Traveling In Our Own Backyard – A Weekend In Chicago

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I’m the oldest of four and my husband is the youngest of three so our children have a robust collection of grandparents, aunts, uncles, and cousins. As the only members of our extended family who move every 1-3 years courtesy of the US Government, we tend to host at least a few visitors at each duty station. Over the years, we’ve taken family members through 30-foot high snowdrifts in northern New York, we’ve hiked with them among American buffalo and Longhorn steer in Oklahoma, and we’ve toured the Smithsonian countless times together in Washington DC. We’ve eaten pounds of Kansas City BBQ, attended multiple rodeos in Texas, and enjoyed the views at Bull Run Winery in Virginia.

As our time in Chicagoland is rapidly approaching to an end (T-minus 60 days), we recently hosted our last visitors – my sister and her family. They hold a very unique title among our family – they’re our only family members who have visited us at every single duty station, which is quite the feat! 

We’re currently stationed at Fort Sheridan, Illinois, which is about 30 miles north from the heart of downtown Chicago. Our little family of four loves to spend time exploring cities – we’ve wandered around the streets of New York City, London, Paris, Washington DC, Munich, and much more over the years and will never turn down the opportunity to visit a major world city. We’ve spent countless hours in downtown Chicago in our almost two-years of being stationed at Fort Sheridan and love to immerse ourselves in the architecture, sports, and food of Second City.

Self-timer fail, November 2021

My parents visited us last summer but had no desire to go to downtown Chicago (womp womp). Clay’s sister and her family visited us this past November and we had a blast spending a couple of nights in downtown Chicago with them so when we suggested doing the same to my sister, Megan, and her family, we were thrilled that they enthusiastically wanted to do the same.

We stayed at the JW Marriott Chicago, which is located in The Loop (Chicago has 77 neighborhoods/community areas). The Loop is the heart of the Chicago business district and surrounded by elevated ‘L’ tracks. It is adjacent to River North, which is a former industrial neighborhood that’s been transformed with spectacular dining and nightlife. It is within walking distance of the famed Magnificent Mile (Michigan Ave.) and The Gold Coast, which has 19th and early 20th century mansions lining the streets. Each family had their own room on different floors – our room had a great view of Willis Tower, much to our son’s and nephew’s delight.

The number one item on our guests Chicago bucket list was a Chicago River Architecture Tour. Our personal favorite is the 90-minute tour offered by Wendella and we were delighted when discovered Jack was our guide. We had him once before – Jack is a Vietnam Veteran who had a robust architecture career and now works for Wendella as a retirement gig. His love for Chicago, design, and history is abundant and he peppers his presentation with humor, wit, and heartwarming stories.

I’m not going to lie – it was cold for mid-April. The forecast was clear when we boarded the boat but 30 minutes into the tour, it started to rain. And then it snowed for bit – I think it was at that point that my sister wished she took her Spring Break vacation in the Caribbean, rather than visit us in Chicago.

After the tour, we had a couple of hours before our dinner reservation so we walked up down Michigan Ave. and popped into Eately for some pre-dinner drinks and snacks. We ate dinner at Harry Caray’s Italian Steakhouse, which is one of our favorite restaurants to eat at in River North with kids.

I adore their shrimp scampi and have yet to order anything else.

In addition to having great food, the restaurant is located in a landmark building the was the home of Al Capone’s enforcer, Frank Nitti. As a result, you can go into the basement of the restaurant and visit Frank Nitti’s vault. In 1998, an electrician drilled a hole in the wall of the basement and uncovered a hidden room that was used as a hideout during the Prohibition era, as well as a passageway to Chicago’s underground tunnel system. Also discovered was a large safe that you can open and close when you visit the vault in the basement.

One reason why I like to stay in The Loop is because the walk from River North to The Loop is one of my favorite views of Chicago at night. I’m a sucker for bright lights and urban landscapes and the Carbide and Carbon building is absolutely gorgeous at night. Located on the far right, it is a shining example of Art Deco brilliance – rumor has it that the architects designed it to look like a green champagne bottle with a foil top.

The SkyDeck on top of the Willis Tower was one of the last things to re-open due to the pandemic so this was our first opportunity to see Chicago from 1,353 feet.

We enjoyed the interactive Chicago-themed queue leading up to the high-speed elevator and felt that the entire Willis Tower experience was worth the cost of admission. We managed to avoid the majority of the crowds by getting there shortly after it opened so by 11am, we had checked off going to the top of the 12th tallest building in the world. 

We’re admittedly not huge fans of Chicago-style deep dish pizza. Our family prefers Giordano’s over Lou Malnati’s but we will choose to eat New York style over deep dish all day everyday. However, we couldn’t let our guests visit Chicago without going deep at least once at Giordano’s.

After lunch, we Uber-ed down to the Museum of Science and Industry, which is a personal favorite of ours. The kids had a blast exploring the interactive exhibits together and excitedly showed their cousins they’re favorite parts of the museum (the U-boat…duh).

We opted to go to the famed original Billy Goat Tavern for dinner that night for our least-expensive meal of the trip. Located on Lower Michigan Avenue, the bar is actually underneath the street and maintains much of the original ‘dive’ mentality, despite being a popular tourist destination.

We had cheezborgers and chips (of course). The kids had Cokes and the adults had draft beer. Billy Goat Tavern has two beers specifically brewed for the restaurant by Miskatonic Brewing Company – an IPA and a Pilsner, both of which are quite good.

Again – how can you not love Chicago at night? This vertical sign on The Chicago Theater is nearly six stories high and one of the few such signs left today. It is one of the unofficial emblems of the city and considered a historical landmark.

We had brunch reservations the following morning at The Smith before making our way back up to Fort Sheridan so we explored Millennium Park and enjoyed the slightly warmer temperatures. If you find yourself at The Smith for brunch, order the jalapeño cheddar shrimp and grits – you won’t be disappointed!

Moving to different places every couple of years has afforded us the opportunity to really get to know various areas beyond what a few-day visit can offer. That being said, I think everyone should travel in their own backyard every so often. Get a hotel room, if you can swing it, and experience your city/town/area the way an out-of-towner would. You know never know – you may not only learn something about your home, you may also learn something about yourself.

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