Chicago's Best Attractions: Iconic, Must-See Places around the City

One of the best ways to see Chicago’s many attractions is by boat. The Chicago Architecture Foundation’s River Cruise takes visitors along the Chicago River while knowledgeable docents share the history of Chicago, its architecture and how it became one of the world's most important crossroads of today.

Another option to see the sites from the museums located on the Museum Campus, including Adler Planetarium, the Shedd Aquarium and the Field Museum to the Lincoln Park Zoo, is to rent a Divvy bike for just $7 which gives you 24 hour bike sharing access.

Using Chicago’s Lakefront Trail, it’s easily possible to stop along the route and view the largest Monet exhibit at The Art Institute or take a picture with The Bean at Millennium Park.

For a different kind of attraction, book a show at Second City, the same comedy troupe that launched the careers of comedians including Gilda Ratner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others.

Rain or shine, Chicago's iconic attractions draw thousands of visitors every day. The city’s excellent transit system, Divvy bike share program and accessible lakefront trail makes it easy to get from one part of Chicago to the other. Cabs are aplenty, too, so a car is unnecessary to enjoy Chicago’s attractions.

10 Chicago Food Planet Tours
If you want to really get intimate with a place, check out its food scene. Chicago Food Planet Tours has done all of the work and its tours have been designed to take its guests through the city's most historic, savory neighborhoods. Restaurants are carefully selected by native food connoisseurs which allow guests to learn all about the neighborhoods, what makes them stand apart while tasting delicious samples. Tours are three hours long and guests can expect to experience foods from one-of-a-kind specialty food stores, famous local restaurants and ethnic eateries while learning about Chicago's culture, history and architecture along the way. (212-209-3370)

9 Art Institute of Chicago
A highlight of any trip to Chicago, this museum is home to one of the best and most diverse art collections in the world. People are drawn first to the vast Impressionist collection, including the world's largest group of Monet paintings. But treasures abound, including the haunting "American Gothic" and Seurat's groundbreaking Pointillist work. The contemporary section has been expanded and now includes pieces by Picasso, Matisse, Dali, Pollock, and Warhol. The temporary shows are also well known and always receive critical acclaim. Kids particularly enjoy the Thorne Rooms, 68 miniature room models with intricately detailed European interiors from the 16th century through the 1930s as well as American furnishings from the 17th century to 1940. (312-443-3600)

8 Adler Planetarium and Astronomy Museum
This eye-catching, twelve-sided building includes two sky theaters, one of which was the first planetarium in the western hemisphere. The theaters depict the night sky and allow visitors an up-close look at distant planets, moons and galaxies. The complex also features exhibition rooms, a cafe and a StarRider theater that offers amazing, interactive, virtual reality shows. In it, visitors use controls in their seats' armrests to participate in a 3-D simulation of space travel. On family-friendly Far Out Fridays, visitors get to see shows, sit in on lectures, view the night sky, play games and learn how to set up and use a telescope. (312-322-0300, 312-922-7827)

7 John G. Shedd Aquarium
The largest indoor aquarium guides the viewer through the world's many marine habitats, from the entertaining colony of Falkland penguins to the exotic Amazon. Watch divers as they feed sea turtles, stingrays, sharks and tropical fish in the Caribbean Reef's circular viewing tank. A perpetual highlight is the Oceanarium where dolphins and beluga whales spread their infectious joy. Finally, the towering Wild Reef tank creates the feeling of being underwater. Get close and eye the sharks of several feet gliding above. For an even more personal experience, schedule a penguin encounter where you'll be introduced to one of the penguins and get close enough to touch its sleek, slick feathers. (312-939-2438)

6 John Hancock Center
After 40 seconds in John Hancock's elevator, visitors are transported 1,000 feet above Chicago. From there, the city's third-largest building offers views that stretch out to 80 miles on a clear day. Food and drink are available in the restaurant and lounge, and informational exhibits are on display in four different languages. Should you be around in April, you may want to skip the elevator ride and run to the top with other participants who "Hustle up the Hancock" to benefit the Respiratory Health Association. Make reservations in advance for dinner or stop for a drink at the famous The Signature Room at the 95th where you can continue to enjoy the spectacular views. New this year: TILT - a new way to see Chicago's skyline. (312-751-3681, 888-875-8439)

