We're going to Chicago! Well, at least Aneesa, Cara, Chris, Keri, Kyle, Theo and Tonya are, and we get to tag along for the ride. We meet Theo and Tonya first and immediately there is tension because Tonya--who is from Walla Walla, Washington--doesn't have much experience with people who are different from her, and Theo happens to be a black man. But they get past the tension without much of a hitch and arrive at the bright orange door of their new home. Aneesa is the next to arrive and Theo is immediately attracted to her. Her vibrant personality and free-spiritedness (that means she likes to walk around naked) has Theo in player mode from their first handshake. When Aneesa reveals that she's a lesbian, Theo is thrown an unexpected loop. But in his mind, the fact that she's not attracted to men seems only a minor hurdle and he continues to flirt shamelessly. ""We're going to be here for four months, anything can happen,"" he reasons.

After the roommates' time in the hot tub, the group wonders what Chris is hiding-they think he must have a secret. Most of them decide that Chris must be the house virgin. Chris shoots that down and shocks them all when he explains that he was deflowered by his baby-sitter when he was 12 years old. Aneesa, however, deciphers the clues and figures out the truth. Her understanding gives Chris a lot of comfort. Kyle also guesses that Chris is gay but only discusses it with Keri--he doesn't want to put Chris on the spot, especially with Theo in the house. While Theo is comfortable with Aneesa's lesbianism, he finds the idea of two men together disgusting. His constant comments about it anger Aneesa while Chris silently listens in. However, Aneesa has an interesting way of showing her unhappiness--instead of telling Theo how she feels, she gets in the shower with him and sleeps naked in bed with him. Despite all of the mixed signals, Theo apparently does understand their dynamic.

Its summertime in the city and our seven strangers are chilling on the sandy Chicago beaches. Newly single Cara is lonely and on a mission…the Boy Hunt is on. First up is Jason, a guy she eyes across the sand castles and through the hard-bodies. She gives him the digits and they plan to make a date out of it. While Cara is excited about the date, she doesn't seem to really know what she wants. She still has feelings for her ex-boyfriend Jared, who apparently wants to marry her. She feels lonely when she's not with someone and needs physical affection to feel good about herself. This week she must feel absolutely great as she spends the night with a ""rock star"" and her friend from home, Nick. As she tells Theo, ""Friends can sleep together.""

Everyone's bonding…except for Tonya. She's not about going out, she's about sitting at home talking on the phone with Justin. The rest of the gang is frustrated that she doesn't spend time with them and thinks she might be making up excuses and drama when things get hard. Kyle remarks, ""My relationship with Tonya is very much a labor of love. Occasionally, with a heavy emphasis on the labor side of things."" Meanwhile, the cast finds out that they will be working as lifeguards for Illinois State Parks and Recreation. They are all excited about the prospect of being on the beach all the time until they realize that they actually have to pass certification. Theo wants to be a lifeguard but doesn't know how to swim very well. Cara's dad is overjoyed that his daughter is following in his footsteps as a saver of lives, but the idea really scares her. She doesn't try very hard because she doesn't want the responsibility and eventually declines getting certified.

It seems pretty obvious to everyone that Keri likes Kyle and Kyle likes Keri, but there's a problem. Kyle has a long-time girlfriend at home that he really loves, Nicole, and he's trying really hard not to do anything to jeopardize their relationship. He says, ""Nicole and I met two and a half years ago and we jumped into this fairy-tale love."" Apparently the fairy tale includes Keri because Kyle seems to enjoy spending a lot of time in the same bed with her, flirting. While Kyle, Keri and the rest of the cast members are bonding in Chicago, Tonya is back in Walla Walla with Justin and her doctors. When she lands, it's pretty clear that homesickness was as big a factor in her coming home as her physical illness. Tonya says that she ""realized that Walla Walla is an incredible place with amazing people that is the closest to a home that [she's] ever had.""

After arguing with Kyle on the train, Keri decides she should start dating other people instead of pining for Kyle. She meets and makes a date with Tyler, and surprise, surprise, Kyle is more than a little bit jealous. His not-so-veiled negative remarks about the boy aren't lost on the other roommates and are definitely not lost on Keri. Which is fine, because she still really likes Kyle. After the date, she decides that Tyler's a nice guy but that playing the pseudo-dating game with Kyle is more fun. Meanwhile, Theo's finally gotten comfortable in the house…maybe a little too comfortable. He's taken to inviting large groups of people over to party, annoy everyone else, and puke in uncool places. The roommates aren't amused, especially Chris and Aneesa, who call Theo out for his actions. Theo refuses to apologize and says he'll ""be damned if these people come down on [him] like [he's] a kid.""

