Last Updated on March 16, 2022 by Jim Ferri
One of the great cities of America, Chicago has plenty of things to do…too many, in fact, to see in a single visit. Here are the most popular you should focus on…
Estimated reading time: 16 minutes
By Jim Ferri
Now that we’re beginning to travel again, many travelers are staying closer to home and planning domestic trips.
For most of us, it’s the sensible thing to do, putting our toes in the water before we make the big plunge. After all, it certainly beats making an 8-10-hour trip overseas, wearing a mask the entire time.
Right now, a great alternative to an overseas trip is a getaway to Chicago. It’s not more than about a four-hour flight from anywhere in the continental U.S. In fact, it’s much less than that from most American cities – just 2½ hours from Dallas, New York, and Denver.
Part of the city’s charisma is beautiful Lake Michigan, at 22,394 square miles (58,000 square kilometers) much more ocean-like than lake. It extends almost into downtown and has quite an impact on the city, providing a shoreline developed into a broad ribbon of beautiful parkland that offers some of the best recreational space anywhere.
Modern Chicago is a city of class, style, and culture that offers a multitude of surprises for travelers, no matter what their interest. The following ten places are the most popular among visitors to the Windy City. If you’re planning a trip to Chicago, put them all at the top of your list.
A Great City in Which to Begin Traveling Again
If you haven’t been to Chicago, you’ll find it’s one of the great cities of America, a sophisticated metropolis with outstanding cuisine, excellent shopping, and vibrant urban life.
It also showcases itself through compelling architecture and scores of world-class museums that provide a cultural legacy second to none.
It’s a city that offers it all and often delivers more than expected.
Part of Chicago’s charisma is that big pond outback, beautiful Lake Michigan. “Lake” is a bit of a misnomer since, at 22,394 square miles (58,000 square kilometers), it’s much more like an ocean than a lake.
It extends almost into downtown and has quite an impact on the city, providing a shoreline that’s been developed into a broad ribbon of parkland. It offers some of the best recreational spaces in the city and is well worth taking a morning walk along a bit of it.
I enjoyed a casual hour-long stroll on the Lakefront Trail from Lincoln Park to Navy Pier, about three miles. It was an enjoyable alternative to a bus trip downtown.
Popular Navy Pier has now reopened to the public.
Said to be the U.S. Midwest’s #1 attraction, the 3,300-foot-long Navy Pier is a colorful amusement wonderland on Lake Michigan. It is Chicago’s Coney Island and Luna Park, complete with a famous Ferris Wheel and other rides.
It is also home to a popular beer garden, not a complete surprise in beer-loving Chicago. What is a surprise is that Navy Pier also has three theaters (including Chicago’s Shakespeare Theater), a Children’s Museum, and a stained-glass window museum.
You’ll find a flotilla of big and small boats along the east side of the pier, some the size of large yachts. Most will take you on a tour up the Chicago River and along the shore or out on Lake Michigan.
During the summer months, fireworks light up the pier every Wednesday and Saturday evening, plus, of course, a special July 4th show celebrating America’s Independence Day.
You’ll find many attractions on the pier. These include:
- Amazing Chicago’s Funhouse Maze (opening late May 2021)
- Chicago Children’s Museum not yet open (visit its website to check current status)
- Chicago Shakespeare Theater
- Hornblower Cruises and Events
- Shoreline Sightseeing
- Tall Ship Windy (scheduled to reopen May 21, 2021)
If You Go:
600 E Grand Avenue
Chicago, IL 60611
Tel: (312) 595-7437
– Suggested duration: 3-5 hours
– Phased Re-opening Hours: Sunday – Thursday 10:00 am – 8:00 pm; Friday – Saturday 11:00 am – 10:00 pm
– Entrance to the pier is free, although there is a charge for many of its attractions
Despite it not being as large as many other zoos, the Lincoln Park Zoo is the second-most-popular attraction in the city after Navy Pier. Established in 1868, it’s the oldest public zoo in the U.S. Beautifully landscaped, it remains one of the last free-admission zoos in the U.S.
