A Guide to the Windy City: Chicago, Illinois

I was lucky enough to visit gorgeous Chicago, Illinois this summer to experience all of the best bites, sights, and sips that the Windy City had to offer. I do not exaggerate when I say I was absolutely blown away (pun intended).

From the beautiful shorefront of Lake Michigan to the innovative sushi art we consumed, Chicago is a dream world for both foodies and travel aficionados alike. I searched high – 103 stories up, in fact – and low for the best views, cocktails, and of course, grub. So sit back and relax as I take you on a journey of sight and glorious smell through this modern Midwestern metropolis.

First Stop:

 Three Dots and A Dash

435 N Clark St. Chicago, IL

It isn’t a trip to Chicago without a stop at the infamous Three Dots and a Dash –a funky fun underground tiki bar – themed hub where summer never ends!

Their creative tropical inspired cocktails are as fun as the restaurant’s  atmosphere itself. Amidst a concrete jungle, guests are transported to a whole new world where they can be a part of one of the world’s greatest beach parties.

For the first elixir, I decided to sip on the “Bali Bali”, a fish bowl full of deliciousness made with passion fruit, orange, falernum, Puerto Rican rum, Armagnac, and London Dry Gin. The cocktail was served over dry ice in a giant bowl adorned with fake octopus tentacles, tropical flowers, and decorative straws. All the components served together made the experience that much more enjoyable and it inspired all the customers around me to order one too! (Travelers tip: this drink is meant for sharing with at least four people).

Make sure to leave room for a bite or two! Even though Three Dots and A Dash is known for its extensive drink menu, they do have some great food options. I highly recommend the ‘Kai’s Crab Rangoon” which was the perfect dish to compliment the sweet flavor of their tropical drinks.


They also feature other menu items such as burgers, coconut shrimp, and spring rolls. Three Dots and a Dash is the perfect spot in Chicago if you’re looking to let loose and have some fun (with or without the sun)!


Millennium Park & Buckingham Fountain

If you’re looking for a free and relaxing activity to enjoy in between all the deep dish pizza and cocktails, Millennium Park is a prime tourist location. The park is filled with collections of architecture, landscape design and art that provide the perfect back drop for hundreds of free events including concerts, exhibitions, tours, and family activities. Don’t forget to make your way to the famous  Chicago Bean – a sculpture that is perfect for a fun photo op.




A 10-minute walk from Millennium Park sits the breathtaking Buckingham Fountain. Situated across from the gorgeous waterfront of Lake Michigan, the fountain is a relaxing oasis right in the middle of the towering city that surrounds it. It definitely gives the Trevi Fountain in Rome a run’s for it’s money! Grab a hot cup of coffee and sit at one of the benches nearby to take in the view.



SmallCakes Cupcakery

3054 N Greenview Ave. Chicago, IL

I’m always on the look-out for the sweetest spots in the places that I visit – literally. So, after seeing SmallCakes Cupcakery on the Food Network show “Cupcake Wars”, I just had to stop by to get in on the action. As soon as I arrived, I was greeted by a beautiful display of gorgeous cupcakes.

With so many to choose from, I decided to go big and try one of their unique menu items called the “Cupcake Smash.”  Featuring one of Small Cake’s giant cupcakes, halved and layered in between homemade ice cream, this beauty should be on everyone’s “must-try” list. With 12 cupcake flavors and 11 ice cream flavors to choose from, there are endless amounts of smashing to to be had! We also recommend grabbing a box of cupcakes to go so the yumminess can continue after you leave the store! (You’ll thank me later).


Chicago River Walk

On a tight budget? Then a stroll down the famous Chicago River Walk should find it’s way on any itinerary! It’s free and has some of the best views of Chicago! Here are some quick snapshots of my stroll around this quaint part of the city:




Yuzu Sushi & Robata Grill

1751 W Chicago Ave. Chicago, IL

If a love sea food and sushi runs as deep as mine, the innovative combination of both at Yuzu Sushi & Robata Grill is an experience not to be missed. I can’t exaggerating when I say that every one of their menu items is a beautiful piece of art and unlike anything I have ever seen. The bright colors and over-the-top designs of their numerous sauces adds a very unique flare to this special hidden gem just outside of the hustle and bustle of the city.

In fact, each dish was so intricately designed, I didn’t know whether to eat it or bring it home to mount on my wall. I’ll let the pictures do the talking because words simply don’t do these dishes justice.

Among the dishes that the talented Itamae’s served were the “Chicago Spring” roll with shrimp tempura, avocado, cream cheese, red tobacco, masago, chili sauce, and wasabi mayo.

The “Thug Life #2” roll with house marinated sake, salmon skin, jalepeno, avocado, cucumber, cilantro topped with inure, and pickled red onion.


And the “Beasty Beets Salad” with parmesan Thai basil cream, candy walnuts, and arugula frisee.

I ended the meal with a delicious presentation of assorted Japanese mochi ice cream in passionfruit, green tea, coconut, and black sesame flavors.

Not only was the food incredible, but the team at Yuzu was extremely accommodating. Everyone (including the wait staff and kitchen staff) constantly had smiles on their faces and it was obvious to us they take a lot of pride in their jobs.

With my tummies full and happy, it was time to head back to the hotel and relax. Check out my review on Hotel Felix, who graciously hosted me during my weekend getaway here.


