City Guide: How To Spend 4 Days In Chicago

Also known as “The Windy City,” Chicago is the third-most populous city in the United States. Four days is the perfect amount of time to see all of the best sights of the city.

Editorial Note: Earth Curious contains affiliate links. If you make a purchase through these links, we will earn a commission at no extra cost to you. Thanks!

Located in the state of Illinois, Chicago is the perfect US city destination for solo travelers, couples, and families due to its abundance and diversity of attractions. Also known as the birthplace of modern architecture, Chicago will leave you amazed by its amazing skyline, food, and culture.

If flying into Chicago, you will arrive at O’Hare International Airport, which is located inside the city. To get downtown, you can order private transport, such as a taxi or Uber, but it will cost you anywhere between $35-50. The most economical option is to hop on the blue line L train which can get you downtown in 45 minutes and costs $5.

Day 1: Arrive in Chicago, Millennium Park, Skydeck Chicago, Chicago Theater

Drop your bags off and head to downtown Chicago, where you can see the famous giant “bean,” aerial views of the city in Skydeck Chicago, and a show at Chicago Theater.

The Chicago Theater mimics classical French architecture. Photo: Clay Banks | Unsplash

Millennium Park

Without a doubt, your first stop on your Chicago adventure should be Millenium Park, which is Chicago’s most popular tourist attraction. Here, you can find the most famous landmark of the city, the Cloud Gate, which is a large metallic archway built in 2006. Because of this shape, the structure is most commonly known as “The Bean.” It’s a great place to stop for a typical Chicago tourist photo.

Other popular attractions at the park include Lurie Garden, Crown Fountain, Maggie Daley Park, and Jay Pritzer Pavilion. If you are visiting during the summer, the Pritzer Pavilion often offers free movie screenings, music performances, and other events.

Skydeck Chicago

After exploring Chicago from the ground, it is time to summit to the top of the 8th highest building in the world, Skydeck Chicago. Located on the 103rd floor, the clear glass platform sits over 1,300 feet above the ground. Tickets cost between $30-40 USD to get to the top, depending on the package you choose. If you want to skip the lines, consider buying an expedited entry ticket, which starts at $55. If you are traveling with children, entry for kids under 3 years old is free.

Chicago Theater

To end your first night in Chicago, head over to Chicago Theater, which frequently hosts live music shows and performances. Built in the 20th century, the theater and its interior were modeled after the Versailles Royal Chapel. It seats over 3,500 people, and the iconic “Chicago” sign in front is a photo opportunity you cannot miss.

Don’t have the opportunity to catch a show? The theater also offers Marquee tours, which go over the museum’s beginnings and history as well as its architectural meanings. You are also able to see the dressing rooms backstage, whose walls contain signatures from famous artists such as Dolly Parton and Frank Sinatra.

Where to eat

Hot Woks Cool Sushi

Millennium Hall

Pizano’s Pizza and Pasta

Where to stay in Chicago?

Day 2: Museum Day

Explore the many educational and cultural museums that Chicago has to offer, such as the Art Institute of Chicago and the Chicago Cultural Center. If you are more into science, go to the Museum of Science and Industry or the Shedd Aquarium. Here are some of the best museums in the city to choose from.

One of the famous lion statues in front of the Art Institute of Chicago. Photo: Wikimedia Commons

Art Institute of Chicago

Known as Chicago’s “#1 Museum,” the Art Institute is one of the oldest and largest art museums in the world. Some notable pieces housed in the museum include American Gothic, The Bedroom, and A Sunday Afternoon on the Island. General admission for adults not from the city of Chicago is $25.

Museum of Science and Industry

Known as the largest science center in the Western Hemisphere, this museum is great for the science geek and those interested in all things innovation. It houses notable exhibits such as a baby chick hatchery, a mirror maze, and a U-505 submarine. Admission for adults starts at $21.95.

Chicago Cultural Center

Only a 3-minute walk from the Cloud Gate, the Chicago Cultural Center is a free community center with various exhibits devoted to visual arts and contemporary culture. Even if you are not interested in the exhibits, the intricate interior of the building is enough of an excuse to visit.

Shedd Aquarium

For the lover of all things aquatic, don’t miss the Shedd Aquarium. The aquarium has over 1,500 species of fish and aquatic life. Some of their permanent exhibits include the Caribbean reef community, Amazonian species, and belugas. At a leisurely pace, you can explore the entirety of the aquarium in about 2-2.5 hours. Tickets start at $44.70 for non-Chicago resident adults, and $33.70 for children aged 3-11.

Lincoln Park Zoo

If you prefer that the exhibits are living, make sure to check out the Lincoln Park Zoo in Chicago, which is the 4th oldest zoo in North America. The zoo has over 1,000 animals, such as penguins, elephants, lions, and camels. It offers self-guided experiences, with special themed routes to explore different types of animals. For the plant enthusiasts, the zoo also has over 1,200 plant species on site.

The zoo is a great attraction for the family and solo traveler alike, and the best part is that it has free admission.

Where to eat

Eggy’s Diner

The Palm Restaurant

Italian Village Restaurant

Day 3: Chicago Riverwalk, Navy Pier, and North Avenue Beach

Have a day near the water by walking the Chicago Riverwalk, riding the Ferris wheel at Navy Pier, and lounging on North Avenue Beach.

