Chicago offers a dynamic mix of stunning architecture, world-class museums, and a thriving food scene. From strolling along the picturesque Riverwalk to admiring the breathtaking views from the Skydeck at Willis Tower, the city is packed with iconic sights and activities. Whether you’re indulging in a deep-dish pizza, exploring Millennium Park, or catching a show or sporting event, the Windy City has something for everyone. This travel guide highlights the best things to see and do in Chicago and includes tips on what to eat, where to stay, and how to get around. Keep scrolling to find our easy-to-customize Chicago travel itinerary to help you plan your adventure.
When to Go
The best times to visit Chicago are between April and May and September through October. During these times, the temperatures are warm but pleasant and crowds are manageable. Chicago’s peak tourist season is during the summer months, from mid-June through August. During these months, you will find higher lodging prices, larger crowds, and hotter temperatures. Chicago experiences frigid temperatures from November through March. However, if you can embrace the cold, you will find more reasonable prices for hotels and airfare.
What to See and Do
The Willis Tower
Formerly known as the Sears Tower, the Willis Tower is a prominent skyscraper on the Chicago skyline and is a symbol of the city’s architectural and engineering accomplishments. It held the title of the world’s tallest building for 25 years after its completion in 1973. Today, it remains one of the tallest buildings in the world reaching 1,450 feet and 110 stories tall.
One of the most popular attractions at Willis Tower is the Skydeck, an observation deck located on the 103rd floor. The Skydeck provides breathtaking views of Chicago and the surrounding area. Visitors can step onto “The Ledge,” a series of glass balconies that extend out from the building’s exterior, giving the illusion of walking on air. At 1,353 feet high, The Ledge is the highest observation deck in the United States. The best times to visit the Skydeck are either just after opening or after sunset. Purchase the timed entry tickets in advance to guarantee admission. You can find more information and purchase tickets here.
Magnificent Mile
The Magnificent Mile is a prestigious and upscale commercial and entertainment district situated along a section of Michigan Avenue. It spans approximately 13 blocks from the Chicago River on the south end to Oak Street on the north end. It is known for its high-end shopping, luxury hotels, and iconic architecture. You can find renowned brands such as Tiffany & Co., Gucci, Louis Vuitton, Apple, and many more along this stretch of Michigan Avenue. There are over 460 stores, 275 restaurants, 60 hotels, and attractions all packed in the Magnificent Mile. In addition to shopping and dining, the district is characterized by its stunning architecture and historic buildings like the Wrigley Building and the John Hancock Center. The district attracts millions of visitors each year, making it one of Chicago’s most popular tourist destinations. You can find more information here.
Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and most renowned art museums in the United States. The museum’s collection spans a wide range of art and cultural items, including paintings, sculptures, textiles, armor, pottery, and more. It is particularly famous for its collection of works by artists like Georges Seurat, Vincent van Gogh, Claude Monet, and Pierre-Auguste Renoir. Other notable artworks include Grant Wood’s American Gothic, Marc Chagall’s America Windows, Mary Cassatt’s The Child’s Bath, and Grant Wood’s Daughters of Revolution. You can find more information here.
Millennium Park
Millennium Park is a renowned public park located in the heart of downtown Chicago. It is one of the city’s most popular and iconic destinations, known for its impressive art installations, stunning architecture, and beautiful gardens. The park is located in the Loop area of Chicago and covers more than 24 acres of land. Perhaps the most iconic feature of the park is “The Bean,” a polished stainless steel sculpture created by Anish Kapoor. Its unique, reflective surface has made it a popular spot for art enthusiasts and tourists. In addition to The Bean, the park features an outdoor concert venue, a beautiful landscaped garden, the Crown Fountain, and temporary art installations and sculptures. You can find more information about Millennium Park here.
The Chicago Theatre
The Chicago Theatre is one of the most iconic and historic entertainment venues in the city. It is renowned for its distinctive architecture, rich history, and its role in hosting a wide range of live performances. Its exterior features a marquee with bright lights and a vertical sign displaying the theatre’s name in large letters, making it a prominent landmark on State Street. It is especially stunning to see at night. The interior is equally impressive, with ornate decorative details, a grand lobby, and a magnificent auditorium. The theatre is designated as a Chicago Landmark and is listed on the National Register of Historic Places. Visitors can book a 60-minute guided tour to learn even more about this magnificent building. You can find more information here.
