The “Must-See-and-Do” list in Chicago is quite extensive – indeed, you could spend years in the city and still not get to explore everything. So how do you choose among all of Chicago’s top restaurants, nightlife, shopping and museums to fit them all into your busy schedule? Let our Classic Chicago itinerary ideas be your guide for all the best that Chicago has to offer.
875 N. Michigan Ave. 94th Floor
Formerly the John Hancock Observatory, 360 CHICAGO is located on the cusp of Lake Michigan, sitting in the heart of the city 1,000 feet above The Magnificent Mile. From the 94th floor of Chicago’s fourth tallest building, 360 CHICAGO delivers incomparable views of the lake and city skyline. Thrill-seekers rejoice with Chicago’s newest epic attraction, TILT, an enclosed glass and steel moveable platform that tips outward at a downward-facing angle that has you looking straight down at the city beneath you. Conquer your fears and take on TILT today!
Buddy Guy’s Legends
700 S. Wabash Ave.
Owned by blues legend Buddy Guy, this is Chicago’s premier blues club, now in a new South Loop location. Local and national blues bands perform every night, ensuring an endless slate of the most talented blues musicians for you to enjoy.
Lincoln Park Zoo
Cannon Dr. at Fullerton Parkway
See roaring lions, playful meerkats and majestic gorillas just minutes from downtown Chicago. Lincoln Park Zoo is free, open and amazing every day of the year. Visitors can go nose-to-nose with chimpanzees, howl with red wolves, peer into a black bear den and immerse themselves in the sights and sounds of Africa with wild dogs, pygmy hippos and black rhinos. In addition to providing a wild home to hundreds of species, the zoo also operates one of the largest zoo-based conservation and science programs in the country.
201 E. Randolph St.
Explore Chicago’s lush Millennium Park, home to the famous Cloud Gate sculpture (affectionately known as “the Bean”), Jay Pritzker Pavilion, Lurie Garden and the Crown Fountain that spouts water from its digital human faces. Millennium Park is constructed on top of a railroad yard and expansive parking garages, making it one of the largest green roofs in the world. It’s simply the perfect spot to spend a relaxing, refreshing day in this beautiful city.
600 E. Grand Ave.
Built in 1916 but reimagined in recent years as a festival destination of shops, dining, cruises and activities, Navy Pier is a Chicago landmark and the city’s most visited destination. This lakefront playground of more than 50 acres has a Ferris Wheel, mini golf course, a children’s museum and an IMAX® Theatre. Stay late for fireworks shows between Memorial Day and Labor Day.
233 S. Wacker Dr.
Picture yourself standing 103 stories and 1,353 feet off the ground with sweeping 360-degree views that span up to 50 miles and four states. Enter the Ledge at Skydeck Chicago, placing you in an enclosed glass box past the building walls of Willis Tower, the second tallest building in North America. The Ledge at Skydeck Chicago is at your feet – literally!
From ancient artifacts and modern photography, to fossils and living organisms, all of it can be found at Chicago’s various museums. With more than 40 in the city, it’s easy to find one that fits your interests.
1300 S. Lake Shore Dr.
The Adler Planetarium is the first museum of its kind in the Western Hemisphere and features a state-of-the-art theater that will take you on a gripping journey through space and time. Fuel your imagination with spectacular exhibitions, leading-edge technology, and hands-on activities for the whole family. You won’t want to phone home after exploring the outer reaches of the Solar System!
The Art Institute of Chicago
111 S. Michigan Ave.
Named the No. 1 museum in the world in TripAdvisor’s 2014 Travelers’ Choice Awards, the Art Institute houses more than 300,000 works of art, including one of the largest collections of Impressionist and post-Impressionist pieces on the planet. Whether you’re up for a trip into antiquity, a fan of Asian or African art, or in the mood for cutting-edge, contemporary works, you’ll find galleries to your liking.
The Field Museum
1400 S. Lake Shore Dr.
What are you curious about? Whatever your answer may be, chances are The Field Museum can answer your burning questions about the world. Discover 26 million artifacts, including Sue, the world’s largest and best-preserved Tyrannosaurus rex ever discovered. Explore dazzling gems, the Aztec empire, 23 Egyptian mummies and a 3D theater. Lose track of time as you traverse centuries of natural history.
