Chicago Labor Day Adventures, Part 1: Eating Italian, Getting Free Stuff & Adventures on Foot

When I first broached the topic of attending the 20sb Summit in Chicago, Andrew’s only complaint was that HE really wanted to visit Chicago, had really wanted to visit, in fact, for, like, ever and that Chicago was actually teetering very, very close to the tippy top of his “Places I Must See Sooner Rather Than Later” list. So, we figured Labor Day weekend would be as good a time as any to get our Chicago adventure on.

Sept. 1. – Chicago Day 1.

The Hotel. -We stayed at the Wit, which was fabulous and which I took approximately zero pictures of. It’s a Doubletree Hotel, which means we got free cookies upon checking in, and really, you just can’t go wrong with that. It was close to both the Red and Blue lines, making travel from Chicago O’Hare and all major tourist attractions almost too easy. I’d stay there again and I’d highly recommend it to anyone who wants a nicely outfitted, moderately priced hotel in a good location with beds that are made for melting into.

Early Adventures. – Andrew and I are big, big fans of exploring new cities on foot. For us, it’s a great way to really get a feel for a city. When we explore on foot, we find that we leave a place feeling like we actually experienced it, if that makes any sense at all. Chances are, if a place we want to check out is within one or two miles, we’ll walk there. So, having arrived in Chicago in the afternoon, we set out on foot to wander aimlessly and explore the area. We:

  • Saw Cloud Gate, or the Bean, pictured above.
  • Heard and watched a bit of jazz at the Jay Pritzker Pavillion in Millenium Park as part of the 33rd Annual Chicago Jazz Festival.
  • Checked out Lake Michigan. Andrew is from Michigan and was raised on stories about the Great Lakes and I’ve developed a love and awe of the Lakes as well.
  • Walked through Millennium Park, seeing the sights and taking in the city.

Dinner. – One cheesy and touristy thing we have the tendency of doing before embarking on any sort of travel adventure, long or short, is to buy the Frommer’s Guide to whatever city we’re getting ready to explore. It might sound silly, and sure, we could probably get a whole bunch of that information on the internets if we spent some time looking for it, but, no matter how silly I feel, I tend to love having the book in my purse and available for quick and easy reference whenever we’re exploring a new city. It’s led us to countless fabulous food finds (like the cured meats shop in Seattle’s Pioneer Square owned by Chef Mario Batali‘s father) and is always helpful when deciding between various tourist attractions.

So, as night fell and we realized our walk had left us absolutely famished, we referred to the book, demanded good Italian, and the book guided us to the Italian Village. The book, as per usual did not disappoint.

The Italian Village (71 W. Monroe, Chicago, Ill.) is actually comprised of three restaurants, each on a separate floor. We opted for the Village, upstairs, and were not disappointed. The wine menu is more book than anything else, the wait staff was exceptionally attentive, the salted breadsticks were heavenly and I’m drooling a little just remembering them. Andrew and I each got baked pasta dishes and finished the night off with a ricotta cheesecake the likes of which I’d consider marrying.

Sept. 2 – Chicago Day 2, Part 1.

Morning Adventures & Free Stuff. – We hit the ground running our second day in Chicago. I woke up excited, knowing I’d get to see Caryn, who I met in Vegas, who I stayed with during the 20sb Summit and who is quickly becoming one of my best friends. Determined to get as much out of our first day in Chicago as possible we set out, on foot again, grabbed a portable breakfast at Dunkin’ Donuts, set out toward Millennium Park, sat down on a bench and planned our attack. We:

  • Checked out Cloud Gate again, just because it’s super cool.
  • Walked the two miles from our hotel to Shedd Aquarium, through Millennium Park.
  • Accidentally happened upon Buckingham Fountain, one of the largest fountains in the world.
  • Got in free to the Aquarium with a military discount. They offer $28 off any ticket to all active military members with a valid military ID. We were hoping for a few dollars off, and we pleasantly surprised with the deep discount.
  • Were awed and amazed at the exhibits at the Shedd Aquarium. We tend to visit the aquarium in every town we visit and the Shedd is by far the best one we’ve ever visited. Among the most amazing things we saw were beluga whales, all manner of snakes and frogs and fishes, tons of jelly fish and even an anaconda.

After the Aquarium, we opted to water taxi back to Navy Pier. As it turns out, with just a flash of a military ID, you can ride for free. Total savings by noon on our first day in Chicago thanks to our military IDs? $70.  Woo-to-the-freaking-Hoo, ya’ll.

Still to come: Hug attacks, a Chicago architecture cruise, even more free stuff, more #Biscuits, Wrigley Field, and loving Chicago so, so much that Andrew and I could pack up and move there tomorrow.

20 thoughts on “Chicago Labor Day Adventures, Part 1: Eating Italian, Getting Free Stuff & Adventures on Foot

  1. TJ

    Wow! Loving it so much that you are considering relocation? That’s great! Did you have that feeling after the first trip, or were you able to appreciate more the second time around? 🙂

    1. I think I had more time to appreciate it the second time – the first time was just super quick and I didn’t get to see too much. The more time I spent there though, the more I loved it.

  2. 1). I’ve still never seen the Bean! A weekend trip to Chicago is a top priority for when I’m back in Nashville full time.
    2) I love that fish. What beautiful colors!
    3) Did the belugas show you their wangs? That happened to me while at the Georgia Aquarium. It was disturbing.
    4) Love that you guys use Frommer’s…and thanks for supporting my company 😉 I buy exclusively Frommer’s, too, after so many letdowns from Lonely Planet and Rough Guides (and not just because I work for them!).
    5) I wish Scott’s military ID was still valid. I’d love me some discounted travel.

    1. The belugas did not show us their wangs. They were just being cute and their trainer came over and and rubbed their tongues. I’d never seen them before so it was pretty cool.

      And I think we’ve officially become exclusively Frommer’s purchasers – we bought a Lonely Planet book on Chicago too but it didn’t have all the stuff I’ve come to love in Frommer’s – the suggested itineraries for short trips are one of my favorite things.

      1. I know what you mean. In the field office on Semester at Sea, we have hundreds of guidebooks for the countries we’re visiting, and they’re a mix of LP, Rough Guides, Frommer’s and others. I try to use them all when I’m looking up answers for students, but everything in the LP ones is just so condensed. How can you get a feel for a place with a one-line hotel description?

        Three years ago, Scott and I went to the GA Aquarium while back in TN for the holidays and were in for a rude awakening when we went to the beluga tank and one started getting frisky (in front of dozens of children, no less). I blogged about it, and not only did several people chime in to say they also saw the beluga wangs while at the very aquarium, but ever since the top search term bringing people to my website has been “animal porn.”

  3. Love that you walk as much as possible. Driving in a strange town is the worst!
    Lots of people have been visiting Chicago lately. You look like you had the most fun! 🙂

  4. gah! I definitely did Chicago wrong the last time I was there. That restaurant! That fountain! The AQUARIUM! I love reading your adventures! I did the bus architecture tour and LOVED it. I can’t wait to hear more.

  5. Ah Chicago! I had a work visit last summer and absolutely did not have enough time. Work was located in Little Village so I did get amazing Mexican food, which I consider a not to miss part of Chicago. Saw the bean, navy pier, etc and of course could not miss the art museum.

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