Chicago, Chicago, that toddling town🎜
For the past couple of decades, the Windy City has served as a connection or brief stopover on many of my travels. Deerfield was a business destination a couple of times. But I never explored the city – until now. I don’t know why I waited so long. My hubby and I were ready to take to the friendly skies for the first time in 2 years and Chicago was our destination choice. So join us as we spend four days in the Windy City starting with…
DAY 1 – Arrival
A morning flight out of LaGuardia went smoothly. Arriving in O-Hare late morning, we bought train tickets and took the “L” train to get to downtown Chicago where our hotel was. The cost was just $5 per person!
The Millennium Knickerbocker, located off the Magnificent Mile (Michigan Ave), was our accommodation choice. We got a great rate, and the hotel served us well in terms of location and comfort.
Since it was before noon, we couldn’t check in yet so we dropped off our luggage and headed out for some brunch. And what a meal this was! Wildberry Pancakes and Cafe serves up an array of breakfast and lunch options. Absolutely delicious and they certainly don’t scrimp on the portions.
With our bellies full, we set out to explore. I always recommend walking around to get a feel of the city. We headed over to Lake Michigan, walking along the shore, amazed by its beautiful blue-green water and beach.
The Chicago skyline is magnificent.
As we walked along this river, we detoured off to Old Town, a beautiful neighborhood that was first settled by German immigrants in 1850. It is very popular with architecture buffs who come to admire its Victorian-era buildings, quaint streets, and shops. Wells Street features the revered Second City comedy club, eateries, pubs, and artisanal coffee shops, as well as quirky boutiques.
Our main destination here was the Chicago History Museum, a must-see stop for any visitor to this great city. It offers an overview of what built this city, its people, and the fire that destroyed it back in 1871.
After our visit, a photo stop at Second City was in order. Unfortunately, we couldn’t get tickets to a show (if you want to, book way ahead of time!) But we got to look at the pictures of all the comedic alumni that graced the iconic place.
It was time to head back to our hotel to check in and wash up before our dinner reservations.
Rick Bayless’ Frontera Grille was our dinner destination. Make sure to book ahead of time. This place gets crowded.
A good night’s rest and we were ready for…
DAY 2 – Cruising, Navy Pier and Al Capone
Breakfast was lighter for us this morning. Some yogurt and fruit that we purchased at Whole Foods the night before.
Of course, some coffee was in order to start our day. So we headed out for a cup of coffee at PEETS and picked up some bottled water to keep us hydrated.
And as you can see, it took me a trip to Chicago to finally get my wings! This beautiful sculpture was a gift to the city from Mexico and was right next to our coffee shop.
Our next adventure was an Architecture River Cruise.
This 90-minute cruise gave an amazing overview of Chicago’s architecture and its history, providing fascinating stories behind more than 50 buildings along the Chicago River.
Learn how the Windy City grew from a small settlement into one of the world’s largest cities in less than 100 years.
And make sure to get tickets to the Chicago Architecture Center in conjunction with the river cruise. We did this the next day and it was worth it.
After the cruise, we walked over to have lunch and explore the Navy Pier, a 3,300-foot-long pier on the shoreline of Lake Michigan.
Navy Pier opened to the public on July 15, 1916, and its original purpose was to serve as a dock for freights, passenger traffic, and indoor and outdoor recreation.
In mid-1918, the pier was also used as a jail for draft dodgers. In 1927, the pier was renamed Navy Pier to honor the naval veterans who served in WWI.
During WWII, the pier became a training center for the U.S. Navy. About 10,000 people worked, trained, and lived there. And over the years was used for different purposes.
In 1995, Navy Pier was redesigned and introduced to the public, incorporating retail, dining, entertainment, and cultural spaces.
Lunch was at IDOF Mediterranean. Great Felafal!
After a full day, we headed back to our hotel before dinner and some ghost and gangster fun!
I booked reservations at The Purple Pig. Plates are meant to be shared and the variety and quality of their food were outstanding. Don’t miss it.
Our 8 pm Al Capone & Ghost Tour was up next on our itinerary. Our tour guide took us on a 1.5-mile walking tour, learning about the infamous Al Capone, places he visited as well locations where ghosts gather. I won’t provide too many details here and spoil the fun in case you’re interested in taking this tour.
Day 3 – Millenium Park, Art, and Incredible Views
After a light breakfast, exploring a famous park was on our itinerary. And that would be, of course, Millenium Park. We explored its art, trails, and fountains. And of course, no trip to this park is complete without taking pictures at The Cloud or Bean as many call it.
Lunch was at the Goddess and the Baker. Fresh, well-prepared ingredients. Yum
The grand Art Institute of Chicago was up next for our afternoon. Advance tickets are necessary, although they were not timed. Our tickets were applicable for the entire day.
After filling our eyes and imaginations with the beautiful art, it was time to eat some famous Chicago eats – deep-dish pizza.
Lou Malnati’s was our dinner destination. This place gets CROWDED, all the time. No reservations are accepted but we put our names on our waiting list on our way over from the Art Institute. This New York girl prefers the traditional Neopolitan slice but this was delicious.
After dinner, we washed up and headed over for a view to die for and some drinks.
The John Hancock building is a 100-story, 1,128-foot supertall skyscraper Located in the Magnificent Mile district, its name was changed to 875 North Michigan Avenue in 2018. Despite this, the building is still colloquially called the John Hancock Center.
Whatever you want to call it, take a ride up to the 96th floor for a drink at the Signature Lounge. Light bites are also offered. If you want, you can eat here as well.
A perfect ending to a perfect day.
Day 4 – Take Me Out to the Ballgame (almost)
Baseball was the plan for our final day but the weather did not cooperate. We booked tickets to see our beloved Mets play the Cubs at Wrigley Field but upon arriving in Wrigleyville, the weather didn’t cooperate. The game was postponed until the following evening. Unfortunately for us, this wasn’t going to work since we were flying home the next day.
But no worries! When on vacation, one must be flexible and be able to adapt to changing plans. Of course, one hopes this doesn’t happen too often, right?
So, we popped open our umbrellas and explored a bit of Wrigleyville, bought some shirts and pins for souvenirs, and took some great photos.
We headed back to our hotel to reevaluate our day. We weren’t going to let the weather and the game cancellation ruin our day.
If we couldn’t get our hotdog at Wrigley Field, we’d eat it somewhere else! So we headed over to Portillo Bros for a late lunch.
Shopping at Water Tower Place and at some delicious ramen at Ramen-San for dinner topped off our day.
Day 5 – Departure
All vacations, unfortunately, come to end. Our flight wasn’t until late afternoon so we headed back to Wildberry Pancakes and Cafe for brunch before our flight. We also picked up some amazing Cuban sandwiches at Cafecito to bring on the plane.
Bye, Chicago. We’ll be back. You’re a helluva town!
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