How to Plan a Trip to Chicago
The complete 2026 guide — flights, hotels, things to do and airport transfers, all in one place. Everything a first-time visitor to USA needs.
Your 4-step Chicago plan
Step 1 — Book flights to ORD
O'Hare Airport (ORD) is the main gateway to Chicago. Compare fares across major airlines and OTAs before locking a date.
See flight deals to ORDStep 2 — Pick a neighborhood
Base yourself in Millennium Park + Cloud Gate ("The Bean") for the best first-time visit — Free downtown sculpture park.
Where to stay in ChicagoStep 3 — Plan your itinerary
Start with Millennium Park + Cloud Gate ("The Bean"), then build outward. Most first-time visitors need 3-5 days to see the highlights of Chicago.
Things to do in ChicagoStep 4 — Sort your airport transfer
CTA Blue Line (to The Loop) is $5 and takes 45 min. Pre-book a private transfer for stress-free arrival.
ORD arrival guideBefore you book — visa check
Same USA rules as ATL — ESTA or full visa required, all connecting passengers must clear US immigration. International-to-international transfers at ORD require leaving + re-entering security.