The Navy Pier in Chicago is even more spectacular at night. Photo: Wikimedia Commons

Walk on Chicago Riverwalk

The Chicago River runs through the city of Chicago, giving you amazing river views. Take advantage of this by visiting the Chicago Riverwalk, which spans 1.25 miles. Visit some of the best bars, restaurants, and shops in the city at the Riverwalk. One of the most popular spots is City Winery, which offers house-made wines and beers with a riverfront patio. You can also get in the water – rent a kayak or join a guided kayak tour along the Chicago River. Don’t want to get wet? Take advantage of Chicago’s multitude of boat tours on the Chicago River, which can be one of the best ways to see the city. One of the most popular tour companies is Shoreline Sightseeing, which passes all major landmarks in Chicago.

Head over to Navy Pier

For a sweet escape of some childlike fun, head over to Navy Pier, a waterfront dock full of amusement park rides. It is most recognized for its 200-foot tall Ferris Wheel, known as Centennial Wheel, which gives you views of Chicago from the top. Dine at one of the many restaurants on the pier for authentic Chicago fare, such as hotdogs, deep-dish pizza, and the famous rainbow ice cream cone.

If you are visiting Chicago in the summer, make sure to check out the fireworks show that is held at the pier every summer! They are held every Wednesday and Saturday night from Memorial Day weekend (last Monday of May) through Labor Day (first Monday of September).

North Avenue Beach

If you want to lounge on a beach with the backdrop of the Chicago skyline, look no further than North Avenue Beach. Located in the city’s Lincoln Park, the beach stretches more than 22,000 square feet and offers plenty of opportunities to go swimming in the water. Although the beach looks like a tropical getaway, it is actually not an ocean at all, but Lake Michigan.

There are plenty of things to do at North Avenue Beach apart from lounging and swimming, the park offers a multitude of activities such as kayak rentals, a nearby hiking trail, and volleyball courts. After spending time at the beach, head over to the nearby strip of restaurants, bars, and souvenir shops. Note that the beach is only open during the summer and that no dogs are allowed. If you are traveling with your pup, head over to the nearby Montrose Beach, which is dog-friendly.

Where to eat

Chicago Brewhouse

River Roast

Harry Caray’s Tavern

Day 4: Chinatown and Chicago Botanic Garden

Munch on some authentic Asian cuisine in Chinatown and smell the flowers in the city’s beautiful botanic garden.

Chinatown is the best spot in the city to find authentic Chinese food. Photo: Wikimedia Commons

Explore and eat in Chinatown

If you love Asian food, then you are in luck, as Chicago has a bustling Chinatown where you will feel transported into another country. Upon arriving, you will find the Nine Dragon Wall, an emblematic arch that marks the beginning of the Chinatown neighborhood. Make sure that you visit while hungry, as Chinatown has some of the most authentic Chinese restaurants in the city. Make sure to try dim sum, a Chinese-style lunch that consists of varied small plates.

Go to Chicago Botanic Garden

For a quiet escape from the city, head over to Chicago Botanic Garden, which houses 27 different gardens on 385 acres of land. It is the most beautiful in the summer, due to the pleasant weather conditions, but the Garden is a wonderful attraction all year round. In the winter, you can visit to see a beautiful light show and Christmas display.

Chicago Botanic Garden also offers a diverse array of activities apart from visiting the gardens – check their website to explore the multitude of classes and workshops they offer which include cooking, yoga, birding, and photography.

Where to eat

Slurp Slurp Noodle House

Phoenix Restaurant

MingHin Cuisine

Useful tips for traveling in Chicago

The best time to visit Chicago

Summer is overall the best time to visit Chicago, as that is when you will find the most attractions and life in the city, as well as the best weather. Temperatures range between 65-85°F (18-29°C). However, summer is when the city receives the most tourists, so there will be higher crowds. To avoid crowds and the brutal Chicago winter, consider visiting during the city’s shoulder seasons of spring (April-May) and fall (October-November).

What is the currency of Chicago?

Chicago uses the US Dollar (USD).

Can you drink tap water in Chicago?

The tap water in Chicago is safe t drink, however, there have been some reports of lead in some water systems in the city. However, if you are only visiting for a few days, it does not pose a risk to you. If you still feel uneasy about this, you can easily buy bottled or filtered water in the city.

The language of Chicago

The language spoken in Chicago is English. Chicago also houses a large immigrant population, adding to the cultural diversity of the city. This means that you will encounter a large Spanish-speaking population, which is the second most commonly spoken language in the city. The third is Polish, thanks to a large population of Eastern Europeans as well.

Is Chicago safe?

A quick google search of Chicago will show that it is a dangerous city. The opposite is true – Chicago is a safe city to visit for tourists. Many of its high crime and murder rates have dropped significantly in the past few decades. Although there still exist some pockets of dangerous neighborhoods, if you stay within the tourist downtown, there is very little risk.

Final thoughts

The skyline of Chicago. Photo: jake grella | Unsplash

If you are looking to visit one of the most popular cities in the United States, Chicago is a mecca for art, culture, and unforgettable experiences. When visiting, make sure that you don’t miss out on trying a slice of the city’s “deep dish” Chicago-style pizza, which is recognized globally. Another must-see is the famous Cloudgate sculpture, charmingly known as “The Bean.”


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Related Posts