Museum of Science & Industry
57th Street and Lake Shore Dr.
Hands-on is the name of the game at one of the largest science museums in the world, a family favorite with 14 acres of exhibits. Explore the human body, ride through a working coal mine and marvel at a 40-foot tornado before your very eyes in the Science Storms exhibit. Make sure to also dive deep into history with the U-505, a real captured WWII German submarine! There’s something for everyone in this fascinating museum.
1200 S. Lake Shore Dr.
Let the animals of the sea connect you to the living world. From whales to snails, tarantulas to turtles, more than 32,500 creatures from aquatic habitats around the world call Shedd Aquarium home. Come face to face with beluga whales, dolphins, sea otters and penguins in the Abbott Oceanarium, talk to a diver in the 90,000-gallon Caribbean Reef and walk through a flooded forest in Amazon Rising. Widely renowned as one of the country’s finest, Shedd Aquarium is a “must-sea” Chicago destination.
Chicago Trolley & Double Decker Co.
Chicago Trolleys have become one of the most recognized elements of the Chicago streetscape and are truly a part of the fabric of the city. Enjoy a quick overview tour of the city and hop-on and hop-off at most major attractions with trolley and open top double decker bus tours. Purchase a multi-day pass for a continuous transportation option during your stay.
Gray Line Sightseeing
For a comprehensive tour of all things Chicago, also consider a ride on the Chicago Gray Line. Their four-hour grand tour covers most of Chicago’s expansive and scenic outer drive, beautiful parks, and includes stops at the Lincoln Park Conservatory and Museum Campus. Multi-day passes may also be used as convenient transportation during your stay.
Notable lake excursions range from dining cruises aboard the Odyssey or Spirit of Chicago cruise ships; a Tall Ship sailing experience with Tall Ship Windy; and a very exciting speedboat tour along the lakefront with Seadog Chicago. With 26 miles of lakefront along the massive Lake Michigan, Chicago has plenty of ways to get out on the water, feel the breeze, and take in some truly remarkable sights of our unforgettable skyline.
Chicago may be most notable for its fabulous architecture. Greats like Daniel Burnham and Mies van der Rohe have lent their talents to some of the major skyscrapers that tower over the city today, many of which are best seen from the Chicago River. Winding through the heart of the city, the river provides an avenue for guided boat tours from Chicago’s First Lady Cruises, Chicago Line Cruises, Shoreline Sightseeing Cruises, and Wendella Boats, led by expert staff and hyper-knowledgeable docents.
Chicago has emerged as one of the great gastronomic cities in the world as noted and rated by the 2015 Michelin Guide – indeed, the city boasts 24 starred restaurants. The range of flavor palettes includes classic fine dining, steakhouses, eclectic trend setters, family casual, and many ethnic dining options. See your concierge for a recommendation which suits your taste.
Gibsons Bar & Steakhouse
1028 N. Rush St.
This classic American steakhouse offers USDA Prime steaks, fresh seafood, huge portions, sides large enough to share, impressively enormous desserts and famously large martinis. Gibsons has been the pinnacle of Gold Coast dining for over 23 years, with an energetic atmosphere and unsurpassable service that makes it a party every night.
Harry Caray’s Italian Steakhouse
You don’t have to be a baseball fan to enjoy the American and Italian cuisine at Harry Caray’s Italian Steakhouse. Named for the late, hall of fame White Sox and Cubs announcer, Harry’s serves the finest prime, aged steaks, chops and Italian favorites in a classic Chicago steakhouse setting. Universally recognized as a Chicago legend, Harry Caray’s has won numerous awards and accolades for its outstanding food and service. Dine at the downtown location in the River North district, or check out Harry Caray’s Tavern at Navy Pier.
Enjoy delicious, direct trade coffee in a cozy atmosphere at Intelligentsia, which provides padded sofas for your espresso sipping experience. Or go all out and join their local roasting tour! What a perfect way to kick start your day, right?
