My kind of town… Chicago

Cover: Chicago, Illinois skyline
Photo: Kim Hull, Cool Adventures © Chasing Light Media
Article by Kim Hull


Chicago has always had a fond place in my heart.

My father grew up on the south side of Chicago during the depression and loved telling stories of his Chicago adventures – from falling through the ice while skating on Lake Michigan and hurrying to the Field Museum to warm up, to going a few rounds with Joe Louis on the Midway, to marching into the Stevens Hotel during World War II, and many more that probably shouldn’t make print. All true? In Chicago style – hardly. All great? Absolutely.

As a little girl, we’d travel to Chicago from the small town where we lived in Kansas to visit my uncle and aunt – and it was magical. Uncle Phil and Aunt Hazel would take me to Marshall Field’s and spoil me with treasures, followed by a stop at their favorite bakery, where we’d pick up a huge layer cake. As we’d drive through the city in Phil’s big sedan with the windows down, all the sounds, colors, sights and energy of the city would mesmerize me.

Has the magic worn off for me over the years? Not in the least. Always one of our favorite places to return to, we recently spent a weekend in the Windy City visiting a few of our favorite spots along the way.

Chicago River, Chicago, Illinois
Chicago River, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

An afternoon stroll

Holy Name Cathedral, seat of the Archdiocese of Chicago, Chicago, Illinois
Holy Name Cathedral, seat of the Archdiocese of Chicago, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Soon after arriving, we headed out for a walk under bright blue spring skies.

Roaming Chicago’s bustling downtown area provides an up close view of Chicago’s beautiful buildings and stunning architecture. As much of Chicago was destroyed in the Great Chicago Fire in 1871, the rebuilding resulted in innovative designs not mired in historical tradition and made Chicago home to some of the first modern skyscrapers.

The Chicago Theatre, Chicago, Illinois
The Chicago Theatre, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Today, Chicago is widely recognized for its landmark buildings of varying styles, with the city frequently voted in polls as having the nation’s best skyline.

Downtown Chicago, Illinois
Downtown Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Finding ourselves on the iconic Wacker Drive, we turned to walk along the famous street that runs along the Chicago River.

The Chicago River, Wacker & Wabash, Chicago, Illinois
The Chicago River, Wacker & Wabash, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Unique in several ways, Wacker Drive is the only street in Chicago that runs in all directions – winding along the river, it has addresses east, north, south, and west. Wacker Drive is also a multi-level street, with Upper Wacker Drive, Lower Wacker Drive and, in a short portion, Lower Lower Wacker Drive.

Strolling in Chicago, Illinois
Strolling in Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

By mid-afternoon on this Friday, the streets that earlier had been filled with those rushing from lunch in business attire began to relax, transitioning to a more casual environment filled with those seeking a stroll in the sunshine or an afternoon jog.

Bridges of Chicago, Illinois
Bridges of Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

As pleasurable as simply wandering amongst the bridges and buildings was, we decided it was time to visit a few attractions and shortly found ourselves at Willis Tower (formerly Sears Tower).

Willis Tower in Chicago, Illinois
Willis Tower in Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Travel tip: Get a CityPASS

Arriving at Willis Tower, we were met with a line that was estimated to be a 3-hour wait before getting access to the Skydeck. Ugh! I spotted a Fast Pass entrance area for those with a CityPASS with no line, so I went to the CityPASS website on my iPhone, bought two passes, and received the confirmation email within one minute. We headed over to the Fast Pass entrance, bypassed the main line, and were on our way to the Skydeck.

In addition to the Skydeck, the Chicago CityPASS allowed us VIP/Fast Pass entry to Shedd Aquarium, The Field Museum, a choice of the Art Institute or the Adler Planetarium, and a choice between 360 Chicago at the John Hancock Tower or the Museum of Science and Industry for $98 per adult, which would have been $208 in regular admission fees. What a sweet deal!


Willis Tower (Sear Tower) Skydeck

View of Chicago from the Skydeck at Willis Tower
View of Chicago from the Skydeck at Willis Tower
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Located on the western edge of Chicago’s Loop, the Sears Tower was completed in 1973, topping out at 1,451 feet (442 meters), making it the tallest building in the world at the time – a title it held for 25 years.

Skydeck Chicago at Willis Tower, Chicago, Illinois
Skydeck Chicago at Willis Tower, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

In 2009, the tower was renamed to Willis Tower, but is still commonly referred to as Sears Tower. Now the 8th tallest building in the world, Willis Tower is the second tallest building in the western hemisphere and offers amazing views of Chicago from the Skydeck on the 103rd floor.

