While you are in the area, do make time to visit one of the city’s gorgeous museums before taking a walk at Michigan Avenue, a famed street in this lively metropolis which will connect you to the posh Gold Cost neighborhood.
This itinerary is best done on weekdays when the office buildings are open and the streets are bustling, so you get to experience the Chicago city rush! The Chicago Architecture Foundation offers a 2 hour walking tour called “Historic Skyscrapers” daily which starts at 10 A.M. This tour takes visitors to the oldest buildings at the Loop and the guide explains why these buildings are ground-breaking. It is also an impeccable way to get a grasp of the Loops layout and scenic vistas.
Fronting the Chicago Architecture Foundation, you can find a prominent cultural institution – The Art Institute. If you are pressed for time, this is one museum you should not miss! Must-see displays here are the galleries of European and American contemporary Art and the Impressionist Collection.
Moving north of The Art Institute is the legendary Millennium Park – a local favourite hang out spot. Do make time to see the colossal video-screen faces situated on the Crown Fountain. Take a stroll around the iconic bean-shaped sculpture known as Cloud Gate by Anish Kapoor and take that obligatory selfie shot. Do check out the legendary works of Frank Gery nearby: the Pritzker Music Pavilion as well as the Serpentine Bridge.
Now take a leisurely north of Michigan Avenue until you reach the stunning Michigan Avenue Bridge which spans the Chicago River. This is a perfect spot for taking photos, it’s like you haven’t been to Chicago if you don’t have these on your travel photos.
If you love shopping, head over to the Magnificent Mile, along Michigan Avenue (from the river to Oak Street). This place is clad by designer boutiques, shops and high-rise malls. If you are not a shopper, you can just scourge through the shops, and observe people.
The Hancock Observatory (now 360Chicago), may not be the city’s tallest buildings, but it is on every bucket-list of tourists visiting Chicago. That’s not surprising given that the view on top is jaw-dropping. If you are lucky enough and the weather is good, you can even see Chicago’s neighboring states such as Michigan, Indiana and Wisconsin. Do try out the famed talking telescope here.
After you’ve had your fill of Chicago’s skyline, it’s about time for Oak Street Beach. You can find this by heading to the spot where Michigan Drive meets Lake Shore Drive at Oak Street. Take the underpass leading to Oak Street Beach, a summer hotspot.
If you are curious about the lifestyle of Chicago’s wealthiest residents, then The Gold Coast is for you. Take a leisurely walk along the tree-lied avenue of this posh village dappled with opulent, historic town homes such as the famous Playboy Mansion.
End the day by having dinner at River North or watch a show and get acquainted with Chicago’s pulsating theater scene.