2 Days in Chicago – What to Eat, See, and Do in the Windy City

With a population of roughly 2.7 million people, Chicago ranks as the 3rd largest city in the United States, and is widely regarded as one of the greatest cities in North America. As I was already spending a couple days in Detroit for the North American International Auto Show, I figured that it would be a great opportunity to spend a 48-hour layover in the Windy City before heading home. With such a short amount of time, I knew I had to be quite calculated with my itinerary in order to maximize my stay. It also helped that my friend Carly was also in town for the first time that week, so I would have a travel pal to enjoy the city with.

I chose to stay at the Hyatt Chicago Magnificent Mile, which is located just off of Michigan Avenue, right in the heart of downtown Chicago. Michigan Avenue is the big shopping street in the city, featuring a great selection of designer and luxury brands, department stores, malls, and boutiques.


Photo credit: John Fulton and John Bellenis

The Four Diamond Hyatt Chicago Magnificent Mile underwent a significant $25 million renovation in 2013, and with 419 guestrooms, their newly renovated rooms and amenities offer contemporary luxury, convenience, and ready access to all of the things that make Chicago one of the finest cities in the world. The guestrooms were clean, modern and well-equipped, with extremely comfortable and plush beds, and I really enjoyed my stay there.

My first order of business was to get a burger at Shake Shack, which is located just a few blocks away from my hotel. This popular burger franchise started in New York, but had just recently opened up a location in Chicago this past November. I ordered the Shack Burger, which was a delicious 100% antibiotic-free Angus beef burger, topped with cheese, lettuce, tomatoes, and their signature Shack sauce, which USA Today describes as “a slightly spicy, sweet and sour blend of mayo, ketchup, mustard and spices.” It truly was a great burger and I’m glad that I had an opportunity to try it.
Shake Shack

Shake Shack on Urbanspoon

I picked up a Chicago CityPASS as well, which allows you to visit 5 different attractions. The pass retails for $94, but you actually end up saving around 50% on admission fares, so it’s actually a really great deal. I also got a CityPASS on our recent trip to San Francisco, as it’s a great way to save some money if you’re planning on seeing a lot of popular city attractions.
One of the attractions included in the CityPASS is 360 Chicago (formerly the John Hancock Observatory), which is a lookout point at the top of John Hancock Center. Looming 94 storeys above the city, it offers breathtaking 360-degree views of Lake Michigan, the North Shore, downtown Chicago, and south to Indiana. At night, you can see the beautiful city lights, while during the day, you can enjoy the sweeping and unobstructed views for as far as your eye can see. While you’re on the observation deck, there are several interactive displays that can help you identify the various landmarks and buildings that are before you.

After 360 Chicago, we headed to Girl & The Goat for dinner, as it had been recommended to us by several friends. Although I found the food was just okay there, word on the street is that Little Goat, which is right across the street and also owned by Stephanie Izard, is a much better, more casual dining spot.

Dinner at Girl & the Goat. This place came highly recommended by many people. Honestly, I thought it fell a bit short, but maybe my expectations were too high. Clockwise top left: sautéed green beans with fish sauce vinaigrette, cashews (way too much sauce, way too big of a portion); wood fired old 1871 oysters with horseradish, bacon, preserved lemon (oysters were cooked, good flavours, but I think it’d be better raw); grilled marinated pork belly with castelfranco, sauce green, blood orange (too chewy and parts were over seasoned); herbs of a feta with hummus​ and feta oil (honestly, really good, the highlight of the meal, probably the best hummus I’ve ever had); goat empanadas with huacatay, grilled mushroom giardiniera, queso fresco (nice flaky wrapper, good flavours, well balanced). Anybody else been here before? #windycitypangs

A photo posted by Dennis Pang (@dennispang) on

Girl & the Goat on Urbanspoon

The next day, we headed to Giordano’s for Chicago-style deep dish pizza. You likely won’t find locals there, but it sure is popular with tourists. A small pizza retails for around $22, and it can feed 2-3 people easily. The pizzas are very unique as the crust is around 2 inches high, with toppings and cheese layered throughout, and tomato sauce on the top, unlike traditional American pizzas, which usually have tomato sauce, followed by toppings, and finished with cheese on top. We both really enjoyed the Special pizza that we ordered, which had sausage, green peppers, onions, and a massive quantity of cheese. We managed to finish the entire pizza, and it was enjoyable until the last bite. I’ve been told that Lou Malnati‘s serves up an amazing deep dish pizza as well, so you know that’s where I’m going next time.

Giordano's Pizza on Urbanspoon

After lunch, we went to The Field Museum (of Natural History), one of the largest natural history museums in the world, which is another attraction included with the CityPASS. It boasts various exhibits containing an extensive variety of scientific specimen and artifact collections. We saw dinosaur bones and gemstones, as well as Egyptian and Haitian vodou artifacts, and even sat in on a 3D short film about Egypt. If you’re into natural history, then this is definitely a family-friendly attraction that you won’t want to miss. You could probably spend an entire day here wandering through the various exhibits and museum floors.

