When a Chicago local turns tourist, she discovers there’s more to Chicago than a gorgeous skyline and Uno’s Pizza (the original Chicago-style deep dish pizza). Follow along as a local takes a Chicago Architecture river cruise, samples some unexpected Chicago pizza places and gazes wistfully upon the field where the not-in-the-World-Series Chicago Cubs play, It all happens during a whirlwind weekend in Chicago.
Disclosure: I was hosted for this weekend in Chicago by Choose Chicago, the city’s tourism office, but the love for this city is all my own. In addition, this post contains some affiliate links. If you click through and buy, TravelingMom will get a small commission at no additional charge to you.
Chicago Architecture and Chicago Pizza
Chicago, the city I call home, has far too many great things to do to cover them all in a weekend. Today we will focus on just two of those world-renowned features: Chicago architecture and Chicago pizza.
Join me on this whirlwind weekend in Chicago. We’ll tour the great skyscrapers that line the Chicago River. And we’ll sample some of the city’s best pizza, including some made in neighborhood haunts far off the beaten path.
[adthrive-in-post-video-player video-id=”H48KFNrE” upload-date=”2018-10-31T19:45:52.000Z” name=”How to Spend a Weekend in Chicago” description=”null”]
Chicago Architecture River Cruise
Chicago is the birthplace of the modern skyscraper. Its soaring skyline (best seen and photographed from the lawn near the Adler Planetarium) is a source of joy and wonder for me. When my kids returned from college for weekend visits, the first order of business was always a drive up Lake Shore Drive. That first glimpse of the city as you come around the bend near Soldier Field always makes me draw a quick breath.
But seeing the skyline from the Chicago River is whole different thrill. Listening to a knowledgeable docent from the Chicago Architecture Foundation aboard the Chicago’s First Lady tour boat offers history and neck-craning views. It’s a great way for Chicago newcomers to get a real feel for my beloved city.
Choose a sunny day and snag a seat on the upper deck of Chicago’s First Lady. That way you can gaze skyward while listening to the informative monologue. It’s the best way to get a full view of the architectural wonders and appreciate this beautiful city.
Weather or Not
Unfortunately, the day we were booked for the cruise, Chicago weather did not cooperate. The temperatures were in the low 50s, the wind was whipping down the river and the rain was blowing sideways. Not ideal conditions for a Chicago River cruise. I toughed it out as long as I could on the upper deck before escaping below for hot chocolate and warmth. Sadly, no matter how close I got to the windows, I couldn’t see more than the first few floors of the sky-high buildings. The cruise runs through mid-November; dress warmly and bring a rain poncho so you can stay up top as long as possible.
I was traveling as an empty nester, but I have taken kids on this trip before. Much of the narrative will be lost on younger kids, although my kids always liked being on the boat.
Chicago Architecure River Cruise Tips
TravelingMom Tip: This cruise is definitely worth the $40+ fee if you’re an architecture buff or if you just want to see the city from the river. But Chicago weather can be unpredictable. On a cold, windy and rainy day, save your money. Instead, opt for a walk along the Chicago Riverwalk, following along on this free self-guided tour. You can walk at your own pace and duck inside for a warm drink when you need to get out of the weather.
TravelingMom Tip 2: Save a few bucks by buying a Groupon for the tour. Enter the Groupon site via this link through Ebates for extra cash back. Even better, if you’re new to Ebates, you’ll get a $10 bonus on your first $25 purchase by using our referral link.
TravelingMom Tip 3: If you plan to spend more than a weekend in Chicago, buy a CityPASS booklet. You’ll get discounted access to many of Chicago’s world-class cultural attractions, including the Art Institute of Chicago and the Shedd Aquarium.
Read More: If you can stay longer than a weekend in Chicago, check out this 3-day itinerary for visiting Chicago with kids.
Chicago Architecture Center
The Chicago Architecture Foundation is the authority on all things architecture in the Windy City. (Fun fact: The city did NOT get this nickname from the winds that blow in off of Lake Michigan. It got the name thanks to its “windy” politicians who fought to bring the 1893 World’s Fair to Chicago.)
