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.

An afternoon stroll

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.

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.

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

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.

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.

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).

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

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.

In 2009, the tower was renamed 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.

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

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.

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.

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.

Water Tower Place and The Magnificent Mile

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.

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.

The Field Museum

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.

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.

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.

Shedd Aquarium

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.

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.

Art Institute of Chicago

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.

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.

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.

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.

Morning stroll along the lake

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.

360 Chicago at John Hancock Center

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.

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.

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.

Back to top

Disclosure & disclaimer: Special thanks to CityPass for hosting us in Chicago. The opinions expressed are entirely our own. Reviews are based only on our assessment and we accept no responsibility for how the information is used. We do not accept paid posts although some posts may contain information regarding businesses where we have previously been compensated.