Chicago Riverwalk
The Chicago Riverwalk is a scenic pedestrian pathway and urban waterfront park located along the Chicago River. It stretches for approximately 1.25 miles, extending from Lake Shore Drive in the east to Lake Street in the west. It is a popular destination for locals and tourists alike, offering a picturesque environment for leisure, dining, and recreation. There are several highlights along the way including a floating garden, the Vietnam Veterans Memorial Plaza, McCormick Bridgehouse and Chicago River Museum, kayak rentals, and public art. Another highlight of the Riverwalk is its vibrant dining scene. You’ll find a variety of restaurants, bars, and cafes offering diverse cuisines, from seafood to barbecue. Many of these establishments have outdoor seating with picturesque river views. Additionally, the Riverwalk often hosts live music performances and special events. You can find more information about the Riverwalk here.
Architecture River Cruise
Chicago is famous for its architecture, and one of the best ways to explore and appreciate the city’s skyline is by taking an architecture cruise along the Chicago River. These boat tours provide a unique perspective on the city’s history, iconic buildings, and architectural innovations. Popular architecture cruise operators include Tours and Boats Architecture Tours, Chicago’s First Lady Cruises, and Wendella Tours and Cruises. Taking an architecture cruise in Chicago is not only a fun and scenic way to explore the city but also an educational experience that deepens your appreciation for its architectural heritage. Whether you’re a tourist or a local, these cruises offer a fresh perspective on Chicago’s iconic buildings and skyline.
Navy Pier
Navy Pier is a popular tourist attraction located along the shoreline of Lake Michigan. It is one of the most visited destinations in the city, offering a wide range of entertainment, dining, and recreational activities. The Navy Pier was originally built in 1916 as a municipal pier and shipping facility. It was named in honor of the naval personnel who served in World War I. Over the years, its functions evolved, and it was later used as a Navy training center during World War II. The pier was eventually transformed into the recreational destination that it is today.
The Centennial Wheel, a giant Ferris wheel offering stunning views of the Chicago skyline and Lake Michigan, is one of Navy Pier’s most iconic features. Additional highlights include the Chicago Children’s Museum, Crystal Gardens, Shakespeare Theater, IMAX Theater, Navy Pier Park, summer firework shows, and a variety of dining and shopping options. You can find more information here.
John Hancock Center
The John Hancock Center is one of the most recognizable landmarks in the city and is known for its distinctive design, impressive height, and prominent location along the Magnificient Mile. The 94th floor of the John Hancock Center houses 360 CHICAGO, an observation deck that offers visitors stunning 360-degree panoramic views of the city and its surroundings. In addition to 360 CHICAGO, visitors can also experience TILT, an enclosed glass platform that tilts outward from the building, allowing visitors to lean out and experience a thrilling view of the city below. Additionally, the 95th floor houses the Signature Room, a renowned restaurant offering fine dining with panoramic views of Chicago. You can find more information about 360 CHICAGO here.
Lincoln Park Zoo
The Lincoln Park Zoo is one of the oldest zoos in North America. It is housed in Lincoln Park, a large public park located along Lake Michigan’s shoreline on the city’s North Side. The zoo covers approximately 35 acres and is home to over 1,100 animals representing nearly 200 different species. Some notable exhibits include big cats, primates, polar bears, penguins, reptiles, and a diverse array of birds and mammals. One of the unique features of the Lincoln Park Zoo is that it offers free admission to the public. Although not required, donations are encouraged to support the zoo’s mission. You can find more information here.
Wrigley Field
Wrigley Field is an iconic Major League Baseball stadium located in the Lakeview neighborhood of Chicago. It is the home ballpark of the Chicago Cubs, one of the oldest and most storied franchises in baseball history. The ballpark has several distinctive features including its iconic red brick exterior, the manually operated scoreboard, the historic marquee at the entrance, and the ivy-covered outfield walls. Wrigley Field is not only a historic sports venue but also an enduring symbol of Chicago and its love for baseball. If you are visiting Chicago during baseball season, attending a game is a must-do experience. To get a behind-the-scenes look at the legendary home of the Chicago Cubs, take a 90-minute guided tour. You can find more information here.
Field Museum of Natural History
The Field Museum of Natural History, commonly known as the Field Museum, is one of the most prominent natural history museums in the world. It is known for its vast and diverse collection of artifacts, specimens, and exhibits related to natural history, anthropology, and cultural history. Some of its most famous exhibits include “Sue,” the world’s largest and most complete Tyrannosaurus rex skeleton, and the 122-foot-long skeleton of a Titanosaurus. Other notable exhibits include Evolving Planet, The Ancient Americas, Inside Ancient Egypt, and Cyrus Tang Hall of China. You can find more information about the museum here.
