As a hub for two major airlines, Chicago is a city many travelers visit during a layover. Chicago’s O’Hare airport is just 45 minutes away from downtown, commonly known as The Loop, making it easy for travelers with a long layover to hop on the “L” train and make the most of their short time in the city center.
There’s way too much to see in Chicago that even a week-long trip might feel short. The city is full of delicious food, renowned architecture and art, exciting history, and a rich culture. But, even on a short stay, you can enjoy at least a few of the iconic activities and places that'll give you a taste of what makes Chicago such a great city.
Formerly known as the Sears Tower, the Willis Tower is the second tallest building in the Western Hemisphere – after One World Trade Center in New York City. While the tower has 110 stories, reaching a total height of 1,450 feet, the attraction here is its famous SkyDeck on the 103rd floor.
If a 360-degree view of the city is not enough for you, you can increase the adrenaline by stepping on The Ledge – a glass box extending out 4.3 feet from the SkyDeck. Once you step on its glass floor, you can see all 1,353 feet of nothingness below your feet. It almost feels like you’re walking on air.
Should your layover allow it, I recommend visiting the SkyDeck during sunset, as you’ll see how the city’s skyline lights up as the sun hides in the horizon. It is also recommended to buy your tickets ahead of time to save time.
Millennium Park is one of the most successful public parks in Chicago, and all of the U.S. Its 25 acres are full of awe-inspiring landscapes, stunning architecture by world-renowned architects, and a varied collection of public art that range from abstract, to modern, and even interactive pieces.
As the most popular green space in the city, the park is always full of free events for the family, outdoor concerts, workout routines, film screenings, and more. Don’t miss seeing two of the most famous art pieces in the park: The Bean and Crown Fountain. The Bean, officially named Cloud Gate, has become a signature landmark of the city. Stand in front of it to see your reflection on its mirror-like surface, but also look beyond, as you’ll also see a distorted reflection of the Chicago skyline. A perfect place for a selfie! Crown Fountain is the famous LCD screen fountain that displays faces spouting water from their mouths. Feel free to frolic in the fountain's water.
Should you go in the winter months, put on some skates and go ice skating in the McCormick Tribune Ice Rink. Should it be summer or a warm day, spread out a blanket at the Pritzker Pavilion where you can watch a live performance or merely relax laying on the lawn. You can see upcoming events in the park on this site.
The Navy Pier is Chicago’s most visited attraction, and once you see it, you’ll understand why. This 3,300-foot-long pier on the Chicago shoreline of Lake Michigan is full of shops, restaurants, family attractions, exhibitions, gardens, and 50 acres of parks.
Beyond the current activities, the Navy Pier also comes with an interesting history. It opened to the public in 1916 as the "Municipal Pier," but in 1927 it was renamed to Navy Pier to honor the naval veterans of World War I. During World War II it even served as a training center for the Navy. It then became a school for the University of Illinois, then back to a pier with actual commercial shipping activities and last, but not least, a public space for locals and tourists.
Today you can ride the Ferris wheel, dine at one of the dinner cruises, look over at art exhibits, get lost in the funhouse maze, and even ice skate during the winter months, among other things.
Chicago’s loop is easy to walk and navigate. At every corner, you’ll see one impressive skyscraper after the other, which is part of what makes this city so visually stunning. But, one of the best ways to see and learn about the city’s architecture is by taking a boat tour.
A few companies offer Architecture tours along the river where you’ll find out how Chicago grew from a small settlement into one of the world’s largest cities in less than a century. The tour’s 90-minute ride is long enough to give you a general history of the city and its architecture, but short enough to do even on a relatively quick layover.
The tour runs several times a day, but should you not be able to hop on an official tour; you can also take the Water Taxi either from the Navy Pier or the site next to the Apple Store and ride up the river sightseeing the city from a different point of view. You might not get a historical explanation on the water taxi, but it will be cheaper than the tour.
These four activities are just a "teaser" of Chicago's greatness. Should you have more time, feel free to add more attractions as you discover them on your city walk.
Note: Available plans and coverages may have changed since this blog was published.
Your bag when backpacking is heavy enough. Here's how travel insurance can help take some weight off your shoulders.
Norbert Figueroa is an architect who hit the pause button on his career in 2011 to do a round the world trip. He's been blogging for over three years at globotreks.com, where he shares his travel experiences, budget travel tips, and a good dose of world architecture. From hiking Mount Kilimanjaro to diving with great white sharks, he is always on the search of adrenaline and adventure. Norbert is originally from Puerto Rico and he is currently based in Milan, Italy... when not roaming around the world, that is. He has traveled to more than 80 countries in 5 continents and his goal is to travel to all 193 U.N. recognized countries. Follow Norbert on Facebook, Twitter, Instagram and Google Plus.
Travel smarter with travel insurance from RoamRight. Get your free, no-obligation quote online today.
View all Blog Authors
View Countries with Blogs
Sign up for RoamRight's FREE monthly email newsletter to get travel tips, tricks, news, ideas, and inspiration!
The RoamRight mark is used by Arch Insurance Company and owned by its parent company, Arch Capital Group (U.S.). Insurance coverages are underwritten by Arch Insurance Company, NAIC #11150, under certain policy series, including LTP 2013 and amendments thereto. Certain terms, conditions, restrictions and exclusions apply and coverages may vary in certain states. In the event of any conflict between your policy terms and coverage descriptions on this website, the terms and conditions of your policy shall govern. Click here for privacy notice.
Copyright© 2023 Arch Insurance Company. All rights reserved.