Oct 30, 20216 min read

C-H-I-C-A-G-O, That Toddlin' Town

I finally made it to Chicago. Finally!

As a first timer, I had a ton of Chicago must-dos planned for the weekend. I'm proud to say I scratched most of them off my list. What are you waiting for? Grab a friend and have the perfect weekend getaway in Chicago like I did!

FRIDAY A.M.

I boarded as A01 on Southwest Airlines (once in a lifetime, right?) to Chicago O'Hare. Brooke and I talked the whole way to Chicago, and got a great glimpse of the towering skyscrapers along the coast of Lake Michigan as we landed.

It was a quick Uber ride to downtown where we checked in to our hotel, 21C Museum Hotel on Ontario Street. 21C is a boutique hotel chain that allows guests to stay with art. The hotel "...offers the local and traveling community unprecedented access to the work of some of today’s emerging artists, every day all day" (21C). We dropped off our bags, freshened up, then hit the town.

It was a short walk down Wabash Ave. to the Chicago River where skyscrapers truly towered overhead. Brooke and I kept laughing at how we were walking with our necks craned back to better see the giant buildings around us. We must look like small-town tourists, we thought.

On our walk we passed the iconic Chicago Theater sign, Goth Target (yep #gothtarget is trending on the socials), and ultimately landed at Revival Food Hall for lunch. The food hall was tucked away on Clark Street and it appeared to be fairly new with mostly local diners. Brooke and I both enjoyed LaShuk Street Food - the hummus was to die for!

FRIDAY P.M.

After lunch, we walked to The Art Institute of Chicago. Their impressionist collection was vast and impressive to say the least. The museum is also home to iconic pieces like Nighthawks, American Gothic, and contemporary pop-art by Andy Warhol.

Just outside of The Art Institute of Chicago is Millennium Park, home to Cloud Gate (AKA The Bean). Hundreds of people were crowded around the iconic sculpture to capture their picture. Tourist hack: Brooke and I found that the back side has less people and the skyline was reflected on the bean, which made for a better photo.

Next we headed north on Michigan Ave back towards the Chicago River where we boarded Chicago's First Lady for a 90-min Chicago River Architecture Tour. The cruise was one of the highlights of our trip. It was narrated by a member of Chicago's Architecture Foundation Center. We learned a ton and got to appreciate over 50 buildings that line the river making up Chicago's iconic skyline.

After the cruise we walked along the Chicago Riverwalk and stopped at Monk's Pub for a quick drink before checking out Art on theMART, the "...largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5 acre river-façade of theMART" (Art on theMART).

By this point, we'd really worked up an appetite. For dinner we enjoyed personal sized deep dish pizzas at Uno Pizzeria & Grill. It was so filling that we couldn't even finish their smallest pizzas!

SATURDAY A.M.

Brooke and I slept in a bit on Saturday before heading to Starbucks Reserve for some breakfast. As expected, we did have to wait in a line outside for about 10-15 minutes before we were allowed inside the 5-story mega Starbucks (the largest Starbucks in the world to be exact). Each floor offered unique drink and dining opportunities. We spent the most time on the top floors where we enjoyed experiential coffees (Nitro Molé Mochas) and cafe items like smoked salmon and cream cheese on brioche. At the bar, I enjoyed my first espresso martini.

We both had a bad case of the zoomies after all that coffee, so we decided to walk to lunch at Portillo's (Clark & Ontario St.) where we enjoyed their famed hot beef sandwiches.

It was a short Uber ride from Portillo's to the Field Museum, where we spent the next few hours exploring world-class exhibits on dinosaurs, mummies, and more.

SATURDAY P.M.

After a day spent primarily inside, we decided to get some fresh air by taking the scenic route back to downtown from the Museum Campus (home to the Field Museum, Adler Planetarium, Shedd Aquarium and Solider Field). It was about an hour walk, but along the way we enjoyed looking out at Lake Michigan, Grant Park, Navy Pier, and the mouth of the Chicago Riverwalk.

Our destination was Three Dots and a Dash, Chicago's famed alleyway tiki bar. "With a thatched faux-roof, colorful mood lighting, and statuesque ceramic mugs, Three Dots and a Dash leaves no doubt about what it is: a tiki bar that's dedicated to the aesthetic without veering too far into the kitsch" (TRAVELER). TD&D was another highlight of our trip. Here's their menu for the curious.

We ended our Saturday with a special treat - a real bucket list experience for me - tickets to see The Second City's 109th review, Together At Last, at The Second City MainStage. The show was absolutely hilarious and a mix of improv and sketch comedy. This was the cast's first revue coming back from the theater's Covid-19 closure, so it was particularly meaningful for all involved. The Second City has roots in Chicago, and was the launching pad for some of the world's most renowned comedy actors, including Dan Aykroyd, John and Jim Belushi, John Candy, Steve Carrell, Steven Colbert, Tina Fey, Keegan-Michael Key, Bill Murray, Mike Myers, Amy Poehler, Gilda Radner, Harold Ramis, Eugene Levy, Catherine O'Hara and Martin Short (to name a few).

SUNDAY A.M.

All good things must come to an end, and such is Sunday's fate. I was booked on an afternoon flight home with just enough time to get a bit more sightseeing done before heading to the airport.

While about a 20 minute ride away from downtown, the Museum of Science and Industry was worth the trek. The museum is the largest science museum in the Western Hemisphere and located in the only remaining building from the 1893 World’s Fair. Like it's sister museums throughout Chicago, the permanent exhibitions here are world-class. My favorites were the captured WWII German U-Boat housing an intact Enigma machine that historians estimate shaved two years off the war; the Boeing 727 1960s air travel exhibit; a restored Pioneer Zephyr train; a twisty mirror maze; and NASA's Apollo 8 module and Aurora 7 capsule.

SUNDAY P.M.

My trip to the airport and through security was a bit arduous, but I safely made it home.

THERE'S ALWAYS NEXT TIME

While I saw most of the things I wanted to see, I left a few things on my list for next time.

The Food:

Let's be honest...this Chicago first-timer could have easily (and gladly) taken it upon herself to spend the entirety of her trip studying the great art of the DEEP dish pizza. I've surveyed friends and natives, watched food travel shows, and even reviewed countless blogs to determine where one will find the best pizza in Chicago. The answer, like the pizza, is not a simple one. But this is certainly a good list to work from (in no particular order):

Lou Malnati's Pizzeria

Chicago Pizza & Oven Grinder

Gino's East Magnificent Mile

Giordano's

The Art of Pizza

Pequods Pizza

While I certainly could eat my fair share of pizza, some alternatives to round out the Chicago food scene may be required. Greektown is home to dozens of Greek restaurants (reminds me...I need to watch My Big Fat Greek Wedding again). Chef Stephanie Izard, of Top Chef fame, has two acclaimed Chicago restaurants, Duck Duck Goat and Girl & The Goat. Also, James Beard awarded Chef Sarah Grueneberg's Monteverde's homemade pasta looks heavenly.

What's vacation without a happy hour? There are so many fantastic places to chose from, but these rose to the top:

Punch Bowl Social Chicago

The Signature Lounge (alternative to the 360 Observation deck)

Lest we forget about dessert...

Scooped Cookie Dough Bar

Margie's Candies

Goddess and The Baker

Garrett Popcorn

Shawn Michelle's Homemade Ice Cream

The Architecture:

Perhaps you're a Frank Lloyd Wright fan, like me. Wright got his start in and around Chicago in the early 1900s, and today you'll find many of his properties open to the public for tours.