CHICAGOin five days
Chicago is one of those cities you enjoy way more when you know how to move through it: which neighborhoods pair well together, where it's worth eating, what to book ahead, and how to get the most out of each day without walking yourself into the ground.
In this itinerary I lay out 5 days organized by neighborhood, with real timings, USD costs, restaurants, direct booking links and practical tips so you can do Chicago with more calm, more intent and less improvising.
The full cost breakdown, before you travel.
All in USD, per person at double occupancy, mid-high hotels, tips included. So you land without surprises on the bill.
Chinatown and back via Magnificent Mile
Four more days to go.
Unlock the remaining 4 days
The full itinerary on a private web page: hour-by-hour stops, costs, transport and neighborhood maps.
When to go?
Plan it yourself vs. let me hand it to you.
Same trip. You decide how much time you want to spend planning it.
You plan it
- —10–15 hours across blogs, TikTok and reels
- —Decisions made mid-day
- —Overpaying at the door for tickets
- —Wishing you'd known about the spots you missed
You use this itinerary
- +Read the whole thing in half an hour
- +Decisions made before you leave
- +Route optimized neighborhood by neighborhood
- +The right spots at the right time
Your itinerary, ready.
- It is a digital guide for the Chicago itinerary, written and built by Stephanie Abreu. Accessed on the web with your email.
- It is not a travel agency. It does not include reservations for flights, hotels, transfers, attraction tickets or insurance. Those bookings are on you, using the links inside.
- Prices and hours are references and can change with season and provider availability. I refresh the route from time to time and updates are free.
- Refunds: because this is a digital product with instant access, purchases are non-refundable once you've accessed the content.
- Personal use. You can't copy, redistribute or resell this guide. Each purchase is for one person.