top of page

Chicago, Illinois


Chicago is positioned on the western side of Lake Michigan and is prone to gusts of frigid winds whirling off the lake and throughout the city. These winds are most commonly believed to be how the city earned the nickname, ‘Windy City,’ but this is considered a misconception. The most popular theory behind the true meaning of the ‘Windy City’ moniker is due to the fact that Chicago was filled with braggadocios politicians who rarely delivered on their promises. Either way, gusty winds or lofty politicians, Chicago is regarded as being one of the most beloved U.S. city destinations given that the city offers a diverse range of land and water attractions, historical landmarks, and eclectic events. Despite being the third largest city in the United States, Chicago feels more compact and easily traversed thanks to the L Train (elevated train). The L Train transports passengers quickly and efficiently from one side of town to the next, which is a valuable resource when you consider the vast amount of attractions that are scattered throughout the city.

From a personal standpoint, outside of San Francisco and Oakland, Chicago would be the city in which I have most frequently visited. In my opinion, I feel that Chicago is hard to beat with all that it has to offer in terms of photography, night life, entertainment, unique dining experiences, and the friendliness of the locals. For this reason, I try to make a point of visiting Chicago every couple of years in order to reconnect with everything that makes this city magnificent. Although the excursions of each trip will lead me back to many of the same places, my encounters and experiences are never duplicated. The attractions that I am particularly fond of are the following:

Willis Tower (Sears Tower) – Willis Tower, more notably known as Sears Tower, is the iconic skyscraper that has become synonymous with the Chicago skyline. It is 108-floors and towers at about 1,450 feet, which makes it the 2nd tallest building in America. At the time of its completion, Willis Tower was the tallest building in the world and held that title for over 25 years. For those who are not acrophobic (fear of heights), Willis Tower has a sky deck and ledge that can be accessed for an entrance fee of $23 per person. The Ledge is a see-through glass box that extends more than 4 feet from the side of the tower so visitors may brave the daunting sight of the street below their feet. The 360-degree view and the experience of being within this iconic structure make the journey to the sky deck memorable.

John Hancock Building - The John Hancock Building is the fourth tallest building in Chicago and adorns the city’s skyline along with the Willis Tower. The building is 100-floors and stands at approximately 1,128 feet tall with arguably the best aerial view of Chicago. For an entrance fee of $20.50 per person, visitors may journey to the building’s 360 observation deck, where they may experience its newest thrill called “Tilt.” Tilt is an exhibit that will literally tilt visitors at a 30-degree over Michigan Ave. This popular attraction rivals the Ledge, at Willis Tower, as being the most hair-raising experience in Chicago. The observation deck at the John Hancock Building offers unmatched views of up to four states on a clear day, Lake Michigan, and Willis Tower over the Chicago skyline, which confirms the unvarying affirmations that this is the best view in the city.

Navy Pier – Navy Pier is a 3,300-foot-long pier that is a 50-acre playground filled with restaurants, souvenir shops, rides, and games. It is a favorite tourist spot that extends along the Chicago coastline and jets out into Lake Michigan. Rides include a Ferris wheel, old-fashioned swing ride, musical carousel, and even miniature golf. During the summer months the pier experiences a peak in boat excursions, which include sightseeing and sunset dining cruises. The boat excursions on Lake Michigan are high in popularity because they offer the public another perspective with the lake and pier in the foreground and the skyline of skyscrapers in the background. This view is particularly majestic when photographed during the sunset and blue hour.

Buckingham Fountain (Bundy Fountain) – Buckingham Fountain lies in the center of Grant Park and is one of the largest fountains in the world. It is a premier location for photographing the essence of the city with the fountain in the foreground and the Chicago skyline in the background. The fountain usually runs from April through mid-October with timed major displays every hour. During sunset, an extravagant music and light display accompanies these major eruptions and is set to go off every hour on the hour. These evening spectaculars last for 20-minutes with the final fountain display running at 10:35 pm.

