Chicago: Your Ultimate Guide to the Cool Windy City
Chicago, the Windy City on the shores of Lake Michigan, is the big metropolis between New York City and Los Angeles that we know as the heart of the United States. Skyscrapers were born here in the late 19th century, using modern construction techniques that were replicated in Manhattan and shaped the dazzling skyline of both cities. Since then, Chicago has evolved into a major cultural, transportation, and culinary hub. Today's city is vibrant, with a vast array of attractions in the Loop (Chicago's downtown) and the Magnificent Mile. The city boasts exquisite dining, delightful shopping, and breathtaking observation decks at the top floors of the Willis Tower (formerly Sears Tower) and the John Hancock Center.
How many days do you need for a trip to Chicago?
For a trip to Chicago, it's worth setting aside at least three full days.
Chicago is a city you must stay in for a few nights, preferably in the city center.
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Here are 8 tours in Chicago that will delightfully and comprehensively present everything you need to see and experience in the big city 🤗
- Cruise on the Chicago River with a guide on the city's skyscrapers
- Guided Sightseeing Tour at Chicago's most famous sites + tastings
- Guided tour in Downtown Chicago following the gangsters
- Guided ride tour in Chicago (Segway, electric bicycles, or regular bicycles for those in shape)
- Guided tour at the Art Institute of Chicago
- Guided tour following the movies and series filmed in Chicago
- Guided culinary tour of downtown Chicago's food scene
- A particularly sweet guided culinary tour following the donuts of Chicago
15 Must-see and do things in Chicago
- Amazing view from the 103rd floor of the Willis Tower (formerly Sears Tower)
- Spend time with the kids at the mall, museum, and restaurants at Navy Pier + stunning city view
- The rare art collection at The Art Institute of Chicago
- View from the 94th floor of the John Hancock Center over the Magnificent Mile
- The light show of Buckingham Fountain at night in the heart of Grant Park
- Selfie with the Bean, Cloud Gate sculpture at Millennium Park
- The unusual architecture of the Jay Pritzker Pavilion
- The stark and imposing view of the Federal Center in downtown Chicago
- Classic shopping at Macy's Chicago
- Wander the Magnificent Mile from DuSable Bridge to the upscale E Oak Street
- The ancient symbol of Chicago – The Historic Water Tower
- The magnificent clock tower of The Wrigley Building
- The jaw-dropping Gothic top of the Tribune Tower
- Stroll in the gallery district of River North neighborhood
- Catch a Bulls basketball game at the United Center or a Bears football game at Soldier Field (or a Cubs or White Sox baseball game)
Click here for all the info on touring the Loop, downtown Chicago
Click here for all you need to know about the Magnificent Mile tour in Chicago…
Click here for all the info on Chicago's professional sports teams…
Click here for the Chicago CityPASS, five top attractions in Chicago at a discount…
What is Chicago?
Chicago is the third largest city in the United States, after New York City and Los Angeles. The city itself is home to nearly three million people, and its vast metropolitan area, known as Chicagoland, includes about nine and a half million residents, extending into the neighboring state of Indiana.
- Chicago is the largest city in the Midwest of the USA and in the state of Illinois (though it is not the state capital, which is Springfield) and the main urban center of the Great Lakes.
- Chicago is located on the western shore of Lake Michigan.
- The Chicago River runs through the city center and flows into the lake at Navy Pier.
- Due to its location on the lake and the intensifying winds between the buildings, it earned its famous nickname, The Windy City.
- The city has a few nicknames, such as the City of Big Shoulders and the somewhat disparaging nickname – The Second City (guess who's first?!)
Click here for a cruise on the Chicago River…
The historic core of the city was Fort Dearborn, established by the American army on the Chicago River in 1803. The fort no longer exists, but its location was at the southern tip of the DuSable Bridge on Michigan Avenue.
About thirty years later, on August 12, 1833, the city was officially established and developed with the construction of the Illinois and Michigan Canal, officially inaugurated in 1848. With the canal opening, the city connected to the railway system and became a critical transportation hub for moving goods westward and developing the Midwest, the Rockies, and the Pacific coast.
