From fabulous parks, museums, and restaurants to world-class skyscrapers, entertainment, and even a Great Lake with beaches – Chicago has all of the ingredients of a wonderful American city. Built on a grid system, with Lake Michigan set as the natural border to the east, the Windy City, (to use one of Chicago’s better-known nicknames), is a favorite destination for many and here you will find out why travelers from all around the world flock to this metropolis.
Art Institute of Chicago
The Art Institute of Chicago, located downtown, is one of the oldest and largest museums in the United States. The building is beautifully connected with Millennium Park, where the billowing Pritzker Pavilion designed by Frank Gehry is situated. The institute houses some iconic American artworks such as American Gothic by Grant Wood and Nighthawks by Edgard Hooper, in addition to many European masterpieces like A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat and The Bedroom by Vincent van Gogh. The modern wing designed by Renzo Piano is definitely worth a visit. The Art Institute’s entrance, flanked by two stone lions, is the starting point of the historic Route 66.
The Loop
Downtown, or The Loop as it is better known, displays several pieces of outdoor sculpture free for members of the public to enjoy as they stroll the streets – works from artists such as Pablo Picasso, Marc Chagall, and Alexander Calder are featured.
Chicago Cultural Center
In the South Loop, walking toward the Chicago River, you will pass the Chicago Cultural Center, and while heading north, you will notice the Art Deco Carbide and Carbon Building which stands out because of its black and green color. Opposite to it, on the other side of the river, is the white Wrigley Building (name after the family who founded the popular chewing gums).
In the area, you will notice 111 East Wacker Drive designed by Mies van der Rohe. The German-born architect worked on 15 different projects in Chicago, starting with the Minerals and Metal Building dated 1943. This was the first building completed in the US by van der Rohe until the IBM Building (also in Chicago) was finished in 1973, four years after the architect’s passing. The Chicago Federal Center (1974) is one of the best examples of his works in the Windy City.
Magnificent Mile
Along the river, you’ll also find the iconic Marina Towers and the Chicago Tribune Building located on Mag Mile (this is the nickname Chicagoans call Michigan Avenue, considered by locals as their ‘Magnificent Mile’ for the beauty of the buildings and stores that face onto this mile-long street).
Chicago Board of Trade
On the West side of downtown, do not miss taking a stroll around the financial district to admire one of the Art Deco masterpieces the city has to offer, the Chicago Board of Trade, with its Cerere statue dominating the building.
Driehaus Museum
The Driehaus Museum exemplifies what the architecture of Chicago’s affluent residents would have looked like in 19th century Chicago. Nestled downtown two blocks west of Mag Mile, this gem of a museum exhibits 19th and early 20th-century art and design with a focus on Art Nouveau posters and Belle Epoque luminaries.
To enjoy Chicago’s architecture at its best, if you are visiting in October, check out Open House Chicago. It is an annual weekend event organized by the Chicago Architecture Foundation where more than 200 hidden gems spread around the city are open to the public for free.
Be sure to dedicate one solid morning or afternoon to strolling around prime residential neighborhood the Gold Coast. During October, Chicago is adorned with pumpkins and spooky Halloween decorations, and a walking tour of the houses in Gold Coast will showcase some of the most elaborate festive schemes in town. The former mansion of Playboy founder Hugh Hefner, on 1340 N. Parkway, is where he hosted legendary parties before moving to L.A. in the 70s.
Frank Lloyd Wright
Before Frank Lloyd Wright was an international name in architecture and design, he spent the formative part of his career in Chicago, as evidenced by some of the buildings and houses peppered throughout the city. But to discover early work, you have to leave downtown and head west, where, approximately half an hour by train or car, you can reach Oak Park, the village where Frank Lloyd Wright had his first house and studio. Here you can tour these buildings and walk around to discover the other projects he designed in this studio.
