Chicago appears to breathe more than its cramped East Coast counterpart, with its lively rooftop restaurants and bars, all the action in Times Square, and the shenanigans of New Year’s Eve in NYC, which is jam-packed with festivities.
Chicago’s main boulevard, Michigan Avenue (the Magnificent Mile), is lushly planted with trees and flowers, and the city stands on the border of Lake Michigan, with the Chicago River flowing through it. In 1900, the city’s filth was running down the river and into the lake, so they reversed the flow!
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1. Shop Magnificent Mile
Mag Mile (as the locals refer to it) is the major thoroughfare, Michigan Avenue, which runs parallel to the lake. There are many office buildings along this route, therefore the finest shopping is on the north side of the Chicago River.
2 Check out Maggie Daley Park
This magnificent green park is connected to Millennium Park by a bridge. It’s an excellent area for recreation. In the winter, visit the Skating Ribbon, play 18 holes of miniature golf, climb the rock climbing wall, and let the kids go in the enchanting Play Garden, which has been lovingly developed for children of all ages and ability levels.
3 Attend a free summer concert
Between June and August, go to Millennium Park for free music. Grab a space on the grass in front of the Jay Pritzker Pavilion and listen to music from both rising and established musicians.
4 Visit the American Girl Store
If you have girls from 3 to roughly 10 years old in your life, they will turn in wonder at the American Girl store. Trust me: go there! Two floors of dolls and accessories, including a hair salon where your favorite dolls can have new hairstyles after sitting on a salon chair draped in a cape. Then you and the dolls can enjoy cupcakes at the cafe.
5. Have lunch at Eataly
But save room for deep-dish pizza for dinner! There are two levels of Italian-inspired food outlets, but seating is dining-style on the second floor – you may choose which of the open-plan restaurants you want. There are also other accessories available for purchase, such as oils and preserves, accessories, and cookbooks.
6. Visit Garrett Popcorn
You must purchase their wonderful and trademark real cheese and caramel popcorn. Seriously, it’s delicious. Sweet and savory all in one. (Don’t judge until you’ve tried it!) I even got a behind-the-scenes tour of Garrett, located off Michigan Avenue, and went into the kitchen to watch how they made this popping delight.
7. Take an architectural cruise
Chicago is known worldwide for its architecture. One of the best ways to experience it is on a building-themed river cruise on the Chicago River. You may hear about the heritage of the city while taking in a few distinctive views as you glide past grand towers and skyscrapers.
8. Take a gangster tour
This is fun! Starting in the Central Business District and stopping at sites of prior gun battles and massacres while the Mob ruled Chicago during prohibition in the 1920s, you’ll learn about gangsters like Al Capone, bootlegging, and all the skulduggery that came with it! Untouchable Tours is highly regarded, and I’ve done it twice, so I recommend it. $38 per person, but book online as they fill up.
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