Click here for a spicy food tour through Chicago Chinatown's culinary gems…
Chicago after the Great Fire of 1871
- On October 8, 1871, the Great Chicago Fire devastated the city's center
- As a result, the city decided on a rehabilitation plan and adopted modern construction plans for the time, including building with concrete and metals
- In 1884, the first modern skyscraper was born in the city – the Home Insurance Building, which rose to a height of 42 meters
- Afterwards, the Chicago School transformed the city's center into the first downtown in the USA characterized by skyscrapers
- The talented architects of the school, such as William Le Baron Jenney, Daniel Burnham, and Louis Sullivan, spread the message throughout the USA, especially in Manhattan. At the start of the 20th century, there was an open and healthy competition between New York and Chicago for building skyscrapers, with Manhattan officially taking the lead only in the 1930s with the construction of the Empire State Building and the Chrysler Building.
Chicago grew rapidly until the end of World War II. The city developed a heavy industry and attracted many immigrants from the southern parts of the U.S. and around the world as a labor force. With suburbanization in the 1950s, the city faced a population flight, and the neighborhoods around the financial district became poorer. It was only in the 1990s that gentrification began, bringing a strong population back to the city. This process has been somewhat disrupted in recent years, and large parts of the downtown are deteriorating again.
Chicago in Popular Culture
Chicago is one of the roughest cities in America, and it's prominently reflected in popular culture. In the 1920s, the Chicago Mafia, or The Chicago Outfit, was active in the city during the turbulent Prohibition era. The most famous of the city's gangsters was Al Capone, who came to the city from New Jersey.
The peak of the mafia's mythology in the city was the event of the Saint Valentine's Day massacre in 1929, where Capone's men murdered the rival gangster Bugs Moran's men. Chicago's mafia stories ignited the imagination, transforming the city into an icon of mob violence.
Click here for a guided bus tour following the mafia and criminals of Chicago…
The roughness of Chicago also continued in popular culture, and the city was home to some of America's most iconic TV shows (although everything was actually filmed in Hollywood). The legendary ‘Married… with Children,' known and pioneering among sitcoms set in the city, expressed the city's spirit through the unforgettable character of Al Bundy (Ed O'Neill). The hospital series genre was very common in the city, including shows like ‘Chicago Hope' and ‘ER.'
The most famous cult movie associated with the city is ‘The Blues Brothers,' filmed in the city in the early eighties. The eighties films by Howard Hughes (starring Molly Ringwald) were also shot in Chicago.
Chicago's Food
Just like its representation in popular culture, Chicago's food scene is also very gritty. The city is known as the birthplace of some of the most iconic and extremely unhealthy foods in the American culinary scene.
Click here for a tour of Chicago's unique culinary secrets….
- In the fast food realm, the city is where McDonald's became the American icon that took over the world. Established in 1940 in San Bernardino, within the Los Angeles metropolitan area, the hamburger restaurant was moved by the initiative of Ray Kroc to Oak Brook, west of Chicago, in the early '60s. Kroc cracked the code, managing to combine speed with an economic franchise system, leading with his own hands the fast food wave that still washes over the globe today. McDonald's headquarters remains in Chicago, a city synonymous with the brand.
- The city boasts a long list of foods identified with it, like the Chicago Deep Dish Pizza. This calorie-loaded pie is a culinary must in the city.
- Additionally, the city is famous for its diverse sausages, linked to the immigrant population such as Polish sausages, German sausages, and collectively known as Chicago hot dogs. The city offers excellent ethnic restaurants, including Chinese restaurants in Chinatown and particularly fine Italian restaurants
- Chicago is considered one of the most attractive cities in the United States from a culinary perspective (not for its sophistication, but mainly for the fun and joy of indulging in greasy, fatty delights). The city's restaurant scene is dynamic and evolving, featuring several long-standing establishments where you'll need to wait in line to taste (and it's definitely worth it)
Click here for a guide to the culinary gems of Chicago's Chinatown…
Click here for a food tour of Chicago's unique culinary secrets….
Map of Chicago
How to Get to Chicago
How to Fly to Chicago?
Chicago O'Hare Airport (ORD) O'Hare International Airport – The largest airport in Chicago is one of the biggest and busiest in the world. It's the home hub for the airline giant United Airlines and a secondary hub for American Airlines. O'Hare was historically ranked as the largest and busiest airport, but now it's ranked fourth after three other American airports (Atlanta, Dallas-Fort Worth, and Denver). It is located on the northwest edge of downtown, about a twenty-minute car ride from the city center.
O'Hare has three terminals connected to each other and linked by an internal light rail line. Chicago's airport is well-connected with all major airports in the USA, key airports in Europe, and also with Ben-Gurion Airport. It is easy to reach the city with a transfer in Europe or direct flights from American Airlines. Access from the airport to downtown is by the blue ‘L' line, which goes to the Loop.
