7 Excellent Ways to See Chicago

Everyone wants to see the sights of New York City, the sounds of Nashville, the architecture of New Orleans, and the natural beauty of San Diego. There’s a city in the middle of the U.S., though, that combines all these things in one: Chicago, Illinois.

Chicago has unique and classic architecture, long stretches of lakefront, enormous parks, astonishing public arts, some of the most iconic buildings in the world, and all the hustle and bustle you’d expect from the third largest city in the country. As a visitor, you want to see as much of Chicago as you can while you are there. Below, we’re going to break down some of the best ways to see it. Here are seven excellent ways to see Chicago.

1. Rooftop bar

Of course, you want to see all that Chicago has to offer while you are there, but you also want to relax, have a drink, and maybe eat a nice meal. Why not do both at one of Chicago’s many rooftop bars? These bars give you an incredible view of the city down below with the added bonus of providing a cocktail, glass of wine, or a cold beer while taking in the city below.

You can sip on one of Cindy’s famous Old Fashioned cocktails at the top of the Chicago Athletic Association Hotel while overlooking Millennium Park and the stunning Lake Michigan. North of Navy Pier you’ll find another hotel rooftop bar, J Parker, that provides great views of Lincoln Park. These are just two of the many rooftop bars you can find in the White City. To see more, Party Slate has a solid guide to Chicago’s best rooftops.

2. Boat tour

The city of Chicago sits on the banks of Lake Michigan and has the mighty Chicago River that runs right through the middle of the city. All this water makes seeing the city by boat a very cool and unique option. Because of the way the water is intertwined with the city landscape, you can take a boat tour that will show you both the natural and man-made beauty of this place.

An architectural boat tour runs up the Chicago River and shows you some of the buildings the town is famous for. At the end of the river, you’ll float into a lock and be taken into Lake Michigan to see the shoreline in all its glory.

3. Bike the lakefront trail

The Chicago Lakefront Trail (LFT) is 18.5 miles long and stretches from Osterman Beach in the north down to South Shore Park. The trail passes by Chicago’s four major lakefront parks and multiple beaches. In the summer, the trail can be walked, biked, skateboarded, and more by upwards of 70,000 people.

On a bicycle, which you can rent on the trail, you can easily see the entire trail on a single day. In addition to the beaches and parks, the LFT also takes you by some of Chicago’s top attractions. This includes Lincoln Park Zoo, Navy Pier, the Museum of Science and Industry, and the home of the Chicago Bears, Soldier Field.

4. Take the El

Taking public transit isn’t always a great way to see a big city. Often it just results in seeing drab, underground subway stations. In Chicago, though, the El or just the L – short for elevated train – is both a cheap and efficient way to get around as well as a perfect way to see the sites of the city.

The transit system, third-largest and second oldest in the U.S., runs 24-hours a day and will take you all around the city including out to both of Chicago’s airports. Taking a ride around the 1.79-mile area known as The Loop enables you to see some of the best of downtown Chicago.

5. Walk the 606

A few miles in from the LFT, another trail runs perpendicular to the lake. The 606 or the Bloomingdale Trail is an elevated trail that repurposed the old Bloomingdale train line into a 2.7-mile elevated walking trail.

The trail cuts through some of Chicago’s hippest neighborhoods such as Wicker Park, Bucktown, Logan Square, and Humboldt Park. There are several parks at street-level below the walkway and you can also check out public art, architecture, scenic lookouts, and Exelon Observatory, one of the best spots in the city to watch the sun rise or set.

6. Take a helicopter tour

If the rooftop bars in Chicago don’t give you enough of a bird’s eye view, you can get an even better vantage point on a Chicago helicopter tour. These tours run multiple times a day from several helipads throughout the city. You can do one of their stock tours around the Northside, Southside, or downtown Chicago, or book a customized one.

You can fly around Chicago during the day and see the whole city and the lake or fly at night and see the incredible lights of the city as the contrast with the lake’s inky blackness. Some of the best sites to see while flying include Soldier and Wrigley Fields, Millennium and Lincoln Parks, Sears Tower, John Hancock Building, Navy Pier, and Montrose Beach.

7. Head to the top of the Willis (aka Sears) Tower or the Hancock

The Second City has several incredibly tall buildings but two stand out and have great observation decks from which the public can see vast stretches of the city. The John Hancock Building at 875 North Michigan Avenue is currently the 13th tallest building in the U.S. but when it was constructed in the 1960s, it was the tallest in the world and the first building outside of New York City to rise to over 1,000-feet.

The Hancock was surpassed as the tallest building in Chicago, and the world, in 1974 by Willis Tower (formerly Sears Tower). At 1,451 feet, this was the tallest building in the world from 1974 to 1988 and is still the tallest in Chicago to this day. The tower has a Skydeck at 1,353-feet which includes a 4.3-foot, glass-bottomed box known as “the Ledge,” for the adventurous to step out and seemingly float over the city below.


Chicago has so many sights to see, it can be hard fitting them all in. The best ways to see a ton of the city at once are with one of the methods above. Whether you’re walking, biking, riding, flying, or taking an elevator up, you can’t go wrong looking at Chicago in one of these special and unique ways.

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