Wrigley Field – Wrigley Field is the iconic baseball stadium that was opened in 1914 as the home of the Chicago Cubs, a MLB baseball franchise. Its ivy-covered red bricked outfield and its signature “Wrigley Field Home of Chicago Cubs” marquee, which hangs above the main entrance, have made this stadium a major tourist destination. Wrigley Field lies on the North Side of Chicago and is situated in a neighborhood that has been given the moniker of Wrigleyville. Throughout Wrigleyville there are souvenir shops, restaurants, bars, and high end residential apartments that line streets. During a home game, Wrigleyville is overflowing with loyal fans and inquisitive tourists who want to be engrossed in one of the most addictive baseball atmospheres around.

Cloud Gate – Cloud Gate, also known as The Bean because of its shape, is a large stainless steel art display that is the centerpiece of the AT&T Plaza in Millennium Park. It quickly became a local favorite due to the distorted reflections of the city, surroundings, and people, which are caused due to its rounded shape. The underside of the sculpture is a particular favorite due to the fact that this is where the concave shape of sculpture multiplies the reflections. The best time to photograph Cloud Gate is during the early morning or late evening when there is minimal foot traffic in the park; however, some may find the presence of crowds, and the reflections they cast, more appealing subjects to photograph.

Adler Planetarium –The Adler Planetarium is a public museum that is dedicated to exhibits detailing astronomic discoveries and observations. Although this is a great place to visit, my purpose for adding this location to my must-see attractions was based on the fact that it offers the best street level view of the Chicago Skyline. The views can be seen just about anywhere along the Lakefront Trail, which is a bike and foot path that traverses the entire peninsula.

Tribune Tower – The Tribune Tower is a neo-Gothic style building that is home to the Chicago Tribune. The characteristics that make this tower unique literally lie within the foundation of the exterior of the building. More specifically, there are nearly 150 pieces of iconic buildings, rocks, and monuments from across the world that are all labeled and embedded around the façade of the tower. The Tribune Tower is especially beautiful when the sun highlights the exterior stone during the early morning or late afternoon hours.

Chicago Theatre – The Chicago Theatre is home to the famous and iconic “CHICAGO” marquee, which has been frequently featured in television, film, and photography. The vibrant colors, bold capital letters, and stylish design makes this an easily photographed landmark at any time of day.

Chicago Water Tower – The Chicago Water Tower is located on Michigan Avenue in the famous Magnificent Mile shopping district and is the second-oldest water tower in the United States. The Chicago Water Tower gained notoriety during the Great Chicago Fire of 1871 when it was one of a handful of buildings to survive the devastation. The building has undergone a couple renovations throughout its tenure in order to preserve its structural integrity. Today, the Chicago Water Tower serves as an art gallery where local artists have their work exhibited.

Chicago Riverwalk – The Chicago Riverwalk is a relaxing pathway that meanders through well-landscaped green space in downtown Chicago. It provides residents with an opportunity to escape the hustle and bustle of the city and replace it with nature and views of Chicago’s iconic buildings. The riverwalk has been expanded to encompass 9-blocks along the Chicago River that are filled with serene sitting areas, cafes, and various outdoor activity rentals that range from bikes to kayaks.

Photography locations for blue hour, sunrise, and sunset:

BLUE HOUR - Cloud Gate at Millennium Park

Cloud Gate at Millennium Park – As I tend to do, I favor the early morning blue hour when there are fewer distractions and obstructions in the shot I am aiming to take. Although there is an element to capturing Cloud Gate with the reflections of large groups of visitors, for the blue hour I preferred the focus to be the reflection of the city skyline and blue sky. Without anyone around I was able to decrease the shutter speed and achieve the exposure and aesthetics that I desired and without any blur from passing foot traffic.