Chinatown
Chinatown is a vibrant and culturally rich neighborhood located just south of Chicago’s downtown area. It is one of the city’s most iconic and historic neighborhoods, known for its Chinese heritage, delicious cuisine, unique architecture, and cultural attractions. Chinatown Chicago was established in the late 19th century by Chinese immigrants who came to the United States seeking better opportunities. Over time, the neighborhood has grown and evolved, becoming a thriving cultural enclave. The neighborhood is known for its iconic Chinatown Gate, which serves as a prominent entrance with its traditional Chinese design and vibrant colors. Visitors can enjoy a wide range of dining options and explore a variety of shops and markets. You can find more information about Chinatown here.
Walking Tours
Chicago offers a wide range of walking tours that allow you to explore the city’s rich history, architecture, culture, and neighborhoods on foot. These tours are led by knowledgeable guides who provide insights and stories about the city’s landmarks and attractions. There are several types of tours that you can take in Chicago including architecture tours, history tours, food tours, neighborhood tours, art tours, and ghost tours. Some popular walking tour companies in Chicago include Gangsters and Ghost Tours, Inside Chicago Walking Tours, and Free Tours by Foot-Chicago.
What to Eat
Chicago is a culinary paradise known for its diverse and delicious food scene. When visiting the city, be sure to try some of these iconic dishes and foods that are synonymous with Chicago’s dining culture.
Chicago-Style Deep-Dish Pizza
Chicago is famous for its deep-dish pizza, characterized by its thick, buttery crust, layers of cheese, chunky tomato sauce, and various toppings. It was developed in the early 1940s and has since become one of Chicago’s signature dishes. The origins of deep-dish pizza are attributed to Ike Sewell and Ric Riccardo, who opened Pizzeria Uno in Chicago in 1943. Popular pizzerias in Chicago for deep-dish pizza include Giordano’s, Lou Malnati’s, Uno Pizzeria, Pequod’s, and Labriola.
Chicago-Style Hot Dog
The Chicago-style hot dog is a beloved and iconic food item that has a rich history dating back to the early 20th century. A classic Chicago-style hot dog is an all-beef frankfurter topped with yellow mustard, chopped onions, bright green relish, tomato slices, pickle spears, sport peppers, and a dash of celery salt, all served on a poppy seed bun. You will find this iconic hot dog at places like Portillo’s, The Wiener’s Circle, Chicago’s Dog House, and Devil Dawgs.
Italian Beef Sandwich
The Italian beef sandwich is a savory and iconic culinary creation that originated in Chicago and has become a beloved staple of the city’s food culture. Its history is closely tied to the Italian-American community and the city’s immigrant roots. This sandwich consists of thinly sliced roast beef soaked in au jus, served on an Italian roll, and often topped with sweet or hot peppers and giardiniera (i.e. a spicy pickled vegetable mix). Try it at Al’s Beef, Johnnie’s Beef, Portillo’s, or Buona Beef.
Where to Stay
Chicago has several great neighborhoods to stay in, depending on your interests and travel style. Here are some of the best areas:
- The Loop (Downtown) – Best for first-time visitors and sightseeing. This area is close to iconic sights such as Millennium Park, the Art Institute of Chicago, and the Riverwalk.
- River North – A trendy area known for its nightlife, upscale dining, and art galleries. It’s near the Magnificient Mile for shopping and offers easy access to downtown attractions.
- Magnificient Mile – Great for luxury travelers and shoppers. This stretch along Michigan Avenue is packed with high-end hotels, designer stores, and excellent dining options.
- Gold Coast – An upscale, quieter area with historic homes, boutique shops, and easy access to Oak Street Beach. It’s perfect for those looking for a more relaxed but still central location.
- Streeterville – Ideal for families and tourists. This area is home to the Navy Pier, the Museum of Contemporary Art, and great lakefront views.
- West Loop – This area is ideal for foodies as it is filled with award-winning restaurants and trendy bars. It is less touristy but still close to downtown.
How to Get Around
Chicago has an impressive network of buses and trains, which are collectively called the L trains (for elevated as many of them are). The combination of buses and L trains should take you as close as a ¼ mile to any destination that you would like to go. Take caution when traveling at night, especially by train. You can pay by ride or purchase 1-day, 3-day, 7-day or 30-day unlimited-ride passes. If you are coming from the airport, the Blue Line service from O’Hare to downtown takes about 40 minutes. The Orange Line service from Midway to downtown takes about 25 minutes. You can find more information and service maps here.
Chicago Itinerary
Are you ready to plan your Chicago adventure? To get started, download our free and easy-to-customize Chicago Travel Itinerary. This is just a sample of what your trip could be like. Easily make changes to make it fit your schedule and interests.