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Chicago Midway International Airport (MDW) – Originally Chicago's main airport, it now complements the massive O'Hare Airport. Located on the southwest side of the metropolis, it's just a 15-minute drive from downtown. The airport is connected to the city center by the orange L line. It's a great option for those looking to fly within the U.S., with excellent connections to key airports nationwide.
How to get to Chicago by car?
The I-90 is the main highway running through Chicago. It's the northernmost road in the highway system, connecting Boston with Seattle. The 90 stretches across the west side of downtown Chicago, with many branches connecting it to all metropolitan cities. Chicago is where the 90 converges with the I-80, the highway linking New York with San Francisco. The 80 runs south to the heart of Chicago. Highway 94 connects Chicago with Milwaukee (Wisconsin) to the north and continues to Minneapolis (Minnesota).
Public Transportation in Chicago
The Chicago L
Chicago's elevated train system, or the ‘L' for short, is the major city's mass transit system. The trains are operated by the CTA (Chicago Transit Authority), the second-largest urban transportation company worldwide (following New York City).
The elevated train system includes 8 different colored lines, all connecting Chicago's financial center and downtown with the city's outer neighborhoods and suburbs within the vast metropolis. These lines connect with the city's legendary Loop system.
The Loop
The Loop is the historic rail line built in 1882 that once encircled Chicago's financial center. Upon its construction, a streetcar line encircled the city's core, serving as the primary mode of transport. By 1897, Chicago's transit network expanded and the ‘L' rail lines were constructed. Even today, the Loop serves as the route for the ‘L' lines in the heart of Chicago, playing a significant role in defining the city's downtown area.
Click here for an updated map of the L line system on the CTA's website…
Click here for an updated map of the L system in the Chicago Loop downtown area…
When is the best time to visit Chicago?
Chicago is generally a city with a gritty character, reflecting its weather. Chicago winters are quite tough, with temperatures dropping below zero from December to February. These months are snowy and the city is usually covered in white. Summers can be hot and humid, as well as pretty rainy. To hit the jackpot with great weather in Chicago, you need a bit of luck.
- Chicago is an active and lively city all year round. Rain or shine, snowy or not, the city never stops.
- The best season to visit Chicago is in the late spring, from May to July. During these months, there are long sunny days, the weather is generally comfortable, but it can also be quite rainy. June is the wettest month in the city, so be sure to have a good umbrella with you.
- Summers in Chicago are amazing, with weather that can be both hot and rainy, but if you catch the sun, the city is incredibly picturesque.
- Winters in Chicago are white and freezing; for those who love the atmosphere, it's really fun, you just have to dress accordingly. Chicago, being a cold city, knows how to operate during snowstorms, including a fleet of snowplows and lots of salt thrown on the roads. During winter, there are particularly tough storms, and temperatures can plummet to bitterly cold levels.
How to Plan a Trip Itinerary in Chicago?
You can combine Chicago with a wide variety of road trip routes in central America. The major and important city in the Midwest serves as a convenient gateway for long trips through the Great Plains and the cities and attractions of the Great Lakes.
- On a trip along the west bank of Lake Michigan, you can also visit the nearby city of Milwaukee, just a reasonable hour and a half drive from Chicago.
- Chicago is the starting point for a grand tour in the northern part of the Great Plains, along the Mississippi-Missouri river route, including stops in Minneapolis, Saint Louis, Kansas City, Indianapolis, Mount Rushmore and the Black Hills and even Yellowstone National Park.
Exploring Chicago itself is easy to plan, focusing almost entirely on its small center. Chicago’s center is comprised of Downtown (The Loop), the Near North Side, and the Near South Side. Within a compact area, all the important buildings in the city, the museums, and a large portion of the must-visit attractions are concentrated.
- The city's main avenue is Michigan Avenue. In its northern part, the street is known as the Magnificent Mile
- From the upscale shopping street East Oak Street to the north and N. South Side, along the avenue or just a short walk from it, you can find nearly all of the city's important sites such as the John Hancock Center, the historic Water Tower, Wrigley Building, Tribune Tower, Navy Pier, Millennium Park, the Art Institute of Chicago, Grant Park, the Field Museum, and more
- A short walk from the avenue, you can also stroll the downtown streets where historic and modern skyscrapers stand, led by the mighty Sears Tower, or explore the elegant North River district
- North of downtown, in Lincoln Park and the Gold Coast district, there's another collection of historic homes and interesting sites
- South of downtown, in the Hyde Park neighborhood, what's known as South Chicago, there's another cluster of important museums like the Museum of Science and Industry, the Smart Museum, and significant historic houses.
