mar 23 / Apr 08 – Apr 11 / Apr 08 – Apr 12 / Apr 08 – Apr 13 / Apr 09 – Apr 13 / Apr 09 – Apr 14 / Apr 10 – Apr 12 / Apr 10 – Apr 13 / Apr 15 – Apr 18 / Apr 15 – Apr 19 / Apr 15 – Apr 20 / Apr 16 – Apr 20 / Apr 16 – Apr 21 / Apr 17 – Apr 19 / Apr 17 – Apr 20 / Apr 22 – Apr 25 / Apr 22 – Apr 26 / Apr 22 – Apr 27 / Apr 23 – Apr 27 / Apr 23 – Apr 28 / Apr 24 – Apr 26 / Apr 24 – Apr 27 / Other dates: There are more dates available than the ones we list here, experiment on your own.

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Tips: The Chase Sapphire Preferred® Card allows for 1-to-1 point transfers to several airline loyalty programs. Booking with points is a good alternative to paying with cash when the price of airfare is high. Here is the current list of Chase Sapphire transfer partners: United, Southwest, jetBlue, British Airways, Iberia, Singapore Airlines, Emirates, Air France, KLM, Virgin Atlantic, Aer Lingus, and Air Canada.

Tips: Vacation rentals on Vrbo are usually cheaper per night for longer stays than shorter stays. This is due to three main factors; The first is that most properties have a cleaning fee that is a fixed rate, the second is that many hosts provide discounts for stays longer than 6-days, the third is that the Vrbo service fee percentage is higher on short stays.

Tips: You can (and should) sort the Vrbo vacation rental search results by “Total” price. Doing so exposes properties with high fees. For example, a $140 per-night property with $100 fees will rank as being more expensive than a $150 per-night property with $30 fees, when sorted. Sorting by “most reviews” is also a good option, as this will show you the most popular properties.

Tips: Use Tripadvisor to create a Hotel “short list”. First, plug in your dates and destination. Then select “Sort by Traveler Ranked”. Finally, select the “Traveler Ranking” filter to show “only 4* and up”. Use this resulting “short list” of hotels to find the cheapest one with a high ranking.

Tips: Hotel rates for Weekend dates are usually higher than the rates for Sunday through Thursday. Tripadvisor has a color-coded date calendar, red when the average hotel price for that day is more expensive, green for less expensive. You can use this to get an overview of what dates in the month are at a discount.

Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on BookingBuddy, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.

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I was able to pull this up on Skyscanner. Screenshot taken when this post was initially created. See timestamps at the top of this post.

Flight Details:

Previous Lowest Price Average: $348
Book this fare on: Priceline, Travelocity, Tripadvisor, Skyscanner, Expedia, Orbitz, Hotwire, CheapTickets.

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Cheap Flights: Chicago to San Jose, Costa Rica $197-$221 r/t – COPA

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