Trip Breakdown: Weekend in Chicago

I recently booked a weekend trip for my girlfriend and I for her birthday. Neither of us have ever been to Chicago, so I thought it was about time we made it up to The Windy City. I was able to get both of us roundtrip flights from Denver to Chicago, and 2 nights in a 4.5 star hotel right downtown, along the river, for a grand total of $300. Here’s a step by step breakdown of how I did it.

The Flights

For the flights, I used one of my favorite travel tools, the Southwest Companion Pass. By using the companion pass, I only had to book one roundtrip flight and then add a companion for just $11.20. I started off by going to and using their low fare calendar to search for a Friday to Sunday trip with lowest cost in points.

southwest low fare calendar

On the low fare calendar, I found an early Friday morning flight with a late Sunday night return for 17,000 Southwest Rapid Rewards points. I had more than enough points left in my account for this, but because my girlfriend is the current holder of our Southwest companion pass, I needed to book the flight with her account in order to be able to add a companion. Unfortunately, my girlfriend only had 16,000 Rapid Rewards left in her Southwest account. I had a few options for topping off her account:

  1. Transfer points from my Southwest account to hers.
    • The minimum amount of points you are allowed to transfer is 2,000 with a fee of $20.
  2. Buy points with her account.
    • The minimum amount of points you are allowed to buy is 2,000 for $60.
  3. Transfer Chase Ultimate Rewards to Southwest Rapid Rewards at a ratio of 1:1.
    • I could transfer exactly the 1,000 points I needed for free.

I decided to go with option 3 and transfer 1,000 Chase Ultimate Rewards to her Southwest account. I now had the 17,000 Southwest Rapid Rewards points that I needed to book the flight. After booking her flight, I added myself as a companion. We both now had flights for our trip.

Total Cost for Flights: $22.40

The Accommodations

For the accommodations, I used the Priceline Name Your Own Price bidding hack. I have used this trick many times and saved thousands on hotel stays over the years. First, I plugged in my dates on Priceline and headed straight to their Express Deals section. I saw there was a 4.5 Star hotel in the Millennium Park Downtown area for $175/night. Priceline Express Deals doesn’t reveal your hotel until you book, and then it is non-refundable. Now I didn’t book this Express Deal, but it gave me an idea of where I should start my bidding and what my maximum bid should be.

My next step was to head over to the Name Your Own Price section of Priceline. Normally, Priceline only allows you one bid every 24 hours, but using the Priceline bidding hack, I can bid many more times than this in a 24 hour period. I began my bidding at $100/night. My first few bids were declined, but then much to my surprise, my bid of $113/night was accepted!

renaissance chicago
The 4.5 Star Renaissance Downtown Chicago Hotel…not too shabby.

Priceline revealed that I got the Renaissance Hotel, a 4.5 star hotel that regularly goes for $300+ per night. According to Pricline, I saved 63% off the normal price of this hotel. That’s 2 nights for less than the price of one.

Total Cost for Accommodations: $281.98

Total Cost for the Trip: $304.38


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