Where the Chicago River and Lake Michigan meet sits the largest city in the midwestern United States – Chicago. Travel + Leisure magazine readers rated Chicago among the top-10 U.S. cities to visit. In a publication called the “World’s Most Amazing Cities”, Chicago placed in the top-10 among “Waterfront Wonders” – category that included cities like Porto, Portugal, San Francisco, and Venice, Italy. 

Some affectionately call Chicago the Second City. This nickname is thought to have emerged as Chicago was chasing New York City to become the largest city in the nation. Others believe it refers to Chicago’s rebuilding after a devastating fire. Another nickname for Chicago is the Windy City. The origin for this nickname is also in dispute. Some claim it is a literal reference to the howling wind blowing off Lake Michigan through the city, especially in winter. Others believe the origin refers to the hot air frequently blown by city officials. Based on my experience, it is the incredible rise from the ashes and pleasant summer breeze off Lake Michigan that most resonate. 

Chicago is the third most populous metro area in the United States with a population of approximately 10 million. Only New York and Los Angeles are larger. I have been fortunate to visit Chicago many times over the years for work-related travel and always try to carve out some time to get out and explore this magnificent city. Theres no better place to start your Chicago visit than with the Magnificent Mile – Chicago’s premier commercial district. Within this 13-block stretch, the Magnificent Mile has over 400 stores, 275 restaurants, 60 hotels, and presents an architectural feast for the eyes. 

I have often found myself in the area shown above (taking far inferior photos) when working my way to the waterfront for a shoreline run. I really like this shot because it features two elements that make Chicago a great destination –  its world-renowned architecture and the Chicago Riverwalk.

It is hard to believe this city began as a 200-person outpost on the shore of Lake Michigan less than 200 years ago in 1830. Chicago’s location on the shore of Lake Michigan set it up for quick growth by allowing for imports and exports. Its river and canal system also afforded access to the Mississippi river which provided access to cities all the way to New Orleans and into the Gulf of Mexico. It’s no surprise Chicago soon became a central hub for railways in the US.

By 1870, Chicago’s economy was booming. Opportunities for good work generated a steady flow of migrants to this fast-growing city as the population approached 500,000 in only 40 years. Then came the great fire. In 1871 a devastating fire swept through downtown Chicago destroying 17,000 buildings, leaving 100,000 people homeless, and killing 300. From these ashes, a new city rose under a carefully designed city plan. A new city grid was designed with new buildings rising up using the latest advances in technology, safety, and architectural advances. With the advent of steel structures to replace brick and stone buildings, building weights were reduced by 60% which allowed the first skyscrapers in the world to rise in Chicago. Only 30 years after the great fire, Chicago was the fifth largest city in the world. 

The tallest building in the image above is the Sears Tower (now officially called the Willis Tower) which was completed in 1973. At that time, it was the tallest building in the world. Today, the Sears Tower (Willis Tower) is the second tallest building in the western hemisphere behind One World Trade Center in New York. I took the image above during a River Architecture Tour as we approached the Sears Tower.

I would highly recommend a river cruise on your trip to Chicago. They will have plenty of drinks and food on board with a guide to tell you all about the history of Chicago, the river’s importance to Chicago’s growth, and the spectacular sights you are seeing. Below are a couple more shots from the river.

If you aren’t into a river cruise, you can easily take in the sights and entertainment along the river by foot. The Chicago River, once primarily used for shipping, now has 1.25 mile path that is a tourist attraction known as the Chicago Riverwalk. The Riverwalk is lined with bars, restaurants, pedestrian ways which are great for sightseeing, and easy access to water activities like kayaking. 

The architectural detail in many of the Chicago buildings is truly impressive and worth slowing down to appreciate. Below are a few buildings that caught my eyes due to their ornate craftsmanship. They don’t seem to make them like this anymore. These aren’t the best images but will, hopefully, at least inspire a closer look when you are in Chicago.

Here are day and night views of the Wrigley Building:

The Chicago Tribune (below) was completed in 1922 and features Gothic Revival details on top. Reportedly, the facade includes fragments from structures such as the Parthenon, Westminster Abbey, the Great Pyramid of Giza, and the Great Wall of China.