The CAF has a shiny new home on Wacker Drive. Don’t miss a chance to visit and learn about the history of Chicago via a brief movie that runs every 20 minutes on the lower floor. Projected onto a screen behind a model of the city as it looks now, the film tells the history of Chicago, including a dramatic depiction of the Great Chicago Fire of 1871 (that did NOT start by Mrs. O’Leary’s cow kicking over a lantern).
The upper level is home to models of some of the world’s most accomplished and innovative buildings, all with a connection to Chicago design, engineering and architecture firms. The entrance features a scary look at the world’s exploding population growth coupled with an inspiring overview of efforts to do more with less, including buildings designed to conserve and reuse natural resources or ones that provide greenspace in a crowded urban environment.
Disappointingly, I didn’t see anything upstairs that is interactive. Keep kids entertained while you read and browse by challenging them to find the tallest building among the impressive models on display.
Love the historic touches @ginslerchicago kept when the design firm took over the former Carson’s store at State & Madison in @choosechicago. It’s just 1 of the cool spaces you can see on #ohc2018 this weekend. #TMOMChicago #architecturelovers #architectanddesign #openhousechicago #openhousechicago2018
Open House Chicago
This is a once-a-year event in Chicago. It’s free and promises a peak inside some of the city’s iconic buildings and tours of the offices of its great design firms. The 2018 event featured access to 250 buildings. Check the website for 2019 dates and information.
I had only a little time to explore, but I did get a peek inside the Seventeenth Church of Christ, Scientist. (As the volunteer docents noted as she began her remarks, “This is not the Church of Scientology.”) I have walked past this tiny rounded building at the corner of Wacker and Wabash my entire life. So I jumped at the chance for a 20-minute tour.
Art on the Mart
The Loop (the central city is called that thanks to the elevated train tracks that run in a “loop” around it), is dotted with works of public art. The most famous is, of course, is The Bean in Millennium Park. No visit to Chicago is complete without a stop for a selfie at The Bean!
But there’s a new art wonder in town: Art on the Mart. The city says it’s the largest digital art project in the world. Certainly, it rivals the projections at Disney World onto Cinderella’s Castle at Magic Kingdom.
Art on the Mart uses 34 projectors to illuminate the river-facing façade of the giant Merchandise Mart. (Another fun fact: The Merchandise Mart is so huge that it used to have its own ZIP code.) The projections run Wednesday-Sunday from 7:15-9:15 p.m. through December 2018. Bundle up. It can get cold along the river. Plan to watch for a least 10 minutes. The best viewing spot is on the south side of Wacker Drive near Wells Street.
Chicago Pizza Tour
It would be wrong to visit Chicago and not eat pizza. After all, Chicago is the home of deep dish pizza. If you were coming to town and asked me where to eat the most famous Chicago-style pizza of all–Chicago deep dish pizza–I would send you to Uno’s. That’s where this delectable delight of chewy dough, stretchy cheese and tomato sauce goodness was created.
Thanks to spending an afternoon with Pizza City USA, a Chicago pizza tour company owned by Steve Dolinksy, a local TV food reporter, I now have two new Chicago pizza places to recommend: Labriola’s on North Michigan Avenue and Pat’s Pizza, a neighborhood joint that was a favorite of that late, great Chicagoan, movie critic Roger Ebert.
We also made stops at two other Chicago pizza places, Pizzeria Bebu, an artisan pizza place, and (gasp!) a New York style pizza place called Dante’s Pizzeria. Frankly, I didn’t even know that anyone in Chicago had stooped so low as to open a New York style pizza place in the Pizza Capital of the World. But they have. It was the last stop on the tour, so I was already stuffed with pizza. Perhaps that’s why I didn’t really care for the huge, dripping, greasy slice you eat by folding in half. But the few out-of-towners on our tour chose that as their favorite pizza stop. Go figure.
But I digress into that age old Chicago vs. New York pizza debate. Back to the tour.
The Pizza Chicagoans Eat
Over the course of the 3.5 hour tour, we sampled 4 of what Dolinksy says is the 10 kinds of pizza you can find in Chicago. Throughout, Dolinsky kept up an entertaining monologue about Chicago pizza, showed off an impressive knowledge of the history of his adopted city and shared foodie insights about some of Chicago’s other food specialties. (Most notable was his hysterical impression of a good ol’ boy Chicagoan ordering a beef sandwich.)
