Playing Tourist: The Chi-Town Girls Trip

Hey All!

I am so excited to finally get this post out. I decided to do this post similar to my Playing Tourist: Gastown post. Basically I’m going to tell you the best places to shop, eat, and play.



{the numerous bridges that run over the two rivers throughout the city}

Where to Eat

(1) RPM Italian : Not only did Guiliana and Bill Rancic get an A+ in their restaurant’s layout and décor, but there food really impressed me as well. It’s not just your typical Italian cuisine—they succeed because they add a personal touch to each entrée (i.e. Mama DePandi’s Pasta & Bill’s Chocolate Budino), nothing is too large to eat, and everything has a ton of flavour…if you’re feeling like a girly drink I suggest the Piccolo Roso, which is a blend of Cocchi Rose, Strawberry and Prosecco. For the main course, I will suggest Mama DePandi’s Bucatini Pomodoro, or the Maine Lobster Ravioli. For—what I thought to be the best part of my experience—dessert, you must try Bill’s Chocolate Budino, which is a salted caramel mouse-like pudding with cocoa nibs (probably the greatest thing I have ever tasted in my life).


{Mama DePandi’s Pasta}


{Maine Lobster Ravioli}


{Bill’s Chocolate Budino}

(2)Pizzeria Due (or Uno). Basically, this is where the Deep Dish Pizza—which Chicago is so famous for—was invented. In 1943 Ike Sewell basically took a pie recipe and substituted Italian spices and ingredients to bake a pizza that takes almost an hour to bake—and from what I tasted, is well worth the wait. Pizzeria Uno and Due are across the street from each other, so simply choose one and wait (you will wait an hour for your pizza regardless, so it’s best to place your order while you are waiting for your table).



(3) While wondering the streets of Chicago, I recommend you find a Crumbs Bake Shop located in several areas around Chicago and try the S’mores Cupcake or the Peanutbutter Cup (especially if you don’t feel like eating dinner that day).

Where to Shop

(4) This may be a no-brainer, but the The Magnificent Mile is pretty frekin Magnificent. It has every shop you can think of with a wide variety of price ranges (Think Burberry and Saks to Zara and Forever 21). It has the majority of department stores (Nordstrom, Macy’s, & Bloomingdales), all the favourite Canadian stores for those who just can’t stay away (Lululemon & Aritzia), and it even has a few patio restaurants along the way to help you freshen up in between stores because we all know shopping can be a bit tiring.

(5) If conventional department stores and shops aren’t your thing,  try taking a short subway ride away from downtown to the Wicker Park/Bucktown area. Go down North Damon street and you’ll experience a wide variety of the cutest storefronts and restaurants including Marc by Marc Jacobs (Ok—maybe this doesn’t go beyond the generic—but still my favourite store), Boutique grocery store The Goddess and the Grocer, and Mindy’s Hot Chocolate. Take a walk just around the corner to find Glazed and Infused, one of Chicago’s best Donut shops. Try the Passionfruit Pistachio or the Classic Chocolate and you’re sure to come back for more.


{The Goddess and the Grocer}


{Wicker Park Apartments}


{Mindy’s Hot Chocolate}


{Marc by Marc Jacobs}

Where to Play

(5) If you’ve never been, you must visit The Navy Pier. A tourist trap for sure, it is still a necessary trip, if not for an hour or two. If the lines aren’t too long, hit the ferris wheel (which, by the way, was first invented at the Navy Pier in Chicago), or try one of the many restaurants lining the pier. If you’re not feeling the touristy vibe, simply go for a run along the pier and take in the pretty views at the end (but beware of high winds). Side note: They often do a firework show, so check the website for a schedule of dates!


{The first ferris wheel}


{Navy Pier}


{Hello Canoes}


{View off the end of the pier—lake for days}

(6) Take an architectural tour because Chicago is famous for it. Check out Frank Lloyd Wright’s (the most famous architect) work on the Chicago Line Cruises. They’ll point out which building was meant to look like a champagne bottle and which was designed to blend in with it’s surroundings (namely the river).


{Chicago Line Cruises via the River}

(7) Visit Millennium Park and the Art Institute of Chicago. Simply snap a pic at the famous Cloud Gate (it strongly resembles the Elsa Peretti Bean at Tiffany’s) while on your way to the Art institute, which is currently showing a Fashion and Modernity exhibit till the end of September.


{The Art Institute}


{The Cloud Gate}

(8) If you’re running low on energy on your way home from the Museum, take a quick pit stop at the famous Magnolia Bakery, which I fell in love with on my trip the big apple. (In case you havn’t noticed, I love cupcakes…)


{Magnolia Cupcakes}

(9) Last, but not least, end off a long day of walking  with a nice big glass of bubbly. Stop by Pops for Champagne, which is a champagne bar that has the largest champagne menu in all of America. It’s also conveniently located just off of the Magnificent Mile, so be sure to end a fabulous day of shopping with a glass of champagne.

On another side note, I would recommend attending a Chicago Cubs game at Wrigley Fields, especially if you’re visiting with your male counterparts—or simply for your own pleasure (unfortunately, none of the girls on my trip wanted to go).

I hope you all enjoyed my post and let me know if you have any suggestions for places to visit in Chicago!



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