SUNRISE - Alder Planetarium

Alder Planetarium – If you ask any local where the best place to watch the sunrise would be, then more often than not the answer would be the Alder Planetarium. This location may not give you the sun rising up from behind the sky scrapers, but it will give photographers the opportunity to capture the changing colors of the sky and the golden hour as it warms up the skyline. Walk along the grounds or the Lakefront Trail to find the vantage point that is most appealing to you, but don’t forget to turn around once in a while to see if there is a shot developing behind you. The Alder Planetarium, or the artistic sundial structure, makes for great foreground elements if you want to capture the sun bursting over the horizon of Lake Michigan.

SUNSET - John Hancock Building’s 360 Observation Deck or Sunset Cruise on Lake Michigan

John Hancock Building’s 360 Observation Deck – The view from the 360 Observation Deck at the top of the John Hancock Building is unmatched when it comes to an aerial perspective of the city. The advantage of the observation deck is that it gives you the freedom to move about the four sides of the building to find the view that works best. Since this is touted as being the best view in Chicago, be prepared to arrive early in order to beat the large crowds, especially during sunset. Another point to note is that tripods are not allowed on the observation deck, but with some creative ingenuity this can be overcome by using a backpack or I’ve even seen some people using suction cup mounts. Whatever method is employed, the view of the skyscrapers bursting skyward over the city streets makes for a visually pleasing photograph.

Sunset Cruise on Lake Michigan – Although this selection is seasonal, it makes for a breathtaking photograph and an unforgettable evening. A number of cruise boat companies offer their version of a sunset cruise, but most of them have a duration ranging from 90 minutes to 180 minutes depending on the services offered. Boarding begins approximately 15-30 minutes before departure and there are no seat reservations, so arriving early will be beneficial in finding a seat to your liking. Once underway, the cruise motors along Lake Michigan giving all passengers on board a sweeping view of the Chicago coastline. As the sun sets and the skyline is illuminated, the radiant sky paired with the reflections of the skyscrapers, buildings, and Navy Pier Ferris wheel, makes for a spectacular photograph.

Publicly acclaimed Chicago dining locations with unique takes on classic dishes:

*Giordano’s – No trip to Chicago can be stamped as complete until you stop by Giordano’s for their famously stuffed, deep dish pizza. The menu offers up a handful of classics, but for those of you who have particular tastes, then there is the option to build your own and fill it with any of the ingredients on the menu. After your first bite it is hard to argue that it is not the best pizza pie you have ever tried.

*Billy Goat Tavern – Made famous by the Saturday Night Live sketch, the Billy Goat Tavern delivers a delicious, no nonsense, 'cheezeborger.' The classic location is found below the city streets with stair access on either side of Michigan Avenue, near the Tribune Building and Chicago River. Billy Goat’s is open late and is the perfect meal after a late night. The simplicity of the hot and tasty ‘cheezeborgers’ are what makes them such a delectable Chicago treat.

*Lucky’s Sandwich Company – Lucky’s Sandwich Company is located in the heart of Wrigleyville and is the perfect place to grab one of their signature stuffed sandwiches and a cold beer before a Cubs game, or just because. All of their stuffed sandwiches are filled with tomatoes, vinaigrette coleslaw, and French fries along with the additional ingredients that come with the sandwich you choose. For those looking to fully maximize the height of their sandwich, they offer extras like double meat, hot peppers, fried egg, onions, bacon, or pickles at an additional cost. It is difficult to choose just one sandwich as all of them are delicious and go incredibly well with the hot sauce that they provide. Be prepared to be fully satiated.

*BIG Bar – The Big Bar is a laid-back, low lit sports bar that lives up to its name by serving ridiculously big drinks with a price tag to match. It can be found on the second floor of the Hyatt Regency Hotel on Wacker Drive with the bar facing the Chicago River to the north. They serve pub-like eats, cocktails that range from big to very big, and a selection of beers that come in three sizes: 16 ounces, 22 ounces, or the 100 ounce beer tower. Bring your appetite, some friends, and anticipate a gratifying night out.

Recent Posts
Search By Tags
No tags yet.
bottom of page