Here’s what I love about Chicago, and why you should go now

If you simply read the headlines about Chicago, you might be scared to visit and question why people live there. Reports of crime and homelessness are plentiful, so it’s a question many of us who willingly live here get asked.

Chicago has lost residents over the past several years, but that is often attributed to high taxes — not to crime or other big-city troubles. There are lots of reasons to live in Chicago and even more reasons to visit. Here’s why I love Chicago and why it might be worth taking a trip there now.

Chicago is one of America’s best big cities

Growing up in St. Louis, Chicago always represented “the big city” to me. I have countless memories of visiting, including when I celebrated my 21st birthday at Carmine’s on Rush (RIP), got on Wrigley Field for my birthday and saw “Happy Birthday Caroline” displayed on the big screen at then-Comiskey Park.

Over time, Chicago became “the big city” I dreamt of living in. In 1998, when walking ahead of my parents as I tended to do, I turned around and declared that I was going to live on Michigan Avenue one day. Twenty-four years later, my dream came true.

Here’s what visitors should know.

It’s the most accessible US metro

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With nearly 3 million people, Chicago is the third most populous city in the U.S., behind New York City and Los Angeles. One of the things I love most about Chicago is that, even with that many people, you don’t need a car to get around.

There are two key transit systems that operate in the greater Chicagoland area: the Chicago Transit Authority L train and bus system services the city, while the Metra connects downtown to the suburbs. The CTA system is easy and cheap to use ($2.50 for L train, $2.25 for bus one-way). The L (short for “elevated” train) is the quickest and most affordable option to get to Chicago Midway International Airport (MDW) and O’Hare International Airport (ORD) via the Orange and Blue lines, respectively.

However, I generally prefer the bus for a few reasons: It’s above ground the entire time (thus more temperature controlled), it’s easier to access and it feels safer to me since it’s a smaller space that remains entirely in view.

If you prefer to travel on foot, that is also possible, particularly if you are starting from one of the downtown neighborhoods, including Streeterville, River North, the West Loop, Gold Coast and the Loop.

My favorite walk to take in Chicago is just under 3 miles. Start at Oak Street Beach in Gold Coast, walk along Lake Shore Drive and Lake Michigan to Lincoln Park, and continue on Stockton Drive through the park to Fullerton Ave before cutting over to North Lakeview Ave, where you can admire some beautiful homes. Be sure to stop by my favorite farmers market — the Green City Market in Lincoln Park — if you’re there on a Saturday in season.

Walking north, south and east is the easiest route. While you can walk from downtown to a western neighborhood, the walk is not nearly as pleasant. Thus, I would recommend public transit if going in that direction.

Uber and Lyft rides are plentiful, while cabs are more limited but available downtown. Chicago traffic can be heavy, particularly heading south on Lake Shore Drive, north on the Kennedy Expressway to ORD and the northwest suburbs, and west to West Town and beyond.

Another alternative to avoid traffic is hopping on a Divvy bike. Chicago is one of the most bike-friendly cities, so much so that even I (someone who hadn’t biked since childhood) was able to navigate across the city. We have the second-highest percentage of bike-to-work commuters, per the city of Chicago, with more than 300 miles of bike lanes, including 19 that border Lake Michigan.

For a city tucked in the middle of the country, Chicago also has an impressive amount of beaches — 29 to be exact — all along the Lake Michigan shoreline. The winding Lakefront Trail knits these beaches together with a series of parks and 18 miles of bike lanes, making for one of the most scenic rides around town. The trail itself is a reason why I think biking is one of the most fun ways to see Chicago.

It’s the most affordable major domestic city

Of the country’s largest urban areas (New York City, Los Angeles, Boston, San Francisco, Miami and Washington, D.C.), Chicago is the most affordable, per data from Bankrate’s Cost of Living Calculator. The cost of living in Chicago compared to other major cities is as follows:

• 50.17% lower than Manhattan
• 32.82% lower than San Francisco
• 23.8% lower than LA
• 21.59% lower than Boston
• 21.27% lower than Washington, D.C.
• 3.62% lower than Miami

The data is based on housing, food and lifestyle costs, including clothing, entertainment and personal expenditures. Having lived in New York and Washington, D.C., the most noticeable cost of living decrease for me has been the cost of renting a large one-bedroom apartment downtown. Various sources cite the average one-bedroom rent in Chicago (across all neighborhoods) to be somewhere between $1,900 and $2,100, per Zillow, Apartments.com and Rent.com.