And, he told me something about Chicago and myself that I never realized was true: Chicago deep dish pizza isn’t really the pizza we Chicagoans eat. We eat “tavern-style” pizza. That’s flat pizza with a crispy crust, cut into squares and topped with whatever we want. That’s the pizza Pat’s specializes in.
Who thinks #Chicagopizza means #deepdishpizza? Wrong! Steve Dolinsky of @pizzacityusa says this tavern style super thin crispy crust pizza is REAL Chicago pizza. It’s true. It’s the pizza we all eat at home. If we ate deep dish all the time we would all weigh 500 lbs! This is from @patspizzachicago. It was Roger Ebert’s fave. The man knew great pizza! #yum #TMOM #TMOMChicago @choosechicago
The minute I heard those words come out of Steve’s mouth, I knew them to be true. We all eat deep dish pizza—generally when our friends come in from out of town and want to eat great Chicago pizza at an iconic Chicago pizza place. We take them to the neighborhood deep dish pizza joint. When there are no guests and it’s just us, we settle on the couch, flip on a movie and order up a tasty, crispy flat pizza to be delivered.
TravelingMom Tip: Skip breakfast before this lunch time tour. And pace yourself. If you eat the entire slice of deep dish pizza, you’ll be too full to properly enjoy the other three Chicago pizza places you’ll visit. And consider booking a walking tour. At least you’ll work off a little of the pizza between bites.
There’s a Chicago Pizza Book!
Dolinsky has taken his passion for Chicago and pizza put it down on paper. The fresh-off-the-press 101 Reasons Why Chicago is America’s Greatest Pizza Town is filled with pizza insights, pizza reviews and, yes, 101 Chicago pizza restaurants I must try. I bought the book and plan to make it my mission to work my way through the list. Except for the New York style pizza places.
Family-Friendly Chicago Hotel
Being a Chicagoan, I rarely get the chance to stay in a Chicago hotel. Being a lifelong Cubs fans, I was sooooo excited at the prospect of checking out the new Hotel Zachary. It’s right across the street from Wrigley Field, home of the Chicago Cubs. The hotel is not downtown, but it is a worthwhile extension of the weekend in Chicago architecture theme. The hotel takes its name from Zachary Taylor Davis, the architect who designed Wrigley Field.
If you’re a Cubs fan, book an east-facing room for a view of the century-old Cubs ballpark. The hotel is park of a $1 billion upgrade to Wrigley and the area around it. Hotel Zachary opened in spring 2018, just in time for the 2018 Cubs season.
Room rates are reasonable by Chicago standards. Expect to pay less than $250 per night for a standard room, assuming you’re not trying to book on nights when the Cubs play at home. The rooms are large for a boutique hotel. Mine had the million-dollar view of Wrigley Field. Had the Cubs been playing, I would have been able to watch batters at the plate through a tiny peekaboo slot in the Wrigley Field stands.
What To Eat
If you get hungry while you’re there, skip the McDonald’s in the building and head straight for Big Star Wrigleyville. This restaurant on the first level of the hotel serves some of the best tacos I’ve ever eaten. If you prefer BBQ, follow your nose next door to Smoke Daddy BBQ. I didn’t have time to try it, but based on smells alone, I plan to go back.
For breakfast, head straight to the Alma Room on the lobby level and order the avocado toast. Just do it. It will make you happy.
2 Things You Need to Know about Hotel Zachary
The only disappointment here was the lack of a coffee pot in the room. Getting a morning cup of tea requires going downstairs to the West Town Bakery. Flash your room key for a free cuppa. That requires getting dressed so you can be presentable when you get downstairs. That is not the way a morning should go. To make matters worse, the line was quite long when I arrived. Everyone was ordering some sort of breakfast, which seemed to take a very long time. I finally managed to snag one of the workers and ask for a plain ol’ cup of tea. But it took close to 10 minutes to get that. People like my husband, who is pretty useless before he downs his first cup of coffee in the morning, may find this to be a real challenge.
Please note that this is a neighborhood hotel. It’s located 4 miles north of the Loop. The good news is that the hotel is a half-block from the Red Line elevated train. The L will get you downtown in a fraction of the time it takes to drive through the thick traffic and find a place to park. And it only costs $2.50 for a safe, quick and easy ride.
TravelingMom Tip: If you must drive, read this first. It will help you find more affordable parking and save you time driving around looking for a parking spot.