Best things to do in Chicago

We believe a 3- to 5-day vacation is the perfect ideal stay to cover the best things to do in Chicago! You'll get plenty of time to explore top attractions like Millennium Park, the Art Institute, and the Magnificent Mile, along with experiencing a boat tour or exploring the city's unique neighborhoods like Lincoln Park or Pilsen. You can definitely hit the must-sees in 3 days, but a trip of 5 days allows for a deeper dive into Chicago's food and cultural picks. To truly soak in the city vibes, don't just see the city; get to know it!

Yes, Chicago is generally safe for tourists, especially in popular areas like The Loop and Magnificent Mile and famous neighborhoods like Lincoln Park and River North. Like anywhere in the world, staying aware of your surroundings and avoiding less busy areas late at unusual hours is imperative. To feel completely secure, stick to tourist-friendly neighborhoods, use well-lit streets and rely on safe transportation options like CTA, rideshares, or licensed taxis. Chicago's tourist spots are patrolled and well-maintained, so with basic safety precautions, you can enjoy the vibrance and attractions worry-free with things to do in Chicago!

The Ventra Card is your key to Chicago’s public transit. It’s a reusable, reloadable card that works on both the CTA (buses and 'L' trains) and Pace buses. You can load it with cash for pay-as-you-go rides or purchase unlimited ride passes (like 1-day, 3-day, or 7-day options). Just tap your card at turnstiles or on buses, and you’re good to go! You can manage your balance and track trains and buses via the Ventra app.

If you are in Chicago for a trip or a short time, you can use a personal, contactless bank card instead. They are more efficient and save you the hassle of registering for a Ventra Card.

The Chicago CityPASS is a different pass that offers discounted entry to top attractions like the Shedd Aquarium and Skydeck Chicago, among others. It doesn’t cover public transit but is perfect for sightseeing on a budget.

Take our advice and use the Ventra Card for transportation and the CityPASS for attractions to save time and money smartly while you have stuff to do in Chicago!

Where you should stay depends on what you want to do in the Windy City.

The Loop is ideal for first-time travelers wondering what to do in Chicago. It is filled with major theaters and different world-class public art. It is also close to iconic sights like Millennium Park, the Art Institute of Chicago, the historic Grant Park, and its spectacular centerpiece, Buckingham Fountain.

Lincoln Park offers attractions like the Lincoln Park Zoo, to name one of many, making it perfect for travelers with family. If you are looking for some luxury shopping, then the Magnificient Mile is your stop! It is an elite commercial district filled with mid- and high-end restaurants, hotels, and bars, along with notable attractions like the Wrigley Building, one of the tallest buildings in the world.

For nightlife, River North has several lively bars, famous nightclubs, entertainment venues, and fine-dining restaurants. West Loop, for foodies, is home to cultural landmarks such as deep-dish pizzas, Chicago-style hot dogs, the Blues, and more. It is the best location for those who want to taste Chicago dishes.

Pro tip: Book your stay a month or two in advance, especially if you are visiting during peak seasons!

Ventra: Essential for public transit. Load your Ventra card, check bus and train schedules, and manage your fares all in one app.

Transit App: Real-time updates on CTA buses, ‘L’ trains, and other public transit options. It even shows bike-sharing and rideshare availability.

Citymapper: Great for navigating Chicago’s public transport, including detailed directions, bike paths, and walking routes.

SpotHero: Helps you find and reserve parking spots across the city, saving time and money.

Divvy Bikes: Ideal for renting bikes from Chicago’s bike-share system, checking available stations, and getting a ride quickly.

Lyft/Uber: For ridesharing to zip around the city when public transport or biking isn’t ideal.

Google Maps: Reliable for directions, transit info, and walking routes, all in one place.