Full spoilers for The Handmaid’s Tale Season 4, Episode 5, “Chicago.”

The Handmaid’s Tale Season 4 episode “Chicago” finally gives June something the show has avoided for a long time: a real choice. Not a plot reaction. Not another obvious survival beat. Not another round of June gets captured, June escapes, June rebels, and June gets pulled right back into the same Gilead spiral.

A real choice.

Moira finds June in Chicago. Canada is suddenly not theoretical anymore. Luke, Nichole, Emily, and a life outside the war are all within reach. But Janine is missing, Gilead is still calling, the Nighthawks are waiting, and June has to decide whether she can actually leave the fight behind.

That is why “Chicago” works. The episode is not just about a bombing. It is about whether June wants freedom anymore — or whether Gilead has turned her into someone who needs the war.

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What Happens In The Handmaid’s Tale Season 4 Episode “Chicago”?

In “Chicago,” June and Janine make their way through the remains of the city after escaping Gilead custody. They find Steven and his resistance group, but Chicago is not exactly the clean freedom fantasy June may have imagined. The city is dangerous, transactional, unstable, and still full of men who think they get to decide what women can and cannot do.

Meanwhile, Gilead is dealing with pressure of its own. Commander Lawrence wants his seat back at the table. Nick wants to protect June. Aunt Lydia wants power over a new crop of Handmaids. The political machinery spins just long enough to create the thing the episode needs: a temporary ceasefire that allows aid workers into Chicago.

Then Gilead bombs the city anyway.

In the aftermath, June wakes up in the rubble. Janine is missing. June stumbles through the destruction looking for help, for answers, and for some kind of next move. Then Moira appears.

That is the episode’s real turn. Not the bombing itself. Not the Nighthawks. Not the deal-making in Gilead. The turn is Moira finding June in Chicago and suddenly making escape possible.

Why Chicago Finally Gives June A Real Choice

Wow.

June is maybe on her way out of the Gilead conflict and on to sweeter pastures in Canada with Moira, Luke, Nichole, and Emily.

Well, that is at least what the show wants you to think.

Nevertheless, Bruce Miller has maneuvered The Handmaid’s Tale into some of its most interesting territory in a long time. June has an actual choice to make here, and for once, it is not just a plot reaction.

First, let’s talk about choice. Not “oh man, should I choose chocolate or vanilla?” A real dramatic choice happens when an obstacle is put in front of a character and there are two valid ways around it. Both sides have pros. Both sides have cons. But the choice reveals who the character is, moves the story forward, and hopefully subverts our expectations.

Most of The Handmaid’s Tale does not work that way. A lot of the show runs on plot reactions. Plot reactions are decisions that are self-evident and obvious. They do not reveal who the character is in any new way. They exist to move the story from one required beat to the next.

When June saves Janine over and over again, those are often plot reactions. When June is faced with Hannah being hurt or giving up the whereabouts of the Handmaids, that is a plot reaction. What other choice does she have? Watch her kid get hurt, or tell Gilead where her friends are? She is always going to choose her kid.

But the ending of “Chicago” feels different.

Why Moira Finding June Changes Everything

The end of this episode is different because June finally has a real choice to make: go to Canada and be with her family, or stay in the fight to search for Janine and continue to lead the resistance.

This is not suggesting she has to leave Hannah behind forever. We have already seen June and Hannah reach the same dead end over and over again. June finds Hannah, or gets close to Hannah, or sees Hannah, and then she has to leave and try again another time.

June can still try to save Hannah from Canada. In fact, she may be able to do it from a more comfortable place, with better resources, a clearer plan, and people who actually have her back.

That is what makes Moira’s arrival so important. Moira is not just a rescue. Moira is a question.

Can June leave?

Can June stop?

Can June accept help?

Can June become something other than the woman Gilead forced her to become?

The real choice is whether June can leave behind not only Gilead, but also the role she now occupies inside the fight against Gilead. Is she the woman responsible for Angel’s Flight? Is she the dutiful wife who can go home to Luke? Is she Nichole’s mother? Is she Hannah’s mother? Is she a resistance leader? Is she a weapon?

And the hardest question of all: does June actually want to be free, or does she enjoy the fight too much now?

What Are The Nighthawks In The Handmaid’s Tale?

The Nighthawks are the resistance fighters June wants to find in Chicago. They represent a more violent, more direct version of the fight against Gilead — the kind of people who are not trying to negotiate, survive politely, or build donor-friendly language around the cause.

They want to burn Gilead down.

That is why June is drawn to them. She is not merely looking for safety anymore. She is looking for a way to hurt Gilead back.

At first, I was annoyed when June kept eyeing the gun and defying Steven’s orders during the search party. Ugh, I thought, it is just June being June. She cannot listen to anyone, and she thinks she is smarter than all her peers.

But ultimately, it is June being June. Not in a bad way, exactly, but in the way she has evolved to become. This entire season has been about that transition.

June no longer has the clean moral high ground of the fight she is fighting. Whether it is Janine, Angel’s Flight, or even saving Hannah, her goal has shifted. She wants to inflict pain on Gilead because Gilead deserves to fall. Poisoning Commanders, hurting Lydia because she can, and wanting to join the Nighthawks all point toward the same thing.

June has transformed into a vengeful killing machine.

And honestly? The show knows it.

Can June Leave Gilead Behind?

It was easy for June to rebuff any attempt to leave Gilead before. She always had the excuse of Hannah being held captive. Or Angel’s Flight. Or the Handmaids. Or the plan. Or the next impossible thing that only June could do.

