The Ultimate Guide to Living With Roommates in Chicago

Living with roommates is always a gamble, but it can end up being a great decision! If you are preparing to share a space with others or are considering doing so, we want to help you succeed. That’s why we’re sharing tips and ideas for making the most of this situation.

You may find yourself in a situation where you want to find a roommate but have no immediate options in front of you.

In this case, start by asking your immediate entourage. Reach out to your friends or family to see if they know anyone in the same boat as you. It’s ideal for someone you know to vouch for a potential roommate, especially one you may not know personally. When you start chatting with other people, you may even meet someone you know who also needs a roommate.

If you’re not lucky enough to find someone this way, consider reaching out to larger networks you’re involved in to try and find someone with overlapping interests. They can be former students, churches or sports groups.

Often the last route is to search online. Start browsing Facebook groups like Roommates in Chicago or download apps like Bedroom to help you get in touch with a potential roommate.

If someone online piques your interest, don’t sign the lease until you’re sure it’s someone you want under the same roof.

You may want to meet this person first in a neutral place, such as a park or a coffee shop. Here you can get to know yourself better and discuss some life expectations and non-negotiables.

If you find yourself living with a stranger, there are a few things to keep in mind.

Even if that person doesn’t become your best friend, communication is still important. Before you even move in or commit to living together, consider these questions:

  • How are rent and charges shared?
  • What are the payment expectations?
  • Can other guests stay overnight?
  • Do lifestyles align?

You may want to establish a verbal or written agreement to honor the most crucial agreed terms.

In addition to communicating, being respectful is also necessary. Recognize that you and your roommate will have different habits and interests.

It’s not your life partner, so even if things end up getting tough, there’s always an end in sight. And in difficult times, remember that being a roommate helps you maximize your money.

You may be in a place where you are looking to take your romantic relationship to the next level. If you and your partner plan to live under one roof, preparing for this relationship transition is essential.

This can turn out to be an exciting growth opportunity if you and your partner are on the same page.

For starters, never underestimate the power of communication. Be sure to start important conversations before you move and continue those conversations once you live together. Discuss expectations, excitements, concerns, or whatever else you need to express before committing.

Meeting and living with the same person requires give and take. Be ready to make sacrifices and give grace. Bad habits are easily exposed when you live with another person, but don’t be quick to judge or get frustrated. We all have them, so be prepared to work with each other when needed and learn to live with some quirks in other cases.

If you’re about to sign a lease with the person you love, chances are you want to spend more time with that person. While living together certainly provides this opportunity, be intentional about setting aside alone time or space for your interests.

Sometimes living with the person you’re dating can help you get “lazy” in the relationship. Plan to always go on dates and treat the person like your significant other, not just a roommate.

Cohabiting with someone you already know and adore can make the season fun. You can skip the “getting to know each other” phase and go straight to sharing a space (and more memories) with your friend.

Although living with your best friend has the potential to improve your friendship, it is crucial to put certain safeguards in place to preserve the relationship.

Good communication is essential in this dynamic. Although you probably know each other pretty well, be sure to express and agree on life expectations.

In your conversations, it doesn’t hurt to set boundaries. Talk about what your ideal life situation will look like. How should you approach visitors? Are there certain days of the week when you need alone time? Answering and honoring these questions will help your friendship and roommate situation.

No matter who you end up living with, work to be a caring housemate.

A recurring and important theme is communication. Your roommate can’t read your mind and vice versa, so share the things that are important to you from the start. Also, make sure you really listen and hear your roommate’s expectations and thoughts.

Help keep the peace by being mindful of your roommate. Whether you’re listening to music, entertaining, or cooking dinner, remember you’re not the only one out there. Check in with your roommate and also respect their space.

Being mindful of your cleanliness can also improve your living situation. Whether or not you are naturally a clean or tidy person, be very aware of how you maintain your accommodation, especially common areas. This can help smooth out potential disagreements or tensions.

Your accommodation is an important decision. If you’re on the fence, consider the pros and cons of living with roommates:


  • Shared rent and charges
  • Integrated business
  • Shared tasks
  • An extra sense of security

The inconvenients:

  • Less privacy
  • No more compromises
  • Different lifestyles under one roof

As you ponder the reality of sharing a space, schedule some real time to weigh the pros and cons.

Ultimately, if you decide that living with a roommate is your best decision, your next step is to find a two-bedroom apartment in Chicago.

Consider taking a look at these luxury buildings in the Windy City:


930 West Altgeld Street, Chicago, IL, USA

Lincoln Park Apartments

727 West Madison

727 West Madison Street, Chicago, IL

West Loop Apartments

High Roosevelt

801 South Financial Place, Chicago, IL, USA

South Loop Apartments


180 North Ada Street, Chicago, IL

West Loop Apartments

500 Lake Shore Drive

500 North Lake Shore Drive, Chicago, IL, USA

Apartments in Streeterville

To visit one of the apartment buildings or to find more options, contact one of our experienced brokers today or follow the link below to get started! We’d love to help you find the perfect apartment for you and your new roommate.

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