Chicago from the Skydeck Chicago, Willis Tower, Chicago, Illinois
Chicago from the Skydeck Chicago, Willis Tower, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

The Ledge at the Skydeck offers visitors the chance to stand in a glass box 1,353 feet over Wacker Drive. Each of the four clear glass boxes extends out 4.3 feet from the Skydeck, providing unobstructed views of the city and the streets below.

Navy Pier

Navy Pier & Chicago Children's Museum, Chicago, Illinois
Navy Pier & Chicago Children’s Museum, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Originally opened in 1916 for shipping and recreation along the shores of Lake Michigan, Navy Pier is a 3,300 foot (1,010 meters) pier that has grown into the #1 leisure destination spot in the Midwest, with nearly nine million visitors annually.

Family Pavilion, Navy Pier, Chicago, Illinois
Family Pavilion, Navy Pier, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media
Navy Pier, Chicago, Illinois
Navy Pier, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Home to a variety of restaurants ranging from sit-down dining to food court fare, Navy Pier also has parks, gardens, shops, and other attractions and entertainment options including the Navy Pier Ferris Wheel, sightseeing tours, dinner cruises, Crystal Gardens and an IMAX theater.

The Crystal Gardens, Navy Pier, Chicago, Illinois
The Crystal Gardens, Navy Pier, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

We stopped by for a beer and a bite at Harry Caray’s Tavern Navy Pier, one of the seven popular dining spots around the city bearing the name of the famous Chicago Cubs announcer.

Harry Caray's Tavern, Navy Pier, Chicago, Illinois
Harry Caray’s Tavern, Navy Pier, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Water Tower Place and The Magnificent Mile

North Michigan Avenue, The Magnificent Mile, Chicago, Illinois
North Michigan Avenue, The Magnificent Mile, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Luxury is ever apparent on the Magnificent Mile. One of the most opulent 13 blocks on the planet, the Magnificent Mile is a stretch of North Michigan Avenue from the Chicago River to the Oaks Street on the north, filled with 460 stores, 275 restaurants, 60 hotels and a wide variety of entertainment options.

Water Tower Place at night, Chicago, Illinois
Magnificent Mile at night, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Anchoring the north end of the Mag Mile is the Water Tower Place shopping mall, named after the nearby Old Chicago Water Tower District. Built in 1869 to conceal a standpipe that held water, the Chicago Water Tower was one of the few buildings to survive the Great Chicago Fire – and is still standing today.

Water Tower Place, Chicago, Illinois
Water Tower Place, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

The Field Museum

The Field Museum, Chicago, Illinois
The Field Museum, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

One of the largest natural history museums in the world, The Field Museum was established in 1893 to house the exhibits and collections from the 1893 World’s Columbian Exposition.

Originally called The Columbian Museum of Chicago, the name was soon changed to recognize its major benefactor, Marshall Field, founder of the Chicago-based department store chain Marshall Field’s.

The Field Museum, Chicago, Illinois
The Field Museum, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Throughout its history, The Field Museum has brought a view of the world and its peoples to the museum to enable visitors to explore the past and present world and its cultural diversity.

Exhibits at The Field Museum, Chicago, Illinois
Exhibits at The Field Museum, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

A highlight of the museum is Sue, the largest Tyrannosaurus rex ever discovered. Measuring 42 feet long, she has 58 teeth and holds court front and center in the museum’s atrium.

Sue the T. rex at The Field Museum, Chicago, Illinois
Sue the T. rex at The Field Museum, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Shedd Aquarium

Shedd Aquarium, Chicago, Illinois
Shedd Aquarium, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Known as “The World’s Aquarium,” the John G. Shedd Aquarium opened in 1930 and, to this day, is one of the largest indoor aquariums in the world.

Penguins, Shedd Aquarium, Chicago, Illinois
Penguins, Shedd Aquarium, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

The Shedd has more than doubled in size since its inception, growing to 480,500 square feet with the addition of the Abbott Oceanarium and Wild Reef.

Home to 32,000 animals representing more than 1,500 species of fish, reptiles, amphibians, invertebrates, birds and mammals from waters around the world, the Shedd is a not-to-be-missed spot, especially for families with children.