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Everything You Need to Know About Staying and Hotels in Chicago
Staying in Chicago is an especially fun urban experience in the shadow of towering skyscrapers and lively streets full of shopping, restaurants, and entertainment venues. In Chicago's Loop and the Magnificent Mile, there are many hotel establishments located within the city's historic skyscrapers. West of the Magnificent Mile, along the Michigan Avenue stretch in the Near North Side, you'll find great urban hotels at more modest prices in the elegant River North district.
The Best Neighborhoods to Stay in Chicago
- The Magnificent Mile – Historic hotel institutions
- River North District – Boutique hotels and three-star hotels in the central district
- Downtown Chicago – The Loop – Urban hotels in the shadow of America's tallest skyscrapers (except Manhattan)
- O'Hare Airport Hotels – Modern business hotels and motels
Map of Accommodation Areas in Chicago
Millennium Park and the Museums of Michigan Avenue
Grant Park has always been the green lung of Chicago. This urban park, which separates the skyscrapers of downtown from the shore of Lake Michigan, is now entirely dedicated to the city's tourism movement. In its past, the park housed two high-profile attractions, the massive Buckingham Fountain and The Art Institute of Chicago, which boasts an utterly impressive collection of paintings significant in art history.
As the millennium drew to a close, the city decided to spice up the tourist space. In the northern part of the park, the unique postmodern attractions of Millennium Park were opened. The park features several amazing structures that quickly became city icons, such as the Cloud Gate sculpture and the chaotic theater pavilion designed by Frank Gehry.
What are Millennium Park and the museums of Michigan Avenue?
Millennium Park is one of Chicago's most popular attractions. The park is part of the city's historic Grant Park, located on the eastern side of the Loop near the shore of Lake Michigan.
- Grant Park is the green lung of downtown Chicago. At the beginning of the 20th century, the city decided it would also be a cultural center for the public's enjoyment
- The Art Institute of Chicago was opened in the park, one of the most important museums in all of the USA
- In the heart of the park stands the monumental Buckingham Fountain, which has become one of the city's symbols
- Toward the end of the second millennium, the city wanted to rejuvenate the park, and its entire northern section was branded anew as Millennium Park. Throughout this section, several attractions were built and positioned, quickly becoming cherished landmarks noted for their stunning beauty
- The shiny Cloud Gate, shaped like a bean, gained popularity and became one of the city's favorite attractions
- Nearby, the pavilion named after Jay Pritzker, an open urban amphitheater, captures the eye with its stunning acoustic shell structure designed by the renowned architect Frank Gehry.
- Today, Grant Park, Millennium Park, and the museums on Michigan Avenue, led by the Art Institute of Chicago, are considered the public and tourist heart of the city, along with Navy Pier located slightly north by the lake.
Click here to purchase online tickets for the Art Institute of Chicago…
Downtown Chicago – Birthplace of Skyscrapers
Downtown Chicago is the towering and historic heart of the grand city. Within the square formed by the Loop, modern urban construction concepts were born at the end of the 19th century. It is in downtown Chicago that the first skyscrapers were built, and where the urban construction techniques characterizing all Western cities were developed.
The early high-rise office buildings were designed as part of the city center's reconstruction after the Great Fire of 1871. The massive Sears building dominates downtown Chicago south of the Chicago River. Nearby are bustling streets filled with restaurants, hotels, and shops, in the shadow of some of the most spectacular skyscrapers in the world.
Click here for all the info on touring the Loop, downtown Chicago
What is the Loop or downtown Chicago?
- This is the legendary area of the Loop elevated train line, Chicago's former tram line
- Downtown Chicago is also the historic core of the city, the part that burned in 1871 and the place where the concept of skyscrapers was born (as a recovery from the fire)
- It is the financial center of the city, home to some of the tallest and most famous skyscrapers in the world
- The main boulevard of downtown is Michigan Avenue, which crosses the city center from north to south. The avenue borders the waterfront's green parks on the west side, adjacent to Lake Michigan. The section in downtown Michigan Avenue is an extension of the Magnificent Mile, north of the riverbank, where you'll find grand institutions such as the city's major museums, key urban hotels, headquarters of large corporations, and various cultural venues.
- Exploring the Loop or downtown Chicago means wandering through bustling streets filled with restaurants, businesses, office buildings, and hotels, all under the towering shadows of Chicago's legendary skyscrapers.
