Oct 15, 20225 min read

Chicago: A Shimmering City Dream

Why You Should Visit The Windy City In The Fall

As summer gives way to idyllic fall, Chicago indulges you in its true beauty. Crowds are sparse, the air is cool and the city sparkles. When I arrived in Chicago during gorgeous September, CityPASS in hand and an adventurous mindset, I was expecting great things — and I was not let down. It’s got the best pizza, the most beautiful skyline, the most delicious hot dogs, and a heart that's as big as the city is beautiful. What exactly makes it a trip to remember? Here are 10 things to do and see in Chicago.

By Allyson Cochran

@allysoncochran

Skydeck & 360 Chicago

No doubt the best sky-high observation decks in Chicago are Skydeck and 360 Chicago, and CityPASS has them both. It’s hard to decide between the two, so my crazy suggestion is: do them both!

Skydeck is located on the 103rd floor of the Willis Tower. Its views are predominantly on the west, so it’s best to go right at dusk to catch the gorgeous orange and purple sunset hues over Chicago’s skyline. You’ll also have the thrilling experience of The Ledge. A glass box that extends 4.3 feet out from the tower, you’ll look down and experience what standing 1,353 feet above the ground feels like. Your heart will jump out of your chest, but you’ll feel like you’re flying above the city.

360 CHICAGO has more of a relaxed vibe. With a bar and plenty of seating, it’s encouraged to slow down and take in the views. Closer to the north, you’ll get a better glimpse of Navy Pier and shimmering Lake Michigan. At night, the city transforms. The skyline lights up and sparkles, so certainly decide to experience the nighttime views. It’s truly a magical experience, and one you won’t want to miss.

The Art Institute of Chicago

The Art Institute of Chicago is a museum in the heart of the city that holds a collection of artwork that spans decades and continents. It’s a real cultural hotspot. Housing one of the largest permanent collections in the U.S., you’ll easily lose hours perusing all the gorgeous artworks.

There are a few pieces that you’ll not want to miss. The depression-era American Gothic, Neo-Impressionist A Sunday on La Grande Jatte, Vincent van Gogh’s The Bedroom and Edward Hopper's Nighthawks are all iconic masterpieces lining the walls. It’s quite the experience seeking them out and discovering unique treasures along the way.

Museum Campus

Three of the top institutions in the city is all housed together on the amazing Museum Campus. Plan to spend a day mingling with Shedd Aquarium's 32,000 aquatic animals (the penguins and otters are so cute!), greeting the largest dinosaur to ever walk the earth at the Field Museum and exploring the dazzling stars at Adler Planetarium. All these are available with the Chicago CityPASS, and will make for an exciting, breathtaking lakefront day.

Want a pro tip? Avoid making your trip out to the Museum Campus on a Chicago Bears game-day. Soldier Field is located there, and it can make transportation a nightmare with all the gathered football fans.

Giordano's

There’s nothing quite like a deep-dish pizza. When you first lay eyes on it, you’re amazed. It’s a 3” thick pie with a buttery crust layered with a somewhat sweet and spicy tomato sauce stuffed to the brim with oozy cheese that endlessly stretches as you grab a slice. This traditional Chicago dish is a behemoth and a legend.

But where to find it? The best location, in my opinion, is nestled right beneath the towering Willis Tower. For a tourist destination, it’s got a real old-style feel and cozy atmosphere. It’s a nice end-of-day meal. The air cools down quite a bit as the sun settles past the horizon, so this pizza is the perfect warm pick-me-up after a day of adventuring.

Navy Pier

Get out of the hustle of downtown and make your way east of the city to Navy Pier. Once you're there, you'll be able to walk along the mile-long pier and take in some of Chicago's most iconic views — including its skyline, which is one of the most photogenic in the world.

You can also take a ride on one of the boats. There are ferries that run across Lake Michigan as well as passenger boats that head up through Chicago's harbor area. The lake seemingly never ends, and the quiet chirping of the seagulls makes it a peaceful escape from the bustling city.

Millennium Park

Millennium Park is home to the iconic Cloud Gate statue aka “The Bean”. The park is infamous for its wild crowds, but I’ll let you in on a little secret: the park nearly empties out on weekday nights.

Experiencing Cloud Gate at night is truly a spectacular experience. This magnificent sculpture’s silky surface reflects the glimmering lights of the city in a dazzling show of the city’s beauty. The quiet peaceful vibe of a weekday night paired with this sight is beyond comparison. It’s one of those “you’ll have to experience yourself” moments.

While at Millennium Park, visit the quirky Crown Fountain and one-of-a-kind Jay Pritzker Pavilion. Both attractions capture the uniqueness of this city and are nice places to rest and relax.

Portillos

Portillos is a Chicago must. The retro-themed restaurant houses the incredibly famous and delicious Chicago-style hotdog. It's tastiness only barely surpasses its reputation. All settled in a poppy seed bun, yellow mustard, sliced white onions, sweet pickle relish, a dill pickle spear, tomato, sport peppers and celery salt tower the top. Veggies who don’t want to miss out should try the delicious plant-based option.

Chicago Theatre

Chicago Theatre is a breathtaking national landmark in the middle of downtown. The distinctive neon marquee acts as an emblem of the city, and the Arc de Triomphe-like facade is lavish and epochal. Even if you don't venture inside for a music or comedy show, the exterior alone is an impressive sight to see. History, theater and architecture buffs have to stop by.

Magnificent Mile

Chicago’s answer to New York's 5th Avenue or Beverly Hills' Rodeo Drive is the vibrant and bustling Magnificent Mile. It’s a dizzying array of restaurants, hotels, stores and architecture all on one single iconic street.

Some of the highlights include trying experimental menu items at the world’s largest Starbucks, shopping at the 8-floor Water Tower Place shopping mall and sipping wine at the Purple Pig. Plan a full day here as this history-packed strip on Michigan Avenue has plenty to do.

Riverwalk

The Chicago River that runs through downtown is part of what makes Chicago so special. It’s a picturesque boardwalk that mesmerizes. While there are endless activities to discover here, a simple stroll through the 1.25-mile stretch is an afternoon spent perfect enough soaking up the watery views.

That isn’t to say that spending some time right on the river isn’t well worth your time. Hopping on the Chicago Water Taxi or taking a Riverwalk Tour is a great way to experience the towering architecture from the best seat in the house — the Chicago River.