Weekend in Chicago Itinerary – 48 Hours in the Windy City

Weekend in Chicago Itinerary – 48 Hours in the Windy City

What Can You See in Chicago in Two Days?

As it turns out, you can see quite a bit. We went to Chicago for my birthday last fall because it was a place I had always been interested in seeing but had never actually visited. Unfortunately, my birthday always falls the week before a major event at work that I am partially responsible for, so my trip couldn’t last much longer than a weekend.

We were able to squeeze quite a lot into just two days of touring. So whether you’re looking for a weekend getaway or you want to extend a flight layover by a couple of days, you can see the city too.  Here’s our itinerary.

Chicago Weekend Itinerary – Day One

First Stop: Art Institute of Chicago

The Art Institute of Chicago, a large and impressive building that contains both art school and museum. It was first built in 1893 as part of the World’s Columbian Exposition. Two huge bronze lions flank the main entrance, where banners also hang to announce the latest exhibits.  The Institute has expanded several times over the years, most recently with the addition of a modern art wing in 2009. That expansion brought the size of the Art Institute to almost 1 million square feet, making it the second largest art museum in the USA. (The first is the Metropolitan Museum of Art in New York.)

Normally, art museums aren’t high on my list of places to visit, but having read The 68 Rooms with my daughter a few years ago, I really wanted to see the Thorne Miniature Rooms in person.

Chicago Weekend Itinerary - Be sure to see the Thorne Miniature Rooms at the Art Institute of Chicago
One of the Thorne Miniature Rooms at the Art Institute of Chicago. This is a shoebox sized rendition of an English cottage kitchen of the Queen Anne period (1702-1714). The blue plates are roughly the size of a dime.

I enjoyed that exhibit, for certain, but there were so many other wonderful things in the museum that I would definitely classify it as a must see in Chicago. They had a great exhibit on glass paperweights, which included this beauty:

Chicago Weekend Itinerary - the Art Institute of Chicago has a beautiful collection of glass paperweights on its lower level.

Naturally, Hubs and I were drawn to the medieval and renaissance armor.

Chicago Weekend Itinerary - the Art Institute of Chicago is a great place to visit, and includes a variety of exhibits, including one on arms and armor.

And there were some famous paintings there as well, like A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat:

Chicago Weekend Itinerary - Be sure to visit the Art Institute of Chicago and see Georges Seurat's famous painting, A Sunday Afternoon on the Island of La Grande Jatte.

and Andy Warhol’s rendition of the Mona Lisa:

Chicago Weekend Itinerary - Be sure to look for Andy Warhol's Four Mona Lisas at the Art Institute of Chicago.

Next Stop: River Cruise and/or Lincoln Park Zoo

We spent a big chunk of time at the Art Institute & Gallery. Afterwards, we explored the riverfront area and toyed with the idea of taking a sightseeing or architecture cruise. This would certainly be a good thing to do if you enjoy water tours and/or architecture. My daughter hates going on boats, however, so we did not.

Instead, we went to the north end of the city and explored Lincoln Park Zoo. Like the zoo in my home town, this zoo does not charge admission for visitors. Plus, they have polar bears, which are one of my favorite animals ever.

Unfortunately, we visited in the middle of a record-breaking heat wave with temperatures over 95 degrees. In late September! The animals were every bit as miserable as we were, and the polar bears looked shell-shocked. I felt so bad for them!

Chicago Weekend Itinerary - Lincoln Park Zoo has free admission ... and polar bears!

That being said, the zoo was in a beautiful park setting and I would definitely like to visit it again in cooler weather.

Dinner: Pizza Pot Pie

Within walking distance of Lincoln Park Zoo, there is a restaurant called the Chicago Pizza and Oven Grinder Company. History buffs will appreciate that it’s located across the street from the site of the 1929 Valentine’s Day Massacre. Foodies will love the Pizza Pot Pie, their signature dish. It is full of cheesy goodness.

Chicago Weekend Itinerary - Dinner at Chicago Pizza and Oven Grinder Company is a must. Try the pizza pot pie!

How good was it? Well, I devoted an entire blog post to it.  It was also the first Chicago post I wrote when I returned. I had the pizza pot pie eight months ago and I still have days where I think I’d love to have it again. Yummm.

