Your First Week in Chicago as a Student: A Day-by-Day Plan

The first week decides more than it should. Invitation rates are at their annual peak, nobody has a friend group yet, and being new is the only social currency everyone accepts. Two weeks later the doors are still open, but you have to knock. Here is how to spend the week you arrive.

Day 1 — Land, unpack, walk

Do the boring things first: SIM or phone plan, bank account, a Ventra card for the CTA. Then walk your own neighbourhood for an hour with no destination. You are looking for three places: a grocery store, a café or library where you would sit for two hours, and somewhere to move your body. These become your anchors.

Day 2 — Introduce yourself to your building and your floor

Knock on doors, prop yours open, sit in the common room instead of your room. If you are in an apartment rather than a dorm, this is the day you introduce yourself to whoever shares your stairwell. The single highest-value sentence of the week is "hey, I just moved in — I''m [name]".

Day 3 — Do every orientation event, including the boring ones

Orientation is not information delivery; it is a friendship market with a very short trading window. Go to the awkward icebreakers. Sit next to someone you do not know. Collect numbers, not impressions — you can sort out who you actually like later.

Day 4 — Learn the L

Ride one line to the end and back. Know which line serves your campus, how long the trip to downtown really takes, and what a night bus costs you in time. Students who understand the CTA in week one say yes to more things all year, because the city stops feeling far away.

Day 5 — Join two things

Go to the activities fair and sign up for two commitments that meet weekly: one social or interest-based (improv, choir, a cultural association, a student paper) and one physical (intramurals, a run club, a climbing wall, a gym class). Frequency beats fit — you can change your mind in October.

Day 6 — Be a tourist on purpose

Spend a Saturday doing the obvious Chicago things with whoever will come: the lakefront path, the Bean, a museum, a neighbourhood you have never seen. Shared first experiences bond faster than shared opinions. Our free things to do and weekend guides are built for exactly this day.

Day 7 — Set your weekly rhythm

Before classes start, write down where you will be at fixed times each week: the same café Tuesday morning, the same gym slot, the same club night, one meal cooked for other people. Chicago rewards regulars. A rhythm turns strangers into familiar faces without any additional effort from you.

Things nobody tells you

• Buy the coat in September, not November. The winter is real and the good coats sell out.
• Neighbourhoods are far apart. A friend twenty minutes away by train will be seen ten times more often than one an hour away.
• Say yes for the first month, then filter. You cannot filter a group you never joined.
• Homesickness peaks in week three, not week one. Plan something social for it in advance.

Where to go next

Read the guide for your own campus — UIC, DePaul, Loyola, UChicago, Northwestern, Columbia College and the rest — then the guide for the neighbourhood you moved into.

Frequently asked questions

What should I do in my first week as a student in Chicago?

Sort your phone, bank and Ventra card, walk your neighbourhood, meet your floor or building, attend every orientation event, learn your CTA line, join two weekly activities, and spend one day seeing the city with new people. Then fix a weekly rhythm before classes begin.

How long does it take to make friends in a new city?

Familiarity takes two to three weeks of repeated contact; real friendship usually takes two to three months. The variable you control is repetition — the same people, the same place, the same time each week.

Do I need a car as a student in Chicago?

No. Chicago has one of the best transit systems in the United States, and parking is expensive and scarce near most campuses. A Ventra pass, a bike in the warm months and occasional rideshares cover almost everything.

When does homesickness usually hit?

Most students feel it hardest in weeks three to five, once the novelty fades and everyone else looks settled. It is nearly universal and temporary. Keep your weekly commitments during it — that is precisely when they pay off.