Best Sightseeing in Chicago

Where the Locals Go Sightseeing in Chicago

Putting together an itinerary for seeing all the best sights in Chicago? There are some obvious spots including Willis Tower (formerly Sears Tower) and the John Hancock Center for those spectacular views from way up high but the real treats lie in the neighborhoods.

Tours like the very popular Chicago Architecture Foundation River Cruise is a great way to see the city’s most famous buildings and skyline while learning some history. Just west of the city is Frank Lloyd Wright’s Home and Studio which is not to be missed if you’re a fan of his architecture.

 A slightly different architectural tour is of the Graceland Cemetery grounds. The cemetery, known as the "Cemetery of Architects," is one of Chicago's best kept secrets and one of the most beautiful places to visit.

It’s hard to miss the city’s stunning Lakefront Trail which stretches from one side of the city to the other in 18.5 paved miles. It gets crowded on warm weekend days but it's one of the best places to bike, run or walk and enjoy the city’s beautiful lakefront. Pack a picnic and enjoy the people watching.

Another great and often overlooked spot is Chinatown’s Ping Tom Memorial Park. Ask for directions (it’s tricky to find by foot). Once you find it, you’ll be rewarded with a quiet sanctuary filled with wildflowers, willow trees, trails and the Chicago River. Or, hop on a water taxi along the Chicago River – the water taxi stops at the park. 


Cemetery hours don't allow guests to verify whether a green-eyed ghoul really howls at the moon. The story of the statue of six-year old Inez Clark disappearing during storms also remains a legend, but a walk through the historical 1860 graveyard during the day is still a worthwhile experience. Inexpensive maps and guides are offered to help visitors identify famous gravesites including the father of skyscrapers and modern masters. The resting place is also home to many of the city's most popular public figures, baseball and boxing greats, merchants and inventors. The grounds were designed in 1861 by prominent landscape architect H.W.S. Cleveland with the intent to create a park-like ambiance. Another landscape architect, Ossian Simonds, added to the plan by using native plants to create the cemetery's pastoral landscape, making the "Cemetery of Architects" one of the most beautiful places in Chicago to visit.

Recommended for Sightseeing because: Known as the "Cemetery of Architects," Graceland is the final resting place of some of Chicago's most famous public figures, including the father of skyscrapers.

Megy's expert tip: As with a visit to almost any cemetery, pets are not allowed on the grounds.

Read more about Graceland Cemetery →

After 40 seconds in John Hancock's elevator, visitors are transported 1,000 feet above Chicago. From there, the city's third-largest building offers views that stretch out to 80 miles on a clear day. Food and drink are available in the restaurant and lounge, and informational exhibits are on display in four different languages. Pop an extra $8 for a ticket to TILT, an enclosed moving platform that tilts you out over Michigan Avenue from the 94th Floor. Should you be around in February, you may want to skip the elevator ride and run to the top with other participants who "Hustle up the Hancock" to benefit charity. Make reservations in advance for dinner or stop for a drink at the famous The Signature Room at the 95th where you can continue to enjoy the spectacular views.

Recommended for Sightseeing because: Visitors can enjoy views up to 80 miles from Chicago on a clear day.

Megy's expert tip: Stop for a cocktail at the famed The Signature Room at the 95th.

Read more about 360 Chicago Observation Deck →

[Due to national security concerns, only pre-arranged group tours are allowed to visit the viewing gallery. The lobby visitor center is, however, open to the general public.] The Chicago Board of Trade, the largest exchange in the world, holds court in an impressive Art Deco building. Visitors may watch the frenzied action of futures and options trading from the 5th-floor viewing center and be enlightened by guides about the seemingly-cryptic gestures used by traders. A small museum and a film offer more insight into the business of trading. While you're there, note the rooftop aluminum statue of Ceres (Roman goddess of harvest) and look for the lovely painting of her that was once on the trading floor and now occupies a place of prominence in the atrium addition.

Recommended for Sightseeing because: A visit to the Chicago Board of Trade is a rare opportunity to see futures and options trading in action.

Megy's expert tip: Tours MUST be planned in advance

Read more about Chicago Board of Trade →


One of Chicago's most unique neighborhoods, Chinatown offers Far Eastern charm in the Midwest. Featuring scores of terrific Chinese and Cantonese restaurants and bakeries, the neighborhood has a special place in the hearts (and stomachs) of folks who visit. Shoppers also enjoy cozy, family-owned bookstores and gift shops. If you're lucky, you'll visit Chinatown during one of its lively festival and perhaps even the colorful Chinese New Year celebration. Within Chinatown is Ping Tom Memorial Park which isn't easy to find but worth the effort. Ask for directions and once you find the entrance you'll be transported to a quiet sanctuary filled with wildflowers, willow trees, trails and the Chicago River. There is a water taxi stop which visitors can pickup and head into the Chicago Loop.

Recommended for Sightseeing because: One of Chicago's most unique neighborhoods, Chinatown is filled with family-owned restaurants, bookstores and gift shops.

Megy's expert tip: Ask for directions to the Ping Tom Memorial Park.

