Chicago Travel Tips

Navigate the Windy City with confidence!

Essential Tips And Hacks For Tourists In Chicago

Navigate Chicago like a local with our comprehensive guide.

From what to pack and how to get around to budget-friendly activities and the best times to drop in on our city, this page covers all the essentials for a traveler in the Windy City.

Make your trip truly Magnifico!

Packing For Your Chicago Trip



Embrace Chicago’s warmth! Pack breathable fabrics, a stylish hat for shade, and don’t forget those sunglasses.



Experience the crisp air in comfort. Layer up with cozy sweaters & sturdy boots, and wrap yourself in scarves.



Brace for the chill! Ensure you have thick coats, snug gloves, and thermal wear to combat the cold.



Prepare for showers and sunshine. Carry a handy raincoat, versatile light layers, and always an umbrella.

Sightseeing Simplified: Chicago’s Best Travel Aids

GoCity & CityPASS

Unlock top attractions with savings! Dive into Chicago’s best with these bundled passes.



Rent a bike on the go! Explore Chicago’s scenic routes with Divvy’s convenient service.


Transit App

Navigate the city with ease! Get real-time updates and route options for buses and trains.



Secure your spot in advance! Find and book parking spaces in busy Chicago areas.



Tap and travel! Use one card for buses, trains, and more across the city’s transit system.

Safety In The City

Tourist Safety Essentials

Always stay alert, avoid flashy jewelry, and keep your belongings secure. Trust your instincts!

Late-Hour Caution Zones

Some neighborhoods can be less safe at night. Research ahead and stick to well-lit areas.

Emergency Contacts

Dial 911 for emergencies. Keep a list of nearby hospitals and clinics for quick access.

Digital Safety Tips

Use secure Wi-Fi networks, avoid public USB charging spots, and update your phone’s GPS.

Exploring Chicago On A Budget

Dine at local favorites like Portillo’s for a taste without the price tag. Museums like the Art Institute offer free days monthly. Check city calendars for no-cost festivals. Hostels and guesthouses in Wicker Park provide affordable stays.

When’s The Best Time To Visit?

Watch The Weather!

Avoid Jan & Feb if you want to steer clear of freezing temperatures. Visit in May-June for mild weather and clear skies.

Events & Festivals

Want to be at events like the Jazz Fest in mid-year and Lollapalooza in July-August? Check local listings before planning your visit!

Tourist Rush Times

July-August sees peak tourist rush. If you’d rather explore on your own pace amidst quieter streets, aim for September or October.

Local Etiquette & Tips

In Chicago, tipping is customary: leave 15-20% for good service. Respect local customs; for instance, stand to the right on escalators, allowing others to pass. Avoid discussing politics or making ‘Windy City’ weather jokes; locals have heard them all!

Tech & Connectivity

Tourist SIM Cards

Opt for tourist SIMs at the airport or local stores. They offer short-term data and call packages.

Best Mobile Networks

Verizon, AT&T, and T-Mobile lead in coverage. Choose based on your stay duration and travel spots.

Public Wi-Fi Spots

Many parks, libraries, and cafes offer free Wi-Fi. Always ensure a secure connection before use.

Charging Stations

Seek out cafes like Starbucks for outlets. Some public areas also feature charging kiosks you can use.


  • The St. Valentine's Day Massacre Site
  • The famous alleyway from a legendary crime
  • The haunted Chicago theatre

And a whole lot more!