As a SINK (single income, no kids), I deeply feel the financial savings of living here.

You can find affordable flights using points or miles

Chicago can be a real bargain when planning a visit, too. Round-trip flights are often less than $300 from most cities in America. Just a few examples: You can find a round-trip ticket from New York to Chicago for a long weekend this June for $123 on Spirit, $189 on Southwest or $225 on American Airlines.

If you’re coming from Houston, we found flights ranging from $138 (on Spirit) to $217 (United, American or Southwest). From San Francisco, there were flights as low as $207 round-trip on United.

Points can make for a great deal option, too — though generally, cash prices are cheap enough that it usually makes more sense to save those points. Still, we found widespread availability for 17,000 American Airlines AAdvantage miles round-trip, and sometimes as low as 12,000 miles for coach tickets from cities like New York.

Hotel prices aren’t cheap, but there are deals to be had

Hotels in Chicago can get pricey depending on the time of year and what conventions are in town, but you can often find some good deals nonetheless, especially compared to other big cities like New York City.

A quick Google search of hotels in June showed lots of great options under $300 a night.

Of course, there are some fabulous points hotels in Chicago, including from Hilton, Hyatt, IHG and Marriott. A quick search of Hyatt hotels for the same weekend showed points bookings for as few as 18,000 World of Hyatt points per night.

One of my favorite Chicago hotels — Park Hyatt Chicago — was just 29,000 World of Hyatt points per night.

Midwest nice is a real thing

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Despite growing up in the Midwest, I had never heard the phrase “Midwest nice” until Chicago. This term refers to the demeanor of Midwesterners, who are generally polite, passive, helpful and nonconfrontational.

I’ve experienced this behavior in random interactions with strangers — people strike up a conversation while standing on a street corner, shopping, eating out or waiting in line for coffee. Chicagoans like to talk — myself included. And, although this is specific to my experience, I have found Chicago to be the easiest place to build a community, including by frequenting fitness studios. In my experience, people in Chicago are social and want to make friends.

If you’re not a student, there are various organizations and activity-based groups where you can meet people, including East Bank Club, Sunday Morning Club, Chicago Girls Who Walk, dating events and running clubs. There’s also a large intramural sports culture, particularly for tennis, with more than 534 public courts. These groups can help Chicago feel less provincial, especially when you are not a Big 10 alumni or from the Chicagoland area.

Having lived in Chicago as a 20-something and a 30-something, I’ve observed the city to be full of transplants like myself looking to make friends if you put yourself in places to meet them.

Chicago is also a huge sports city. Whether it’s rallying around the city’s teams or your local NFL or college football team, there is likely a designated neighborhood bar where you can cheer on your team. Even if you don’t like the sport, go to a bar with vibes you do like, and you’ll likely end up talking to new people at the very least.

And if all else fails, take yourself for a walk around one of Chicago’s 100 neighborhoods. Walking around and enjoying the architecture is my favorite Chicago activity.

There is a lot to do (for free, too)

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Even though Chicago feels distinctively Midwestern, it offers all that you would find in a cosmopolitan city, from diverse restaurants, national theater performances, music shows and festivals, year-round professional sports games (two MLB teams, one NFL team, one NHL team, one NBA team, one WNBA team and one MLS team), 80-plus farmers markets, and many cultural institutions/museums and international events.

