Chicago Travel Checklist. Before You Go, Packing List, Preparation

Important Preparations

Strategic planning for your Chicago visit minimizes last-minute stress.

Chronological Planning

Follow these time markers for comprehensive trip organization.

Months Before

Passport Validity

Ensure your passport is valid for at least six months beyond your travel dates.

Flight Bookings

Secure international flights as early as possible for favorable pricing.

Accommodation

Book your lodging, especially during peak season or major events.

Month Before

Domestic Travel

Reserve any connecting domestic flights or train tickets.

Tours & Dining

Book must-do tours and make restaurant reservations for popular spots.

Travel Insurance

Secure travel insurance for medical events, cancellations, or lost luggage. Get a quote from World Nomads.

Week Before

Confirmations

Reconfirm all flight, hotel, and tour reservations.

Bank Notification

Inform your bank and credit card companies of your travel dates.

Packing & Apps

Begin packing and download necessary apps for navigation and transit.

Required Advance Bookings

Certain popular attractions and services require early booking.

Reservations

Flights and accommodation secure your travel framework.
Architectural Boat Tours often sell out; book well in advance.
Fine dining establishments require reservations, sometimes weeks ahead.
Consider museum tickets or city passes for popular venues.

Pre-Trip Research

Familiarity with Chicago's layout and culture enhances your visit.

Areas of Study

Read about Chicago's rich history and architectural heritage.
Familiarize yourself with the CTA map for efficient navigation.
Check for major events or festivals during your visit.
Understand Chicago's diverse neighborhood characteristics.

Home Preparation

Final domestic arrangements for peace of mind while away.

Mail & Deliveries

Arrange for mail to be held by postal service.
Coordinate package deliveries or pick-ups.
Ask a trusted person to collect newspapers or flyers.
Update subscriptions for temporary holds.

Pet & Plant Care

Organize pet sitting or boarding services.
Arrange for plant watering, especially for delicate species.
Provide detailed instructions for pet care providers.
Leave emergency contacts for pet sitters.

Home Security & Bills

Secure all doors and windows before leaving.
Set timers for lights to deter intruders.
Plan for any bill payments due during your absence.
Unplug non-essential electronics to save energy.

Final Check

Double-check all essential documents before walking out the door. A quick review avoids major travel disruptions.

Arrival Checklist

The first few hours in Chicago set the tone for your trip; follow these steps for a smooth transition.

First Steps Upon Arrival

1
Clear Customs
Navigate customs and immigration upon international arrival.
2
Collect Luggage
Retrieve your baggage from the claim area.
3
Proceed to Transport
Locate your chosen method for reaching downtown.

Orientation Strategies

Locate Accommodation
Pinpoint your lodging on a digital or physical map.
Ventra Card
Purchase a Ventra Card for seamless CTA public transport access.
Physical Map
Consider a backup physical map alongside digital options.

Initial Finances & Transport

Currency Exchange

Withdraw some cash from an airport or city ATM for immediate small purchases upon arrival.

Avoid airport exchange booths due to unfavorable rates.

CTA Passes

Purchase a multi-day CTA pass if your stay exceeds one day; it offers both convenience and savings.

Passes are available at Ventra vending machines in 'L' stations.

Airport Transport

Utilize the CTA Blue Line from O'Hare or Orange Line from Midway for cost-effective transfers downtown.

These lines avoid traffic and are often quicker than taxis.

Departure Preparation

Ensure a smooth departure by handling last-minute details and logistics.

Souvenirs & Shipping

Plan souvenir shopping throughout your trip to avoid rushing.
Inquire about shipping options from retailers for large items.
Consider shipping services for fragile or bulky purchases.
Be aware of customs regulations for items entering your home country.

Pre-Departure Timing

Arrive well in advance for international flights (3 hours before).
Check-in online if your airline permits to save time.
Pack liquids according to airport security rules for carry-on.
Keep all travel documents easily accessible.

Departure Logistics

Final checks for a seamless exit from Chicago.

Check-out Procedures

Settle any outstanding hotel charges.
Return any rented items (e.g., bikes).
Confirm airport transfer arrangements.
Double-check your room for forgotten items.

Return Trip Preparation

Reconfirm your flight or train details.
Have boarding passes ready, either printed or on your phone.
Consider downloading entertainment for your journey.
Anticipate any home tasks upon your return.

Smooth Exit

A planned departure ensures your final moments in Chicago are relaxed.

It completes the cycle of a well-executed trip.

Chicago Travel Checklist