An All-Expense-Spared Trip to Chicago

On Sunday I submitted my 2018 tax return. I’m eagerly awaiting a $2 refund from the Feds.

The tax refund got me into a parsimonious frame of mind. I decided to assemble an inexpensive trip.

Incentives for a cheap trip

The stars were in alignment:

  • An email from Hyatt Hotels warned me that a bunch of loyalty points would expire at the end of this month. 
  • An email from Chicago’s gorgeous new Wrightwood 659 exhibition space offered free (as in “no charge”) time slots this week for their new socially engaged architecture exhibition.
  • My partner, Dwight, would be flying to New Orleans for a wedding. I generally don’t do weddings; besides, the last time I went to a wedding in that city, the bride fell into a hot tub in full wedding regalia. No, I don’t do weddings, but I do travel. 

This week, in a frugal mindset, I decided I would go on a trip for one night, leaving on Friday, the same day Dwight heads for The Big Easy.

Chicago works well for a quick trip. I know my way around, and have favorite places to explore. But fares were steep: the cheapest were north of $300. Delta Airlines started around $530. 

It was time to see what I could get with frequent flyer miles. To my surprise and delight, many Delta flights to The Windy City this weekend were available for 12,000 miles round-trip. This is much less than the usual 25,000+ miles.

So, I booked flights in Economy for a total of $12 in fees and 12,000 SkyMiles. For that price, I would gratefully stand in the aisle holding onto a strap, subway-style. Later, a message from my Delta app popped up saying I’d been moved to First each way. I appreciate the treat.

I used most of the expiring Hyatt loyalty points on a room at the downtown Hyatt Regency on Wacker. Surprisingly, there were no hidden fees or taxes. 

I forgot my rewards.

Finally I went online and reserved a free visit to the Wrightwood.

This trip was meant.

The trip begins

I flew to Chicago this morning (Friday). My flight pulled back at the same time as Dwight’s, so we took the train to the airport together.

I had requested an early hotel check-in. When I arrived in Chicago, mid-morning, the Hyatt app announced my room was ready.

I stuffed down a sandwich for lunch in my room, then headed out to do an app-based walking tour of select Loop buildings. The tour was produced by Chicago’s public television station, and, of course, it was free.

A big reason to travel

Tomorrow, around the time I fly home, a big snowstorm is forecast for Minneapolis.

Delta has been offering weather waivers which would allow me to cancel or change my flights at no cost. The Delta app makes it easy to change flights, but I’m sticking to my original plans for now.

I may be spending an extra night or two in Chicago. This might blow my minimal budget, but it would turn my routine trip into a bigger adventure.

I get a kick out of making lemonade out of lemons when traveling. When things don’t go according to plan, my instinct to make the best of it shifts into high gear. If the snow wins, I will not be pacing an airport gate area, pouting.

The unexpected is a big reason to travel.

Postscript

Added March 10, 2019.

The day after I posted this piece, I rode the L back to Chicago’s Midway Airport, as planned. I noted that an earlier flight to Minneapolis was still at the gate, but would be departing in 15 minutes. The Minneapolis airport, MSP, had instigated ground delays for inbound flights. I didn’t have checked bags, so I got myself a seat on this flight, and arrived back in Minneapolis earlier than planned.

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