Read more about Chinatown →


Since 1916, Navy Pier has been home not only to the military but to scores of special attractions. Now purely commercial, the Pier offers everything from an IMAX theater to performances by a Shakespeare troupe. You can view dancing in a grand ballroom, ride the splendor of a fifteen-story Ferris Wheel (a replica of the one at Chicago's 1893 World's Fair), or relax to the sounds of waves quietly lapping on the lakeshore. The Chicago Children's Museum is on the second floor and there are dining options on the premises. A series of special events happen throughout the year including seasonal celebrations, festivals and cultural events to public shows in the exhibition hall space. The website has an up-to-date calendar worth checking out in advance of a visit.

Recommended for Sightseeing because: Navy Pier is home to an IMAX theater, Chicago Shakespeare Theater, the Chicago Children's Museum and year-round special events.

Megy's expert tip: Free Trolleys run between State Street and Navy Pier between Memorial Day and Labor Day.

Read more about Navy Pier →

The architectural genius of Frank Lloyd Wright is showcased on this variety of tours. Eager visitors learn about Wright's background and his design philosophies while touring the interior of his home and studio. The guided home tours showcase his studio and its chain-hung balcony, along with a playroom designed for his children that offers treetop views. The architect's signature style and taste are clearly evident throughout the intricately designed home. Other tour options promote an exploration of Oak Park itself, which has a preponderance of homes that Wright designed. The historic neighborhood also showcases Prairie-style homes and Victorian structures. Oak Park, where the home and tours are located, is just west of Chicago.

Recommended for Sightseeing because: Architecture and history lovers can view several Frank Lloyd Wright as well as the birth home of Ernest Hemingway.

Megy's expert tip: Check out the charming downtown Oak Park area before or after the tours.

Read more about Frank Lloyd Wright Home & Studio and Historic District Tours →

A highlight of any trip to Chicago, this museum is home to one of the best and most diverse art collections in the world. People are drawn first to the vast Impressionist collection, including the world's largest group of Monet paintings. But treasures abound, including the haunting "American Gothic" and Seurat's groundbreaking Pointillist work. The contemporary section has been expanded and now includes pieces by Picasso, Matisse, Dali, Pollock, and Warhol. The temporary shows are also well known and always receive critical acclaim. Kids particularly enjoy the Thorne Rooms, 68 miniature room models with intricately detailed European interiors from the 16th century through the 1930s as well as American furnishings from the 17th century to 1940.

Recommended for Sightseeing because: Visitors to the Art Institute of Chicago can view the haunting "American Gothic" and Seurat's groundbreaking Pointillist work.

Megy's expert tip: Check out the world's largest Monet collection.

Read more about Art Institute of Chicago →

Standing 1454 feet high, this skyscraper is easily Chicago's most dominant structure and still holds the title of tallest building in the Western Hemisphere. Visitors can shoot to the top of the 110-story building via a 70-second elevator ride and catch magnificent views into Indiana, Michigan and Wisconsin from the 103rd floor Skydeck. If you are looking for thrill, step out onto "The Ledge," glass boxes extended from the side of the Skydeck with views 1,353 feet straight down. Informational exhibits for both adults and children teach the history of Chicago, the construction of the tower and interesting "did you know" facts.

Recommended for Sightseeing because: Still holding the title of the tallest building in the Western Hemisphere, show proof that you were there by taking a picture on The Ledge.

Megy's expert tip: Get a photo on The Ledge as a souvenir.

Read more about Willis Tower (formerly Sears Tower) →

The city really comes alive when the weather warms up enough for its residents to hit the Lakefront Path. Located east of Lake Shore Drive, the Lakefront Trail is an 18.5 mile linear path that stretches from the far north part of the city to the south side. Neighborhoods dot the path as well as notable cultural landmarks including the Museum of Science and Industry; the Field Museum of Natural History; Shedd Aquarium; Adler Planetarium & Astronomy Museum; the Chicago Children's Museum; the Peggy Notebaert Nature Museum; Lincoln Park Zoo, and the South Shore Cultural Center. The paved path is very popular among walkers, joggers and bicyclists and it will and does get crowded during the warm weekends. Expect to slow down around Navy Pier, one of the most congested points on the trail. Still, the Lakefront Path is one of Chicago's best and free sightseeing attractions.

Recommended for Sightseeing because: One of Chicago's best free attractions, the 18.5 mile linear path stretches from one part of the city to the other.

Megy's expert tip: Metered parking is available at almost all of the parks along the trail.

Read more about Chicago Lakefront Trail →

Seeing Chicago's architectural beauty from the decks of a river cruiser is a must for both locals and visitors. One of the city's most unique tours, the CAF River Cruise takes visitors along the north and south shores of the lake. Guests will learn about more than 50 buildings and their significance to Chicago's architectural landscape as well as general history about Chicago and how it grew from a small back-country outpost to one of the world's most important crossroads of today. Tours are available late April through mid-November and run about an hour and a half in length. Be sure to purchase tickets in advance as they often sell out.

Recommended for Sightseeing because: CAF River Cruise tours takes visitors along the north and south shores of Lake Michigan and learn the significance of more than 50 buildings.

Megy's expert tip: Tickets sell out fast so book them as soon as you can.

Read more about Chicago Architecture Center River Cruise →


Meet Megy Karydes

Megy Karydes has spent more than 20 years as a professional writer and most of her life in Chicago. While she’s traveled extensively internationally, visiting each of the 50 states is on her...  More About Megy