Chicago is known for pizza, bold architecture, lively communities, and endless entertainment— but is Chicago a good place to live? We did some digging to bring you the scoop on life in the Windy City. From the quality of life and cost of living to main attractions and commute times, we’re here to answer one question: Is Chicago a good place to live?

Our team of Chicago experts has one goal: to make finding an apartment in Chicago easy, stress-free, and maybe even a little fun. To do this, we’ve created resources with information that you can’t find anywhere else. We answer questions like: “Why doesn’t everyone live here?” “How do locals afford luxury apartments?” and “Can I find a Chicago apartment from an entirely different state?” We also provide free apartment locating assistance.

Now, back to the big question at hand: Is Chicago a good place to live? Let’s find out.

What Should I know About Living in Chicago?

Quality of Life

Bustling urban hub’. Because Chicago is such a melting pot of culture; you can find all kinds of different activities, entertainment, and food within the city limits. No matter which way you turn, there is always something going on. It also makes for a great place to create connections – business, creative, friendships, and so much more!

Lakefront. The lakefront is what makes Chicago the perfect blend of urban living and natural relaxation. If you want an active beach experience, check out North Avenue Beach or Montrose Beach. At North Avenue Beach, you can rent a sand volleyball court and enjoy amazing views of the downtown skyline.

Montrose Beach is very dog-friendly and has a fenced beach just for pups! Enjoy a cold beer and live music at The Dock, a dog-friendly beach-side favorite. If relaxation is your goal, Hollywood beach is for you— due to minimal boat traffic, you can rent paddle boards and soak up the sun in this quiet spot.

Getting to the beach is easy, all you have to do is jump on the CTA and head east until you hit the water. Hop between beaches via the Lakefront trail, which stretches 19 miles from north to south. Just make sure that you pack some sunscreen!

Highly active communities. Every Chicago neighborhood has their own calendar of activities and events planned throughout the year. From the Edgewater Arts Festival every fall to the Logan Square Farmers Market— open every Sunday, year round— the variety of community activities and organizations that take place in Chicago are astounding.

Stop by the Green Mill for some live jazz weekly, or drop into an improv show hosted by Second City. There is something for everyone in the city. Whether you want to peruse or participate, it is very easy to get involved in your neighborhood.

Vibrant startup scene. Chicago is filled with hundreds of successful family-run businesses. Because of this, there is a definite want amongst Chicagoans to support local startups. You’ll find new pop-up ventures, co-ops featuring up-and-coming artists, and local alternatives to big-box stores.

Many tech start-ups are popping up around Chicago (AptAmigo included!) And even more are moving their offices here from San Francisco or New York. With the number of Chicago-based businesses growing, job hunting here is easier than most cities.

Things to Do

Foodie Central. Almost any type of craving can be satisfied in this city. So, if you and your partner have a hard time picking a dinner spot, buckle up. Chicago offers almost endless options. Phodega, for example, is a Wicker Park pho restaurant that doubles as a corner store and sells a variety of Asian snacks, sweets, and drinks.

Or, if you’re hungry for some pizza with a view, you can saunter down to Pizzeria Portofino. Nestled by the Chicago Riverwalk, Pizzeria Portofino serves up crispy thin crust pizza with amazing skyline views.

Skydeck. Searching for something that is both beautiful and terrifying? Have you considered standing on a glass ledge 103 floors above the city’s sidewalks? Well, at the top of the Willis tower, you can do exactly that.

This Chicago staple provides a jaw-dropping view of the lake, panoramic city skylines, and an amazing selfie opportunity. It can be considered a “touristy” activity, but you shouldn’t let that stop you from seeing it at least once!   

Chicago River Cruise. If you’ve ever found yourself thinking: “This drink is delicious, but it would be better if I was drinking it while wearing a sun hat on a boat,” we’ve got just the thing for you: the Chicago River. There are a couple different river-cruising options to choose from, depending on your mood.

The Odyssey Chicago River Dinner Cruise, a glass-encased boat that offers a three-course meal and cash bar. Or, there is the Chicago Line Jazz Cocktail Cruise, which is just as classy as it sounds. Drift down the river with a cocktail in hand while the sun sets and live jazz plays in the background.

Dine at one of the famous Chicago rooftops. There’s nothing better than the wind in your hair and an aperol spritz in your hand on a hot Chicago day. Good news: you can have exactly that at one of Chicago’s exquisite rooftop bars! Our first stop is located off Michigan Ave. Cindy’s is a local favorite, has an amazing view of the downtown skyline, and a luxurious aesthetic to match.

