Are you planning a 3-day trip to Chicago? This 3-day Chicago itinerary is fantastic whether you’re a first-time visitor or coming back to explore more in this iconic city.
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Chicago, also known as the “Windy City“, is one of the most well-known cities in the United States. It is located in Illinois and is close to the East Coast. Chicago is located on Lake Michigan and is known for many iconic landmarks, delicious food like the famous deep dish pizzas and Chicago-style hot dogs, stunning architecture, mesmerizing jazz music, and so much more.
In this post, you will see the ultimate 3-day Chicago travel guide, including where to stay and what to eat. Also, explore Chicago must-see landmarks, the best things to do in Chicago, the best sightseeing itineraries and tours, and more.
This 3-day Chicago itinerary will take you to the best views of Chicago, the iconic Millennium Park and the Chicago Bean, the beautiful Chicago Riverwalk, the Willis Tower Skydeck, shopping at the Magnificent Mile, the 360 Chicago John Hancock Observatory, and so much more.
This post is all about the ultimate 3-day Chicago itinerary.
Start your 3-day Chicago itinerary by heading to Millennium Park. Millennium Park in Chicago has so much to offer, including beautiful art, amazing architecture, and more. In the centre of this one-of-a-kind park is “Cloud Gate,” which is also known as “The Bean“. This magnificent bean structure is mirror-like, and it copies the city’s skyscape in it. Such a unique piece of art that people from all over the world come to see.
Millennium Park is the biggest cultural hub in Chicago as it always hosts live music, has many art exhibits, and many community events. The Bean is a great place to get some memorable photos. The park is full of scenic beauty like stunning landscaped gardens. This is a great spot to relax and take in the stunning views of a bustling part of Chicago.
Next, enjoy a walk along the Chicago Riverwalk. The Chicago Riverwalk is a lively urban hub that circles along the Chicago River in the centre of downtown. There is lots to do here, including relaxing, dining, and sightseeing. One of the best things to do at the Riverwalk is a leisurely walk along the river to see the iconic skyline and some amazing architecture. There are also self-guided architectural tours that you can do that take you through iconic landmarks like the Tribune Tower and the Wrigley Building. The Chicago Riverwalk also has public art installations and live events multiple times a week. It’s a great area to enjoy some entertainment. Also grab something to eat here or a drink at one of the many riverside restaurants, ars, and cafes.
After strolling along the Chicago Riverwalk, head to the Art Institute of Chicago. The Art Institute of Chicago is a world-renowned museum and cultural jewel in Chicago. It is also one of the oldest and biggest museums in the United States. Enjoy World-Class Collections like works of art from Van Gogh, Monet, and Grant Wood. Explore the many iconic exhibits, like “American Gothic“. There are many educational opportunities here, many hands-on workshops, tons of ancient artifacts, and lots of modern installations.
Once you’ve seen all the amazing exhibits of the Art Institute of Chicago, make your way to Willis Tower Skydeck. This is an absolute must-do attraction when visiting Chicago. This unique experience is on the 103rd floor of one of the most iconic buildings in the city. This is the best way to get panoramic views of Chicago’s amazing skyline, the beautiful suburbs of Chicago, and the glistening Lake Michigan. Step out onto “The Ledge“, which is the glass box that extends just outside the tower for one-of-a-kind photo opportunities. The Willis Tower was once known as the famous Sears Tower and is a testament to Chicago’s architectural history and innovation.
To end the evening, discover the magic of Navy Pier. Navy Pier is one of Chicago’s most vibrant neighborhoods and an absolute must-visit. This beautiful pier stretches along Lake Michigan and has so much entertainment, culture, and beauty that it is great for all visitors. This is a great place to watch the sunset on Lake Michigan while taking a leisurely stroll. There are also many family-friendly things to do here, like children’s exhibits and attractions. Also, there are lots of shopping boutiques, boat tours, outdoor concerts and performances, festivals, and many great dining options to explore.
Start day 2 of your 3-day Chicago itinerary by heading to the Field Museum. This iconic museum has an impressive collection of world-class history and unique wonders from around the planet. The Field Museum is a must-visit when here because of its one-of-a-kind exhibits. One of these famous exhibits is “Sue“, the largest and most complete T. Rex skeleton that was ever discovered on earth. There are lots of cultural and historical treasures to explore, like Egyptian relics, natural wonders, Native American artifacts, the evolution of life, and so much more. This museum is great for all visitors, including kids and adults, and has many interactive exhibits for everyone of all ages to enjoy.
