23 Best Sights in Near North and River North, Chicago

Designed by Skidmore, Owings & Merrill, this multipurpose skyscraper is distinguished by its tapering shape and enormous X braces, which help stabilize its 100 stories. Soon after it went up in 1970, it earned the nickname "Big John." No wonder: it's 1,127 feet tall (the taller east tower is 1,506 feet counting its antennae). Packed with retail space, parking, offices, a restaurant, and residences, it has been likened to a city within a city. Like the Willis Tower, which was designed by the same architectural team, this skyscraper offers views of four states on clear days. To see them, ascend to the 94th-floor observatory—now dubbed 360 Chicago ($30). While there, visitors can grab a cocktail, beer, wine, hot drink or nonalcoholic beverage at Bar 94, which can only be accessed with a General Admission ticket. Thrill seekers can pay an additional fee to take advantage of the tower's most exciting feature, The Tilt ($8), which has eight windows that tilt downward to a 30-degree angle, giving you a unique perspective on the city below. Those with vertigo might prefer a seat in the bar of the 96th-floor Signature Lounge; the tab will be steep, but you don't pay the observatory fee and you'll be steady on your feet.

Michigan Avenue, or Mag Mile as some call it, is a potpourri of historic buildings, upscale boutiques, department stores, and posh hotels. (It is also the city's most popular place for people-watching.) Among its jewels are the Tribune Tower, the Wrigley Building, 875 North Michigan Avenue (formerly the John Hancock Center), the Drake Hotel, and the Historic Water Tower.

A group of art patrons who felt the great Art Institute was unresponsive to modern work founded the MCA in 1967, and it has remained a renegade art museum ever since. It doesn't have any permanent exhibits; this lends a feeling of freshness but also makes it impossible to predict what will be on display at any given time. Special exhibits are devoted mostly to original shows you can't see anywhere else.

Big changes have arrived at this iconic tower, which opened in 1925 to house the Chicago Tribune. Sold by the Tribune Company to CIM Group and Golub & Company for $240 million in 2016, the neo-gothic structure is no longer home to the newspaper, and WGN’s final broadcast there took place in 2018. Now the interior is 162 luxury residences with more than 55,000 square feet of indoor amenities. Visitors can still see fragments from famous sites, including the Taj Mahal and the Alamo, embedded in the building’s façade.

"Hands-on" is the operative concept at this brightly colored Navy Pier anchor. Kids can tinker with tools, climb through three stories of tunnels, play at being a firefighter, dig for dinosaur fossils, and create a masterpiece in the Art Studio.

The gleaming white landmark—designed by Graham, Anderson, Probst & White and the former headquarters of the chewing-gum company—was instrumental in transforming Michigan Avenue from an area of warehouses to one of the most desirable spots in the city. Its two structures were built several years apart and later connected, and its clock tower was inspired by the bell tower of the Giralda Tower in Seville, Spain. Be sure to check it out at night, when lamps bounce light off the 1920s terracotta facade.

These 26-story twin apartment towers overlooking Lake Michigan were an early and eloquent realization of Mies van der Rohe's "less is more" credo, expressed in high-rise form. I-beams running up the facade underscore their verticality; inside, mechanical systems are housed in the center so as to leave the rest of each floor free and open to the spectacular views. Completed in 1951, the buildings, called “flat-chested architecture" by Frank Lloyd Wright, are a prominent example of the International Style, which played a key role in transforming the look of American cities.

Built in 1912 for the Shriners, the former Medinah Temple is a Middle Eastern fantasy, with horseshoe-shape arches, stained-glass windows, and intricate geometric patterns around windows and doors (it once also held a 4,200-seat auditorium). Vacant for many years, it was transformed into a Bloomingdale's Home & Furniture Store in 2003.

Designed by Louis Sullivan and his protégé Frank Lloyd Wright, this almost austere residence is one of the few extant buildings that displays the combined talents of these two architectural innovators. Historians still squabble about who contributed what here, but it's easy to imagine that the young go-getter had a hand in the cleanly rendered interior. Note how the geometric exterior looks unmistakably modern next to its traditional neighbors. Public tours of both the interior and exterior are available and last about one hour. The complimentary Wednesday tours are less comprehensive than the paid ones on Saturday; reservations are required for all tours. Check the website for reservations and pricing.

Chicago is a city of bridges—and this one, completed in 1920, is among the most graceful. The structure's four pylons are decorated with impressive sculptures representing major Chicago events: its exploration by Marquette and Joliet, its settlement by trader Jean Baptiste Point du Sable, the Fort Dearborn Massacre of 1812, and the rebuilding of the city after the Great Chicago Fire of 1871. The site of the fort, at the south end of the bridge, is marked by a commemorative plaque. As you stroll Michigan Avenue, be prepared for a possible delay; the bridge rises about 50 times a year between April and November to allow boat traffic to pass underneath.

A welcome visual and physical oasis amid the high-rise hubbub of North Michigan Avenue, this Gothic Revival house of worship is the oldest building on North Michigan Avenue apart from the Old Water Tower complex (which survived the Chicago Fire of 1871). Designed by Ralph Adams Cram, the church drew many of its congregants from the city's elite but now reflects the city's diversity. Local architect Howard Van Doren Shaw devised the cloister and companion buildings.

