I totally messed up on this leg of the road trip by booking only a one-night stay in this incredible city. Coming from New York City, I am a bit of a city snob and tend to zip through other cities never expecting any to have more to offer than the city I come from. Boy was I wrong with Chicago. This may be arguably the best city in the United States (minus the winter season that is). The city is quite large with many neighborhoods to explore, holds the title for one of the most creative food scenes in the country, is extremely clean and well-kept, and has an incredible energy that keeps visitors outdoors as much as possible. Oh wait, and how can I forget to mention, it is situated along an entire stretch of the most aqua waters and beaches; real beaches with sand and everything! Now, that is my idea of perfection – the combination of a thriving city with a beach! The East River in New York City can’t even begin to compete with the vast, blue waters of Lake Michigan in this part of the country. Had I known how awesome Chicago is, I would have totally booked a few more nights here. Learn from my mistake and make sure you allow yourself at least three nights to become more intimate with this utopic city.

Here’s what our twenty-hour itinerary looked like. I am quite impressed by how much we fit in!

Walk the city, wear comfortable shoes!

In a jiffy, our initial walking tour looked like this * this is about five hours of walking time*

Navy Pier
Lake Front Trail along the Gold Coast and further

Alfred Caldwell Lily Pool
Oz Park
Old Town (stop at Jeni’s Splendid Ice Cream on way to next stop)
Maginifect Mile

Millennium Park- The Bean

Chicago River Walk

We started our journey at Navy Pier, a three-thousand-foot long pier along Lake Michigan bustling with people strolling along to enjoy the views, grabbing a drink at one of the several outdoor bars, or riding the Ferris wheel which is a staple in the city skyline.

From there we continued along the well-paved water promenade on the Lake Front Trail which spans eighteen miles of waterfront lanes for cyclists, joggers, and nature lovers to enjoy breathtaking views of the lake. The lanes are wide, leaving plenty of room for all types of commuters who soak in the spectacular vistas of the crystal waters on their route. We continued our walk into the Gold Coast, one of the more affluent neighborhoods in the city, with stately homes and towering skyrises. If you’re up for additional walking, cross over into the neighborhood to soak in its vibe by walking through the streets. This neighborhood offers plenty of stunning architectural landmarks, notable restaurants, and high-end shopping. Once you are back on Lake Front Trail, make sure to take a moment to pause at Oak Street Beach, in the heart of the Gold Coast, which is a gorgeous part of the coast with ample sand and waters that are reminiscent of the Caribbean. We continued walking along the trail for approximately another two miles reveling at the pristine body of water, adventurous swimmers, sunbathers, volleyball players, and all the locals who get to enjoy a spectacular city AND a sea simultaneously!

From Lake Front Trail we crossed over to the Alfred Caldwell Lily Pool, a beautiful three-acre enclave lavishly landscaped in the middle of the city. The stone steps, wild-flower-filled trails, animal life, and a pond overtaken with lilies all offer a perfect retrieve from city life.

We had ambitious goals to head over to Oz Park from here and then cross down to Old Town along Wells Street, then to Jeni’s Splendid Ice-Cream, and then ultimately over to Magnificent Mile but honestly, our feet were sore by now so we Ubered our way down to Millenium Park instead. This park is a magnificent urban oasis with the most striking amphitheater and of course, the iconic “Bean” that draws thousands of people each day. When we arrived at the park on a Tuesday afternoon in July, The Chicago Symphony Orchestra was rehearsing and visitors were treated to a free concert! Oddly, there were only a handful of audience members while just a few feet over at “The Bean” hundreds were waiting to take the perfect Instagram capture of the pretty awesome sculpture.

A short walk from Millenium Park will take you to The Chicago Riverwalk, a scenic stroll along the bright green waters of The Chicago River. Make sure to grab a great shot over the De Sable Bridge which incidentally shakes vehemently with each truck that drives by!

Where to Stay:

The Peninsula Hotel is the ultimate hotel for luxurious accommodations, comfort, and a superb location in the River North section of the city with easy access to many of Chicago’s most desirable sites. The hotel exudes glamourous vacationing with doting staff, enormous attention to detail, and rooms refitted with the most modern touches available. They even delivered the most delicious selection of treats prepared by their pastry chef to welcome our children. This place thinks of it all. Our stay here was perfect and my only complaint is that we didn’t stay long enough.

Where to Eat:

Breakfast: Beatrix This local’s favorite offers a healthy selection of breakfast items, including fresh-pressed juices, in a trendy environment that will keep you sipping your green juice as slowly as you possibly can. The restaurant opens early allowing eager tourists like me to start their day bright and early to soak in as much of the city as possible! The food here is fresh, delicious, and just what you’ll need to start your day! We opted for a selection of juices: blueberry juice with white grape and basil; mango, orange, and pineapple nectar; pineapple yuzu lemonade. For our meal we noshed on the Greek yogurt and berries; avocado and jalapeno toast topped with radish and crispy quinoa; egg white sandwich with shishito peppers, jalapenos, organic kale, and spinach. Everything was beyond delicious.

Lunch: Giordano’s You can’t leave Chicago without trying Giordano’s famous stuffed deep-dish pizza. This is a pie like no other and will absolutely knock your socks off. The cheese is baked into the crust and topped with a homemade marinara sauce for an explosive pizza-eating experience. For $10.99 you can get your own personalized deep dish pizza with a side dish. Now that’s a deep steal!

Dinner: Galit I spent a lot of time researching where we should eat for our only dinner while in Chicago and am happy to share that all my hard work paid off. Galit offers a four-course Prix-fix menu for $65 per person that will take you on a culinary ride of innovative Middle Eastern flavors and ingredients that blows even the best restaurants in Tel Aviv out of the park. We haven’t eaten Israeli food this good since our travels to Israel. Our dining experience was comprised of non-stop delivery of large portions of typical Israeli dishes with a unique twist. We ate too many decadent dishes to list here but trust me when I tell you every bite was sensational. In my opinion, you don’t want to miss an opportunity to eat here when in town.

I didn’t have many expectations of Chicago. Had I known how impressive the city is, how much it offers, and how much fun it is to walk around here, I would have booked a longer stay. I have booked over nine and a half months’ worth of traveling throughout the United States and have made very few decisions that I regret in my planning. Not staying longer in Chicago is one of them.