For the afternoon, do some shopping at the famous Magnificent Mile. This is one of Chicago’s most iconic areas along Michigan Avenue, which has a blend of luxury shops, fine dining, architectural wonders, and more. Michigan Avenue is known for world-class shopping with its flagship stores, upscale designer boutiques, large department stores, and more. Be sure to stop by Water Tower Place as well, which is a huge shopping mall. There is something for every style and price. This is also a great area to see some architectural wonders along the Chicago skyline. Also a great area to take a leisurely walk and check out the window displays and art exhibits. Be sure to grab some lunch at one of the stunning high-end restaurants for an iconic meal.
Before leaving the Magnificent Mile, you need to explore the 360 Chicago John Hancock Observatory. Located on the 94th floor, the observatory offers panoramic views of the beautiful skyline and Lake Michigan. From there, you can see Millenium Park and the Magnificent Mile. There is also a TILT experience, which is a glass platform that tilts where you can see the city. Such a great and unique thrilling experience. There are lots of great photo opportunities here as well.
For the early evening, explore the vibrant River North Neighborhood. This area is Chicago’s most dynamic and vibrant street for dining, nightlife, and entertainment. It is filled with delightful restaurants, art galleries, stylish boutiques, cute cafes, fun nightlife, and more. It is a great place to grab some dinner and relax along the river at one of the cocktail lounges or bars.
For the rest of the evening, you could catch a show at the Chicago Theatre. The Chicago Theatre puts on lots of entertaining shows like a Broadway show, a comedy act, concerts, world-class performers of many interests, jazz shows, and many more. This is also one of the most photographed landmarks in Chicago with the bright CHICAGO lights that light up the night.
For the last day of your 3-day Chicago itinerary, start off by exploring Lincoln Park and Lincoln Park Zoo. Enjoy a quiet walk in Lincoln Park, this is a fresh escape from the busy city streets. There is so much natural beauty in Lincoln Park that you will enjoy. The Lincoln Park Zoo is a must when visiting Chicago. This zoo is free to enter and is home to over 1,000 animals, ranging from majestic lions to playful monkeys and more. It is a great place to see many diverse animals while taking in the beauty of the nature all around.
After enjoying a relaxing morning at Lincoln Park and the Lincoln Park Zoo, make your way to the areas that are covered in beautiful street art and murals. The Chicago streets are filled with creativity, color, and character. Whether you’re looking to get some great pictures or are an artist yourself, this is a really cool experience you need to do. Some of the best spots to see street art and murals are Wabash Arts Corridor on the South Loop, This is “Chicago’s living urban canvas” that is full of murals from locals and international artists. The Pilsen Neighborhood is a Mexican-inspired mural. The Bloomimgdale Trail is a scenic walking route full of beautiful murals along the entire path. Logan Square and Bucktown are filled with indie art, graffiti, creative pieces of art, and the “Greetings from Chicago” mural (pictured above). There are many more art-filled neighborhood areas in Chicago; these are just the biggest and most popular ones.
After wandering the vibrant neighborhoods filled with street art and murals, head to Oak Street Beach for some relaxation. Enjoy the breathtaking views of the Chicago skyline and the lake while enjoying a walk or a bike ride along the Lakefront Trail. If the weather calls for it, you can relax on the beach or go for a swim in the lake. There are also many places to grab a coffee or a drink along the beach.
To end your 3-day Chicago itinerary, make your way to Montrose Harbor for sunset. This is the best place to catch a sunset in Chicago, right along the water with all the boats in the beautiful harbor. It is located close to Lincoln Park and has the best unobstructed views of Lake Michigan. Take some photos of the stunning Chicago Skyline illuminated by the evening glow. Take in the peaceful atmosphere and reflect on your amazing trip to Chicago. Then head to your last dinner in Chicago. I would suggest enjoying some delicious traditional Chicago deep-dish pizza. Chicago is famous for its deep-dish pizza with its signature thick crust and fresh ingredients.
Budget-Friendly – There are many budget-friendly hotels to stay in in Chicago. Some of the best ones are Kinzie Hotel and Hilton Chicago Magnificent Mile Suites. These are both great hotels that go for a great price, and both have breakfast options to include with your stay.
Mid-Range Hotels – Some mid-range hotels in Chicago are the Embassy Suites Chicago – Downtown River North and Loews Chicago Hotel. Great hotels in great areas are packed with many amenities.
Luxury Hotels – Some of the best luxury hotels in Chicago are Virgin Hotels Chicago, Best Western Chicago Downtown-River North, and The Hoxton, Chicago. All of these hotels have high-end furnishings, are located in prime locations, and have many amenities like restaurants, spas, rooftop pools, and so much more.
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