I frequently get asked about my favorite local restaurants. This is a city of restaurants (7,300-plus), and so many of them are amazing. My personal favorites by neighborhood include:

• Lincoln Park: Armitage Alehouse, Athenian Room
• West Loop/Fulton Market: Duck Duck Goat, Kumiko
• River North: Planta
• Old Town: Doma Cafe
• Logan Square: Lula Cafe
• Lakeview: Wheat’s End
• Southport: GC’s Chicken Shop
• Wicker Park: Handlebar, Bloom

I also have many recommendations for bakeries, coffee, health food stores, smoothies and juices:

• Bakeries: Raw and Ingrained (River North), both of which serve my gluten-dairy-free needs
• Coffee: Ground Up (River North and the West Loop)
• Health stores: Bonne Sante (Hyde Park) and Chicago Health Foods (Gold Coast)
• Juice: Dharma Delights, primarily sold online but also available at certain outposts, including Zen Yoga Garage (my favorite yoga spot)
• Smoothies: Pure Green (multiple locations)

Many tourist attractions are free, including my top walk spots — the Riverwalk and Lakefront Trail. Other free highlights include Millennium Park, the Bean, the Chicago Cultural Center, the Buckingham Fountain, Garfield Park Conservatory, Harold Washington Library Center (one of largest public libraries in the U.S.), Lincoln Park Zoo and Conservatory, and the 606 Trail.

Visit Chicago on a summer weekend, and you’re pretty much guaranteed to run into an event, such as Lollapalooza, EEEEEATSCON, Pride Parade, Windy City Smokeout, NASCAR Street Race Weekend, Pitchfork Musical Festival, and Chicago Air and Water Show to name a few. Nearly every neighborhood has a food fest during the summer, too. Seasonal events continue in the fall and winter, such as ice skating in Millennium Park, Christkindlmarket and ZooLights, among others.

Music and arts fans can enjoy one of the 40 annual film festivals, 74 yearly music festivals and 250 live music venues.

If you’re going to visit Chicago and pay for one thing, I recommend booking an architecture boat tour (at night). These boat tours never get old to me: You can enjoy an open-air upper deck and interior views of some of the city’s most beautiful buildings while hearing their history narrated in a funny and informative way. Tours are offered year-round, weather permitting.

With more than 600 parks and 500 playgrounds, Chicago is family-friendly.

Chicago has its cons

The city is racially and ethnically diverse but segregated

Chicago is neighborhood-centric, and many residents stick to their neighborhoods day-to-day. Like many other U.S. cities, Chicago has gentrified over time. Nearly half of Chicago neighborhoods experienced a “rapid increase in housing costs (an increase above the regional median) between 2000 and 2017,” per the Urban Displacement Project.

Based on 2023 U.S. Census data, the largest racial makeup of Chicago residents are white (42%), black (29%) and Hispanic/Latino (32%). But lower-income households continue to be priced out from the city’s moderate-to-high-income neighborhoods that offer desirable schools, grocery stores, parks and other community advantages. As a result, neighborhoods in Chicago can largely be homogenous, depending on where you live.

Even so, Chicago has several culturally diverse neighborhoods, including Little Italy, Chinatown, Pilsen, Uptown, Rogers Park, Albany Park, Hyde Park and Humboldt Park.

Leaving my neighborhood has helped me appreciate the melting pot that makes Chicago a great place to live.

Chicago generally feels safe, despite statistics

One of the most common narratives about Chicago is that it is not safe. Crime statistics suggest some things are getting better, though some violent crime has increased.

In 2023, homicides and nonfatal shootings decreased by 12% and 14%, respectively, while overall violent crime and citywide robberies increased (14% and 40%) from the previous year, per the University of Chicago Crime Lab End of Year report. This report notes that crime disproportionately affects black victims and areas with minority residents, including District 11, which includes Humboldt Park, West Garfield Park and East Garfield Park. Even so, the data shows violent and property crime trending down in the area, with 150 fewer shooting victims year over year.

Overall, I feel safe in Chicago while adhering to basic safety principles, including keeping my head on a swivel at all times, avoiding the L train alone at night and walking with a Birdie alarm. It’s the same advice you’d give for any big city — just use your common sense.

Bottom line

Chicago can become a really big small town if you let it be. If you get out of your neighborhood (and comfort zone), you’ll find diverse opportunities for community, culture, entertainment and inspiration among neighborhoods.

It’s a stunning city to visit, thanks to its plentiful museums, bike paths and public beaches. And don’t forget to take a river cruise — it’s one of the best ways to see the city.

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