Ultimate Guide to Chicago

Windy City Travel Guide

Chicago is one of those cities that you need to experience at least once in your life. It’s known for having a Midwest personality with big city vibes. Windy City is the 3rd largest city in the US, yet still manages to have that smaller, home-town feel. From Jazz, to deep-dish pizzas, to the world’s first skyscraper, to the Cubs, Chi-Town is made up of several different neighborhoods and they are all equally unique. It’s busting with delicious restaurants, trendy nightclubs and bars, breweries galore, endless shopping, a huge art scene and history, architecture and character behind each corner.

The Best Views!

Test your fear of heights on one of Chicago’s newest thrill rides. 360 Chicago is located on the 94th floor of the John Hancock Building and features a tilting glass lookout. 1000 feet above Magnificent Mile, you’ll not only be able to get the best view of the Windy City but come face to face with the ground below. Experience the TILT, where you’ll be enclosed in a glass box that’s moveable platform slowly tilts outwards and downwards, for an adventurous angle of the city below. This thrill-seeking adventure is not for the faint of heart, but trust me, it’s worth facing your fears for.
360 Chicago 360 Chicago 360 Chicago

If you’re looking for another way to experience the breathtaking skyline, that’s a little less scary and more “traditional”, try the top of the Navy Pier Ferris Wheel. Although the Pier tends to get quite busy during the hot summer months, it is a fun way to escape the busy city-vibes and relax by the water. It’s located right on the beach, so you’ll be surrounded by Lake Michigan the entire time. The Wave Swinger is another popular ride, as it hoists you up 14-feet in the air and then whips you around in circles. The Musical Carousel is always a favourite, you can’t help but feel nostalgic when you’re on it.
Navy Pier Ferris Wheel Navy Pier Ferris Wheel Navy Pier Ferris Wheel Navy Pier Ferris Wheel Navy Pier Ferris Wheel

The Skydeck in the iconic Willis Tower, formerly known as Sears Tower, is another place for those that love heights and want the best city view. Ride up to the 103rd floor to the tallest lookout in the Western Hemisphere. Step out onto “The Ledge” which is a collection of glass boxes that extend outwards (4-feet) from the side of the building, allowing you to look directly down at the city below. That’s right, a glass floor that sores over 1300-feet above the city. Don’t worry if the glass floor freaks you out, you can still enjoy a 360 view, allowing you to see upwards of 50 miles and 4 different states.
Skydeck in the iconic Willis Tower Skydeck in the iconic Willis Tower Skydeck in the iconic Willis Tower Skydeck in the iconic Willis Tower

Major Attractions!

I don’t think you can come to Chicago without visiting the Cloud Gate Sculpture, also known as the “bean,”. It’s one of the highlights in Millennium Park, thanks to its 168 highly polished stainless-steel plates, giving the effect of liquid mercury. Get creative with your photos and try to get the reflection of the famous Chicago skyline in the background. Of course, this is an extremely busy tourist destination, so if you want no-one in your photo, plan to get there before 6AM.

Cloud Gate Cloud Gate

Sitting along beautiful Lake Michigan, just North of downtown, you’ll find Lincoln Park. With rich history, greenery, ornate homes and even the Chicago Zoo, it’s the perfect way to spend an afternoon. It’s actually almost a third larger than New York’s Central Park, and filled with canopies of trees, chirping birds, and peaceful places to take a mental hiatus. Be sure to check out the conservatory, which houses over 40,000 plants under a glass dome and greenhouse.
Windy City Travel Guide

While you’re in Lincoln Park, be sure to stop by the Chicago Zoo…it’s free. It’s home to over 1200 animals, anything from zebras and apes, to Diana monkeys to Madagascar hedgehogs, this lively zoo has it all. It’s open 365 days of the year, rain or shine. Waddle on in to see the African penguins or stay to hear the Lions roar at dinner time, either way, it’s a free oasis for any animal lover.
Chicago Zoo Chicago Zoo Chicago Zoo

Shopping!

If you’ve come to shop, Magnificent Mile will feed all your shopping addiction. Michigan Ave is lined with both high-end boutiques such as Chanel, Gucci and Burberry, as well as mainstream and fast-fashion stores like Forever 21, H&M and Zara. You can literary spend all afternoon strolling the one-mile strip. You’ll also find chic cafés and trendy restaurants when you want to fuel up and take a load-off.

