Chicago is among the best cities in the United States. Chicago is a place you just must visit because of its amazing architecture, top-notch museums, amazing observation decks, and gorgeous waterways. I’ve provided tips on how to have the ideal four days in Chicago in this guide.
This is the perfect amount of time to truly experience this stunning city. You have plenty of time to see the main attractions and go further afield in four days. The itinerary below offers the top things to see and do in Chicago, regardless of whether you’re visiting for a long weekend or as part of a longer trip.
Table of Contents
The best time to Visit Chicago
The months of April through October are the ideal times to travel to Chicago. The best weather and the fewest crowds occur during this time of year.
It’s best to avoid the winter months November through March unless you enjoy the cold, as Chicago is known for its long, harsh winters. The majority of the attractions will remain open throughout the winter, but some events, like the sunset cruise and kayaking, might not.
But if you want to take advantage of the beaches, the summertime in Chicago can be a wonderful time to visit. But now is also the most popular time of year to go there. In July, I went to Chicago, but the heat was too much for me. In addition, the attractions were packed to capacity. The ideal times to visit are in April, May, September, and October, which are the cooler months. The crowds are acceptable, and the weather shouldn’t be too bad.
Is traveling to Chicago safe?
Chicago has become known as one of the riskiest American cities. It suggests that a lot of new visitors wonder if traveling to Chicago is safe. But if you look past the headlines, it will become apparent that most acts occur in particular parts of the city. These are easy-to-avoid areas as they are not used by tourists.
The parts of Chicago that are popular with tourists and included in the 4-day Chicago itinerary below are extremely safe. Police patrol the downtown area, which doesn’t see many serious crimes. I’ve gone to on multiple occasions without any problems. Chicago actually makes me feel safer to walk around than London does.
How to get around Chicago
The Chicago Transit Authority, or CTA, runs trains and buses all over the city. An easy way to get around the city and to some suburbs is to take the ‘L’ train system, which stands for elevated trains. Routes that the ‘L’ might not service are covered by buses.
- Taxis: In taxis are a common form of transportation that provide a comfortable means of getting around the city. Taxis are readily available for hailing on the street, in particular in crowded areas, or at designated taxi stands. Traditional taxis give their customers versatility by taking credit cards in addition to cash. Taxis are still an excellent choice for people who want the familiarity of metered fares and the ability to pay with cash, even though rideshare services have grown in popularity.
- Metra Rail: Metra commuter trains are a good option if you have to travel to the suburbs. They link different suburban areas with Chicago’s downtown.
- Water Taxis: During the warmer months, water taxis along the Chicago River and Lake Michigan run, offering a distinctive and picturesque mode of transportation.
1 Day in Chicago
Chicago Architecture River Cruise
A popular and learning approach to taking in the amazing skyline of the city and finding its architectural past is the Architecture River Cruise. This boat tour, which usually lasts 90 minutes, offers a unique viewpoint of the famous structures that define the city as it moves along the Chicago River.
Many of the city’s attractions, such as the News Tribune Tower, the Willis Tower, and the Old Post Office Building, are apparent as the cruise sails along the Chicago River. As you come to the end, walk out into the marina to see Lake Michigan and the Skyline.
Willis Tower
When referred to as the Sears Tower, the Willis Tower is a famous illustration of urban environment and architectural skill. With a height of 1,450 feet (442 meters), this skyscraper was completed in 1973, and for 25 years after that, it was the tallest building in the world.
The Willis Tower is famous for its unique bundled-tube structural design, which groups nine interrelated tubes together to offer support and stability. The tower, with its sleek black exterior and unique stepped design, is a prominent feature of the Chicago skyline. The Skydeck, situated on the 103rd floor of the Willis Tower, offers visitors stunning views of the city and Lake Michigan.
The Chicago Riverwalk
A popular urban go for both residents and tourists, the Chicago Riverwalk is a colorful and beautiful promenade that runs with the Chicago River. The Riverwalk, which stretches 1.25 miles through the center of downtown Chicago, provides a lovely environment with a variety of parks, gardens, eateries, and leisure areas.
An appealing urban experience is produced by the harmonious flow of the Chicago River and the architectural beauty of the surrounding buildings. Whether you’re taking a leisurely stroll, grabbing some food, or just taking in the beautiful surroundings, the Riverwalk is a vibrant and welcoming location that perfectly encapsulates the riverfront culture of the city.