It's the first official day of work for everyone. Keri, Chris and Kyle are on the beach with their lifeguarding duties while Cara, Tonya, Aneesa and Theo are working with the Chicago Parks program helping to design and paint a mural with a children's program. Everyone seems happy with their jobs, although Kyle notes that being a lifeguard mostly means having to be a jerk. Kurt comes down to spend a week with Chris. At first, Chris seems a little overwhelmed with the amount of time and attention Kurt wants. Chris is about moving slow and Kurt is about being in a relationship and falling in love. Tonya tells Chris that she would be ""sketched"" if a guy was acting like that towards her. But Tonya is also sketched by the idea of two guys being in love with each other so what does she know about it?

Aneesa and her mom continue to struggle with issues during their phone calls. Aneesa's mom wants Aneesa to try and not be ""gay"" while she's in Chicago and to just have a good time. Aneesa, however, just wants to be free to be who she is…especially when she meets Veronica at gay night at Red Dog. They make an immediate connection and end up hooking up in the elevator of the loft. Meanwhile, it's the first real day of work for the non-lifeguards. They meet the kids who are going to be painting the mural with them along with Lara, the Chicago Parks District Manager, who is their boss. They get the kids to start brainstorming on the mural and they all start to realize, especially Tonya and Theo, the impact that they might have on these kids lives.

They've had the fight to end all fights but Veronica is still on Aneesa's mind. Aneesa looks for sympathy and understanding from everyone but no one is interested. Her mom doesn't want to hear any more bad news, Tonya and Chris think that Aneesa should just be glad to be rid of her. But Aneesa really wants Veronica to call. Cara empathizes with her, saying, ""I don't blame Aneesa at all for still having feelings for Veronica. Sometimes when people push you away, it makes you that much more likely to attach yourself to them."" Cara may know a thing or two about this phenomenon. Her dad comes in for a quick visit and takes everyone out to dinner. Cara reveals that her dad is now living in Indiana while the rest of her family is in St. Louis, which isn't ideal. She had never felt close to her father until recently and is very appreciative of his love. After her dad leaves, she's also really appreciative of Kyle's friend Djordje.

Just as Justin is planning to visit Tonya in Chicago, she relapses with her kidney problem. The situation is so bad that Cara rushes her from work to the emergency room. Tonya is in an incredible amount of pain and explains to Cara that this was the reason that she went home the first time. After getting treated she decides she should stay home for the rest of the week, which happens to include the time that Justin will be there. Theo thinks that ""Tonya's illness is absolutely real…she's not faking it. But…her not going to work has more to do with sex with her boyfriend."" Meanwhile, Kyle is planning a trip to his father's lakeside cabin. Everyone is planning to go and it seems like couples are forming--Tonya & Justin, Chris & Kurt…and Keri & Kyle. Kyle is concerned about how this might appear and begs Theo and Aneesa to come up early with him and Keri so it doesn't look like he's going on a ""romantic retreat"" with her.

The gang all heads up to Kyle's lake house for a weekend of sun and fun. The couples--Justin and Tonya and Chris and Kurt--find time for sex and other activities, while the single roommates hang together. Even with Nicole out of the way, however, Kyle won't give in to his urges and hook up with Keri. They sleep in separate rooms and don't spend much time together over the weekend. Kyle explains, ""I have a great time with Keri and I really like being with her...but Nicole is still very, very with me."" When everyone is back in Chicago, the happy romances and the cautious flirting turn sour. Chris realizes that Kurt wants a lot more out of their relationship than he is able to give. Chris wants to focus on his recovery and on trying to stay sober while he bartends, but Kurt wants a commitment. Chris calls Kurt and ends it.

The gang is continuing to work with the kids in Humboldt Park with varying degrees of success. The kids think Tonya is like a drill sergeant, always nagging and never playing. One of the kids most at risk, Nelson, isn't coming around as much as he should. Theo is worried and lets Nelson know that ""he should be working on the mural again...instead of getting into trouble."" Meanwhile, Keri is having the post-Kyle blues and is getting homesick. When she gets the opportunity to go home for the weekend, she jumps at it. She wants to feel some closeness and intimacy with people who didn't go to Princeton and get her head together. While Keri's away, Kyle and Cara get closer. Cara admits that though she and Kyle are just friends, if Keri weren't in the picture, she and Kyle might ""share a drunken kiss.""

