Chicago

[updated september 2024]

SO, roomiematch.com's Chicago roommate rundown:

Chicago looms large, because it is, along with its place in America's imagination . . . blues, jazz, improv comedy, America's largest lake next to a modern art skyline looming large over modern art parks. And some of those parks feature their very own professional sports teams.

Chicago isn't cheap, some neighborhoods now obviously more than others. But for how big it is plus all it features, it should seem cheap-ish? Compared to NYC and San Francisco?

If you can handle extreme weather, you and your roommates will be rewarded with cheaper rent, lower cost of living, and almost everything else you and your roommates could possibly need accessible from "The L." That's The L that makes Chicago one of the best cities to live without a car, The L that connects an astonishingly diverse collection of communities, and The L that is generally beloved.

From all the beachfront still free to browse, to the public transport arriving reliably, to the dive bar food that's delicious, there's so much about Chicago that seems better than it strictly needs to be. So much art, so much history, so much black culture . . . near the most delicious hot dogs and pizza humanly possible.

What's NOT to love? Not much, except how do you feel about riding The L in extreme weather, hot and cold?

Awesome? Or if not all the way to awesome, you can most definitely deal?

This Windy City is for you.

The rest of the Chicago roommate lowdown:

• Chicago is the hub and most populous Midwestern city. It has about 3 million residents, and an impressively modern art/modern architectural skyline you can see from all the way across Lake Michigan.
• "Chicagoland" (Chicago plus surrounding areas) includes about 10 million.
• home to Barat College, East-West University, Elmhurst College, Illinois College of Optometry, Industrial Engineering College, Judson College, Kendall College, Robert Morris College, Trinity Christian College, Aurora University, Chicago College of Osteopathic Medicine, Chicago State University, Columbia College, Concordia University, Governors State University, John Marshall Law School, Lake Forest College, Lewis University, North Central College, Northeastern Illinois University, Saint Xavier University, School of Art Institute of Chicago, Adler School of Professional Psychology, Depaul University, Illinois Institute of Technology, Loyola University of Chicago, Northern Illinois University, Northwestern University, Roosevelt University, Rush University, Trinity College, University of Chicago, University of Health Sciences, University of Illinois at Chicago, and Wheaton College
• There may be other cities as diverse as Chicago . . . maybe? You won't find any more diverse in the United States. Representatives from most global communities live in Chicago today.
• Navigating Chicago is way easier than most American cities as block numbers and block sizes are standardized, with all flowing from the zero point (the intersection of State and Madison).
• Metro Chicago residents identify more strongly with their neighborhoods than most cities, with North Side vs. South Side being the most prominent division, but many feel pretty strongly about East vs. West as well.
• Their massive public transport system makes Chicago one of the best places to live in the US without a car. The Chicago Transit Authority (CTA) operates many trains and buses throughout Chicago plus a few suburbs. All the trains together are "The L," and their lines radiate from "The Loop" all over the city. Chicago and NYC are the only American cities with some rail service operating around the clock. Crime on the CTA is low, but if you feel unsafe or need to travel late at night you'll be safer sitting near the driver.
• Even with severely cold winters, extremely hot and humid summers, and thunderstorms with heavy winds surprising residents year round, Chicago rarely slows down for weather, including city services and public transport. However, the weather is often so severe you and your roommates will need to keep climate in mind when considering any activity almost all the time anyway.
• Avoid driving downtown if possible. Traffic is awful and parking is expensive while also confusing. Tickets and towing for parking violations afflict many, even more when it's snowing.
• Chicago's black population is #2 in the US, after NYC. Chicago's larger South Side area is the largest black neighborhood with the largest number of black-owned businesses in the country too!
• Chicago has a lot of passionate bicyclers, many gathering along the 18-mile scenic lakefront trail or "Hipster Highway," a popular bike route along Milwaukee Avenue.
• Chicago is one of the best restaurant cities. Is it known for deep dish pizza, Chicago-style hot dogs, Italian Beef sandwiches, jibarito sandwiches, frozen custard, fried chicken, and dive bars and lounges with decent pub food? Yes, it is! But just about everything else is being served somewhere in Chicago too.

After you're settled down, you and your roommates should experience Chicago's:

• Museum Campus: Chicago has a lot of museums worth visiting, but three of the best are within walking distance of each other and along the lake: Adler Planetarium, Field Museum of Natural History, and the Shedd Aquarium.
• Lake Michigan: Free (no fees, hardly any private beaches getting in the way) for miles within walking distance of the Red Line. It's the largest freshwater lake in the US, and you can show up, walk around, and swim for free . . . but mostly in the summer and early fall if you want to maximize lifeguards = yes while freezing to death = no. It's beautiful!
• Offshore Views: In the summer, you and your roommates can enjoy great views for cheap by taking a water taxi around downtown.
• Loop Art Tour: Free open air art museum of famous modern artists! Their itinerary will guide you along the walking tour that's an efficient route to visit Calder, Chagall, Lewitt, Miro, Moore, Oldenburg, Picasso and many others . . . all this magnificent modernism on display in Chicago's commercial center.
• Blues and Jazz: As Chicago is considered the home of both, you've got extreme options. Really, so many options it's likely there will be a major music festival most weekends. If you like walking around, you'll likely stumble right into one, eventually. If that's not a "Fest" celebrating one or more musical traditions, it'll likely be a "Taste" or a "Lollapalooza!"
• Park & Boulevard System: Ring of parks connected by boulevards (streets with wide medians with plants and pedestrian walkways) winding throughout the city, over 25 miles of greenbelt. And then even along those 25 miles there are other connected gardens and lakes. If you or your roommates want to walk longish distances in very green but still accessible and connected spaces, this is a absolute must ramble.

Here's the city of Chicago's list of services for renters and landlords, which you'll hopefully never need if you choose the right roommates.

Notes

1.   The non-traditional roommate rent average for this city we've experienced over the last 3 years. We can't predict future rental availability, because we're neither in control of any rental market nor psychic, sorry!

But in most cities most of the time, the recent and relatively recent past are the best predictors.


2.   This idea came from smartasset.com's ranking of what a roommate saves you in 50 cities. They ranked where roommates will save you the most money, based on the average cost of a 1BR as opposed to a 2BR ÷ 2. Unsurprisingly, the more expensive the city, the more you can save, but the savings are significant in all larger metros. So we got the data for the rest of our cities from Zumper too.

This is really the minimum you could save, as you could live with more than one roommate, split more services, share food or other supplies, etc. More sharing tends to lead to more savings too, as per our roommate roadmap.

As per the rest of the description at the top of this page, we're calling this "traditional" roommate rent.


3.   From zumper.com.


4.   Directly quoted from the Trust for Public Land's parkland rating system.

"The ParkScore index awards each city up to 100 points for acreage based on the average of two equally weighted measures: median park size and parkland as a percentage of city area. Factoring park acreage into each city’s ParkScore rating helps account for the importance of larger “destination parks” that serve many users who live farther than ten minutes’ walking distance."

While each city's rundown already includes their individual ParkScore, nature lovers might like to see all roommate cities ranked for parkland.


5.   Directly quoted from Walk Score's Cities and Neighborhoods Ranking. They've ranked "more than 2,800 cities and over 10,000 neighborhoods so you can find a walkable home or apartment."

While each city's rundown already includes their individual Walk Score, dedicated pedestrians might like to see all roommate cities ranked for walkability.


6.   From various lists here on our own best roommate cities.


7.   From hoodmaps.com: a collaborative map where residents use tags describing social situations you're likely to find. Other users can thumb up or down, so the largest tags have been thumbed up the most.