The Ultimate Guide to Living With Roommates in Chicago

October 17, 2022 | By Lauren Bozarth
Reading Time: 5 Minutes

Living with roommates is always a gamble- but it may end up being a great decision! If you’re preparing to share a space with others or considering it, we want to help set you up for success. That’s why we’re sharing tips and insight into making the most out of this situation.

How to Find a Roommate in Chicago

You may find yourself in a situation where you want to find a roommate but don’t have immediate options right in front of you.

In this case, start by asking around your immediate circle. Reach out to 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 personally know. As you start chatting with others, you may even come across someone you know who also needs a roommate.

If you don’t have luck finding someone that way, then consider reaching out to larger networks you’re involved in to try and find someone with overlapping interests. This may be college alumni, church, or sports groups.

Often the last route involves looking online. Start browsing Facebook groups like Chicago Roommates or downloading apps like Roomster to help you connect with a potential roommate.

If someone online piques your interest, don’t sign the lease until you’re sure this is a person you want under the same roof.

You may want to first meet this person at a neutral place, like a park or coffee shop. Here you can better get to know one another and discuss some living expectations and non-negotiables.

Living With a Random Roommate

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

Even if this person does not become your best friend, communication is still important. Even before moving in or committing to live together, consider these questions:

  • How are rent and utilities being split?
  • What are payment expectations?
  • Can other guests spend the night?
  • Do lifestyles align? 

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

Along with communicating, being respectful is equally necessary. Recognize that you and your roommate will have different habits and interests.

This is not your lifelong partner, so even if the situation ends up being difficult, there is always an end in sight. And in the challenging moments, remind yourself that the roommate situation is helping stretch your dollars.

Living With a Significant Other

You may be in a place where you’re looking to take your romantic relationship to the next step. If you and your significant other are considering living under one roof, it’s critical to prepare for this relational transition.

This can prove 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 moving, and keep these talks going once you live together. Discuss expectations, excitements, concerns, or whatever you need to express before making the commitment.

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

If you’re about to sign a lease with the person you love, chances are you’re looking forward to spending more time with that person. While living together certainly provides this opportunity, be intentional about carving out alone time or space for your interests.

Sometimes, living with the person you’re dating can make it easy to get “lazy” in the relationship. Be intentional about still going on dates and treating the person like your significant other, not just a roommate.

Living With Your Best Friend

Cohabitating with someone you already know and adore can make for a fun season. You can avoid the “getting to know you” phase and jump straight into sharing a space (and more memories) with your friend.

While living with your BFF has the potential to enhance your friendship, it’s crucial to set some safeguards in place to preserve the relationship.

Good communication is essential in this dynamic. Although you likely know quite about each other, make sure you express and agree upon living expectations.

In your conversations, it doesn’t hurt to set boundaries. Talk about what your ideal living situation will look like. How should you approach having 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.

How to Be a Good Roommate

Regardless of who you end up living with it, work to be a considerate roommate.

One 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 to listen and really hear your roommate’s expectations and thoughts.

Help keep the peace by being mindful of your roommate. Whether you’re listening to music, having people over, or making dinner, remember that you’re not the only one there. Check-in with your roommate and be respectful of their space as well.

Being considerate of your cleanliness can also help your living situation. Whether or not you’re naturally a clean or tidy person, be extra cognizant of the way you maintain your place, especially the common areas. This may help alleviate potential disagreements or tension.

Living With Roommates Vs. Living Alone

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


  • Shared rent and utility costs
  • Built-in company
  • Shared chores
  • An extra sense of safety


  • Less privacy
  • More compromise
  • Different lifestyles under one roof

As you think through the reality of sharing a space, carve out real time to weigh the advantages and disadvantages.

Finding 2-Bedroom Apartments in Chicago

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

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


930 West Altgeld Street, Chicago, IL, USA

Lincoln Park apartments

727 West Madison

727 West Madison Street, Chicago, IL, USA

West Loop apartments

Alta Roosevelt

801 South Financial Place, Chicago, IL, USA

South Loop apartments

The Mason

180 North Ada Street, Chicago, IL, USA

West Loop apartments

500 Lake Shore Drive

500 North Lake Shore Drive, Chicago, IL, USA

Streeterville apartments

To tour any of the apartment buildings or to find more options, connect with 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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