201 East Randolph Street, Chicago, IL 60601-6530

Three square blocks of open lakefront complete with a Ferris Wheel, outdoor music pavillion and ice skating rink; expected to become one of the city's most popular sites.

111 S Michigan Ave, Chicago, IL 60603-6110

See why the Art Institute of Chicago is the only museum in the world to be top-ranked by TripAdvisor four years in a row! Experience the greatest Impressionist collection outside Paris, and view contemporary masterpieces in the spectacular Modern Wing. Stand before classics like Nighthawks, and travel the globe through galleries devoted to the art of ancient Greece, Japan, Africa, and the Americas.

201 E. Randolph St. Millenium Park, Chicago, IL 60602

Nicknamed "The Bean" for its sleek kidney shape, this Anish Kapoor sculpture is the centerpiece of AT&T Plaza in Millenium Park.

233 S Wacker Drive entrance on Jackson Blvd (south side of building), Chicago, IL 60606-7147

Skydeck Chicago is the breathtaking, thrilling observatory atop the iconic Willis Tower. The highest observation deck in the United States, Skydeck provides views of the city spanning up to four states and 50 miles on a clear day. Skydeck features The Ledge; five glass floor balconies extending 4.3 feet from Willis Tower and made up of three layers of half-inch thick glass laminated into one seamless unit. After an extensive transformation, Skydeck offers a can’t miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The revamped attraction features a brand-new, lower-level, museum-like interactive experience that celebrates the unique personality, history, neighborhoods, and sites of Chicago.

North Michigan Avenue, Chicago, IL 60611

The Magnificent Mile is a prime hospitality, dining and retail destination in the heart of Chicago. This section of Michigan Avenue, running from the banks of the Chicago River to Oak Street, features more than 460 shops, from high-end boutiques like Gucci and Burberry to pocket-friendly department stores. Amid lots of shopping and fine dining options, don’t miss the avenue’s historic landmarks like the Wrigley Building and the Chicago Water Tower. You can also take a walking tour of the area to make sure you’ll cover all the must-sees or stay in a room with an impressive view of downtown Chicago. – Tripadvisor

600 E Grand Ave, Chicago, IL 60611-3419

Opened in 1995, Navy Pier is a 50-acre scenic waterfront destination that’s home to countless restaurants, exhibitions, shops, entertainment, and more. Take a ride on the 200-foot-tall Ferris wheel, explore the interactive Chicago Children’s Museum, enjoy a free concert, or go on an art and mural hunt—all against the spectacular views of Lake Michigan and the Chicago skyline. Adrenaline seekers will love the speedboat tours; otherwise, unwind on a sightseeing cruise. Parking can be rather pricey, so it’s best to make your way there via public transportation. You'll likely pass by the pier on a cruise of the Chicago River. – Tripadvisor

5700 S. Lake Shore Dr, Chicago, IL 60637-2093

The largest science museum in the Western Hemisphere! Housed in the only remaining building from the 1893 World’s Fair, MSI is a Chicago must-see. You’ll experience 14 acres of hands-on exhibits and have the chance to stand before a 40-foot tornado; climb aboard a World War II German submarine; take a run in a human-sized hamster wheel; descend into an Illinois coal mine; tour a fully functioning eco-friendly home; board a 727 hanging from the ceiling; transmit your pulse to a 13-foot, 3-D beating heart; and much more! MSI is not a place where you walk around quietly and observe. No way! You get involved in the fun—and learn—by doing. Just a few miles from downtown with convenient underground parking.

875 N Michigan Avenue 94th Floor, Chicago, IL 60611-1803

Located on the 94th floor of the John Hancock Center, 360 CHICAGO offers breathtaking views of Chicago’s skyline, the lakefront, and four states. It’s the only place you can enjoy Chicago’s highest thrill ride, TILT – a giant moving platform that literally TILTs visitors over the edge of the building. Relax at BAR 94 with local favorites, a large cocktail selection, and front-row seating to the city’s best views from 1,000 feet up. Explore HD interactive touch screens in seven languages and learn more about the Windy City. If you really want to experience Chicago, make your first stop 360 CHICAGO.

1060 W. Addison St., Chicago, IL 60613-4566

Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.

1400 S Lake Shore Dr, Chicago, IL 60605-2827

The Field Museum fuels a journey of discovery across time to enable solutions for a brighter future rich in nature and culture. With almost 40 million specimens and artifacts in our collections—including SUE, the world's most complete Tyrannosaurus rex—there's something for everyone. Start planning your visit at fieldmuseum.org.

2001 N Clark St, Chicago, IL 60614-4757

Founded in 1868, the Lincoln Park Zoo is one of the country's last free-admission zoos. There are over 1,200 animal residents, self-guided tours, and interactive activities with seals, polar bears, and penguins—check the schedule for timings. Don’t miss the Regenstein Center for African Apes—a popular habitat showcasing cheeky chimpanzees and majestic gorillas. Navigating the zoo is a breeze with multiple points of entry and wide paths to boot. Check for early closures before visiting and arrive in the morning to cover the majority of the exhibits. – Tripadvisor

301 S. Columbus Dr., Chicago, IL 60601

Chicago's landmark is considered one of America's finest fountains due to its Beaux-Arts-style landscape design, finely wrought bronze sculpture and innovative use of technology.

Chicago, IL 60601

Located on the south bank of the Chicago River, this bustling urban space is filled with public art, museums, water activities, and more.

78 E Washington St, Chicago, IL 60602-4801

The Chicago Cultural Center is the nation's first free municipal cultural center and one of the most visited attractions in Chicago. The stunning landmark building, opened in 1897 as the city's first public library, is home to two magnificent stained-glass domes, and annually presents hundreds of free cultural exhibits and performances. Admission is free.

540 N Lake Shore Dr, Chicago, IL 60611-3414

The Chicago Lakefront Bicycle Trail is roughly 22 miles of bike paths, stretching from Indiana border up to Evanston. The trail rides through many parks including Jackson Park (including U of Chicago), Grant Park (including Buckingham Fountain/Museum Campus) Millennium Park, and Lincoln Park with its Free Zoo. Plenty of beaches and bike rentals available at Bobby's Bike Hike - 540 N. Lake Shore Drive, Chicago IL 60611 (free maps, helmets).