Tip:  Be at the Chicago Pizza and Oven Grinder Company when they open for dinner at 4:00 pm. It’s small and fills up quickly. Besides, you’ll want to have enough time to walk off some of those calories before dessert…

Next Stop: Millennium Park

I hadn’t intended to go to Millennium Park around sunset… it just worked out that way because we got out of dinner early. As it turns out, sunset is a pretty cool time to approach the park, because you can get a photo like this:

Chicago Weekend Itinerary - Arriving at Millennium Park late in the day provides some great photo opportunities.

Yeah, I know it’s a little off-center. I would have had to fight off at least four people with tripods in order to get a better spot.

But that’s not the reason we went to Millennium Park, obviously. We went to see “The Bean,” which is actually an art installation called Cloud Gate. This is one of those things that if you don’t do it, you’ll end up regretting it after you’ve left. It’s iconic, and you pretty much have to see it.  Besides which, it’s really cool.

Chicago Weekend Itinerary - Be sure to stop by Millennium Park to see Cloud Gate (better known as "The Bean").

The mom in me wants to know how it stays so clean and shiny.  Clearly, it’s not made out of the same stuff as my kitchen sink.

The photo above is the end of the Bean.  The sides have an indentation big enough to pass through it.  When you do, be sure to look up. You might not be sure what you’re looking at, because it’s almost psychedelic.

Chicago Weekend Itinerary - Walk inside the center of the Bean at Millennium Park and be sure to look up!

Explore the rest of the park too… it has many other great things to see in addition to the Bean!

Dessert: Smallcakes Smash

If you saved room for dessert, head on over to Smallcakes for a cupcake, ice cream, or the most decadent dessert in town. (You might want to take a couple of people to share it with you.)

Now, Smallcakes is a national chain, not a uniquely Chicago business.  However, it’s worth a visit because of their signature, over-the-top dessert called the Smallcakes Smash.

Choose a cupcake and one or two flavors of ice cream. There are at least a dozen of each to choose from.  Then, sit back and watch as they construct the “Smash” before your very eyes.

A scoop of ice cream goes in the bottom of the cup, followed by the bottom half of the cupcake. A second scoop of ice cream tops that, followed by some whipped cream and syrup in a complementary flavor. Then the whole concoction is topped with the remainder of the cupcake. It is a masterpiece!  Behold!

Chicago Weekend Itinerary - Get a Smallcakes Smash at Smallcakes!

I recommend sharing one with a friend. It’s a lot for just one person!

Chicago Weekend Itinerary – Day Two

First Stop: Chicago Tribune Tower

In the morning, we walked over to see the Chicago Tribune Tower which is in the heart of downtown Chicago. Normally, I wouldn’t make a special trip to see just a building, but the Tribune Tower is a building like no other. Pieces of famous landmarks and buildings from all over the world are embedded in its walls.

Chicago Weekend Itinerary: Look for fragments of world landmarks at the Chicago Tribune Tower.

And I don’t mean a dozen or so… I mean almost 150. It was great fun to stand there looking for these special stones – we saw pieces of Westminster Abbey, the Taj Mahal, and the Great Wall of China, to name just a few.

Next Stop: Museum of Science & Industry (with Kids)

If you don’t have children with you, you might not enjoy the Museum of Science & Industry all that much. We only went because I’ve had a bit of an obsession with Colleen Moore’s Fairy Castle for over 15 years, and it happens to be on display at Science & Industry. Otherwise, I would have found a different activity, such as the Field Museum, or one of those river cruises, or something else.

That being said, the Fairy Castle did not disappoint.

Chicago Weekend Itinerary - Families will enjoy a visit to the Museum of Science & Industry, home to Colleen Moore's Fairy Castle

I circled it three times and was constantly finding new details each time I looked inside the rooms. An audio recording plays while you are going around the castle, and it’s worth listening to, because it has some very interesting details. The castle is full of authentic items, some of them hundreds of years old. Other items are not as old, but are just as valuable, like the miniature chair that is made of platinum and diamonds.

We looked at a few other exhibits after the fairy castle, including one on bicycle design that Hubs found very interesting, and a mirror maze. But we still had more to see and do, so we didn’t stay too long.

Next Stop: Street Art & Lunch in Logan Square

Street art makes for great photo opportunities. I found out that there was a “Greetings from Chicago” style postcard mural and knew we had to get our pictures in front of it, so that was where we headed next.

Chicago Weekend Itinerary - snap a pic with the Greetings from Chicago mural as your backdrop.