Aneesa's openness is becoming a problem for Tonya. Everyone loves a beautiful body, but Tonya is a little tired of seeing Aneesa's all the time. Aneesa's open door policy for the bathroom and frank discussions about sex put Tonya over the edge, and they have a conversation about it. Aneesa is immediately defensive, refusing to understand how her nudity could be a problem for someone else. Tonya begrudgingly agrees to try to learn to be more accepting, while Aneesa compromises as well, saying that she is ""sorry if Tonya was made to feel uncomfortable."" Meanwhile, Cara's ex-boyfriend Ali comes to visit. He's ""evil."" He's ""the boyfriend from hell."" He's…cute! Cara is a very forgiving ex-girlfriend, apparently. Though Ali supposedly ""crushed"" her the last time, she doesn't hold any ill will, and after a brief tug of war, they are touching and groping.

Things seem to be okay with Aneesa and Tonya. They aren't the best of friends by any stretch but they are at least talking and sharing and being nice roommates to one another. Aneesa, however, does seem to be annoying everyone else. She won't do the chores when its her turn, taking days and days to wash the dishes. Theo wants to ‘ground' her but Cara decides to just wash the dishes for her instead of confronting Aneesa about it. Kyle asks Cara, 'When am I gonna see you pissed off?' Meanwhile, all isn't well in Walla Walla. Tonya passes a kidney stone and has to return to the hospital. She's scared to go though because she's already in tremendous medical debt and doesn't want to get deeper in. Plus, she's worried she's going to lose her waitressing job. But she's sick and the roommates take her to the hospital so she can get well. They are all very concerned for her. Theo even writes her a note and goes to visit her while she's there.

It's the last day of working with the Summer Parks Programs. Kyle, Keri and Chris are bummed that they are done lifeguarding. Kyle is really going to miss it because he doesn't think that the next job is 'going to afford him a lot of peace.' Its also the last night with the kids as they present their mural for their parents. Theo is worried that Nelson won't show but he does eventually and even participates in the presentation. The roommates decide to celebrate the end of their jobs with a night out with drinks. Chris isn't interested in celebrating that way and heads home to the chagrin of Kyle. Kyle doesn't know how to deal with someone who's battling alcoholism and is struggling to understand. Kyle asks if he can attend an AA meeting with Chris and Chris is very excited to have the opportunity to share that with him. The meeting proves to be a revelation for Kyle. He tells Chris that 'he was planning on clubbing and getting wasted that night but [he's] glad [he] did this.'

09.10.01 – It's the day before Aneesa's birthday, late at night and she's hoping to get some phone time to talk to friends and family so that she can celebrate her birthday a bit before going to bed. Tonya, as usual, is dominating the phone with phone calls from Justin who is calling her from a tanning salon. The two argue about the phone and Tonya wins this round, refusing to debate the issue while she talks with Justin. Kyle encourages her to get off the phone so that Aneesa can use it and Tonya begrudgingly agrees to do so…in a little while. 09.11.01 – The cast, like most of the rest of the world, is glued to a television set watching the tragedy of the day. They go from supporting each other to desperately trying to find friends and family to trying to find meaning amongst the senseless violence. Kyle is desperate to find Nicole and his sister, both of whom live in New York near the World Trade Center.

After the events of 9.11, some of the roommates' priorities have changed, Kyle's in particular. He's realized that he wants to be with Nicole and he is trying to get back together with her. Part of that means changing his relationship with Keri. Even though their relationship supposedly ended a few weeks ago, Keri reveals that they still hook up pretty regularly and that Kyle is always interested in her after she comes back from going out on dates. And sure enough, after Keri goes out on a blind date with a friend of Cara's, Kyle is all over her again. Meanwhile, after going out on a date with Danielle, Aneesa loses the keys to the minivan. Everyone is looking to her to take care of the problem and Aneesa stresses out about it. She cries to her mother about how much it's going to cost. She whines to her brother that getting it fixed won't happen fast enough, but eventually she gets it done.

While discussing her relationship with Jared to Kyle, Cara realizes that she needs closure with him. He was her 'true love', her 'fairy tale romance' and she wants to know that she's doing the right thing by pursuing her dreams instead of spending her life with him. The roommates then all decide to join Cara on a trip to St. Louis to meet her family and support her while she spends some time with Jared. Chris can't go because he has a family emergency and Tonya chooses not to go so she can work. The roommates are annoyed that Tonya would rather spend her time alone in the house than spend time with them. The time away from each other provides ample opportunity to be 'chatty.' Tonya spends much of her time on the phone completely railing on Cara, Aneesa, Keri and Kyle to Justin. It's not to unfair though, considering how the others spend much of their car ride to St. Louis ragging on her.