As expected, you’ll see the typical lineup of animals in the 35-acre zoo – lions, apes, polar bears, etc. But don’t miss the Great Ape House – it’s one of the most significant collections of gorillas and chimpanzees in the world.
You’ll also find that it’s the zoo’s setting in Lincoln Park that adds to its allure. Walkabout the park near the zoo, and you’ll enjoy a beautiful view of the city skyline reflecting in the lake, almost as if you were on an oasis.
If You Go:
2001 North Clark Street
Chicago, IL 60614-4757
Tel: (312) 742-2000
– Suggested duration: 2-3 hours
– Open 10 am – 5 pm every day of the year
– Admission is free, but reservations are required. And you must plan ahead since reservation slots are released at 4:30 pm every Sunday and Thursday for the following three to four days
The Shedd is a fantastic aquarium, one of the best in the country. When I arrived, I saw just how popular it was since the admissions line stretched for about 200 yards. I was lucky enough to have a CityPASS, though, which allowed me to bypass the line and enter immediately.
(At the risk of sounding like a shill for CityPASS, I use these passes whenever I can since they not only save you a lot of money but also allow you to skip long lines).
The aquarium’s 3-million-gallon Oceanarium, home to Beluga whales, dolphins, sea otters, and seals, is the largest marine mammal habitat in the world.
You can reach it via bus or taxi or by an $8 water taxi ride from Navy Pier. I took the water taxi and enjoyed a mini-cruise on Lake Michigan.
If You Go:
1200 South Lake Shore Drive
Chicago, IL 60605-2490
Tel: (312) 939-2438 or email at firstname.lastname@example.org
– Suggested Duration:2-3 hours
– Open: Tuesday – Thursday 9am to 5pm; Friday – Monday 9am – 6pm
– Admission: $29.95-39.95 ($14.95-19.95 for Chicago residents). A wide variety of discount tickets are also available. Go to https://www.sheddaquarium.org/plan-a-visit/get-tickets/discount-and-free-days
– Note that purchase of timed tickets before your visit is required
– Illinois residents enjoy free admission to Shedd Aquarium on special days throughout the year
– Chicago police officers and firefighters receive free on-site general admission with proper ID
– Active-duty U.S. military personnel receive free general admission with proper ID
Adjacent to the Shedd is the Field Museum, a natural history museum rated one of the best in the United States. Its collection contains almost 40 million specimens and artifacts.
Among its treasures is the largest and most complete T-rex ever unearthed, a behemoth named Sue. Sue is joined by several top-notch exhibits, including one devoted to the cultures of Pacific islands.
Another provides an “underground” view of the earth’s subterranean ecosystem, a fascinating bug’s-eye view of the world beneath our feet.
Other interesting displays include exhibits devoted to Africa, the ancient Americas, ancient Egypt, gems, and the evolution of our planet.
If You Go:
1400 S Lake Shore Drive
Chicago, IL 60605-2827
Tel: (312) 922-9410
– Suggested Duration: more than 3 hours
– Open 9am – 5pm; closed Tuesday and Wednesday
– Admission is $26-40 for out-of-state visitors; residents of Illinois and Chicago are given discounted admission
Chicago’s “Magnificent Mile,” a glitzy 13-block stretch of shopping Nirvana on North Michigan Avenue, is as famous as New York’s Fifth Avenue and Beverley Hills’ Rodeo Drive. It is Chicago’s premier commercial district.
The Magnificent Mile begins at the Chicago River on North Michigan Avenue. It continues north for about a mile (1.6 km) to Oak Street near the famous Drake Hotel. It is actually one square mile, extending eastward from the avenue to the shore of Lake Michigan.
Within this square mile, you’ll find more than 460 stores, 275 restaurants, 60 hotels, and more. Think Bloomingdale’s, Cartier, David Yurman, Marshalls, Saks, Tiffany, et al.
After you’ve shopped yourself to near death and are ready to leave the Mile, go back to the Chicago River, cross over the bridge and walk down to nearby Millennium Park. There you’ll find Cloud Gate, a magnificent sculpture nicknamed “The Bean” by Chicagoans for its kidney shape. See below…
If You Go:
The Mile begins on North Michigan Avenue at the Chicago River and stretches north 13 blocks to Oak Street / East Lake Shore Drive.
– Stores and restaurants open during regular business hours
Another Thing to Do in Chicago – See Cloud Gate
Cloud Gate, aka “The Bean,” is a magnificent sculpture, unlike anything I’ve seen before. As I walked around and under it, I could hear others describing it as “unbelievable” and “so uniquely beautiful.” Even those descriptions fall well short of sufficiently describing this beautiful but simplistic work of art.
In AT&T Plaza at Millennium Park, it was created in 2006 by Indian-born British artist Sir Anish Kapoor. Designed in 2006, the 110-ton elliptical sculpture of highly polished stainless-steel plates is among the largest of this type of sculpture in the world.
Its name is derived from the reflection of the clouds and city skyline. The “gate” is the 12-foot-high arch under the sculpture. Walk through it, and you’ll see yourself and the city in an ever-changing perspective.
It’s pretty fascinating and photogenic.
If You Go:
201 East Randolph Street (between Michigan and Columbus Avenues)
Chicago, IL 60602
– Admission: free
– Suggested Duration: ½ hour
– Open 6 am – 11 pm daily
Fabulous…Chicago Architecture Foundation River Cruise
One morning I went down to the river to take the Chicago Architecture Foundation River Cruise, which had been highly recommended to me by friends. (By the way, the Chicago River is the only river in the world that flows backward. It’s the result of a massive public works project undertaken to protect the city from water-borne diseases in the early 1900s.)
The 90-minute tour is an excellent and lively introduction to Chicago, and a comfortable and fascinating way to see the city. What makes the tour so popular is that Chicago is a living museum of 20th-century architectural history since the city was rebuilt after the Great Fire of 1871.
The fire is said to have started when Mrs. O’Leary’s cow kicked over a lantern, a spot also pointed out by the excellent guide. This is a great and interesting tour aboard Chicago’s First Lady.
If You Go:
The meeting point is on the northeast corner of Michigan Avenue and East Wacker Drive. Look for the blue awning marking the stairway entrance at 112 East Wacker Drive.
Tel: (312) 922.343
– Duration: 1½ hours
– Admission: Tickets are $48.18 plus tax for a day cruise, $52.91 plus tax for an evening cruise (after 5pm)
– All tours depart rain or shine
Not for Acrophobics: Willis Tower and the Hancock Tower
Chicago and New York continually compete for the bragging rights for America’s tallest skyscraper. But Chicago, however, can lay claim to having built the world’s very first skyscraper, the 10-story Home Insurance Building, in 1885.
The tallest building in the city today is the Willis Tower, aka the Sears Tower, once the tallest in the world.
Today, though, it’s famous for its Skydeck, glass boxes in which you walk out the side of the building and look straight down to the street, 103 floors below. It’s the highest observation deck in the United States and not for the acrophobic, but remains a trendy Chicago attraction.
You can also get an adrenaline rush at the “Tilt” ride at the John Hancock Center. As the name implies, Tilt is a box that tilts out of the side of the building, providing another adrenaline rush. You’ll find it on the 360° Chicago Observation Deck on the 94th floor of the John Hancock Center.
The difference between it and the Willis is the much better 360° view of the city from the Hancock Tower. And the Center also has a bar and restaurant, providing a more relaxing view, especially at sunset.
If You Go:
Skydeck Chicago in the Willis Tower
233 South Wacker Drive
Chicago, IL 60606
Tel: (312) 875-9447
– Duration: 1½ hours
– Open 9am – 10pm
– Admission: $22–30 purchased online. Advanced tickets are strongly recommended
360 Chicago – John Hancock Center
875 N Michigan Avenue 94th Floor
Chicago, IL 60611-1803
Tel: (888) 875-8439
– Duration: 1½ hours
– Admission: $20–30 (has reopened to the public at limited capacity; tickets are very limited)
– Open Thursday – Monday 9am – 9pm; closed Tuesday and Wednesday
Simply Incredible: the Museum of Science and Industry
The incredible Chicago Museum of Science and Industry is further from downtown Chicago than other sights, but it’s worth the trip. That’s because its home is in the only remaining building from the 1893 World’s Fair. Furthermore, it’s the largest science museum in the Western Hemisphere and one of the most captivating. And it’s big: 14 acres of exhibits, many of which are hands-on.
The first museum in North America to introduce interactive exhibits, it’s a fascinating place that can easily take up most of the day, if not all of it. Learn about genetics and farms, trains and coal mines, and take a walk through a heart.
Watch a 40’ (12 m) tornado form inside a two-floor exhibit and see the Apollo 8 Command Module. And don’t miss a tour through the U-505, the only German U-boat captured intact during World War II.
If You Go:
5700 South Lake Shore Drive
Chicago, IL 60637-2093
Tel: (773) 684-1414
– Open: Wednesdays through Sundays, 9:30 am to 5:30 pm
– Suggested Duration: at least ½ day
– Admission: adults $21.95, children (3-11 years) $12.95
– At this time, you must reserve timed-entry tickets to enter
Culture on Steriods: Art Institute of Chicago
Set in an original 1893 Beaux-Arts building and guarded by a pair of iconic lions on South Michigan Avenue, the Art Institute of Chicago Is home to one of the finest collections of French Impressionist art in the world.
For many Americans, however, one of its greatest treasures is Grant Wood’s American Gothic, which for some reason I expected to be much larger. Another is Nighthawks, Edward Hopper’s depiction of a New York diner near his home in New York’s Greenwich Village.
Other treasures include Seurat’s A Sunday on La Grande Jatte – 1884, Renoir’s Acrobats at the Cirque Fernando, and Toulouse-Lautrec’s At the Molin Rouge, to name just three. It has the most outstanding collection of Impressionist paintings outside Paris.
If You Go:
111 South Michigan Avenue
Chicago, IL 60603-6110
Tel: (312) 443-3600
– Open Thursday – Monday 11 am-6 pm; closed Tuesday and Wednesday
– Admission: $19-25; free with CityPASS
Chicago has a great music tradition, which continues to this day (in fact, it’s purported that the term “jazz” was coined in the city in the early 1900s). I capped off my visit to the Windy City with something quintessentially Chicago: a visit to a Blues club.
My choice was Kingston Mines, considered one of the best blues clubs in Chicago. Right after arriving in the dimly lit place, I grabbed a beer and some ribs, along with delicious fries and coleslaw.
I sat down at one of the long narrow 8” bar tables. I was soon engrossed in conversation with two couples from South Dakota who were in the middle of a baseball-tour vacation.
I stayed for several enjoyable hours but had to leave at 11 pm since I had a flight to catch the next morning. The band, I later was told, kept playing until 4 am.
It’s that popular.
If You Go:
2548 North Halsted Street
Chicago, IL 60614
Tel: (773) 477-4646
– Open Thursday – Saturday; show start at 6:30 pm
– Admission: due to the pandemic, all seats are reserved, and shows are limited to 90 minutes. There is a cover charge of $20.00 per person/ per show. A current, valid photo ID is required for entry to the club. Tickets can be bought online. Those tickets not sold online are sold at the door. Obviously, it’s best to buy online than take a chance at the door.