My tricks getting to Chicago Frequent Traveler University

If you read my previous article, you know I’m in Chicago now to attend FTU. Here to gain some tips and tricks to share with you in the coming weeks.

Let me tell you a bunch of travel tricks, hacks, and maneuvering I’ve done to take advantage of miles, points, and promotions that are out there.

Getting to Chicago

Originally I had a flight on AA from SFO to ORD, purchased a number of months ago for $110 US. Realized I needed to stop by LA before heading to Chicago so I needed to change my flight.

Lucky for my, American had a schedule change over 1 hour, so I was able to get a refund on that flight.

Now how do I get from SF – LA – Chicago? I was thinking I’d book a one way via Alaska who has 5K award redemptions between SF and LA, then buy a ticket from LAX to ORD. Normally it would be fine, but with Thanksgiving the week after, the prices were sky high, about $200-300 one way which I didn’t want to pay out of pocket.

Therefore, my Alaska miles came to the rescue. I booked SFO-LAX-ORD all on one ticket for 20K miles. LAX-ORD alone was 20K miles since it wasn’t at the lowest redemption level, but I was able to add SFO-LAX for free since Alaska allows free stopovers. I felt this was well worth it 20K miles. (btw the flights were on Virgin America, soon to be Alaska)

Staying in Chicago

I’m here for three nights, Fri, Sat, and Sun. The conference had a $109 special rate at the Marriott O’hare. I originally booked two nights there, but I didn’t really want to pay any $.

So, what I did was book my first night at the Four Points O’hare. It’s only category 2 so it’s a really good deal. Only 3000 SPG Starpoints on a Friday night stay (vs 4000 on a weekday.) SCORE!

Sat night I kept at the Marriott since I wanted to be convenient to the conference.

I could’ve stayed there another night, but Marriott is having a stay twice, get one night free promo. So I decided to stay my last night in downtown Chicago. Found the Fairfield Inn at only 68USD, near Michigan Ave, what a steal. I’ll get a free night at up to Cat 5 hotel after both stays. Much better than staying two nights at the same hotel.


The reason I’m sharing this is to show you to shop around for awards, promos, and regular paid flights and hotels each time you’re looking to travel. You can play around with different programs and try to maximise value. I’m glad to have paid nothing for my airfare, only $200 in total for 2 nights hotel, and get 1 night back in a Marriott certificate!

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