The Midwest's largest city can overwhelm with its array of activities and sights. So to get you started, we've compiled a list of must-see attractions--some quirky, some iconic--based on Midwest Living's travel editors' experiences. The list is arranged by interest; whether you are a sports fan, art aficionado or history buff, you'll find plenty to love about Chicago.
Being in the country's third largest city (population: 2,695,598) means you have a lot of territory to wrap your brain around. Start by taking time to get an overview. Choose a tour that caters to your interest.
Loop Tour Train A ride on the El (pictured) illustrates why Chicago's heart is called The Loop--the tracks lasso the city's financial heart. Get a special deal on Saturdays, May through September, if you're able to snag a free ticket from the Chicago Cultural Center at Randolph and Michigan. The transit authority also has a downloadable sightseeing guide. transitchicago.com 
Chicago Greeters Volunteers lead free two- to four-hour neighborhood walking tours. Choose from more than 25 neighborhoods and 40 interests, including fashion, film, ethnic and public art. chicagogreeter.com 
Bobby's Bike Hike Offers guided bike tours of neighborhoods, a great way to learn more about the city's history. bobbysbikehike.com 
Seadog Zip along on a speedboat while a stand-up comic leads an informative architectural tour. seadogcruises.com 
Sure, these spaces provide a little breathing room in a major metropolitan city, but they also offer a bounty of activities.
Millennium Park (pictured) Concerts, gardens, sculpture and free events draw people to this 24.5-acre corner of Grant Park. A free downloadable tour tells how and why Millennium Park was built, the secrets beneath the park, and the reasons Millennium Park is one of the world's most spectacular public spaces. millenniumpark.org ; downloadchicagotours.com 
Grant Park Chicago's front yard, Grant Park is among the city's loveliest and most prominent parks. Three world-class museums--the Art Institute, the Field Museum of Natural History and Shedd Aquarium--call it home. Check out the Buckingham Fountain, one of the world's largest fountains, with 20-minute water shows on the hour 8 a.m. to 10 p.m. Also in the park: trails for walking, jogging, and biking; a skate park; a dog-friendly area; baseball fields; tennis courts; and more. chicagoparkdistrict.com 
Oak Street Beach This stretch of Lake Michigan shore offers a carpet of white sand against a backdrop of skyscrapers. chicagoparkdistrict.com 
Millennium Park 
Grant Park 
Oak Street Beach 
World-class collections abound, but the up-and-coming are here, too.
Art Institute of Chicago The Modern Wing opened in 2009 to showcase 20th- and 21st-century. Older galleries have been renovated, making it easier to see the collections, which span 5,000 years and include some of the world's major works of art, including American Gothic. Free admission first and second Wednesdays. Pictured. artinstituteofchicago.org 
Museum of Contemporary Art An edgy, fun venue offering free admission Tuesdays and jazz concerts during the summer. mcachicago.org 
National Museum of Mexican Art A collection of more than 6,000 objects, including textiles, folk art, photography, paintings and sculptures, tells the Hispanic story. Free admission. nationalmuseumofmexicanart.org 
Indie art galleries Featuring a wide range of art styles and media in different neighborhoods. You'll find a lot along North Michigan Avenue in River North. chicagogallerynews.com 
Indie art galleries 
Take a look at what makes Chicago one of the top vacation destinations in the Midwest. This video highlights some of the most talked about attractions, such as Millennium Park, The Field Museum, Macy’s on State Street, the Sky deck at Willis Tower, and Navy Pier.
Chicago has an incredible concentration of world-renowned cultural institutions. Even better, several are concentrated on the museum campus: the Field Museum (pictured), John G. Shedd Aquarium and Adler Planetarium.
The Field Museum Basically it contains 4.6 billion years of history, including the 67-million-year-old T. rex Sue, under one roof. fieldmuseum.org 
Adler Planetarium Caters to space buffs, but the movies shine. adlerplanetarium.org 
John G. Shedd Aquarium See Nunavik, the beluga whale, and other Pacific Northwest coast creatures at the Abbott Oceanarium exhibit and aquatic shows. sheddaquarium.org 
Museum of Science and Industry You'll love the exhibits on technology and transportation, but Science Storms is way cool, too. msichicago.org 
DuSable Museum Gain insight into the African American experience through paintings, sculpture, print works, and historical memorabilia. dusablemuseum.org 
Field Museum 
Adler Planetarium 
DuSable Museum 
The fact that there is a whole class of architecture called the Chicago School indicates just how important this city is in the world of architecture. You can see prime examples of Art Deco, neoclassical, Prairie, Gothic, Queen Anne and others.
Chicago Architecture Foundation Explore modern skyscrapers, historic downtown, Art Deco landmarks and more by foot, boat or bus. The most popular outing is the 90-minute river tour (pictured), which will help you discover the city's many architectural masterpieces. architecture.org 
Willis Tower Visit the tallest building in North America, and then step outside on The Ledge on the 103rd floor. theskydeck.com 
John Hancock Observatory North America's fastest elevator whisks you to the 94th floor where you look out labeled window walls and use multimedia devices providing stories about the views. A cafe serves appetizers, drinks and coffee at 1,000 feet up. hancockobservatory.com 
Willis Tower 
These family-friendly attractions may be just as fun for adults as kids.