In July and August, free concerts are staged every Friday at 12:10 beside the courtyard fountain off Michigan Avenue; other months they're performed in the sanctuary.

This famous Michigan Avenue structure, designed by William W. Boyington (who also designed the Pumping Station to the East) and completed in 1869, was originally built to house a 135-foot iron standpipe that equalized the pressure of the water pumped by the similar pumping station across the street. Oscar Wilde uncharitably called it "a castellated monstrosity" studded with pepper shakers. One of the few buildings that survived the Great Chicago Fire, it remains a civic landmark and a symbol of the city's spirit. The small gallery inside hosts rotating art exhibitions of local interest.

Likened to everything from corncobs to the spires of Antonio Gaudí's Sagrada Família in Barcelona, these twin towers were a bold departure from the severity of the International Style, which began to dominate high-rise architecture beginning in the 1950s. Designed by Bertrand Goldberg and completed in 1968, they contain condominiums (all pie-shaped, with curving balconies); the bottom 19 stories of each tower are given over to exposed spiral parking garages. The complex is also home to six restaurants, including the House of Blues, plus Hotel Chicago, a huge bowling alley, and the marina.

This massive art deco building takes up nearly two square blocks and was the world's largest building when it opened in 1930. These days the neighborhood landmark is known as ground zero for home-design shopping, with the first floor given over to LuxeHome, a vast collection of high-end kitchen, bath, and building showrooms open to the public. The upper floors are lined with trade-only showrooms.

Located in the southwest tower of the DuSable (Michigan Avenue Bridge), this engaging museum provides a glimpse into the complicated history of the Chicago River System and its movable bridges---and has some great city views, too. The Chicago River has undergone an incredible transformation over the past 40 years, from a polluted waterway to a thriving, living river full of wildlife. On lift days visitors can see the gears that still raise the bridge put to work. This is the only bridge house in Chicago that is open to the public. See the website for a lift schedule; reservations are recommended on lift days.

No matter the season, Navy Pier is a fun place to spend a few hours, especially with kids in tow. Opened in 1916 as a commercial-shipping pier and part of Daniel Burnham's Master Plan of Chicago, it stretches more than a half a mile into Lake Michigan. Redesigned and reopened in 1995, Navy Pier underwent another major transformation for its 100th anniversary in 2016, which included the opening of the Polk Bros Park, the Fifth Third Bank Family Pavilion, and the Peoples Energy Welcome Pavilion. Other popular activities and venues on the pier include tour boats and cruises, the Centennial Wheel, the Chicago Children's Museum, and the Chicago Shakespeare Theatre.

This 1989 limestone-and-granite edifice by Skidmore, Owings & Merrill looks back to the art deco days without becoming a victim of fashion's past. Four floors of the 38-story tower are dedicated to a radio and television broadcasting facility.

On the northwest corner of Astor and Burton places in the swanky Gold Coast, you'll find this Georgian building. It was commissioned in 1891 by Chicago Tribune chief Joseph Medill and built by Stanford White. You can't go inside, though, because it's been converted into condos.

Curious about how the wealthy built their urban palaces during America's Gilded Age? Steps away from the Magnificent Mile, the former Samuel Mayo Nickerson mansion has lavish interiors with 19th-century furniture and objets d'art, including pieces by Louis Comfort Tiffany and George Schastey, along with rotating exhibitions related to art, architecture, and design.

North of the Merchandise Mart and south of Chicago Avenue, between Orleans and Dearborn, is a concentration of art galleries carrying just about every kind of work imaginable. Virtually every building on Superior Street between Wells and Orleans houses at least one gallery, and visitors are welcome to stop in. Free tours leave from Addington Gallery at 704 N. Wells on the second Saturday of the month at 11 am; galleries also coordinate their exhibitions to showcase new works typically on "First Fridays" (check the Chicago Gallery News for dates). Although many artists have left this high-rent district for the less expensive, more industrial West Town, there is still a lot to see here, just a 10-minute walk from Michigan Avenue.

Built in 1894 with a courtyard and annexes constructed in 1911 and 1912, the nation's oldest surviving artist studios have been restored and designated a Chicago landmark. Shops, galleries, and event spaces now fill the studios.

Water is still pumped to some city residents at a rate of about 250 million gallons per day from this Gothic-style structure, which, along with the Water Tower across the street, survived the 1871 conflagration. Lookingglass Theatre, located in the same complex, has called this place home since 2013.

The Chicago Sun-Times Building was torn down to make way for this 92-story tower, which was designed by Skidmore, Owings & Merrill and opened in 2008. A spire that elevates its height to a whopping 1,392 feet makes it the city's second-tallest building. The concrete-reinforced structure (the former Sears Tower and John Hancock Center are reinforced by steel) is a glassy, tiered monolith whose biggest attribute is an idyllic riverfront location. Although there's no viewing deck, the public can get picturesque views of downtown through the floor-to-ceiling windows of its 16th-floor restaurant, Sixteen, or the Terrace (open seasonally); Rebar, on the mezzanine level, provides lovely views of the Chicago River and Michigan Avenue Bridge.