My $5 three-day trip to Chicago (courtesy of points and miles).

One of my best friends in the whole wide world lives in Boston. Ginger and I only see each other once a year (twice if we’re really lucky!), but she is the kind of friend you wait your whole life to find: once you make a friend like this, you’re friends forever. We love to travel together because we’ve got a very similar travel style – active, adventurous, slightly kooky, and willing to go out of our way for a delicious meal.

For the past several years, we’ve met up in New Orleans, but this year we decided it was time for a change. Our destination: Chicago. Our style for this trip: luxury chic. My challenge: make it free. My success: boom! Here’s how I did it:

Hotels

Since we’re luxury-loving but budget-minded, I had my eye on a few different properties in Chicago, which is brimming with amazing choices. Through a rigorous and competitive process of elimination (which I will write about soon, because I’m sure some of you would appreciate it, or at least get a good laugh out of it), we managed to whittle down our choices (with great difficulty!) and finally settled on the Radisson Blu Aqua and the Park Hyatt.

Rooms at the Radisson Blu go for around $300/night, but because I have the Club Carlson Visa, I was able to lock in a rate of 50,000 points for a night, then get the second night for free. Yay!

Rooms at the Park Hyatt are even pricier, with an average nightly rate of $400-$500, so I decided to redeem 25,000 Hyatt points for a free night. Since my Hyatt account was a little light after a few major redemptions, I transferred Chase Ultimate Rewards points to my Hyatt account (they transfer at a 1:1 ratio) to make up the difference.

Flights

I know I say this every chance I get, but the cost of flights was why I got into points and miles collecting in the first place. When I was booking this trip, a nonstop flight from San Francisco to Chicago on American Airlines was pricing out at $438 each way!

Seriously? That is so much money.

Using AA miles, direct flights from San Francisco to Chicago were 25K each way, or if I wanted to stop in Dallas, 12.5K each way.

Using British Airways Avios, the same direct flights from San Francisco to Chicago were 10K each way.

Guess which one I chose?

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I was especially thrilled with this redemption because I earned 9,000 of these miles from a retention bonus phone call in December.

So there you have it – another free trip, thanks to points and miles. I’m looking forward to every bit of it, and I’m also looking forward to posting my tips and thoughts as it happens, and hearing what you have to say.

What fabulous trips have you planned lately? Anything you are especially looking forward to?

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Comments

  1. Sigh, I love these stories. We never plan a trip that doesn’t have majorly free stuff going on.

    This is the summer we explore the “flyover” states. We are west coast babies and have had very little experience of the Midwest although we have been longing to for some time.

    Later this month we fly to Ohio and spend a week there on our Southwest Companion pass and free Marriot and IHG nights. Our companion pass is good only for this year and husband has knee surgery in the fall so we want to cram in at least one, possibly two more trips to the Midwest.

    We particularly adore small towns that are still viable. Any suggestions, anyone?

    • Meagan Thomas says:

      Anne,
      If you’re looking for somewhere in the midwest that’s a bit quirky and small, but still close to the city, I’d suggest Lawrence, Kansas. Massachusetts Street (Mass street to the locals and college kids) has PHENOMENAL local restaurants and if you go the third Thursday in July they have something called Sidewalk Sales – basically a sun up to sun down clearance sale outside of all the stores on the downtown strip. Tons of great deals and lots of fun. It’s also about 40 minutes from Kansas City which has some great BBQ and decent shopping, especially at the Plaza.

      • Points Pixie says:

        Meagan – I want to go to the Sidewalk Sales!! Lawrence, Kansas sounds like a great trip. Do they have a Hyatt? 😉

    • Points Pixie says:

      Anne – I bet you’ll have great weather for your Ohio trip. Nice timing.

      I remember that you and I are similar in that we both lie awake at night planning trips. 🙂

  2. JustSaying says:

    8 night Waldorf Hilton London using 280k points, 2 nt weekend cert from Citi, 1 call center free nt (please don’t ask), Hyatt Vendome 6 nights 132k pts, Relais and Chateau 4 nt PAID on cheap year out rates, United FC 270k +$290 taxes and fees. Kids COACH 1 US Air 60k 1 UA one way 30k + 1 AA one way 30k Air Tahiti Nui using Lucky booking service $150.
    Definitely agree that Kansas City is a prime Midwest spot…….also think the hills of Arkansas can be beautiful……..Siloam Springs………..and the obvious midwest spot is chicago with great art museums, great food and a great vibe on Rush Street for night life…………

    • Points Pixie says:

      JustSaying – Wow, info packed comment! I need time to digest it all.

      And I’m asking about the call center free night…but you can save that story for another time. 😉

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