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The 5 Must-See Spots to Hit Up on Your First Trip to Chicago

Chicago Insider Guides
by Christine Pundavela Jun 8, 2018

Chicago is loaded with some 5,000+ restaurants, over 60 museums, 580 parks, 250 theatres, 225 music venues, over 100 festivals, nearly 400 landmarks — you get the gist…the list goes on and on. So it’s remarkable how many directions you can take your trip. If you’re a beer geek, you can have a totally different experience than the architecture nerd. If you plan entire itineraries around eating, you may not want to fit in hours gawking around art galleries. But if this is your first time to Chicago, here’s a few to start your bucket list and ease into the trip planning.

Every city has them: iconic sights and ever popular things for visitors to do. This list of five spots to hit up on your first trip to Chicago is decidedly touristy. But for good reason. They stand the test of time, plus have the popular vote and critical acclaim behind them. So it’s a no-fail way to make a stellar first impression on your inaugural visit.

1. The number one attraction in the Midwest: Millennium Park.

Everyone comes to see “The Bean” in Millennium Park. The giant silver sculpture is actually called Cloud Gate — a playful take on liquid mercury by renowned artist Anish Kapoor that draws millions of visitors each year. But the park didn’t become one of the top 10 most visited sites in the US on the looks of this alone. Free concerts, film screenings, exhibitions, festivals, and family activities keep the lakefront park activated year round. So get the requisite selfies here on your first trip to Chicago and also plan a few hours exploring the whole Millennium Park Campus, home to another must-see attraction…

2. Art Institute of Chicago: top ranked museum in the world by TripAdvisor, four years in a row.

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Two mega attractions sit practically side by side so knock them out together in one day. The Art Institute of Chicago connects to Millennium Park via the beautifully arching Nichols Bridgeway. Take that into the Modern Wing then off you go to start your study of European sculpture, Mesoamerican ceramics, Pre-Columbian textiles, and more. To help focus — since you’re surrounded by an overwhelming 300,000 works of art — you can pick a general theme or stick to the icons in the collection by the biggest names like Pablo Picasso and Jackson Pollock.

3. The most popular tour in America: Chicago Architecture River Cruise.

Chicago, you’ve done it again. Another accolade to add to the mantel. In 2017, TripAdvisor tallied up all their booking data and named the architecture boat tours on the Chicago River the most popular tour in the US. With all that amazing architecture lining the waterways, it’s not that big of a surprise. See for yourself with a ride on Shoreline Sightseeing, Chicago Line Cruises, Wendella, or Chicago’s First Lady.

4. The Magnificent Mile: a shopping district that packs 460 stores into 13 city blocks.

The main boulevard when people think “downtown Chicago” is North Michigan Avenue and that goes by a pretty stately moniker, The Magnificent Mile. First time visitors often stay on or around this stretch (there are more than 70 area hotels here alone) and find themselves shopping for hours. Big brands and massive malls are the anchors — like Water Tower Place, The Shops at North Bridge, and 900 North Michigan Shops — but there’s a mix of stops you can add to your itinerary like spas, museums, galleries, restaurants, and bars.

5. Skydeck Chicago at Willis Tower: the tallest building in Chicago.

The 110-story Willis Tower, the apex in Chicago’s great skyline, goes up 1,450 feet high and the building’s Skydeck observatory goes up 1,353 feet high so expect impressive views. Exhibits point out that you can see up to four states from where you stand, but it’s The Ledge that gets all the attention. Jump up, strike a pose, and strut around the glass boxes that extend four feet out — there’s nothing between the transparent floor and the city streets down below except a lot of air.

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