Monday, September 15, 2014

Cheap Chicago Weekend

Well, to be completely fair, we didn't actually go into downtown Chicago. We spent 4 days (3 nights) in the Northwest suburbs for my father's small business and to visit my friends Jack & Connor.

Nevertheless, including flights, transportation and hotels, we got through this weekend trip having spent just $143 out of pocket. Here's how we did it.

We had to get from our apartment in Manhattan (Flatiron/Chelsea) to LaGuardia at 6AM. LGA Airport is the closest NYC airport and has the shortest security lines, though it also has the least amenities. But to save time and money, we prefer flying out of LGA. We just caught a regular NYC Yellow Cab and it cost us $41 including tolls and tip. Since it was a business trip expense, we put it on my father's Business Starwood American Express.

Cash out of pocket: $41

From LGA-ORD, we used 7,500 Avios + $5.60 for each one way tickets on American Airlines. We were lucky that the aircraft used was one of American's newer configurations, with a revamped main cabin seat and sleek touch screen in-flight entertainment system. Unfortunately, they charged for most shows and movies, so we just caught up on our sleep.

Our return flight home used the same British Airways Avios redemption scheme. So another 7,500 Avios + $5.60 per person. Unfortunately, the return flight was less than ideal: (a) not on the new aircraft with no entertainment system, (b) we were seated in the very last row, (c) it ended up delayed 2 hours and (d) being 2.5 years old, I had a screaming fit for a good 30 minutes for an unknown reason. But it still cost us just $17 in taxes for 3 passengers.

Cash out of pocket: $34

Given my father was just 3 nights away from hitting 2015 Starwood Platinum status, we decided to focus all our hotel stays with them. Fortunately, we had a Sheraton Suites nearby in Elk Grove Village and they had availability to book with points. Thursday and Friday nights were 3,000 and 4,000 SPG points, respectively, for a free night award. So 7,000 SPG points got us 2 free nights with no cash out of pocket. Because my father was a 2014 SPG Platinum elite, we also received (a) 500 SPG points as a welcome gift, (b) free wifi, (c) free access to the Sheraton Club Lounge where we could have complimentary breakfast and evening snacks and soft drinks.

For our final night, we decided to stay closer to O'Hare Airport given we didn't want to be rushed in the morning. So we stayed at another Starwood hotel - Four Points O'Hare in Schiller Park. While not the most glamorous location, behind an office building construction site and BP gas station, it served its purpose of having a clean place to sleep the night before our flight home. For just 3,000 SPG points, we had another free hotel night with (a) 250 SPG as a welcome gift and (b) free wifi internet. The Four Points did not, however, have a lounge for free breakfast in the morning, but they did offer a free airport shuttle every 20 minutes.

Cash out of pocket: $0

To get from our friend's place to The Four Points in Schiller Park, we used my father's Uber account. They're currently giving away Free Rides (up to $30) for new sign ups. We weren't entirely sure how much the ride would be, but it ended up being just $23 (including tolls)! By way of comparison, a few months earlier when my father took a regular taxi from ORD Airport to Rolling Meadows (15 miles or about 20 minutes), it ran him about $55 (more than double).

And after we landed in NYC, to get home, we took a regular NYC taxi from the "secret" taxi stand and it ran us another $45 (including tip and toll).

Cash out of pocket: $68

So for a 3 night long weekend vacation/work trip, we only spent $143 in cash in travel (of which $86 for NYC taxi rides to/from LGA Airport). That's just $48/night! Obviously, we spent money on food, but we would have spent that anyway had we stayed at home. But it was a great way to see my best friends for a very reasonable amount of money.

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