But now she has Moira standing in front of her in Chicago.

How does June turn Moira down after everything they have endured together? Is she really going to reject a clear opportunity to see Luke, see Nichole, and continue a more manageable fight from the comfort of New America?

This is a real choice. It will affect the plot. It will tell us something meaningful about June’s character. And if the show is smart, it will subvert what we expect from her.

What is also important is where this choice happens. “Chicago” lands at the exact midpoint of the season, when the drama should reach a story-altering moment that fuels everything going forward. With only ten episodes in the season, it makes sense that Moira potentially saves June here.

But just because June is saved does not mean she will stay that way.

You can take the person out of Gilead, but can you take Gilead out of the person?

It is no coincidence that we have watched other survivors struggle with freedom. It is no coincidence that Rita has had to navigate life after Gilead. It is no coincidence that the Waterfords are pregnant and potentially drifting toward reconciliation. And it is certainly no coincidence that everything Luke and Moira have been doing to raise funds against Gilead has felt small compared to what June has been living through.

While June was fighting, Luke and Moira were having dinners with donors and giving speeches about June.

That is not nothing. But to June, it may feel like nothing.

So even if June chooses to leave Gilead, the real question is whether she can stay in Canada once the fight starts calling out to her again. That becomes even more complicated if Janine is still missing because, as Aunt Lydia reminds us, Handmaids always walk together.

Why Gilead Bombs Chicago

Many people will probably quibble over the logic behind the deal-making between Lawrence, Nick, and Aunt Lydia. I get it. Who gets what when one person gives X and the other person gets Y? It is all Plotty McPlot stuff that ultimately gets us to the actual thing.

Chicago is not going well. Gilead is under fiscal pressure and needs relief, so the Commanders authorize a ceasefire and allow aid workers into the battle zone to garner international support. Nick has the potential to save June. Lawrence gets a seat back at the table. Lydia gets authority over a new crop of Handmaids.

Some will probably also argue about the logic behind the bombing of Chicago right before relief arrives. It does not make a ton of sense off the jump.

But my answer is: why should it have to make perfect sense?

Nothing Gilead does makes clean moral sense. Gilead is a system built on power pretending to be principle. It wants international support, but it also wants domination. It wants children, but it destroys families. It wants order, but it creates chaos everywhere it goes.

So if Gilead sees a chance to bomb Chicago and call it strategy, of course it does.

That is the point. Gilead does not need to be rational. It needs to remain in control.

Steven, Chicago, And The World Outside Gilead

Steven is useful because he reminds us that leaving Gilead does not mean entering paradise.

Chicago is not Gilead, but it is not safe. Steven is not a Commander, but he still tries to impose his will. The rules are different, but the power dynamics are familiar. Just because June has escaped one cage does not mean every man outside that cage suddenly becomes noble.

There will always be a Steven holding June back, telling her she cannot do something, or imposing his will on women who are not strong enough to fight him off.

That matters because June’s choice is not simply “Gilead or freedom.” It is more complicated than that. The world outside Gilead is damaged too. It has war zones, opportunists, weak alliances, donor dinners, political compromises, and men who still mistake survival for permission.

That does not mean Canada is meaningless. It means freedom is not magic.

And for someone like June, that may make the fight feel easier to understand than the recovery.

Moira Saves June — But Does June Want To Be Saved?

The final 20 minutes of “Chicago” are incredible.

June walking alone to find the Nighthawks has this quiet paranoia to it. Then Janine finds her. Then the bombing happens. Then the aftermath becomes pure disorientation. The episode finally creates the kind of uncertainty I have been waiting for.

And then Moira sees June.

Now, are the odds of Moira finding June on the exact right street, at the exact right time, in the exact right city astronomically low? Of course. But I will go along to get along. Sometimes narrativium has to happen.

The reason I can accept it is because the result is strong enough to matter. Moira’s arrival is not just convenient. It is clarifying. It takes all of June’s excuses and puts them under pressure.

June says she wants out.

Now out is standing in front of her.

So what does she do?

Why Chicago Is A Turning Point For The Season

“Chicago” gives Season 4 its sharpest pivot yet because it forces June out of the repetitive Gilead loop and into an identity crisis.

She can go home. But home may not feel like home anymore.

She can fight. But the fight may be changing her into someone who only knows how to hurt back.

She can look for Janine. But Janine may now be one more reason June cannot leave.

She can try to save Hannah from Canada. But doing it from a distance may feel like surrender.

That is why the episode works. It gives June a door and then makes the door feel terrifying. It gives her rescue and then makes rescue feel like a threat to the identity she has built inside the war.

For the first time in a while, I do not know exactly where The Handmaid’s Tale is going.

And that is refreshing.

Apropos Of Nothing

• The final 20 minutes or so, when June is walking to find the Nighthawks alone, are incredible. From the quiet paranoia, to Janine finding June, to the bombing and the aftermath, I was on the edge of my seat.
• I was genuinely surprised that Moira sees June. Again, the odds are absurdly low, but sometimes narrativium has to happen.
• I love the purposeful contrast between June and Lydia, with both women trying to find their war and fight back toward the leadership roles they once had.
• Another incredible benefit of this episode is that it injects some gray back into Commander Lawrence. Whose side is he actually on? Why does he want a seat at the table so badly? Is it an excuse to do what he does best and fix the economy? Or is it because he, like Nick, wants to save June? Now that he has lost his wife, his job, and his stature, why is he trying so hard to reform a country he knows is dead in the water?

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