Willis Tower Skydeck 

Is it even a trip to Chi-town without a visit to the iconic observatory deck of the Willis Tower? Nah. (Tip: set aside plenty of time because during the busy season as the wait can be up to 3-4 hours long). In order to save some time, I recommend purchasing the CityPass which allows visitors to fast track the line both at the Willis Tower and many other attractions in Chicago. The process of getting up to the tower can be frustrating to say the least, but the views more than made up for it.



For those feeling brave, photos on top of the glass floors that extend out from the observatory deck are an option. This one was the money shot!


Waiting in line for three hours to make it to the top of the Willis Tower can work up an appetite, so I made my way to my final Chicago destination.


Seven Lions

130 S Michigan Ave. Chicago, IL

The last stop on the Chicago food train before hauling it back to the airport – and reality – was Seven Lions. Since brunch is my favorite meal (and most everyone else’s favorite meal), the menu items that Seven Lions features on their brunch menu did not disappoint. Given my high expectations for brunch dishes, Seven Lions surpassed them all – and then some.

I kicked things off with drinks because lets face it: brunch isn’t the same without some booze. I sipped on the “Aperol Spritz” with Aperol orange liqueur, sparkling wine, and soda, as well as the “Strawberry Lemonade” spiked with vodka. Both made for a great and refreshing start to our day and the meal.

For an appetizer, I ordered the ooey-gooey skillet of warm cinnamon rolls. This dish is what dreams are made of! Flaky cinnamon encrusted bread topped with a thick layer of cream cheese frosting that melts into every crevice of the rolls — literal heaven!


For the main brunch dishes, I was served a variety of their house favorites which consisted of the “New England Style Lobster Roll” and the “Strawberry Nutella Pancakes.” The lobster roll was served up on a toasted and buttered hoagie roll, and generously stuffed with sweet and tender chunks of Maine Lobster salad (golden fried steak-fries were the perfect side addition).

The pancakes (which are often seasonal and are subject to change), were warm and fluffy with a light golden brown crust. Generously topped with sweet whipped cream, diced berries, and drizzles of Nutella, these pancakes rank among the best ones I’ve ever sunk my teeth into.

As the time to head back to the airport neared, i reserved an UberPool (this is an extremely efficient way to get around the city fast!) back to the hotel to grab my belongings. While I always yearn to see and experience more, two nights in Chicago was the perfect length of time to fit in almost all of the restaurants and tourism hot-spots I had planned to.

Looking to for an adorable boutique hotel to stay at in the center of the Chicago? Check out my experience at Hotel Fleix.

One of the top cities for foodies in the nation, a trip to the Windy City to experience the dishes, culture, and hospitality of one (or all) of the partners mentioned above, will not disappoint. When you do, don’t forget to tell them that East Coast Contessa sent you.


12 replies to “A Guide to the Windy City: Chicago, Illinois”

  1. All I can say is you all should be professional photographers. All the Windy City pics make me want to book a Chicago trip of fun and food today. Thanks for the great review!

  2. I LOVE Chicago. I am planning on just recreating your trip the next time I am there. That Tiki Bar looks amazingly random for Chicago. Who doesn’t love an amazing cupcake shop?! And I’ve wanted to go to the Skydeck and hyperventilate before completely loving it. Ha! LOVE your blog!!

  3. I am from Chicago (but currently stuck in Alaska) and your post made me so homesick! The Riverwalk, Millenium Park, and ahem *Sears Tower 😉 are definitely a must for any visitors! I have never been to the tiki place, I’m going to have to check it out next time I am home.

  4. if there are places in the state that gives you a feel of coming back again, it gotta be chicago… alot of nice places and cool stuffs to get you in the groove. nice pictures for the post too.

  5. Chicago always impresses me, and your post convinces me even more of why I should put Chicago on the bucket list. What a great trip you had! For the love of Bali I would not mind to try “Bali Bali”

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If I learned anything during my recent trip to @visitchatt, it’s that there’s so much more to the city than meets the eye. It’s home to some of the most popular attractions in the US, sure, but it also boasts plenty of hidden gems and unique local experiences. Add these 5 locations to your Chattanooga itinerary (you won’t regret it!):

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- 1885 Grill @1885grillstelmo. This southern coastal restaurant specializes in fresh seafood, high quality steaks, and comforting soul food. Order their wings with Carolina Gold BBQ!
- Rock City Gardens @seerockcity. Located on Lookout Mountain, Rock City Gardens features a 4,100-foot Enchanted Trail with incredible rock formations, magical caves, native plant species, waterfalls, and a panoramic view of Seven States!
- Massey’s Kitchen @masseyskitchenlookout. This Mediterranean inspired restaurant just opened in June and is Chattanooga’s new hot spot. The food is incredible and their outdoor patio is perfect for dining al fresco. Order the baked feta 🤤
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If you’re looking for the perfect end of summer U.S. vacation destination, Chattanooga, Tennessee is it. @visitchatt 🇺🇸 

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📍Walnut Street Bridge. With a 1/2-mile span, it’s one of the longest pedestrian bridges in the world and provides amazing view of the riverfront. 

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Welcome to one of the most underrated southern cities in the U.S.: @visitchatt! 

While most travelers flock to Music City year after year, just a couple hours drive southeast you’ll find a true gem hidden in the lively city of Chattanooga, Tennessee. 

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✧ MoonPies were invented here! These graham cracker marshmallow sandwiches are covered entirely in melted chocolate and are so delicious.

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✧ Chattanooga boasts one of the largest collections of American art in the country at the Hunter Museum. 

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Food and travel are intertwined. Almost any memorable journey starts (and ends) with a great meal, and my trip to Cartagena was no exception 🇨🇴 

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