Chicago functions in Esther Greenwood’s imagination as a place where she might escape the identity and expectations attached to her life in Boston. She has never been there, but pictures it as a city where she could begin again as “Elly Higgenbottom,” an orphan loved for her quiet nature rather than judged by her academic record or marriage prospects. The contrast between this imagined refuge and the real, difficult journey she considers making gives Chicago its decisive significance: it is a possibility of self-invention, not an experienced destination.

An Imagined City

Esther first names Chicago to a sailor she meets in Boston Common. Asked where she comes from, she answers “Chicago,” despite never having been there. The false answer makes the city immediately available as a story about herself: it is, she thinks, the sort of place unconventional, mixed-up people might come from. Her invented origin lets her step briefly outside the Boston identity she fears being recognized by, while walking through the Common with the sailor’s arm around her waist.

The city’s appeal is bound up with anonymity. Esther imagines that in Chicago nobody would know she had thrown up a scholarship at a big eastern women’s college, spoiled a month in New York, or refused a solid medical student who might become a member of the AMA and earn a great deal of money. These details turn Chicago into the inverse of a life measured by credentials, public success, and conventional security. She wants to be taken for what she is, but the self she imagines presenting is itself a fiction: a new name and a new biography designed to make judgment seem less inevitable.

The Elly Higgenbottom Fantasy

In Chicago, Esther pictures herself as “simple Elly Higgenbottom, the orphan.” She imagines being loved for a sweet, quiet nature and no longer being expected to read books or write long papers on the twins in James Joyce. The fantasy is strikingly specific: she could marry a virile but tender garage mechanic and have a large, “cowy” family like Dodo Conway—if she happened to feel like it. The condition at the end matters. Even as the fantasy borrows the language of domestic life, Esther reserves the right not to choose it.

This imagined future offers a sharp counter-image to the achievement-oriented identity she has been given. Instead of scholarship, prizes, intellectual work, and an economically promising husband, Elly would have a quiet disposition, a mechanic, and a family. Yet Esther does not simply endorse that alternative. Her qualification leaves choice unresolved: Chicago represents the ability to imagine another life, not a settled desire to exchange one prescribed role for another.

From Daydream to Practical Plan

The prospect becomes more concrete when Esther considers leaving home for Chicago. With her mother and Dodo Conway due to drive her to Walton the next morning, she recognizes that this may be her chance to run away. She counts the money in her pocketbook—one dollar and seventy-nine cents in bills, dimes, nickels, and pennies—and tries to work out how to get to the city. The imagined destination now has a fare and a route, but not yet a workable means of arrival.

Esther does not know how much the journey will cost and is afraid to withdraw all her money from the bank. She suspects that Doctor Gordon may have warned the bank clerk to intercept her if she makes an obvious move. Hitchhiking occurs to her, but she does not know which routes out of Boston lead to Chicago; even judging direction is difficult when the sun is hidden or it is night. Her inability to orient herself geographically gives the attempted escape a practical dimension: the city she has made into a fresh beginning remains remote, and departure requires knowledge and resources she does not have at hand.

She settles on a more deliberate step: walk to the bus terminal, ask the fares to Chicago, and then withdraw precisely that amount from the bank. At the terminal she browses colored tour leaflets and schedules, only to realize that the bank in her home town has already closed for the day. Her appointment at Walton is set for ten o’clock. The sequence narrows the distance between fantasy and action, then closes it again through money, timing, and the obligations of the next morning. Chicago remains a contemplated escape rather than an accomplished one.

Meaning and Contrast

Chicago’s imagined promise also develops in contrast with the public images of success that surround Esther elsewhere. In New York, the magazine contest winners receive month-long jobs, gifts, fashion opportunities, and access to successful people; the spectacle suggests a ready-made story of upward mobility. Esther, however, describes herself as moving numbingly between hotel, work, and parties, unable to feel the excitement the story is supposed to inspire. Against that glossy public narrative, Chicago offers a private, invented biography without an audience that knows her record.

The city is therefore less a portrait of Chicago than a measure of how urgently Esther wants distance from the self others can identify and evaluate. Its imagined freedom is incomplete: she expresses it through a disguise, and her alternative future still borrows conventional images of marriage and family. But the phrase “If I happened to feel like it” prevents the fantasy from closing into a prescription. Chicago matters as the space in which Esther can at least conceive of choosing—or declining—a future for herself.