5 Second City
The world's premier comedy troupe, The Second City has launched some of the biggest names in the business. You may have heard of them: Gilda Ratner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others. The Second City imprint is felt across every entertainment medium. Since its creation in 1959, the show claimed Old Town its home when the founders wanted a theater to practice their own, Chicago-style routine of sketch and improv. The small audience gets an intimate vibe; half theater, half comedy lounge. Expect bits that cover all facets of societal satire and of course, long running jokes. (312-337-3992, 312-664-4032)

4 Chicago Lakefront Trail
The city really comes alive when the weather warms up enough for its residents to hit the Lakefront Path. Located east of Lake Shore Drive, the Lakefront Trail is an 18.5 mile linear path that stretches from the far north part of the city to the south side. Neighborhoods dot the path as well as notable cultural landmarks including the Museum of Science and Industry; the Field Museum of Natural History; Shedd Aquarium; Adler Planetarium & Astronomy Museum; the Chicago Children's Museum; the Peggy Notebaert Nature Museum; Lincoln Park Zoo, and the South Shore Cultural Center. The paved path is very popular among walkers, joggers and bicyclists and it will and does get crowded during the warm weekends. Expect to slow down around Navy Pier, one of the most congested points on the trail. Still, the Lakefront Path is one of Chicago's best and free sightseeing attractions. ((312) 742-PLAY (7529)

3 Lincoln Park Zoo
An ape house, a birdhouse and a working model of a five-acre Midwestern farm are just a few examples of what makes this zoo special. Founded in 1868 and known as America's oldest free public zoo, the Lincoln Park Zoo still manages to charge no admission and remains open year-round. Set on scenic park grounds with lush lawns and pleasant walkways, the zoo greets visitors with the beauty of Georgian Revival buildings and a spectacular greenhouse. Prominent zoo residents include elephants, giraffes, sea lions, gorillas, reptiles and an endangered Siberian tiger. The Zoo is open 365 days a year and constantly hosts events and activities. (312-742-2000)

2 Millennium Park
Millennium Park is Chicago's crown jewel. With the change of seasons, the park attracts thousands every day. Summertime means a stellar line-up of concerts at Jay Pritzker Pavilion (during the day, on most Tuesdays through Fridays, the Grant Park Orchestra and Chorus can be heard for free in the Pavilion as musicians rehearse for upcoming concerts). Winter brings out the ice-skating rink and Christmas lights. Get a picture with the Cloud Gate sculpture, or 'The Bean' as we call it in Chicago and at Crown Fountain, two 50-foot glass block towers at each end of a shallow reflecting pool. The towers project video of faces of Chicago citizens on LED screens and having water flow through an outlet in the screen to give the illusion of water spouting from their mouths. At the southern tip is Lurie Garden, a 5-acre urban oasis featuring perennials, bulbs, grasses, shrubs and trees. (312-742-1168)

1 Chicago Architecture Foundation River Cruise
Seeing Chicago's architectural beauty from the decks of a river cruiser is a must for both locals and visitors. One of the city's most unique tours, the CAF River Cruise takes visitors along the north and south shores of the lake. Guests will learn about more than 50 buildings and their significance to Chicago's architectural landscape as well as general history about Chicago and how it grew from a small back-country outpost to one of the world's most important crossroads of today. Tours are available late April through mid-November and run about an hour and a half in length. Be sure to purchase tickets in advance as they often sell out. (312-922-3432, 312-902-1500)


Megy Karydes has spent more than 20 years as a professional writer and most of her life in Chicago. While she’s traveled extensively internationally, visiting each of the 50 states is on her bucket list. An adventure seeker, she’s game for anything from mixed martial arts training to competing in obstacle course races. A self-proclaimed coffee snob and “greenie” who loves farmer-grown food and locally-grown craft beers & wine. She’s yet to find an outdoor beer garden she doesn’t like.  Mixing writing and food/drink is her specialty, especially when it involves travel. Visit her musings on her insatiable appetite for life at www.WanderingTastes.com or www.KarydesConsulting.com.

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Maps and Directions

3
Adler Planetarium and Astronomy Museum 10Best List Arrow
Type: Museums, Planetarium / Observatory, Science Museums
Neighborhood: Airport - Cgx
7
Chicago Lakefront Trail 10Best List Arrow
Type: Attractions, Beaches, Family Friendly, Free Attractions, Great Views, Outdoor Activities - Summer, Outdoor Activities - Winter, Parks, Public Spaces, Romantic, Uniquely Here
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Chicago Architecture Foundation River Cruise 10Best List Arrow
Type: Architecture, Tours and Excursions
Neighborhood: River North