Top tips: If you are in the area at lunchtime, pop into Winberie’s which offers a broad traditional American menu with great choices for vegans and anyone with food allergies. On your way back, stop at the Garfield Park Conservatory, an oasis of plants from all around the world displayed both inside and outside.
The Rookery
On your stroll around Chicago following Frank Lloyd Wright’s works, do not miss the chance to visit the financial district of Chicago, particularly The Rookery, a historical landmark famous for its lobby and one of the most iconic buildings in the city. Then head south and visit Hyde Park. Here is one of the better-preserved examples of Wright’s architecture in the city, Robie House. The house is near the historic campus of the University of Chicago, also worth a visit for its buildings designed by some of the world’s most renowned architects (you can click on the university’s official link for a complete map of buildings to visit).
While taking your stroll around the south part of Chicago, do not miss the opportunity to capture the city’s stunning skyline on camera. Head to Promontory Point in Burnham Park for a photography session and while in the area, check out the Museum of Science and Industry.
Boat Cruise
If you’re looking to discover Chicago’s rich architecture from a different perspective, take a boat cruise along the river. Various companies offer architecture tours but try to book one through the Chicago Architecture Foundation. They offer the most comprehensive tours and their expert guides are second to none. Through this tour, you will enjoy spectacular views of the Merchandise Mart as well as heading southwest to discover River City, a magnificent riverside residential project by the architect Bertrand Goldberg.
River tours usually start in spring and end between October and November. Due to unpredictable weather conditions, check the schedule on the company’s website before you book.
Chicago Music Scene
Chicago has an almost century-long blues tradition with the city’s plethora of clubs and venues offering many opportunities to experience the music. Kingstone Mines with its two stages is undoubtedly one of the most popular destinations, while the neighboring B.L.U.E.S. offers a more intimate atmosphere. In the River North area, Blue Chicago is a great place to go to discover more about the history of this genre. The city celebrates its bond with blues with the Chicago Blues Festival, an annual music extravaganza held in June in Millennium Park.
On the other side of Millenium Park is the Orchestra Hall, home to the Chicago Symphony Orchestra directed by Riccardo Muti. On the west side of the Loop is the Lyric Opera housed in an Art Deco building. If you are a fan of rock, punk, metal or hip-hop, you are probably aware that Chicago proudly hosts the Lollapalooza Festival every summer in Grant Park.
Chicago Parks
Beautiful parks spread across the city provide a great escape from the traditional tourist attractions. My favorite season, I have to confess, is autumn when the red and yellow foliage makes every stroll around Millenium Park, Lincoln Park, the Chicago Riverwalk, and the Morton Arboretum nothing short of magical. During Indian summer, if you are lucky enough to be in Chicago when the weather is not too chilly, you can have a lovely time walking outdoors among the beautiful skyscrapers or parks.
Morton Arboretum
Do not miss a visit to Morton Arboretum, the best botanical garden in the city (but to reach it you need to go by car) with a wide variety of species and settings. I find the Japanese garden particularly inspiring because of its origins – it was created shortly after World War II when the two countries fought one another.
Grant Park
Grant Park in the Loop is without a doubt the city’s most famous tourist destination and I am pretty sure that during your stay in Chicago you will pass there at least twice. It includes among its most notable attractions: the Museum Campus, Buckingham Fountain, the Art Institute, Millennium Park and Maggie Delay Park. Another great park is Lincoln Park with its zoo, ponds, and museums. Do not miss the chance to run along the east side of Lincoln Park on Lake Shore Drive for a spectacular view of the green and the blue (or icy, depending on the season) waters of Lake Michigan.
It’s not just leaves and grass that are green in Chicago. Green also refers to the color of the Chicago River on the 17th of March when it is dyed green to celebrate Saint Patrick’s Day.
