Last year, Mrs. TIL's brother found some Sprit "$9 fare club" fares to Chicago, and asked us to join him for a weekend in January. He's the one guy I know who probably a) travels more than we do for leisure and b) always seems to find lower rates. So, I knew the weekend would be far more than just a "visit", especially after he announced he had scored the Doubletree Magnificent Mile for around $50. The competition was on!
Last year, two free round-trip Amtrak tickets from my hometown, a free night at the Hotel Indigo (great property!), and a free tour of the city made for a great inexpensive vacation. We even found a couple of incredible happy hours for dinner and a bar where we were able to score free drinks.
This year, the competition is on again, and Mrs. TIL is being a bit more particular about what she wants -- two nights in a hotel on Magnificent Mile (at least 4 star), easy transportation from our hometown to Chicago (no driving!), and the hotels must be close together so we don't need to haul luggage all over the city. Reasonable requests, for sure.
So, the challenge is on for 2013. My goal is to get two nights in a 4+ star hotel (preferably suites or breakfast included) with no out-of-pocket expense or points spent. I'd also like to get cheap or free transportation to and from Chicago without blowing a bunch of points. Finally, I'd like to get free transportation within the city, and at least one free tour. Paying for reasonable meals and drinks is okay (soup kitchens are out), but meals should not cost more than what we'd spend at home for food.
Can I do it? Stay tuned!