I Paid Just ~$214 Out-of-Pocket For My 3 Favorite Trips in 2018. You Can Do the Same With Chase Ultimate Rewards & the Southwest Companion Pass!

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I Paid Just ~$214 Out-of-Pocket For My 3 Favorite Trips in 2018. You Can Do the Same With Chase Ultimate Rewards & the Southwest Companion Pass!

EmilyI Paid Just ~$214 Out-of-Pocket For My 3 Favorite Trips in 2018. You Can Do the Same With Chase Ultimate Rewards & the Southwest Companion Pass!Million Mile Secrets Team

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Sometimes I think about the miles & points hobby and wonder how saving so much money on flights is possible.  But it IS possible, and I haven’t had to pay full price for a flight in years thanks to the rewards earned from the best travel credit cards.  Southwest is one of my favorite airlines, and I frequently transfer Chase Ultimate Rewards points to Southwest and get 2-for-1 flights because I have the Southwest Companion Pass!

I’m sharing a few of my favorite trips from 2018, which I booked using 71,000 Chase Ultimate Rewards points.  To put that into perspective, Ink Business Preferred℠ Credit Card sign-up bonus is 80,000 Chase Ultimate Rewards points after meeting minimum spending requirements.  So just 1 credit card sign-up bonus can get you a lot of travel!

I Used Chase Ultimate Rewards Points for Several Fun Trips in 2018!

~$214 TOTAL for My 3 Favorite Trips on Southwest Using Chase Ultimate Rewards

My 3 favorite trips of 2018 cost me a total of 71,000 Chase Ultimate Rewards points.  These points covered airfare for 2 people!  That’s because I got 2-for-1 flights with the Southwest Companion Pass.  Taxes and fees added up to ~$107 per person (~$85 for Costa Rica, ~$11 for San Diego, and ~$11 for Washington, D.C.)

You can also take trips using points earned from credit cards like the Ink Business Preferred℠ Credit Card and Chase Sapphire Preferred® Card.  You can transfer points from these cards directly to your Southwest account.  Or you can earn Southwest points directly with the Chase Southwest credit cards.  Right now, you can earn up to 60,000 Southwest points on all 4 Chase Southwest credit cards, and these points count towards the Southwest Companion Pass!

Here’s how many points I used for my 3 favorite trips:

  • Costa Rica – 22,000 Chase Ultimate Rewards points
  • San Diego – 17,000 Chase Ultimate Rewards points
  • Washington, D.C. – 32,000 points

1.   Costa Rica – 22,000 Chase Ultimate Rewards Points Transferred to Southwest

My partner and I went to Costa Rica for a post-baby couples’ getaway.  It was our first time in Costa Rica and we had an amazing time!  We went white water rafting, hiking through the jungle, and explored the hanging bridge canopies.

We flew to Costa Rica using 22,000 Southwest points TOTAL for 2 people.  Taxes and fees were ~$85 per person which are high for Southwest flights, but we still saved a lot of money, because the flights were ~$450 per person or ~$900 total!

We Used Southwest Points to Fly Down to Costa Rica and Stayed in a Magical Treehouse!

2.   San Diego – 17,000 Chase Points Transferred to Southwest

We went to San Diego for a 5-day family vacation over the summer.  Our round-trip flights were ~17,000 Southwest points total for 2 people, and we paid just ~$22 in taxes and fees!

We also used Hyatt points (that we transferred from credit cards like the Ink Business Preferred℠ Credit Card) to stay at the Hyatt House San Diego/Sorrento Mesa for just 12,000 Hyatt points per night!  There are tons of family activities in San Diego.  We had a lot of fun visiting the San Diego Zoo, Balboa Park, and the Birch Aquarium in La Jolla.

We Used Just 17,000 Chase Ultimate Rewards Points TOTAL for Our Family Vacation to San Diego

3.   Washington, DC – 32,000 Chase Points Transferred to Southwest

I used 32,000 Southwest points to attend my best friend’s baby shower in the Washington, D. C. area.  Taxes and fees were just ~$11 for my ticket.  I had a great weekend helping her prepare for the shower and getting things organized for her baby, who is due to make her appearance in a little over a month!

I Attended My Best Friend’s Baby Shower Thanks to Chase Points!

Using miles and points doesn’t have to be about taking big family vacations.  This was the most expensive Southwest Airlines points purchase of the year, but it was well worth it!

What are your favorite Southwest flight trips from 2018?  Share with us in the comments below!

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Ink Business Preferred℠ Credit Card

Ink Business Preferred℠ Credit Card

  • Earn 80,000 bonus points after you spend $5,000 on purchases in the first 3 months from account opening. That's $1,000 toward travel when you redeem through Chase Ultimate Rewards®
  • Earn 3 points per $1 on the first $150,000 spent on travel and select business categories each account anniversary year
  • Earn 1 point per $1 on all other purchases–with no limit to the amount you can earn
  • Points are worth 25% more when you redeem for travel through Chase Ultimate Rewards
  • Redeem points for travel, cash back, gift cards and more – your points don't expire as long as your account is open
  • No foreign transaction fees
  • Employee cards at no additional cost
  • $95 Annual Fee

More Info

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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11,000 points to costa round trip is so amazing. I haven’t seen that.

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It helps being flexible with your dates. I also went during the rainy season, when demand might have been lower.