Chicago, IL

Settled in the 1780s, it's possible that Chicago was explored as early as 1679 -- when the first reference to the city was made by Robert de LaSalle, a French explorer who focused on the Great Lakes Region. He wrote about a place called "Checagou" in his memoir, where he claimed the name came from the "quantity of garlic which grows in the forests."

By 1833, the town had roughly 200 residents. Within seven years, that number had exploded to more than 4,000 -- mainly due to the important lakefront location. In 1893, the city hosted the very first World's Fair. The event set a world record for attendance, with more than 751,000 attending.

During the 1920s and the era of Prohibition, Chicago became the setting for some infamous gangsters, including Al Capone and Bugs Moran. In 1929, the St. Valentine's Day Massacre took place in the city, when Al Capone and his gang took on Bugs Moran and his gang.

Chicago's culinary scene is nothing short of legendary, earning its reputation as one of America’s great food cities. The city is world-famous for two iconic staples: deep-dish pizza, with its buttery thick crust and layers of cheese and toppings, and the Chicago-style hot dog — a beef frank loaded with toppings and served on a poppy seed bun (just don’t ask for ketchup). Beyond these beloved classics, Chicago’s diverse neighborhoods serve up a host of global cuisines. From 18th Street taquerias in the vibrant Pilsen neighborhood to Michelin-recognized dining in the West Loop’s Fulton Market district, there’s something for every palate and every budget.

Food lovers will also find no shortage of culinary events to keep them engaged year-round. Grant Park’s Taste of Chicago, the city’s largest food festival, showcases Chicago’s dining diversity across a wide range of vendors and local restaurants. Whether you’re craving Polish, Vietnamese, Italian, or New American cuisine, Chicago’s diverse heritage and neighborhood food traditions mean bold flavors are never far away.

Chicago is one of the most transit-friendly cities in the United States, and many residents rely on the Chicago Transit Authority (CTA) to get around. The CTA's iconic "L" train system, named for its elevated tracks, runs eight color-coded lines that connect neighborhoods across the city to the downtown Loop, with two of those lines extending directly to O'Hare International Airport and Midway Airport, making air travel incredibly convenient. The CTA also operates an extensive network of bus routes that fill in the gaps the train doesn't cover, giving residents a comprehensive public transit system no matter where they live. For those commuting beyond city limits, the Metra commuter rail connects Chicago to the broader region, making it a go-to option for suburban workers.

For drivers, major interstates like I-90 and I-290 serve as key arteries in and out of the city, though like most major metros, peak-hour congestion is something commuters learn to plan around. Chicago is also a remarkably walkable and bikeable city, with extensive sidewalks, dedicated bike lanes, and the beloved Chicago Lakefront Trail stretching nearly 18 miles along the shores of Lake Michigan. Cyclists and runners also love the 606, an elevated greenway trail in Logan Square that winds through vibrant neighborhoods. The city's Divvy bike-share program adds even more flexibility, letting residents and visitors pick up and drop off bikes at hundreds of stations citywide. Whether you're commuting downtown or exploring neighborhoods on a weekend, Chicago offers a wealth of ways to get where you're going.

Chicago is a city where green spaces thrive alongside its iconic urban landscape. Millennium Park, one of the most visited parks in the country, anchors the lakefront experience with its famous "Cloud Gate" sculpture (affectionately known as "The Bean"), an outdoor concert pavilion, and a seasonal ice skating rink all just steps from the Art Institute of Chicago and the Loop neighborhood.

Nearby, Grant Park serves as the city's "front yard," hosting major annual events like the Taste of Chicago culinary festival and Lollapalooza, the internationally renowned music festival. On the North Side, Lincoln Park is home to the beloved Lincoln Park Zoo, one of the few free admission zoos in the country, offering up-close encounters with apes, big cats, sea animals, reptiles, and more, along with seasonal events like Zoo Lights during the holidays and outdoor summer concerts.

Beyond these marquee destinations, Chicago's park system stretches along miles of stunning Lake Michigan shoreline, giving residents access to beaches like Oak Street Beach and 12th Street Beach, perfect for summer relaxation. The 606 Trail in Logan Square offers a popular elevated greenway for walking, running, and cycling through vibrant neighborhoods. Chicago also sits within driving distance of the Indiana Dunes National Park, roughly 50 miles southeast of the city, a stunning natural escape featuring towering sand dunes, scenic hiking trails, and freshwater beaches along Lake Michigan, offering a welcome contrast to the bustling city life.

The average rent in Chicago is $2,008 per month, based on one-bedroom pricing, though costs vary depending on the size of the unit. Studio apartments average $1,599 per month, one-bedrooms come in at $1,966, two-bedrooms average $2,480, three-bedrooms average $3,010, and four-bedroom units average $3,838 per month. Rent prices have been trending upward across all unit sizes, with year-over-year increases ranging from 3.4% to 5.7%. The median household income in Chicago is $69,230, providing some context for the city's overall affordability.

Chicago's rental market sits notably above the Illinois state average of $1,672 per month for a one-bedroom apartment, reflecting the city's status as a major metropolitan hub. With a population of over 2.5 million residents and a population density of approximately 10,757 people per square mile, Chicago ranks among the most densely populated cities in the country, factors that contribute to its rental pricing.

No conversation about shopping in Chicago is complete without mentioning the Magnificent Mile, the city's most celebrated stretch of Michigan Avenue. Spanning several blocks through the heart of the city, the Mag Mile draws millions of visitors and locals alike with its designer boutiques, major department stores, and multilevel urban shopping centers. Anchoring the strip is Water Tower Place, a six-story indoor shopping destination that has been a Chicago institution since 1975, situated next to the historic Water Tower and the John Hancock Building. Beyond the Magnificent Mile, the State Street corridor in the Loop has long been a shopping destination in its own right, home to storied department stores and a lively street-level retail scene that reflects the city's commercial roots.

Chicago's neighborhoods round out the shopping experience with distinct personalities. Wicker Park and Bucktown along Milwaukee Avenue attract shoppers with their eclectic mix of independent boutiques, vintage shops, and local designers, while Lincoln Park and Lakeview offer a walkable blend of retail and restaurants perfect for an afternoon out. For those who love open-air markets, the city hosts a robust Chicago Farmers Market program at multiple locations throughout the summer and fall, including popular spots at Daley Plaza and Logan Square. Shoppers who want it all at once can take advantage of the Chicago Pedway, a six-mile network of underground and indoor walkways connecting major retail hubs across downtown, making it easy to explore the city's shopping scene no matter the weather.

When comparing Chicago to cities in Canada, Toronto is very similar with access to the Great Lakes and diverse communities.