Ein Blick auf die Skyline von Chicago vom Lincoln Park aus.

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3 Days in Chicago for First Timers

Organisiert von Lori Zainowho was born and raised in the Windy City.

I’ve always thought that Chicago has one of the most impressive skylines of any city. Combine that with world-class museums, the stunning Chicago River, and the Lake Michigan shoreline, and it’s clear that the Windy City is an incredible vacation spot. Plus, chowing down on a slice of piping hot, deep-dish pizza is one of my favorite Chicago pastimes.

My preferred way of exploring the city’s grid-like streets is on foot, always looking up to admire Chicago’s grand architecture. Although the midwestern hub is large, with many unique neighborhoods, most of the key attractions to check out during your first visit are fairly close to one another and accessible on foot.

Chicago has extremely cold winters and very hot summers, as well as distinct spring and fall seasons, so pack and dress appropriately for each season.

If you only have time for one thing, visit the 360 Chicago Observation Deck to see Chicago’s expansive skyline (and view the Willis Tower) from above.

Day 1

Start with getting your bearings in this large city with an architectural boat cruise along the Chicago River. This way, you can admire the skyscrapers, such as the Willis Tower and the Wrigley Building, without having to navigate Chicago’s busy streets on foot.

Then, spend the rest of your day riding around the city on a double-decker hop-on, hop-off bus. A bus tour will give you even more insight into the lay of the land and allows you to cover more ground, passing spots like Buckingham Fountain, Grant Park, Millennium Park, Soldier Field, and Navy Pier.

Day 2

It can be tough to decide which of Chicago’s many museums to visit, from the history-heavy Field Museum—complete with a T-Rex skeleton—to the family-friendly Shedd Aquarium and Museum of Science and Industry to the Art Institute of Chicago, with works from impressionist masters. If you want to visit several, consider a Chicago CityPASS™, which offers free admissions and discounts.

Take a break at lakefront Millennium Park, a quick taxi ride from most of the museums. Snap photos of Lake Michigan, the skyline, and the famous Bean (Cloud Gate) statue, a mirrored monument that reflects the city and its visitors.

Day 3

Chicago’s immense skyscrapers can be viewed from the ground, but seeing them from up above is a magical experience. Although you can visit the top of the Willis Tower, Chicago’s tallest building, it’s best to catch panoramic views of the city from the 360 Chicago Observation Deck in the John Hancock Building so you can spot Willis Tower.

Chicago’s food scene has a little bit of everything, from Chinatown to Greek Town to Little Italy. But you can’t leave without sampling a Chicago hot dog or a slice of Chicago-style, deep-dish pizza drenched in cheese and tomato sauce in a buttery crust.

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