Where To Eat!

The best things in life are sweet, and if you have a sweet tooth, head to Sweet Mandy B’s. Not only is this the most photographable café I’ve ever seen, it has the most unique and delicious desserts. Spend an hour in their pastel bakeshop, sipping coffee and enjoy one too many sweet treats. From cakes, cupcakes and brownies, to cookies, puddings and pies, the possibilities are endless.
Sweet Mandy B’s Sweet Mandy B’s

If you’re craving rosé, or looking for a beachy place to eat, stop by the Hampton Social River North. It’s become quite famous for its “rosé all day”, but people keep coming back for the food. It somehow manages to bring the calm and peacefulness of the Hamptons to a busy city like Chicago. I highly suggest getting their famous Frosé, which is a mixture between vodka, peach puree and rosé of course. I actually ordered off the kids menu, grilled cheese and macaroni and cheese, and I can honestly say it’s one of the best meals I’ve had in a long time.
Hampton Social River North Hampton Social River North Hampton Social River North Hampton Social River North

Looking for a funky and ultra-trendy place to dine, check out Broken English Taco Pub (75 E Lake Street). Think street meat meets street graffiti. Colourful Mexican street art covers every inch of this restaurant, Piñatas hang from the ceilings, and red retro booths along the walls. Although the menu may seem small, it’s filled with tasty options, even vegetarians one’s too. Of course, we went traditional with the vegetarian tacos, cool beers and margaritas.
Broken English Taco Pub Broken English Taco Pub Broken English Taco Pub Broken English Taco Pub

Snacks!

Even if you don’t love popcorn, Garrett Popcorn is a must. If you happen to love popcorn, you’ll be in heaven. There’s a reason why the line is incredibly long, the popcorn is delicious. Chicago Mix is the reason why there’s a lineup around the corner, as it’s the perfect mix between sweet and salty. It features both caramel and cheese flavored popcorn and is the very best handcrafted popcorn I’ve ever had.

Garrett Popcorn

If you’re looking for a truly unique dessert experience, stop by Snow Dragon Shavery at Navy Pier and try their shaved snow. It’s not quite ice cream, yet it’s not frozen yogurt, and it’s not your basic snow cone, it’s unlike anything you’ve tried before. Its velvety smooth texture, paired with its unique toppings, it’s simply irresistible. It’s honestly a work of art. Have fun picking your favourite flavours and toppings, and then indulge in this delicious soft treat.
Snow Dragon Shavery at Navy Pier Snow Dragon Shavery at Navy Pier

Stan’s Donuts serves up freshly, handmade, exotic doughnuts all day long. It’s lovingly created and fried fresh and comes in an array of yummy flavours. With a menu and display cabinet full of the most amazing looking donuts you’ll ever see, the only problem you’ll have is picking which ones you want. From Captain Crunch, to Peanut Butter Pocket, to Lemon Pistachio to the classic Old Fashion, it’s a struggle to pick a fave. Plus, the entire space just screams Instagram me.

Stan's Donuts Stan's Donuts Stan's Donuts

Have you ever had a dessert taco? It’s kinda a game changer, and Dessert Dealer at Parlor Pizza Bar serves up the best cocktails, alongside dessert tacos. It’s located at 108 N. Green Street.

Dessert Dealer at Parlor Pizza Bar Dessert Dealer at Parlor Pizza Bar

My fave Instagram murals!

Flamingo Wall at 2601 W Division St.
Flamingo Wall at 2601 W Division St

Pink Garage with White Arrow at 1670 N Ada St.

Pink Garage with White Arrow at 1670 N Ada St.

Pink and Red Heart Wall at 2214 N. Elston Ave.

Pink and Red Heart Wall at 2214 N. Elston Ave.

Pastel Butterfly Wall at 2912 N Milwaukee Ave.

Pastel Butterfly Wall at 2912 N Milwaukee Ave

Chris Uphues Wall located at the corner of Ravenswood & Winona.
Chris Uphues Wall located at the corner of Ravenswood & Winona

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