When you get the itch for a road trip and want to be sure there’s a memorable climax, where do you go? One of our favorite travel memories of all time was in Chicago – we packed up on a weekend and drove a couple days to the Windy City to enjoy its sights, sounds, and quintessentially Chicago vibe. If you need a getaway, we recommend heading here – and spending some time at the 5 best Chicago landmarks in the whole city.
1: Navy Pier
Poking out into Lake Michigan from the center of the city is the inimitable Navy Pier, an iconic Chicago landmark with scads of history. The pier was opened to the public in 1916 with a threefold purpose: allow for the docking of freight ships, provide passenger transport, and create a recreational area for the city. It’s done that and more, also serving as a temporary jail for draft dodgers, a training center for the U.S. military, and a teaching center for the University of Illinois at Chicago. While commercial activity ebbed in the ’60 and ’70s, the pier saw a revitalization in the late ’80s.
Today, the Navy Pier boasts multiple restaurants, rides, games, public art – even open-air workouts and concerts. We spent a whole afternoon here, swinging in circles on the fair rides between bites at RIVA Crabhouse (get yourself a steam pot of mussels with garlic toast) and drinks at Offshore Rooftop & Bar. The views are just amazing – you can people-watch to your heart’s content or lose yourself in the gentle waves of Lake Michigan.
If you really want to do it up, consider a cruise – there are a few that depart from the pier, including a dinner cruise. Or, just time your dockside visit to align with a pier event – like fireworks or performances – that you can watch from a restaurant booth. Check the Navy Pier website for a full calendar of events and all the details.
2: Millennium Park (and the Giant Bean)
The bean! Who hasn’t heard of the glossy, reflective bean that grounds Millennium Park? If you want more outdoor time – accompanied by exceptional views of the city, some quirky-fun public art, and perhaps a picnic – then there’s no better place than Millennium Park.
Designed to celebrate the third Millennium, this 24-acre public area is a boon to both Chicagoans and visitors who love outdoor adventures and sight-seeing. As part of your trek, you can walk underneath the crisscrossed canopy of the Jay Pritzker Pavilion and Giant Lawn, admire the flora in Lurie Garden, and of course, spend time snapping photos of yourself in the giant metallic bean (actually called the Cloud Gate).
Depending on how much time you want to spend in Millennium Park, there are other pavilions to view and fountains to ogle – it’s all open and most sites are free, so make yourself at home. If you come in the winter, you’ll notice an ice rink on the south side; we highly recommend a few laps, preferably at night under the glow of the Chicago skyline.
3: Magnificent Mile
The Magnificent Mile is not really a traditional Chicago landmark – or at least, few think of it that way. We included it because it is an iconic stretch in the heart of the city that gives you views of the Chicago River at the start and the impressive downtown skyline that ascends as you head into the city via North Michigan Avenue.
The Mag Mile got its name in the 1940s from a real estate developer, and now serves as the posh go-to for shopping in the city. You can also see some Chicago landmarks along the street, including the Wrigley Building, 875 North Michigan Avenue (formerly the John Hancock Center), and the luxe Drake Hotel.
If you’re a shopping nut, this will be your mecca. Bloomingdales, Neiman Marcus, Saks Fifth Avenue, Armani, Chanel, Dolce & Gabbana, Harry Winston, and dozens of other top brands line the Mag Mile, not to mention a mix of both casual and fine-dining restaurants. Bring some extra cash – you’ll need it.
4: Skydeck Chicago (Willis Tower)
As the second tallest building in the Western Hemisphere, Willis Tower is unquestionably a Chicago landmark. Opened in 1973, the tower stands 110 stories tall and serves about 25,000 people every day. Little surprise, then, that this mammoth building also boasts an observation deck – the Skydeck, to be exact.
The Skydeck is not for the faint of heart, as it actually gives you a chance to step out onto a “ledge” with a glass floor – perfect for staring at the city between your feet and taking Insta-wowing photos. We also recommend doing a little Chicago landmark hunting – can you spot the key sights you’ve already visited from the 1,300-feet-above-ground ledge?
(Keep in mind visitors are limited to 60-90 seconds on the Skydeck to make sure everyone has a chance to experience it.)
Last but not least on your adventures in the Windy City, make a point to visit the Art Institute of Chicago. It was founded in 1879 – evident in the original building’s classic architecture, popular at the time – and has housed some of the most famous works of art in the world for over a century.
Among its more notable pieces is Edwards Hopper’s “Nighthawks,” painted in 1942; Picasso’s “The Old Guitarist,” painted in 1903; and George Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte,” painted between 1884 and 1886. While these classics are darlings of the art world, one of the Art Institute’s biggest draws is its diversity; you can find exhibits stretching from African Art to Byzantine statuary, textiles, and photos. In fact, the museum boasts a collection of almost 300,000 individual pieces of art. There really is something for everyone.
Heck, you can even find outdoor art – if you just want to admire creativity in the open-air. We do recommend purchasing a ticket and experiencing the full Institute, however; these run from $20-25, but check the website for up-to-date pricing.