The mural is located at 2226 N Milwaukee Ave, in the Logan Square neighborhood of Chicago.  Nearby, we saw another great series of paintings titled “Never Give Up” on the side of a family dollar store.

Chicago Weekend Itinerary - There are all types of street art to amuse and inspire you in Logan Square.

It had the stories of five famous people who had, at various points in their lives, encountered setbacks and failures. Despite those challenges, they went on to achieve great success.  It was a good reminder to hang in there when the going gets tough.

Logan Square is a racially diverse and artistic neighborhood with lots of beautiful architecture, great restaurants, and street art. Unlike some city neighborhoods I’ve visited, Logan Square seemed to have a strong sense of community. There are many great restaurants, bars, churches, and local is the key word when describing many aspects of the scene. Ingredients are sourced locally at restaurants; bars serve local craft brews; galleries showcase local artists; and concerts and street fests promote local, upstart bands.

There is no shortage of good restaurants in the Logan Square area, and in a wide variety of ethnic cuisines as well. We had lunch at the Logan Bar & Grill, which had an amazing outdoor seating area. I almost forgot that it was insanely hot while we enjoyed our burgers.

Feeling refreshed and at least a little rested (not to mention re-hydrated!), we got an Uber to take us to…

Next Stop: The Tower Formerly Known as Sears

As you may have read in my blog post about the Willis Tower, I wasn’t completely sold on the idea of going to the top to see the views. But eventually I did make the decision to do it, because I figured it was another one of those iconic Chicago things, like The Bean.

I wish I had paid attention to the time when we first went in to see how long we waiting in line before actually making it to the Skydeck. It was at least an hour. It felt like two. Let’s split the difference and call it ninety minutes, waiting in line, moving at a snail’s pace through the basement of one of the most famous buildings in America.

By the time we got to the Skydeck, the sun was beginning to drop in the sky, and the Golden Hour was upon us.

Chicago Weekend Itinerary - Catch the view from the (Sears) Willis Tower Skydeck.

With the setting sun behind us, the shadows of the skyscrapers were cast across the city and the lake. It was stunning! Suddenly, I didn’t resent that two hour 90 minute wait quite as much.

Dinner: Deep Dish Pizza

You can’t leave Chicago without eating deep dish pizza at least once, right? Well, there is apparently some debate as to who has the best deep dish in Chicago. I’m not a big fan of deep dish style pizza, so I didn’t put a lot of effort into choosing a restaurant for this meal. The first place I saw a recommendation for was the lucky winner: Gino’s East.

I don’t know if Gino’s East has the best pizza, but it’s probably got the most fun atmosphere. The entire restaurant has been covered in graffiti from past customers.

Chicago Weekend Itinerary - Make one meal a deep dish pizza, the city's signature dish. Gino's East is one of the best, and has an interior that is completely covered in graffiti.

Our server was great as he welcomed us and explained the different options. When the food arrived, we dug in and managed to finish the whole thing, thanks to his recommendations on what size we needed.Chicago Weekend Itinerary - Deep Dish pizza is the Windy City's signature dish.

However, that being said, do be careful when ordering a deep dish pizza.  Because it is so thick, eating one slice is equivalent to eating two or three slices of regular pizza. I saw a lot of tourists walking around Chicago carrying pizza boxes because they didn’t take this into consideration. It’s much better to order the right size and not have to worry about leftovers.

Next Stop: Strolling the Magnificent Mile

After dinner we walked along the area of Michigan Avenue known as The Magnificent Mile. (Can you hear that in any voice but Oprah’s? I can’t.) There are loads of shops along this stretch of road, most of which I cannot afford. Still, it makes for good window shopping and people watching.

Between there and our hotel, we stopped at Eataly, which I’ve always been curious about but have never had an opportunity to visit. Then we returned to the hotel to pack our bags for the next morning, when we would wish a fond farewell to the city of Chicago. It was our first visit there, but we all agreed that we didn’t want it to be our last.

Summary Infographic:

Chicago Weekend Itinerary in list form

Chicago Weekend Itinerary at Travel As Much
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Chicago Weekend Itinerary - What You Should See, Do, and Eat in the Windy City
Article Name
Chicago Weekend Itinerary - What You Should See, Do, and Eat in the Windy City
Description
Visiting Chicago for a weekend? Here's a two day itinerary that will help you hit all the high points and feel like you've seen a lot of the city in just two days.
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Travel As Much
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