Navy Pier (pictured) A 150-foot Ferris wheel, the Chicago Children's Museum, the Chicago Shakespeare Theater, restaurants and boat cruises draw visitors to this lakefront spot. There are twice-weekly fireworks in summer. navypier.com ; chichildrensmuseum.org 
Peggy Notebaert Nature Museum Kids love playing with the boats and locks at water tables and checking out the critters. The highlight, though, is the Butterfly Haven. Free on Thursdays. naturemuseum.org 
Lincoln Park Zoo This North Side zoo often prompts visitors to marvel that it is free. A new nature boardwalk opened recently; the children's zoo and carousel are reliably entertaining. lpzoo.org 
American Girl Place It's mecca for tween girls. Find historical-theme dolls, a salon for your little one's doll, and a cafe serving brunch, lunch, tea and dinner. americangirl.com 
Navy Pier 
Lincoln Park Zoo 
American Girl Place 
For a city renowned for its buildings, Chicago offers notable greenspace.
Chicago Botanic Garden Monthly exhibits round out an already-hefty offering of walks, birding, bicycling and blooms. chicago-botanic.org 
Lurie Garden A living prairiescape framed by landmark Chicago architecture, this free garden not only illustrates Illinois' tallgrass prairie plants but also demonstrates beautiful possibilities for Midwest gardens. luriegarden.org 
Garfield Park Conservatory This free garden emphasizes Midwest native plants and materials. Parts of the conservatory were heavily damaged in a summer 2011 hailstorm; check the website for updates. garfield-conservatory.com 
Lurie Garden 
Blues, jazz, gospel, soul, country ... Chicago fosters them all.
Andy's Jazz Club In a city known for its live music, this place has a reputation for sophisticated dinners and a 40-year track record of pulling in crowds. andysjazzclub.com 
The Green Mill Music lovers throng to this speakeasy-style setting for blues and jazz and a poetry slam. greenmilljazz.com 
Symphony Center The center is home to the Chicago Symphony Orchestra, which is recognized as one of the finest in the world. cso.org 
Ravinia Festival In Highland Park, the summer home of the CSO has $10 lawn seats and big-name shows. ravinia.org 
Blues Tour Rock and Roll Hall of Famer Buddy Guy narrates a free, downloadable walking tour of South Side places where the blues took root. downloadchicagotours.com 
Andy's Jazz Club 
The Green Mill 
Symphony Center 
Ravinia Festival 
Blues Tour 
Major players call Chicago home. Major fans love that.
Cubs Try to catch a fly ball at Wrigley Field (pictured), the historic ballpark built in 1914. Tours of the field are available. cubs.com 
Bears This NFL championship team plays on Soldier Field along the lakefront. chicagobears.com 
Bulls They play ball at the United Center, where you can see the statue of Michael Jordan, unveiled when his No. 23 was retired. unitedcenter.com/bulls 
Blackhawks Cheer on the 2010 Stanley Cup champs at the United Center. blackhawks.nhl.com 
Home to Native Americans, military posts, fur traders and others through the years, Chicago opens America's history book in a tangible way.
Chicago Cultural Center This landmark building (pictured) is home to free events, including tours, dance, films and lectures. explorechicago.org 
Old Chicago Water Tower District The Old Water Tower and the Chicago Avenue Pumping Station are two of only seven buildings to survive the Great Chicago Fire of 1871. Both were built in the castellated-Gothic Revival style. cityofchicago.org 
Chicago History Museum Start here in your study of Chicago history, both as an urban center and as part of the United States. chicagohistory.org 
Chicago History Museum 
Location and selection combine to make retail king.
Loop shopping In an area of downtown named for the circling elevated train tracks, bargains and browsing abound. Macy's (pictured) anchors it all on State Street. visittheloop.com 
Oak Street Offers a trendy mix of designer shops and indie boutiques. oakstreetchicago.com 
Mag Mile More than 400 high-end stores, including boutiques, department stores and high-rise shopping malls, line North Michigan Avenue. themagnificentmile.com 
Loop shopping 
Mag Mile 
The theater district hops with plays, musicals and live acts. Get tickets cheap at Hot Tix, which lets you purchase last-minute, half-price tickets online. hottix.com 
Second City A training ground for comics, it features smart shows that skewer current events. secondcity.com 
Steppenwolf Theater For more than three decades this artist-driven theater has offered groundbreaking, innovative works. steppenwolf.org 
Chicago Shakespeare Theater As indicated in the theater's name, the works of Shakespeare remain at its core. But classics and new pieces by gifted artists are also preformed. chicagoshakes.com 
Broadway in Chicago Save on airfare and see blockbusters here. broadwayinchicago.com 
Second City 
Steppenwolf Theater 
Broadway in Chicago 
Time your visit to mingle with the masses at one of these outdoor events.
Air and Water Show A free show by the awe-inspiring likes of U.S. U.S. Air Force Thunderbirds (pictured), U.S. Army Parachute Team Golden Knights, Chicago Fire Department Air and Sea Rescue Team. Held one weekend in August along Lake Michigan. explorechicago.org 
Tall Ships Learn about barks, brigantines and schooners when tall ships dock at Navy Pier. The festival isn't every year, but the tall ship Windy calls the pier home. tallshipwindy.com 
St. Patrick's Day Watch the Chicago River run green and see the downtown parade. chicagostpatsparade.com 
Taste of Chicago A 10-day family-oriented celebration of food--ethnic to exotic--in Grant Park. explorechicago.org 
Air and Water Show 
Tall Ships 
St. Patrick's Day 
Taste of Chicago 
Chicago has more than 7,300 restaurants, everything from mom-and-pop diners to cutting-edge fine-dining establishments. Click on the links below to read about our favorites for breakfast, for a bargain, for a splurge and for an only-in-Chicago experience.
Best Alfresco Dining 
ExploreChicago.org is your comprehensive source for all there is to see and do in Chicago this summer. Discover amazing festivals and events like the Taste of Chicago, Chicago Blues Festival, and Air and Water Show, to world-class restaurants, shopping and hundreds of attractions, museums, concerts, and more.
Start planning your trip today!