Shedd Aquarium, Chicago, Illinois
Shedd Aquarium, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Art Institute of Chicago

The Art Institute of Chicago, Chicago, Illinois
The Art Institute of Chicago, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

Founded as both a museum and school for the fine arts in 1879, the Art Institute of Chicago has grown to house nearly 300,000 works of art, with the School of the Art Institute of Chicago and the Museum of the Art Institute of Chicago internationally recognized leading fine-arts institutions in the United States.

A Sunday Afternoon on the Island of La Grande Jatte, Georges Seurat, Art Institute of Chicago, Chicago, Illinois
A Sunday Afternoon on the Island of La Grande Jatte, Georges Seurat, Art Institute of Chicago, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Well-known for its fabulous Impressionist and Post-Impressionist collection, the Art Institute also has a broad selection of American art, Old Masters, and contemporary art.

Elizabeth - Like the Queen, Andy Warhol, Art Institute of Chicago, Chicago, Illinois
Elizabeth – Like the Queen, Andy Warhol, Art Institute of Chicago, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

One of the most visited museums in the world, the Art Institute welcomes 1.5 million visitors each year to its one million square feet of space spanning eight buildings.

Nighthawks, Edward Hopper, Art Institute of Chicago, Chicago, Illinois
Nighthawks, Edward Hopper, Art Institute of Chicago, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

In addition to housing one of the finest collections in the country, the museum regularly hosts guest exhibitions. On our most recent visit, the museum presented Van Gogh’s Bedroom exhibition, which brings together all three versions of The Bedroom for the first time in North America.

Van Gogh's Bedroom Exhibit, Art Institute of Chicago, Chicago, Illinois
Van Gogh’s Bedroom Exhibit, Art Institute of Chicago, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Morning stroll along the lake

Lake Michigan, Chicago, Illinois
Lake Michigan, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

A walk or run along Lake Michigan is the perfect start to any day in Chicago.

With spectacular views of the city and the sound of the lake splashing against the shore, the 18-mile multi-use path running along the eastern edge of Grant Park and continuing along the Lake Michigan shoreline, is a beautiful way to start your day.

A Sunday afternoon in Chicago, Illinois
A Sunday afternoon in Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

360 Chicago at John Hancock Center

360 Chicago at John Hancock Center, Chicago, Illinois
360 Chicago at John Hancock Center, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

We ended our Chicago visit at 360 Chicago on the 94th floor of John Hancock Center.

It had started to rain and we questioned if we should go or not. We decided yes. We were rewarded with a nearly vacant Sunday night experience observing the city as it wound down from the weekend under the cover of clouds.

Night view, 360 Chicago Observation Deck, John Hancock Center, Chicago, Illinois
Night view, 360 Chicago Observation Deck, John Hancock Center, Chicago, Illinois
Photo: Greg K. Hull, Cool Adventures © Chasing Light Media

We wandered over to Tilt and watched as about half of the evening’s visitors decided to try out the glass and steel moveable platform that tilts visitors to an angle, with downward-facing views of Chicago and the Magnificent Mile.

Tilt at 360 Chicago at John Hancock Center, Chicago, Illinois
Tilt at 360 Chicago at John Hancock Center, Chicago, Illinois
Photo: Kim Hull, Cool Adventures © Chasing Light Media

Wandering over to the bar, we grabbed a couple of vodka sodas, selected a table (they all have stunning views), and relaxed as we enjoyed our elevated happy hour above the windy, and tonight rainy, city.

Know before you go

Fly into Midway if you can. Located on the southwest side of Chicago, Midway is smaller than O’Hare, is closer to the city, and sees far fewer delays than busier O’Hare.

Bring your walking shoes. Chicago is very walkable, so put on some comfortable shoes, get some exercise, and enjoy the view.

Don’t put ketchup on your hotdog. A Chicago dog (and yes, veggie dogs are widely available) includes mustard, onions, slices of tomato, relish, peppers and a dill pickle slice. Chicagoans have strong feelings about ketchup and hotdogs – just don’t go there.

There’s wind chill and then there’s Chicago’s wind chill. Chicago didn’t earn the nickname “The Windy City” by accident. When the wind blows across Lake Michigan, it feels much colder than the actual temperature. If visiting any time other than summer, be prepared to bundle up.

Cool Adventures

Photographers Kim and Greg Hull travel the world full time looking for cool adventures. CoolAdventures.com is the site for exploring amazing places to go and things to do across the world. From mountains to cities to beaches, join us as we roam the globe in pursuit of the best experiences the world has to offer.