Union Station
Chicago has been the location for many beautiful films over the years. Do not miss a trip to Union Station – it’s here on the stairs that filmmaker Brian De Palma shot the famous Untouchables’ gunfight between Eliot Ness, played by Kevin Costner, and Al Capone’s sidekick. The Great Hall and the newly restored Burlington Room are beautiful examples of architecture of the mid-1920s. Besides The Untouchables, Chicago has been the setting of many movies from The Blues Brothers and Ferris Bueller’s Day Off to My Best Friend’s Wedding, The Dark Knight, and Transformers: Dark of the Moon. Chicago and its suburbs are also where Home Alone was filmed with the iconic airport scene shot at the O’Hare International.
Chicago Neighborhoods
Pilsen in the Southwest Side of Chicago is definitely worth visiting. Formerly where Mexican immigrants settled in the city (the National Museum of Mexican Art is a testament to the activism of one of the largest Latino organizations in the US), Pilsen is now the Chicago Arts District with a myriad of galleries and street art. Heading downtown, you can spend time taking a stroll around Printers Row, a historic area that used to house publishing businesses. Now a residential area, Printers Row celebrates its roots with The Printers Row Lit Fest, an annual book fair held at the beginning of June.
Chinatown
Among the lesser-known areas of Chicago, Chinatown in the south is worth seeking out especially if you are visiting the town between January and February, during the Chinese New Lunar Year. Besides viewing the traditional parade, you should visit the Chinese American Museum of Chicago which tells the story of Chinese migration to the US and Chicago. While you’re there, have one of the friendly museum staff members read your fortune for the New Year ahead.
Andersonville
In the north of the city is Andersonville, an area first settled by Swedish immigrants. Traces of this heritage are still visible while taking a stroll around the neighborhood with picturesque Scandinavian restaurants and bakeries, charming antique shops, cafés, and furniture shops. The lovely Swedish American Museum tells the story of the immigrant communities. The area is also home to one of Chicago’s largest gay and lesbian communities.
Christmas in Chicago
I know, Chicago winter weather can be brutal (I was there when the city reached its lowest temperature at minus 23 F, and wasn’t pleasant at all, which is an understatement!), but even so, anytime after Thanksgiving is still a great time to visit. Chicago is dressed up in the most beautiful of these seasonal vests and in the weeks leading up to Christmas, some years with the first snowfall already on the ground, there is the most magical feeling throughout the city. Festive vibes abound when the ice rinks open around town, usually about the 18th of November or so. From this time, the Christmas atmosphere illuminates the city, both metaphorically and literally. The main events are the Christmas tree lighting ceremony in Millennium Park, the Magnificent Mile Lights Festival and the Zoo Lights at Lincoln Park. Different seasonal markets pop up around the city, especially in the church halls. The biggest indoor fair (you don’t have to freeze!) is One of a Kind, the event hosted by The Mart, with a vast selection of handcrafted items made by more than 600 hundred artisans from around the US.
One of the better-preserved traditions in Chicago is a lunch at the Walnut Room, the restaurant in Macy’s on State Street, where the Christmas fairies come to each table to sprinkle stardust on the guests to make a wish. Chicago is a city with well-founded commercial roots and also where the famous childhood character Rudolph the red-nosed reindeer was originally created.
Summer in Chicago
Summer is every Chicagoan’s favorite season, and the reason is simple. The weather is finally hot, and people tend to stay in town, enjoying tons of activities, from concerts to movies in the parks, from sunbathing on one of the beautiful beaches to sailing on the lake. The evenings spent relaxing on the city’s rooftops are one of the highlights of the season. Another high point is attending Tuesdays on the Terrace, the Jazz concert summer season organized by the Museum of Contemporary Art. Enjoy music and food whilst lying on the grass. It’s a kid-friendly event too. The summer season ends with the Chicago Expo at Navy Pier, the leading contemporary art fair in the Windy City.
Have you ever been to Chicago? Are you planning a visit soon? I have lived in Chicago for nine years so this city guide written from a local point of view and not exhaustive of tons of entertainment opportunities, restaurants, shopping malls, and restaurants.