Chicago Food tour
The food tour of Chicago, known for its varied and popular food, offers a delicious introduction to the city’s rich culinary scene. A food journey expressing its melting pot of cultures can be found in the Windy City, from the famous deep-dish pizza to the traditional Chicago-style hot dog.
the best food in the United States. Joining a food tour is the best way to experience this, especially when you only have four days in Chicago.
2 days in Chicago
Millennium Park
Situated in the center of downtown Millennium Park is a vibrant and popular urban area that attracts both residents and visitors. The remarkable public sculpture known as Cloud Gate, dubbed “The Bean” for its unique kidney bean shape, is a major attraction. Anish Kapoor, a British artist, created Cloud Gate, a work of art made of reflective stainless steel that captures the captivating reflections of the park’s lush surroundings and the city skyline.
With its beautifully designed gardens, interactive art shows, and outdoor areas that are used for year-round concerts, festivals, and cultural events, Millennium Park enhances this creative focal point.
Grant Park
Located in the center of downtown, Grant Park is a vast urban retreat that provides a variety of leisure areas, cultural attractions, and incredible views of the city’s famous skyline. The 319-acre park is a lush haven that offers a wide range of events and activities all year.
Popular places such as the Art Institute of the Museum Campus, which houses the Field Museum, Shedd Aquarium, and Adler Planetarium, are located in Grant Park, which is also a center of culture.
Museum Campus
A haven of outstanding facilities mixed with scenic beauty, the Museum Campus in is a haven for culture and education. This 57-acre park serves as a center for scientific research, marine life, and astronomy. It is home to three significant museums: the Field Museum, the Shedd Aquarium, and the Adler Planetarium. The Museum Campus offers expansive views of Lake Michigan in addition to a breathtaking skyline backdrop, fostering a tranquil environment ideal for leisurely strolls and outdoor activities.
3 Days in Chicago
Cycling the Lakefront Trail
On the third day of this four-day itinerary in Chicago, rent a bike and ride along the popular Lakefront Trail. This beautiful trail is ideal for walking or cycling.
Cycling Chicago’s Lakefront Trail is a beautiful and reviving experience that lets riders take in the amazing shoreline of the city and expansive views of Lake Michigan. The Lakefront Trail is a legally designated path that stretches around eighteen miles around the lake, providing a path specifically for people walking, walkers, and riders.
For cyclists of all skill levels, the Lakefront Trail offers a combination of beautiful paths and paved surfaces, making for a comfortable and enjoyable ride. Accessing bicycles and exploring this scenic route is made simple for visitors by the numerous bike rental stations located along the trail.
Explore Lincoln Park
Lincoln Park offers an exciting blend of recreation, culture, and nature within the dynamic landscape of the city. With more than 1,200 acres, Lincoln Park is one of the biggest and most varied public areas in the city, providing a wide range of activities for both residents and tourists.
A network of paths and trails makes up Lincoln Park, providing a great place for leisurely strolls, biking, and jogging. The park’s sandy beaches encourage leisure and waterfront activities, and its lakefront stretch offers stunning views of Lake Michigan. The Lincoln Park Zoo’s Nature Boardwalk showcases local flora and fauna while enveloping visitors in an urban oasis.
There are many museums in the park, such as the biology and environmental education-focused Peggy Notebaert Nature Museum. Moreover, the historic Alfred Caldwell Lily Pool, with its prairie-style landscaping and water features, provides a tranquil haven.
North Avenue Beach
North Avenue Beach, which is located along the picturesque Lake Michigan shoreline, is a bustling, popular location that epitomizes the lakefront culture of the city. The beach is a year-round favorite for recreation because of its wide sandy beaches and amazing skyline views. In the summer, North Avenue Beach is a popular destination for swimmers and sun worshippers who want to play beach volleyball, kayak, and paddleboard, as well as just soak up some sun.
The beach is more than just a place to soak up the sun; it is a vibrant, social area that highlights the city’s passion for outdoor recreation and community involvement.
Navy Pier
With its majestic reach into Lake Michigan, Navy Pier is a colorful and popular location that perfectly captures the energetic vibe of Chicago’s lakefront. Navy Pier is a cultural hub and a hub for recreation, with a wide range of attractions to suit all age groups. The pier is home to a Ferris wheel that is referred to as the Centennial Wheel and offers stunning views of Lake Michigan and the city skyline.
Family-friendly attractions abound at Navy Pier, such as the Play Theater and the place Children’s Museum. With tropical foliage and changing floral displays, the pier’s charming Crystal Gardens, a botanical oasis housed in a glass atrium, provide a peaceful haven.
Sunset cruise
Take a Lake Michigan sunset cruise to cap off your day. the skyline illuminates the sky as the sun sets. A sunset cruise around Lake Michigan on the renowned Tall Ship Windy is what I would suggest.
