Return to the Windy City


SpotHero was, in fact, my hero for parking in Chi-Town.

Living so close to Chicago throughout my entire life, it was always a given I’d wind up there at least once a year, if not more. For whatever reason — growing up, getting a puppy and so on — Caitlyn and I are currently in our longest stretch in memory between Chicago trips.

I’m happy to say that stretch will end next month.

While allocating all my vacation time to fixing up The Frankfort House is useful, we both missed Chicago and realized we needed a weekend trip. Of course, we’re poor now thanks to this Frankfort house, so we needed to pull out the big guns for an affordable trip.

I really didn’t want to use Hotwire. Don’t get me wrong, I absolutely LOVE Hotwire, but, for once, I thought it’d be nice to pick out a hotel ourselves instead of being told where we’ll be staying after hitting the “book now” button. Unfortunately, hotel rates in Chicago fluctuate wildly from one weekend to another, based on the city’s event lineup. That said, I really wanted to stay at the Hotel Allegro, a trendy-looking boutique hotel in the Loop and, as luck would have it, it turned out to be the Hotwire deal I selected! Thanks to Hotwire, we saved $50 a night off the standard rate.


It’s been a few years since I’ve driven to Chicago but, if memory serves me, you’ll sometimes pay just as much for parking as you will for one night’s sleep in some parts of town. Thankfully, I found a snazzy website/app called SpotHero that lets you see the parking garages and lots in the city, hours and rates, while allowing you to pay and book your parking in advance. Through SpotHero, I found a great spot a block from the hotel for $30 … for the ENTIRE WEEKEND. That’s what we call a “woot, woot.”

No deals here, but thanks to the money I saved on lodging and parking, this was a little easier to stomach. We snagged two tickets to see comedian Chelsea Handler rip off inappropriate jokes the first evening in town. Caitlyn was especially happy about this, which makes me a happy husband.

Stay tuned to the Rover for a recap of our trip next month!


2 Comments on “Return to the Windy City

  1. I’ve stayed at Hotel Allegro! Make sure to go to the complimentary Happy Hour. They have local beer too. Also, for the next trip, have you ever tried Airbnb for lodging? Lastly, another parking option would be to park for free on the street in Chinatown near the Red Line stop and take that north to the Loop. Have fun in Chi-town and looking forward to reading about the trip! 🙂

    • Thanks for the tips! I did look at parking further away and taking transit into town, but we’re going to be on a very tight schedule that first night (getting from Indy to Chicago, checking in at the hotel, dinner and then the show), so I figured it was best to grab parking nearby.

      I did look at Airbnb and some other sites — also good alternatives!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s

%d bloggers like this: