13 Best Things to Do in Chicago for First-Time Visitors

Chicago offers world-class architecture, major museums, historic hotels, and distinctive neighborhoods. It is also an excellent city to explore on foot. I especially loved experiencing the city through its architecture. The city feels like an outdoor museum of American design.

I traveled to Chicago multiple times on business over the years. But those trips never gave me much time to explore. On this visit, everything changed when I slowed down and discovered the city’s iconic architecture.

I spent my days looking up at skyscrapers, walking beside the river, and learning about the city’s architectural history. This trip showed me a Chicago I had missed on all those earlier visits.

Here are 13 of my favorite things to do in Chicago.

Take the Chicago Architecture Center River Cruise

If you do only one tour, make it an architecture cruise. The Chicago Architecture Center (CAC) offers its river cruise aboard Chicago’s First Lady. Volunteer docents explain the buildings lining the river.

The cruise that puts Architecture First. Voted the #1 best boat tour in the United States by USA Today, as well as Chicago Reader’s Best Tour for over 10 years!”-Chicago Architecture Center

Learn about the architects who created our city’s magnificent buildings and the stories behind them. Along the way, you’ll also hear how the city grew from a small settlement into one of the world’s largest cities.

The Chicago’s First Lady architecture cruise highlights over 50 iconic landmarks along the Chicago River. The five most famous buildings featured on the tour are the Willis Tower, the Wrigley Building, the Tribune Tower, Marina City, and the Merchandise Mart.

The views are unforgettable. Expect a stiff neck at the end of the cruise from staring in awe at so many highrises. The cruise offers a different perspective than exploring the city on foot. I recommend doing both.

Tip: I also wrote a separate guide, Chicago Architecture: What to See, for readers who want to explore further.

Visit the Chicago Architecture Center

Architecture lovers should also visit the CAC near the river. Its exhibits explain how it became one of the world’s most important architecture cities. You can also learn about famous architects.

The large-scale city model is a highlight. It helps visitors understand the city before exploring outside. The center also offers walking tours focused on different neighborhoods, architects, and building styles.

Step Inside the Palmer House

The historic Palmer House offers a glimpse into Chicago’s grand hotel era. Real estate magnate Potter Palmer built the hotel for his fiancée, Bertha. This 225-room hotel operated for only 12 months at State and Quincy Streets. Potter spent a staggering $100,000 on furnishings. He was also building a second Palmer House nearby. Both hotels burned to the ground on October 8, 1871.

Palmer House is famous for many things. “It was the first hotel to incorporate the light bulb, the telephone, and the vertical steam lift (elevator) as well as being the creator of one of the world’s most adored confections, the brownie,” according to Palmer House.

The current hotel opened in 1873 and later underwent major changes. Its ornate lobby remains the main attraction for visitors. Look up at the ceiling while standing in the lobby. The painted panels and chandeliers create an impressive setting.

You do not need to stay overnight to appreciate this historic Chicago landmark. I recommend visiting the Palmer House to enjoy afternoon tea or an evening cocktail in the lobby.

Explore the Chicago Cultural Center

The CCC is one of my favorite free places to visit downtown. Its nickname is the “People’s Palace.” The building opened in 1897 as Chicago’s first central public library. Today, it hosts exhibitions, performances, and cultural programs.

The country’s top architects and craftsmen used the most sumptuous materials, such as rare imported marbles, polished brass, fine hardwoods, and mosaics of Favrile glass, mother-of-pearl and colored stone, to create an architectural showplace.”―Chicago Cultural Center

Located on the south side of the building, the world’s largest stained-glass Tiffany dome (which measures 38 feet in diameter and features some 30,000 pieces of glass) was restored to its original splendor in 2008.

The building also features mosaics, marble staircases, and decorative details. It is open daily from 10 a.m. to 5 p.m. Admission is free. The Cultural Center sits across from Millennium Park, making it easy to combine both attractions.

Walk the Riverwalk

The Riverwalk provides another way to experience the city’s architecture. The pedestrian walkway follows the river through downtown. Restaurants, public art, seating areas, and boat docks line the route.

You can walk a short section or spend several hours exploring. Bring your walking shoes.

Tip: I recommend returning after your architecture cruise. You will recognize many of the buildings you learned about from your guide.

See Millennium Park and Cloud Gate

Millennium Park belongs on almost every first-time city itinerary.

Its best-known attraction is Cloud Gate, commonly called “The Bean.” Artist Anish Kapoor created the stainless-steel sculpture.

Artist Anish Kapoor described its concave, dome-like underside—called the omphalos—as a ‘gate that traditionally implies a or a kind of a coming together.'”

Its mirrored surface reflects Chicago’s skyline and the people surrounding it. Everyone takes this photograph.

You can also explore the gardens, public art, and nearby lakefront while visiting Millennium Park.

Tour the Art Institute of Chicago

The Art Institute of Chicago houses one of America’s major art collections.

Its galleries feature works by Monet, Renoir, Van Gogh, Seurat, Picasso, Hopper, and many other artists.

Georges Seurat’s A Sunday on La Grande Jatte is one of the museum’s most recognizable paintings. (Credit: Georges Seurat. A Sunday on La Grande Jatte, 1884. The Art Institute of Chicago.)

You can also see Grant Wood’s American Gothic and Edward Hopper’s Nighthawks.

Allow several hours inside. Admission: $32 adults; $26 seniors 65+.

The museum sits beside Millennium Park, so you can easily visit both attractions on the same day.

Visit Wrigley Field

Baseball fans should make time for historic Wrigley Field. The Chicago Cubs have played at Wrigley since 1916. The ballpark is known for its ivy-covered outfield walls. You can attend a Cubs game during baseball season. Stadium tours are another option when your schedule permits.

Spend some time walking around Wrigleyville before or after your visit.

Tip: The Chicago Architecture Center features a gallery exhibit on the historic ballpark at their downtown location. Official stadium tours are available directly through the Chicago Cubs.

See the Historic Chicago Theatre

The Chicago Theatre’s famous marquee has become a city landmark. The building is a French Baroque Revival movie palace, designed by Chicago architects Cornelius W. Rapp and George L. Rapp. The Rapp brothers became nationally known for elaborate movie theaters during the 1920s. Their designs often borrowed from French Renaissance and Louis XIV-era architecture.

The theater opened in 1921 as part of the Balaban & Katz theater chain. Today, it hosts concerts, comedy performances, and other events.

Even if you do not attend a performance, stop outside for a photograph. You can also check whether theater tours are available during your visit.

Take a Route 66 Selfie

Chicago marks the eastern starting point of historic Route 66. Look for the “Begin Historic Route 66” sign near Michigan Avenue and Adams Street. It is across the street from The Art Institute.

The sign provides an easy photo opportunity while exploring downtown. It’s a classic Chicago selfie.

Route 66 celebrates its 100th anniversary in 2026, marking a century since the legendary highway was established. The original route stretched about 2,400 miles from Chicago to Los Angeles and became a symbol of the American road trip. Centennial events are taking place throughout 2026 along the historic “Mother Road.”

Sample Chicago Food

Food is part of the Chicago experience. A traditional Chicago-style hot dog comes loaded with toppings. Expect mustard, onions, relish, tomatoes, pickles, peppers, and celery salt.

One important rule separates the Chicago dog from many others. Don’t ask for ketchup. Trying one is an inexpensive way to sample a local tradition during a busy sightseeing day.

Tip: I ordered my Chicago hot dog at Jimmy’s Gyros & Grill. This takeout joint operates from the location of the oldest hot-dog stand in the Chicago Loop. Its menu includes the classic Chicago-style dog.

You should also try Chicago’s famous deep-dish pizza at least once. Deep dish originated in Chicago in the 1940s, with Pizzeria Uno commonly credited with popularizing the style.

Chicago deep-dish pizza resembles a savory pie, with a thick crust baked in a deep pan. Cheese and toppings sit beneath a layer of chunky tomato sauce. One of the city’s signature foods, it is closer to a meal than a quick pizza slice.

Tip: I headed to Gino’s East to try one of Chicago’s most famous foods: deep-dish pizza. The Chicago institution has served its thick, cheesy pies since 1966. Its buttery crust holds layers of cheese, toppings, and chunky tomato sauce.

Take a Chicago Walking Tour

Chicago is an ideal city for walking tours. Architecture tours remain the obvious choice, but they are not your only option. You can find tours focused on food, history, neighborhoods, public art, skyscrapers, and Chicago’s past.

Multiple companies offer architectural walking tours in Chicago. However, I took two Inside Chicago Walking Tours. The company is a woman-owned, small local business that pioneered the “interior architecture tour” concept in Chicago. I also recommend the Chicago Architecture Center’s walking tours, such as the “Historic Treasures of Chicago’s Golden Age. An adult ticket costs $35; it is free for CAC members.

Visit the New Obama Presidential Center

The Obama Presidential Center opened in June 2026 on Chicago’s South Side. I haven’t visited yet, but it is already on my list for my next trip to Chicago. The 19-acre campus in Jackson Park includes the Obama Presidential Center Museum and a Chicago Public Library branch. Visitors can also explore gardens, walking trails, public art, and the Great Lawn.

Built on the South Side where the Obamas’ journey began, this 19.3 acre campus was designed with you in mind. Find inspiration in a one-of-a-kind Museum, dive into a story at the public library, or hang with friends on the Great Lawn.”

Most of the campus is free and open to the public. The museum requires a timed-entry ticket. The Center celebrates Barack and Michelle Obama’s Chicago roots while exploring the Obama presidency, democracy, and civic engagement.

Frequently Asked Questions About Visiting Chicago

What is the best way to get around Chicago?

Walking and public transportation work well for most visitors. Chicago’s CTA trains and buses connect downtown with many popular neighborhoods. You probably will not need a rental car. Rideshare services can fill occasional transportation gaps. I prefer exploring on foot. Walking also lets you appreciate Chicago’s architecture and public spaces at a slower pace.

What are the best months to visit Chicago?

May, June, September, and early October are excellent months for sightseeing. Temperatures are generally comfortable for walking. Summer brings warmer weather, festivals, and larger crowds. Winter can be very cold. Spring and fall are especially appealing if you plan to spend much of your visit outdoors.

Is Chicago safe for a solo female traveler?

Many solo women visit Chicago without problems, particularly in busy tourist areas. Stay aware of your surroundings and research neighborhoods before traveling beyond central sightseeing areas. Avoid isolated streets late at night. Consider a taxi or rideshare when you feel uncomfortable walking. Trust your instincts while traveling. Keep your phone charged and avoid displaying valuables unnecessarily on public transportation.

How many days do you need in Chicago?

Three days provide enough time to see many of Chicago’s major attractions. Four or five days allow more time for museums, neighborhoods, architecture tours, and the lakefront. Architecture and art lovers could easily fill several additional days.

What should first-time visitors not miss in Chicago?

Start with the Chicago Architecture Center River Cruise. It provides an excellent introduction to the city’s architectural history. Also visit the Art Institute, Millennium Park, Chicago Cultural Center, and Chicago Riverwalk. Try the local food too. Add Wrigley Field, the Chicago Theatre, and a neighborhood walking tour if your schedule allows.

More City Guides

Love exploring cities on foot? You might also enjoy these city guides:

• San Francisco
• Boston
• St. Petersburg
• Alexandria (Old Town)
• Washington, DC

Final Thoughts

Chicago surprised me with how much I enjoyed simply walking around and looking at buildings. The architecture cruise gave me a new appreciation for the city’s skyline and history. The Art Institute was another highlight. Chicago is made for exploring.

But some of my favorite moments happened between the major attractions. I loved walking the Riverwalk and discovering architectural details downtown. I also enjoyed Chicago’s traditions, from eating deep-dish pizza to taking my Route 66 selfie. Give yourself time to wander. Chicago offers enough museums, architecture, food, and neighborhoods to fill several days. I already have reasons to return.