After spending some time at the museum, we crossed the street and visited the Shedd Aquarium, which as you guessed is also included with the CityPASS. Built in the 1930s, the Shedd Aquarium is now home to over 25,000 fish. The aquarium is big and has some nice permanent exhibits featuring various regions of the world like the Amazon and the Caribbean. You’ll also find sharks, belugas, stingrays, and penguins here. The facilities did feel a tad bit dated though, compared to the Vancouver Aquarium or Aquarium of the Bay in San Francisco.

For dinner, we decided to go to The Purple Pig, which is a Mediterranean restaurant that was highly recommended by many of my friends who had visited Chicago. As this place fills up pretty quickly in the evening, we made an effort to arrive at around 5:30pm, which was perfect as we got seated immediately. By the time we left, there was already a decent sized lineup forming. I highly recommend this restaurant, as the service is good, and thedishes are well executed without being overcomplicated. I particularly enjoyed the pork fried almonds, and you can bet that I’ll be stealing that recipe for myself.
Left: Pork Fried Almonds with Rosemary & Garlic; Right: Roasted Bone Marrow with Herbs
Left: Razor Clams with Oregano, Lemon & Olive Oil; Right: Wagyu Sirloin Tip with Fingerling Potatoes, Cippolini Onions, Olives & Bone Marrow Vinaigrette

The Purple Pig on Urbanspoon

With teams in all of the major sports leagues, Chicago is a great city for sports fans. As a hockey fan, I really wanted to go watch a Chicago Blackhawks game, however their schedule just didn’t line up with our itinerary. We did however attend a Chicago Bulls game at the United Center. The United Center is an iconic arena, and one look up into the rafters will be a telling sign of how many championship teams have called this arena home over the past several decades. In the main concourse, there’s even a display window showing off the 6 NBA Championship trophies the Bulls brought home during the Jordan dynasty era. The arena itself is fairly old, but it has lots of character and history, not to mention it’s huge, with 6 levels of seating for nearly 23,000 people. The Bulls played a good game against the Washington Wizards despite losing 105-99.
Chicago Bulls
We started the next day by visiting Skydeck, which is the observation lookout at the top of Willis Tower (still commonly referred to as Sears Tower). At 1,450 feet, it is the second-tallest building in the United States, and it happens to be another attraction included with the CityPASS. The observation deck is located on the 103rd floor, offering stunning panoramic views of the city. As we enjoyed a great nighttime view of the city at 360 Chicago, today we would get to enjoy another amazing daytime view of the city.
After Skydeck, we headed to The Art Institute of Chicago, an art museum featuring a variety of art from around the world. With priceless works from the Impressionist and the Post-Impressionist era, to Japanese and Roman art, and American modern and contemporary art, this is a great attraction for art lovers. Having been to many art museums around the world, I have to say that this museum is definitely one that you don’t want to miss. As the second largest art museum in the United States, you could probably spend an entire day here, but as time was of the essence, rather than visit every square inch of the building, we decided to just check out the exhibits that appealed to us.
Above: Some famous works that we saw included Caillebotte’s ‘Paris Street; Rainy Day‘ (1877), Monet’s ‘Water Lily Pond‘ (1900), and Wood’s ‘American Gothic‘ (1930).
Across the street from the Art Institute is Millenium Park, where you can find the famous art sculpture Cloud Gate, commonly referred to as The Bean, along with other notable public art works. In front of The Bean is the McCormick Tribune Ice Skating Rink. If we had time to spare, I would have wanted to go ice skating, as it was such a beautiful sunny day.
Cloud Gate
After Cloud Gate, we headed to Portillo’s for lunch, a franchise made famous for their hot dogs and Italian beef sandwiches. Portillo’s is located primarily throughout the Chicago suburbs, but they also have a couple locations in southern California and Phoenix. I decided to get both the hot dog and the beef sandwich, as they’re both staples of Chicagoans’ diets. The beef sandwich was served on French bread with hot and sweet peppers, and it was pre-dipped in au jus. It’s a bit of a messy sandwich, so prepare to roll up your sleeves for it. The hot dog was sensational, as the sausage had a great snap to every bite, and the toppings were fresh and delicious. Tip: NEVER ask for ketchup for your Chicago hot dog. That’s a big no-no.

Portillo's on Urbanspoon
We used Uber to commute around the city, and it was really great. Everything was a $8-12 ride away, and we never waited for more than 5 minutes for an Uber car to pick us up. An airport ride from downtown will take around 30 minutes and set you back around $25, or you can take a CTA mass transit for $5, but it’ll get you there in around an hour.

With so much to eat, see, and do, there’s no way I could have packed in everything that I wanted to do in 48 hours. Chicago exceeded my expectations in every way, and I can’t wait to come back again to explore more of the city. My only wish is that the weather was warmer, as the winter chill was quite brutal at times. But even despite the cold weather, it’s easy to see why so many people are so fond of this city. I fell head over heels in love with this city in just 2 days. And now I need to hit the gym to burn off all these calories. 😉

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I am the CEO & Marketing Strategist for Motive8 Media Inc. and Popcorn. This is my personal blog, which contains highlights of my personal life. I'm into all things food, wine, and travel related.

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