4 Days in Chicago
Morning culture
There are several options available to you on the fourth and last day of this four-day Chicago itinerary to visit the attractions of your choice. I suggest visiting the Art Institute of and the Chicago Cultural Center if you’re interested in culture and art. Since they are close to each other, it would be easy to see them both.
One popular framework is the Cultural Center. Amazing architecture and a variety of historical shows and displays can be found inside. You can enter many of these for free. One of the oldest art museums in the country, the Art Institute of is located just down the street.
The Magnificent Mile
In the heart of downtown Chicago, Michigan Avenue is a popular destination for tourists and locals alike for its exceptional shopping and cultural offerings. This famous avenue is well-known for its high-end retail establishments, which include a variety of designer flagship stores, department stores, and luxury boutiques. The Magnificent Mile is a shopping haven, with everything from jewelry and high-end clothing to electronics and fine dining.
Sunset at The John Hancock Centre
There is nothing quite like seeing the sunset at John Hancock Center. The famous skyscraper, which is now formally known as 875 North Michigan Avenue, provides an unrivaled vantage point to watch the sun set and cast a warm, ethereal glow over the city as the day draws to an end.
Other Chicago itinerary ideas
1. Cultural Exploration
Starting a cultural exploration in Chicago allows you to become fully immersed in the rich past and diverse artistic landscape of the city. Visit the Art Institute first thing in the morning to see works of art from all over the world. Admire renowned pieces created by painters such as Monet and Van Gogh, and delve into the varied exhibits of the museum. Visit the neighboring Chicago Cultural Center in the Loop for a change of scenery. It’s a free architectural treasure.
2. Neighborhood Food Tour
In the trendy Wicked Park or Logan Square areas, where local eateries and cafes serve up a wide array of delicious options, start your day with a hearty breakfast. Savor artisanal coffee and inventive brunch dishes while taking in the lively vibe of the area.
3. Chinatown
Admire renowned pieces created by painters such as Monet and Van Gogh, and delve into the varied exhibits of the museum. Visit the neighboring Cultural Center in the Loop for a change of scenery. It’s a free architectural treasure. Admire the elaborate Tiffany glass dome and get a peek at the cultural events and changing shows.
Relaxing on the beach
Chicago’s beaches provide the ideal fusion of urban leisure and scenic beauty for a tranquil and restorative beach experience. You can find a peaceful haven along Lake Michigan’s shores, whether it’s the wide waterfront at Oak Street Beach or the sandy shores of North Avenue Beach. The gentle sound of the waves breaking on the soft sand creates a calming soundtrack as you relax and take a break from the bustle of the city.
Where to stay in Chicago
Given that is a large city, choosing a place to stay can be a little difficult. It is a good idea to stay in the downtown area if this is your first time visiting the place. This implies that every major attraction listed in this 4-day Chicago itinerary will be within easy reach of you. It’s important to remember that this is also one of the safest parts of the city.
The Loop and Magnificent Mile
Chicago’s vibrant center is made up of the Loop and Magnificent Mile neighborhoods, which provide a unique fusion of famous buildings, business, and culture. Aptly named for the loop formed by the “L” train tracks that encircle it, The Loop is located in the central business district. The skyline is broken up here by towering skyscrapers like the historic Board of Trade Building and the Willis Tower.
River North
Located immediately north of the River and next to the Magnificent Mile, River North is a vibrant and fashionable neighborhood right in the middle of the city. With its blend of modern skyscrapers, repurposed warehouses, and art galleries, River North has proven itself as a vibrant hub for culture and entertainment.
Is the Chicago City Pass worth it?
The attractions you intend to visit and your personal travel preferences will determine whether the CityPASS is worthwhile. A ticket booklet that bundles discounts for entry to some popular attractions is called CityPASS.
- Shedd Aquarium
- Skydeck Chicago (Willis Tower)
- Field Museum
- Museum of Science and Industry OR 360 CHICAGO Observation Deck
- Adler Planetarium OR Art Institute of Chicago
If you want to visit all of the attractions and stick to the above 4-day itinerary for Chicago, then purchasing a Chicago CityPASS is highly suggested. I’m sure you’ll save a tonne of cash. You can still save money with the pass even if visiting the Shedd Aquarium isn’t at the top of your list of things to do.
For instance, depending on the cruise and time of year, admission to Skydeck Chicago, the Adler Planetarium, Chicago 360, and a river cruise costs approximately $141 USD. You essentially get the Shedd Aquarium for free because that isn’t included.
