The Windy City is the perfect destination for a long weekend BUT there is so much to see and do, that it’s hard to fit it all in. Whether you are there for business or pleasure, take some time to get to know the city. With incredible architecture, world-class museums, a beautiful river and a Great Lake, you will never be bored with so many must-visit attractions in Chicago. Like many world-class cities, you will never be able to see everything in one visit, but you need a place to start. We are sharing our top 5 must-visit attractions in Chicago to help you plan your itinerary:
The Magnificent Mile
The Magnificent Mile literally is one square mile and is also known as Michigan Avenue. It is a 13-block stretch that will take you from the Chicago River to Oak Street with it’s views of Lake Michigan. This is a shopper’s paradise with more than 400 stores, hidden gems, museums and some of the city’s most stunning architecture. You will also find some of Chicago’s finest restaurants and theatres on or near The Magnificent Mile. You may even dare to “TILT” at 360 Chicago’s Observation Deck.
DIVINE Tips: Walk The Magnificent Mile on the first day of your first visit to the Windy City. It will help you orient yourself since it’s close to or houses some of the must-visit attractions in Chicago. It truly is breath-taking to see skyscrapers like The Wrigley Building and 360 Chicago. Keep your eyes open – from the planters along the sides of the streets to a surprise pop-up, you never know what you will see along The Magnificent Mile.
A Chicago River Cruise
This is a must! It is the best way to see and learn about Chicago’s stunning architecture and the people behind it. Viewing the massive skyscrapers from the water gives you a unique perspective that you can’t appreciate by foot or by car. You will see famous buildings like the 62-story Marina City Towers, the Willis Tower which is one of our must-visit attractions in Chicago and 150 N. Riverside which seems to defy the laws of physics.
We took Chicago’s First Lady Cruise. You can board their boats on Chicago’s Riverwalk. Their vessels have a spacious, open-air upper deck, a salon and full-bar. It was rated #1 boat tour by Trip Advisor for a reason. The volunteer CAC docents (guides) know the city very well and will give you the history behind the views that you are seeing. Tours run from April 1st-November 20th.
Go for a stroll along Chicago’s Riverwalk afterwards. It will help you tick another bucket list item off of your itinerary. Trust us, this is a highlight that you won’t want to miss.
DIVINE Tips: Dress warmly – especially if you are sitting on the upper deck. Even if the temperature is moderate, it can get windy and cool on the river. Bring sunglasses as the sun can be reflective and make it difficult to appreciate the architecture.
Millennium Park
Located in Chicago’s downtown Loop, Millennium Park was Chicago’s top tourist destination in 2017 and is really considered the “people’s park” by natives of the Windy City. It houses the iconic Cloud Gate statue, otherwise known as “The Bean”, Jay Pritzker Pavilion & The Great Lawn which is home to some of the best festivals in the city, the interactive Crown Fountain, art installations and so much more.
You absolutely cannot visit Chicago without seeing “The Bean” first hand. The Anish Kapoor creation is a reflective steel sculpture reflects both the skyline of Chicago and the visitors to the park. You will marvel at how it has no visible seams.
Speaking of marvels, Jay Pritzker Pavilion & The Great Lawn houses Frank Gehry’s one-of-a-kind bandshell. It is truly an amazing sight with steel structures that are works of art. Music festivals like the Chicago Jazz Festival and Chicago Blues Festival feature performances at the pavilion which has a state-of-the-art sound system designed to mimic the acoustics of an indoor theatre.
Crown Fountain is Conceptual artist Jaume Plensa’s video sculpture and features a granite reflecting pool between two 50-foot glass brick towers. It appears that water is coming out of the mouths of the Chicago residents who appear in the video. It’s an artsy splashing pool where you can cool down on a hot summer’s day.
DIVINE Tips: If you have kids, Millennium Park is right next to Maggie Daley Park which has lots of fun activities for children. Take them there first so that they can play and then cool off at Crown Fountain.
The Art Institute of Chicago
Located in the Loop across from Millennium Park, The Art Institute of Chicago is one of the oldest and largest art museums in the world. Unlike some museums, though, it is so well curated that it never feels overwhelming like The Met in New York can. With everything from modern art to the best of The Impressionists, even discerning art lovers will be satisfied. The America Windows by Marc Chagall are a must-see. Spend some time in the Thorne Miniature Rooms too.
DIVINE Tips: Take your time and really enjoy the museum. Go to Millennium Park in the morning and the museum in the afternoon. The close proximity will help you see two highlights in one day. Buy your tickets in advance – most Chicago attractions recommend it.
Willis Tower
Willis Tower is also located in the Loop. It is a must-visit attraction in Chicago for a number of reasons. Willis Tower is the tallest building in Chicago, the second tallest building in North America, and best of all, it is home to the Skydeck AND The Ledge! Skydeck located on the 103rd floor of the building, gives you 360-degree views of the city. If it’s a clear day, you may even see up to four other States. The Ledge consists of glass boxes that extend 4.3 feet out from the Skydeck. You can look straight down to the street or up to the clouds. Either way, it’s not for the faint of heart. I did it and it was thrilling!
DIVINE Tips: Buy your tickets in advance. If you are brave enough to step out onto The Ledge, have someone take a picture of you sitting on the floor. It’s part of the experience and a different perspective.
Our 5 Must-Visit Attractions in Chicago only scratch the surface, so check back for our 5 Hidden Gems in Chicago.