Lou Malnati’s Pizzeria
Considered the oldest family name in Chicago pizza, Lou Malnati’s has stayed true to the original Chicago style deep dish pizza recipe first created in the 1940s. If you’re craving the best deep dish Chicago has to offer, stop by and savor the buttery, flaky crust, tangy tomato sauce and gooey mozzarella that make Lou’s so famous.
Portillo’s Hot Dogs
Ready for a true Chicago culinary classic? Sample a juicy Italian Beef sandwich or a famous Chicago-style hot dog at Portillo’s in River North. This 1930s and ‘40s themed diner is located on a corner with Hard Rock Café, Rainforest Café, and Chicago’s most famous contribution to dining in the world, a throwback Rock N Roll McDonald’s. Not to distract from the delicious food at hand, but Portillo’s has some tempting restaurants for neighbors.
Any shopping adventure in Chicago should begin with the granddaddy of all Chicago retail: The Magnificent Mile. This cosmopolitan, history-packed section of Michigan Avenue teems with shopping, dining and entertainment treasures that make any vacation unforgettable. That’s not to leave out the other diverse neighborhood hot spots where you can find luxury brands, independent and trendy boutiques, and great vintage items at any number of Chicago’s street fairs.
The Magnificent Mile
North Michigan Avenue
For a shopping experience that’s as diverse as Chicago itself, head to The Magnificent Mile. This retail mecca is home to more than 460 retail stores, 275 dining options, and almost 60 hotels filling the district with vibrant options for any taste. Luxury retailers on Michigan Avenue and Oak Street include Prada, Ferragamo, Escada, Burberry, Louis Vuitton, Marlowe, Jimmy Choo and many more. You will also find very accessible American shopping favorites and brands from around the globe in places such as the world’s first vertical shopping mall, Water Tower Place, as well as 900 North Michigan Shops and The Shops at North Bridge.
Theatrical fare, from lavish Broadway musicals to serious stories told in intimate settings, is one of the magnets that attract the world to Chicago. With five Tony Award®-winning regional theater companies and more than 250 professional theaters, it’s always show time somewhere. Chicago also abounds with first-rate comedy venues offering the very best in stand-up, sketch and improv. You’ll leave delirious from laughter.
Broadway in Chicago
The best of Broadway lights up downtown’s grand theaters as Broadway In Chicago showcases dozens of hit musicals every season. See shows direct from Broadway and world premieres destined for the big stage. From “Jersey Boys” to “The Book of Mormon,” Broadway In Chicago features a number of must-see performances. Off to the show!
Chicago Symphony Orchestra
220 S. Michigan St.
Consistently acclaimed as one of the best orchestras in the world, the Chicago Symphony Orchestra collaborates with internationally renowned conductors and guest artists, putting on more than 100 concerts each year. During the summer, don’t miss the free orchestral performance at the Pritzker Pavilion in Millennium Park, where you can spread out a picnic blanket and listen to classical music under the stars.
170 N. Dearborn St.
Chicago’s oldest and largest not-for-profit theater has won international renown for the quality of its productions, and the depth and diversity of artistic leadership. The Pulitzer Prize-winning Goodman Theatre is an essential cultural institution in Chicago, providing productions of tremendous range and unsurpassed theatrical experience.
Lookingglass Theatre Company
821 N. Michigan Ave.
Recipient of the 2011 Regional Theatre Tony Award®, the Lookingglass Theatre Company is a critically acclaimed live theater on The Magnificent Mile. Prepare yourself for visually stunning, physical and dynamic productions of unmatched excellence.
The Second City
1616 N. Wells St.
No trip to Chicago would be complete without a visit to The Second City, our world-famous comedy club known as the birthplace of improv. With an impressive roster of celebrity alums, such as Mike Myers, Tina Fey, Stephen Colbert and Steve Carrell, this full-time training ground for Saturday Night Live is sure to lead to some laughs.
Steppenwolf Theatre Company
1650 N. Halsted St.
You will be challenged to think harder, laugh longer and feel more. True to its mission, Steppenwolf Theatre Company consistently delivers dynamic and exciting theater that will hit you hard. Chicago’s prized local theater has nine Tony Awards® and a host of famous ensemble members under its belt – make it a priority to check out a performance here.