3 Crazy Nights in Chicago: Chapter 3 – Pride and Joy

Posted on July 3, 2008 No Comments

As a native Chicagoan, I get a lot of questions from potential visitors (through the blog and personally) about what to do and where to go in the city if you’re on a budget or not looking to spend your life savings on a weekend here. And with the recent trend of staycations, Chicago’s at the top of a lot of people’s summer destination lists. So I hope those of you considering a trip to the city found these last couple posts helpful.

For the final day of their trip, my friends and I took in two extremes of Chicago tourism: A $12 guided architectural boat tour, a long-standing pillar of city tourism for all ages, and the $0 gay pride parade, a more adult and more recently popular addition to the city’s tourism scene.

For $12, the dazzling architectural tour shares the history of the city’s most celebrated buildings, sprinkled with sparkling conversation pieces. I can now tell you exactly how tall the Chicago Spire will be when it’s completed, and provide a visual reference for just how high 2,000 feet really is. For those of you looking for activities for your families in the city, this is a four-star treat. Though we rushed to our next destination, you could always follow up the tour with a trip to Navy Pier, or a nice afternoon lunch at Grand Lux on Michigan, easily walkable from the boat docks on Wacker and a great spot for parents, aunts, in-laws or grandparents.

Following the boat tour, we made our way via el train to the colorful gay pride parade. Despite living here for 28 years, I had never seen it and was thrilled to experience the joyful pageantry of the day — dancers, mardi gras costumes, bikers, floats, costumes and oh-the-glitter — on such a beautiful morning. To see pictures of the event, go here. The downside was that organizationally, with more than 500,000 people in attendance, we spent the first hour hot, crowded and barely able to see anything until we walked a half-mile north to find an open spot. Unfortunately at that point someone fell off a float, it started to rain and the entire parade stopped for 40 minutes. (Luckily we were standing near a radio station float jamming to “Bootie Call,” “Yolanda,” and “Percolater,” so the time passed quickly), but eventually we had to get back into the city and so instead of waiting for the floats to move again, we strolled down the street along the parade route, seeing the rockin’ floats up close and personal (thank you Minibar). Next year I’ll definitely get there earlier, research better places to stand or potentially try to find somebody along the route with an apartment from which to get some good pictures!

As with any large-scale city event, it’s important, both for your safety and your wallet, to be prepared before you go. Whether it’s the Taste of Chicago, the South Side Irish Parade or simply a Cubs game, research everything online before you get there – public transportation, weather, dining, good spots to stand – and go with a game plan. We didn’t and I think my friends were a little overwhelmed by the whole thing.

One more trip for pizza before boarding the train for the airport and I said good-bye to my friends. I can’t wait for them to come again.

I recently wrote that shacking up with a friend is a great way to save money, but I sort of forgot how much work goes into being a great host. As host, you’re at least partially responsible for making sure out-of-towners leave with a smile on their faces and great stories to tell. I suggest offering budget-friendly options that combine local mainstays with more off-the-beaten-path activities, planning days based on their interests and staying away from editorializing too much. Allow guests to experience everything your city has to offer and form their own opinions about what they love.

And if at all possible, try to keep a handle on your cell phone while guests are in town.

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