The Magnificent Mile – Magnificent Mile
The Magnificent Mile is the liveliest and most attractive part of Chicago. Along Michigan Avenue, an incredible array of everything luxurious and stunning in Chicago unfolds. Towering above the avenue is the dark and iconic John Hancock Center. Beneath it lies the historic Water Tower and Pumping Station, a magnificent neo-Gothic structure that is the only one on the avenue to have survived the Great Fire of 1871. In the southern part of the Magnificent Mile, a line of vintage skyscrapers can be found, headed by the Tribune Tower, the InterContinental Hotel Tower, and the stunning Wrigley Building.
Click here for all the information on touring Chicago's Magnificent Mile, north of the river…
What is Chicago's Magnificent Mile?
- The Magnificent Mile is the prestigious part of Chicago. It stretches in the southern section of the Near North Side district, with Michigan Avenue being the main thoroughfare of the area.
- The stretch between the Chicago River and the DuSable Bridge to the south and Oak Street to the north is often referred to as the Magnificent Mile.
- Along the avenue, you'll find a stunning array of historic skyscrapers, modern high-rises, breathtaking neo-Gothic churches, the charming Water Tower, and the towering John Hancock Center.
- The area suffered greatly from the Great Chicago Fire in October 1871, and its restoration played a key role in the city's revival.
- This is Chicago's upscale district with luxury shops, luxurious hotels, gourmet restaurants, and (luxury) galleries.
- Just north of where the Chicago River meets Lake Michigan is Navy Pier, the bustling pier now considered a top city attraction alongside nearby Millennium Park (a bit to the south in the Loop).
- To the west, the River North neighborhood is a fantastic place to explore, filled with amazing galleries and restaurants.
Near North Side and North Chicago
Chicago's Near North Side brilliantly combines luxury residences, towering modern skyscrapers, vintage skyscrapers from the early century, upscale shopping, and plenty of attractions. North of the Magnificent Mile, the legendary Michigan Avenue, lie more luxurious and less grandiose neighborhoods. The Gold Coast is a fascinating neighborhood, a hub of luxury residences in the late 19th century, north of it is the large Lincoln Park and the Old Town Triangle district.
What is Chicago's Near North Side and North City?
Chicago's center is divided into three major districts from north to south – the Near North Side, the Loop (downtown), and the Near South Side. Within these major districts are autonomous neighborhoods and areas meant for urban living. These areas boast a bustling main street filled with restaurants, shops, and entertainment venues.
- North of the Chicago River, in the southern part of the Near North Side, is the Magnificent Mile, one of the most upscale and bustling areas in all of America.
- Michigan Avenue north of the river is the third most expensive street (in terms of rent per square meter for a business) in the USA, following Rodeo Drive in Beverly Hills near Los Angeles and Fifth Avenue in New York City. This area features an astonishing concentration of skyscrapers, some vintage from the late 19th and early 20th centuries and some sleek and modern.
The northern part of the Near North Side is less crowded and intense in terms of skyscrapers, corporate headquarters, and additional commercial functions. The neighborhood area of Gold Coast, Old Town Triangle, and North La Salle Drive is characterized by luxury residences, historic mansions, and wonderful museums.
This part of the upscale district (Near North Side) is bordered to the north by the large Lincoln Park, which houses the city's zoo and excellent beaches for swimming, known as North Avenue Beach.
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Sports Events and Teams in Chicago
Sports in Chicago are part of the very fabric of this proud city. Chicago boasts major professional sports teams in all popular sports – basketball, baseball, football, and hockey. Chicago's teams are considered among the elite and most renowned in professional sports leagues across the board.
Click here to purchase online tickets for the Cubs baseball games at Wrigley Field…
Click here to purchase online tickets for the Chicago White Sox games…
- The Chicago Bears, one of the crucial historic football teams, represent the city in the NFL.
- The tough hockey team, the Blackhawks, represents Chicago in the NHL.
- The city's two baseball teams – the White Sox and the Cubs – bring a longstanding rivalry and electrifying games (especially for this not-so-intense sport)
- The legendary sports team of Chicago is undoubtedly the city's representative in the NBA league. The Chicago Bulls are closely linked to the mythical figure of Michael Jordan, the greatest basketball player in history and one of the most famous and important athletes in the world. Jordan was the one who turned the athlete into a mega-celebrity and led the Bulls to total dominance in the NBA during the 1990s.
- The city's women's basketball team in the WNBA, Chicago Sky, is also considered one of the best in the league.
- The city's soccer team in the MLS, Chicago Fire FC, is also regarded as one of the top teams in the less exciting professional league (soccer is best saved for a trip to Europe).
Click here for all the info on Chicago's professional sports teams…
