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A Luxury Weekend in Chicago for $5

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A Luxury Weekend in Chicago for $5

Before I discovered the world of points and miles collecting, planning a weekend trip with a friend required some serious budgeting. I needed to start saving months in advance, and even then I was always shocked by the final cost. Back then, more often than not, my trips were short and local—and far from luxurious.

All that has changed, thanks to having a nice balance of points and miles in my award program accounts. Recently I booked a weekend trip to Chicago with a friend. I took a nonstop flight from San Francisco to Chicago, stayed at the Radisson Blu and the Park Hyatt, and paid a whopping total of $5. How did I do it?


When I was looking to book this trip, a nonstop flight from San Francisco to Chicago on American Airlines was $438 each way!

If I’d used AA miles, direct flights from San Francisco to Chicago would have been 25,000 miles each way. Stopping in Dallas, 12,500 miles each way.

Booking with Avios
Booking with Avios

But with  British Airways Avios, those direct flights from San Francisco to Chicago were only 10,000 Avios points each way.

No contest!

Because British Airways is not a domestic airline, using Avios is not the obvious choice. But because Avios is a distance-based reward program, the redemption rate is based on miles flown. So, while the minimum cost of a North American award flight on other major airlines is 25,000 miles (no matter what the city pairs are), if you use Avios and the distance of your flight does not exceed 2,000 miles, you can get a great deal. Also, because British Airways is part of the oneworld alliance, you can use Avios on American Airlines, US Airways and Alaska Airlines.

Tip: You can sometimes add to your stash of miles with a quick phone call. I was especially happy with this particular redemption because I earned 9,000 of these Avios points when I called Chase last December, to ask if they might offer me anything to “to help offset the annual fee” on my British Airways Visa. Their offer was sweet: If I spent $1,500/month on the card for the next three months, I would get an additional 9,000 Avios. Since I knew those Avios would go a long way toward a pretty pricey flight (such as the $438 SFO-ORD example above), I was happy to accept the offer.


Chicago has so many amazing hotels! I had my eye on two in particular: the Radisson Blu Aqua and the Park Hyatt Chicago. Both are luxurious, unique and easily bookable with points.

Radisson Blu rooms go for about $300 a night, but because I have the Club Carlson Visa, I was able to get a rate of 50,000 points a night—with the second night free.

Park Hyatt Chicago

Rooms at the Park Hyatt are usually $400-$500, so I redeemed 25,000 Hyatt points for a free night. If you don’t have enough in your Hyatt account, you can transfer Chase Ultimate Rewards points to it (they transfer at a 1:1 ratio) to make up the difference.

The Weekend

Chicago weekend
Chicago weekend

Our trip was fantastic. Because I was traveling for free, I felt fine about making reservations at some of Chicago’s top restaurants. We went to Girl and the Goat, The Publican, and Purple Pig, and they were all worth the splurge! We also enjoyed some shopping (there were great sales over the Memorial Day weekend!), and some fun touristy stuff. The Architectural Boat Tour is a must-do.
I’ll definitely return to Chicago, especially since the cost for my trip was less than my latte in the airport.

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