As time passes in the Chicago house, Tonya becomes more removed from the group. Her illness has kept her from group trips, from participating fully at work and from becoming a part of the close-knit group of friends. When she informs them that she can't go on the trip to New England, the gang wonders whether or not she is using her sickness as an excuse because it just so happens that Justin is coming to Chicago at the same time. While everyone else makes fun of Tonya when she's not there, Theo has had enough and lets her know what he and everyone else thinks about how she's handling things. The argument brings Tonya to tears. When Justin arrives, he confronts Theo about the incident. The two have an intense discussion and come to some agreement. Justin tells Tonya that she needs to avoid interacting with Theo and she gets defensive. Later, when the gang leaves, Tonya and Justin argue about Tonya's friend Darren and her relationship with him.

While the rest of the gang is in Boston visiting haunted houses, including 'Spooky World,' Tonya is in Chicago working on their assignment there. Neither party seems to missing one another very much. However, Kyle feels pangs of guilt for not staying in contact with Tonya and Chris feels bad that he has been participating in the Tonya bashing. Cara then reveals that the only reason she defends Tonya is because she thinks 'someone has to'. Everyone is tense as they return to the house, not knowing what to expect from the relationship between Tonya and the rest of the gang. When they return, they all come to the realization that they have very little time to get their performances together. When they see the space they are going to be performing in, it's a shock. They expected something like spooky world and instead its just a very 'not-so-spooky' tent. They hanker down, and begin practicing with Cara taking the lead as the director.

There are just a few days until the gang begins their Halloween performances for the Chicago parks program. Things seem to be running smoothly except for one thing, Keri hasn't finished her skit, 'Bloody Mary' and Cara and Kyle are giving her grief because of it. Keri's feeling a little off put because Cara keeps remarking that Kyle is the playwright for the other two skits when they both worked on them. There is also something else going on between Cara and Kyle and the new coupling seems to be adept at keeping Keri on the outside looking in. When it gets down to the wire and Keri's skit isn't where Cara wants it. She asks Keri if they can cut it. Keri, who seems to let things roll off her back with ease, agrees, although she thinks that it is going to have to happen anyway because their job requires them to do three. When Cara explains to Laura, their boss, that she wants to cut the skit, she claims that one of the major reasons is that Tonya is going into surgery.

After years of repression, Aneesa feels her father should learn her true sexual orientation. Aneesa asks her mother to set up and mediate a phone conversation, but her mother refuses to get involved. Aneesa gets upset and admits her mother's immature attitude has emotionally destroyed her. Desperate for help, Aneesa seeks refuge in Chris, who confesses his parents were appalled when he revealed his sexual orientation. With time, however, Chris's parents warmed up to their son's homosexuality, and learned to love and accept his lifestyle. However, Aneesa's problems go beyond her parents. She's torn between the two women she's been dating, Danielle and Latonia. On the one hand Danielle is physically attractive and outgoing, but Aneesa is fed up with her pretentiousness. On the other hand, Latonia is fun and down-to-earth, but doesn't interact well with Aneesa's personality. Aneesa fears the single life, and doesn't know if she can deal with an emotional breakup with either women.

Kyle's younger brother, Austin, watches the Halloween performance and stays at the house for an overnight visit. It's a sweet moment, but Tonya and Keri think that it's being done for the cameras. They rarely think that Kyle is sincere, and as their time gets shorter in the house, it's getting harder for them to keep up appearances for his benefit. Kyle's actions don't help much as he worries that he's used his time in Chicago poorly and worries more about how he will be perceived if he participates in a charity fashion show. The rehearsal process makes Kyle feel like he is ""gay,"" but he learns to enjoy the ""acting"" element of modeling, and because it's for a good cause, he participates. Everyone in the house shows up at the fashion show to support Chris and Kyle's successful walks on the runway.

While the rest of the gang starts to get sentimental about leaving the loft and Chicago, Tonya's ready to go. She gleefully packs up her boxes and is excited about getting home to Justin. She hasn't made any strong friendships in the house and doesn't understand why everyone is getting sappy sentimental. She tells Justin that she can't stand all this 'mushiness.' Everyone else is all about the mush though as Cara sets up a night in a coffee house with her friend Matt to sing a few songs and sing one, in particular, for her roommates. When Tonya and Chris blow off the event to go to the gym, Cara and the rest of the roommates are very upset. Chris, who had debated not going before hand, realizes he's made the wrong decision and immediately apologizes to Cara. Tonya, however, puts up her usual defensive walls and refuses to say she's sorry. Cara, unwilling to take it anymore, calls Tonya on her attitude and asks her to move away from her so that she can enjoy the evening.

MTV’s Damien Fahey hosts all seven cast members from The Real World Chicago to dish the dirt on what went down and the roommates have the opportunity to clear the air on some of the most controversial moments from the season.