Chicago Tribune Tower

The building behind the Tribune Tower, (image above, left side) is the Intercontinental Hotel located on Michigan Ave. This is where I have stayed most often and definitely recommend it. The building itself is a landmark building completed in 1929. The globe on top of the building was originally envisioned to be a docking station for airships. Looking out of my Intercontinental hotel room window (below), we can see the ornate detail on the Intercontinental with the Wrigley Building just beyond it. 

The building below, theMART, caught my attention because of its shear mass. This one single building covers two square blocks all by itself. The building was originally designed by Marshall Field & Co to be a venue where retailers could view and buy their merchandise.

While summers are typically amazing in Chicago, the weather will surprise you on occasion. This is a shot I must have taken over 10 years ago and really like it. This is the John Hancock Center disappearing into the heavens. 

The black building (below) is the Hancock Center on a better day taken from a shoreline park on a sunny, summer Chicago day.

Visit the top of the Hancock Center for 360 views of Chicago and Lake Michigan. 

Taking in all the architecture and Riverwalk will be more than enough to fill your days. But, I have to mention the  parks and waterfront. City planners showed great foresight in setting aside land devoted to parks and relaxation/fitness. Chicago’s Lakefront Trail is an 18-mile paved path along Lake Michigan’s shoreline. The licensed image below provides a shot of the Chicago Bears’ Soldier Field and off the right you can get a flavor for the shoreline, parks, and Lakefront Trail.

Along the trail, you’ll find plenty of parks, art, lake and skyline vistas, and even beaches for swimming. In the photo above, the beaches and larger parks I mentioned are around the corner from those building in the top right of the image. Want to go for a long run without needing to worry about traffic? The Lakefront Trail is the place to go. Here are a few photos from a run during my last trip to Chicago which also include a few glimpses at the beach areas.

Chicago is also a great sports town with two MLB teams, Chicago Cubs and White Sox; NFL team, Chicago Bears; NHL team, Chicago Blackhawks; and the NBA team, Chicago Bulls. I was fortunate to catch a Chicago Cubs baseball game at Wrigley Field during one visit.

Wrigley Field was built in 1914 and considered an iconic baseball stadium. The red marquee shown above is well known among sorts enthusiasts. Looking at the stadium from inside in the image below, you can see the scoreboard in the top right. In this digital age, Wrigley’s hand-turned scoreboard remains as nod to the past. Looking down to the bottom left at the outfield, you can see the ivy-covered wall (brick wall) which is also unique among baseball parks. Finally, the stadium is located in a residential area. People can access the rooftops of their buildings to take in a game.

Built in 1914, the Navy Pier is another of Chicago’s must see attractions. Food, theater performances, boat cruises, museums, and fireworks are among the attractions. A bit of notable history on the Navy Pier includes the Ferris wheel. Back in 1893, Chicago hosted the World Fair and one of the featured attractions was designed and built by George Washington Ferris. We know his invention today as the Ferris Wheel. The original Ferris wheel is, surprisingly, long gone – not sure how they could have possibly let that bit of history just roll away. A smaller (but still large) replica is located on the Navy Pier and is a nod to Chicago’s gift to the world – the Ferris wheel.

I took the below photo probably 15 years ago during my first trip to Chicago. As I recall, I was on a river cruise and maybe a half mile or so from the bustling downtown area. This metal structure offered a glimpse into Chicago’s industrial past where revitalization efforts hadn’t yet touched. The clouds were swirling around in the strong breeze of the day and the structure vividly contrasted with the skyscrapers and dazzling sights further down the river. I felt such an overwhelming sense around the passing of time – including my own.

As we come to end, I have only scratched the surface of all Chicago has to offer. The city has been selected as America’s “Best Large City” by Conde Nast Traveler for the last four years. With such an endorsement, there is clearly far more to experience. Chicago has an abundance of restaurants, music, and art to explore along with dozens of neighborhoods (Wicker Park, Bucktown, Pilsen, Greektown, West Loop, Chinatown, Japanese Garden, and Randolph Street’s restaurant row) offering their own distinct cultural experiences.

After revisiting my memories of Chicago, I find myself eager to return and explore more of this great American city. I hope your path leads you there as well some day – you won’t be disappointed.