Next up is the tri-level rooftop bar located at LondonHouse Chicago. Have you ever had afternoon tea 23 floors above Lake Michigan? No?! Well now you can say that you have. After LondonHousewe have The J. Parker with an exceptional view of the Lincoln Park Zoo and Lake Michigan. The J. Parker is located atop the famous Hotel Lincoln and boasts an energetic rooftop bar.

(For even more things to do, read our guide to Touring Chicago Like a Local and check out our Exploring Chicago series.)

Main Attractions

Millenium Park. While it tends to become crowded on a clear summer day, this touristy stop will still ‘wow’ you every time. Not only does the Cloud Gate sculpture (AKA, The Bean) provide the ultimate mirror selfie, the Jay Pritzker Pavilion offers free music all summer long. Just a short walk away is the Maggie Daley Park, which has rock-climbing walls in the summer and an ice skating rink in the winter!

Garfield Park Conservatory. The windy city might be known for its brutal winters, but nothing thaws the heart like tropical plants in December. Located off the green line, this hidden treasure is a place that you can easily get lost in.

While it is free admission, the Garfield Park Conservatory accepts donations to maintain the plants and the property. It houses 30 exhibits at a time, and in the summer the outdoor gardens will take your breath away. Garfield Park Observatory is a worth a visit any time of the year.

Art Institute of Chicago. The Art Institute is, without a doubt, the best place to go on a rainy day. With free admission to Chicago residents (on designated days), you can spend as long as you want wandering the exhibits. With hundreds of exhibits, there’s no shortage of things to see here.

The Art Institute boasts the largest collection of Impressionist paintings outside of Paris and includes Renoir, Van Gogh, Seurat, and Monet. If you find yourself in a funkier mood, wander over to the Modern wing and see works by Dalí, Matisse, Picasso, and Pollock. No matter your mood, the Art Institute is sure to have something you enjoy.

Chicago Riverwalk. What was once Chicago’s main shipping channel is now the city’s main attraction! Split into six distinct areas, the Riverwalk is an excellent place for a date night or a solo excursion. Featuring restaurants, tons of Instagrammable spots, kayaking, museums, and so much more— there is plenty to do when you visit the Riverwalk.

How to Get Around

Leave your car. Quite frankly: Chicago is not a car-friendly city. Parking is expensive, difficult to find, and never guaranteed. With an abundance of rideshare options, rental bikes, scooters, and the CTA— you won’t even miss having a car.

However, if you choose to bring your car and need a reliable place to park, you can still rent a parking spot on a monthly or yearly basis. With a cost ranging $50 to $300 or more a month, it’s not always an affordable option.

Public transportation is aplenty. Once you have your vehicle all squared away, the CTA will provide you with an efficient way to get around Chicago. Although it might be hard to give up your car in the short-term: Chicago’s public transit is cheaper and less stressful than owning a car in the long-term.

With routes going to almost every suburb and hundreds of stations, you’ll rarely need anything else! Convinced yet? If so, check out these Chicago Apartments Near The Blue Line.

Is Chicago Expensive?

It depends. If you’re moving from New York or San Francisco: no, it’s not that expensive. But if you’re moving from anywhere else, it might be. Keep in mind, however, that salaries are generally higher here than smaller cities and can balance out a hefty cost of living.

Chicago was ranked No. 15 for most expensive cities in the U.S. but 23rd for highest salaries. So as long as you look at the big picture, you can make Chicago work for you. Living expenses will likely be the most expensive part of moving to Chicago.

The average rent price as of January 2020 is $1,948 and the average cost of utilities is $191 per month. Of course, not only are these prices variable, but Chicago itself has an astoundingly wide range of options. If you want specifics, check out our Is it expensive to live in Chicago? article

Next Step: Find a Chicago Apartment

If you need help finding an apartment in Chicago, AptAmigo is here to help. We take the stress out of apartment hunting by giving you VIP service, a team of helpful locals, and expert apartment knowledge. The best part? It’s completely free. Just contact us, tell us your preferences, and your dedicated apartment experts will handle the rest. Click here or contact us below to get started!

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About the Author
Rebecca Denham

Rebecca is a freelance writer with eight years of journalism experience. She recently graduated with a BA in Communications and a minor in journalism. She currently bartends in downtown Chicago and spends her free time exploring the city and making connections.