Planning your first trip to Chicago can feel overwhelming because the city has so much to offer.
From its world-class architecture and deep-dish pizza to the stunning lakefront and lively neighborhoods, Chicago is a destination that blends culture, food, and history seamlessly.
To help you make the most of your visit, here are 15 local tips every first-time traveler should know before exploring the Windy City.
1. Dress for the Weather – It Changes Fast
Chicago weather is famously unpredictable. You could experience sunshine, rain, and strong winds all in the same day.
Locals recommend wearing layers and carrying a light jacket, even in the summer.
Winters can be brutally cold, so if you’re visiting between December and March, pack thermal gear, gloves, and boots.
2. Use Public Transit Instead of Driving
Parking in downtown Chicago is expensive and traffic can be stressful.
Locals prefer using the “L” trains or buses, which are affordable and reliable.
Buy a Ventra card for easy access, and you’ll save time while exploring neighborhoods without worrying about parking tickets.
3. Try More Than Just Deep-Dish Pizza
While Chicago is famous for deep-dish pizza, locals often prefer thin-crust tavern-style pizza.
Don’t miss out on tasting Italian beef sandwiches, Chicago-style hot dogs (no ketchup allowed!), and Garrett’s popcorn mix for a true food experience beyond the tourist favorites.
4. Explore Neighborhoods Beyond Downtown
Downtown has iconic spots like Millennium Park and the Magnificent Mile, but locals encourage you to explore neighborhoods like Pilsen for its murals, Andersonville for unique shops, or Chinatown for authentic cuisine.
Each neighborhood feels like a small city of its own.
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5. Visit Millennium Park Early in the Morning
The “Bean” (Cloud Gate sculpture) is one of Chicago’s most photographed landmarks, but it gets very crowded during the day.
Arrive early in the morning for a quieter experience and better photos without crowds in the background.
6. Take an Architecture River Cruise
Chicago is known for its architectural beauty, and locals say the best way to appreciate it is from the Chicago River.
An architecture boat tour offers stunning views of historic and modern buildings while providing fascinating insights into the city’s history.
7. Walk Along the Lakefront Trail
The Lakefront Trail stretches for 18 miles and is a local favorite for walking, running, or biking.
Even if you’re not into exercise, strolling along the lake gives you beautiful skyline views and a chance to experience Chicago like a resident.
8. Check Out Free Attractions
Chicago offers plenty of free attractions. Millennium Park, Lincoln Park Zoo, and the Chicago Cultural Center are all free to enter.
These are perfect for budget travelers and still give you a rich cultural experience without spending extra.
9. Plan for the Museums – They’re Huge
The Field Museum, Museum of Science and Industry, and Art Institute of Chicago are massive.
Locals suggest dedicating at least half a day to each instead of trying to rush through.
Pick one or two based on your interests and enjoy them fully.
10. Try the Local Breweries
Chicago has a thriving craft beer scene.
Goose Island is the most famous, but neighborhoods like Logan Square and Ravenswood have plenty of smaller breweries worth visiting.
It’s a great way to meet locals and taste unique flavors you won’t find elsewhere.
11. Respect the Chicago-Style Hot Dog Rules
Locals take their hot dogs seriously.
A true Chicago-style hot dog comes with mustard, relish, onion, tomato, pickles, peppers, and celery salt—but never ketchup.
If you want to blend in, follow this unspoken rule when you order.
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12. Don’t Skip the Skyline Views
Chicago has one of the most iconic skylines in the world.
Instead of just going to Willis Tower, locals recommend checking out the 360 CHICAGO Observation Deck at the John Hancock Center or heading to Cindy’s Rooftop Bar for skyline views with a cocktail.
13. Learn the Grid System for Easier Navigation
Chicago’s streets are organized on a grid, making navigation easier once you understand it.
Madison Street divides north and south, while State Street divides east and west.
Locals use street numbers to know exactly where they are in the city.
14. Attend a Street Festival if You Can
Chicago hosts dozens of street festivals, especially in the summer. From music to food festivals, these events are where locals gather.
Check local event calendars—you might stumble upon live music, amazing food, and a vibrant neighborhood celebration.
15. Be Ready for the Wind
The nickname “Windy City” is real. While it originally referred to politics, the breeze from Lake Michigan can be strong.
Hold onto hats, avoid umbrellas on really gusty days, and be prepared for that signature Chicago wind when you’re walking downtown.
Final Thoughts
Your first trip to Chicago can be unforgettable if you know what to expect and follow a few insider tips.
From understanding how to get around to sampling local food favorites and exploring hidden gems, these 15 tips will help you experience the city like a local.
Embrace the energy, prepare for the weather, and enjoy everything the Windy City has to offer.
FAQs About Visiting Chicago for the First Time
1. What is the best time of year to visit Chicago?
The best times to visit are late spring (May–June) and early fall (September–October). The weather is pleasant, festivals are in full swing, and you’ll avoid the harsh winter cold or peak summer humidity. If you love holiday lights and don’t mind the cold, December is also magical.
2. Is Chicago safe for first-time visitors?
Yes, Chicago is generally safe if you stick to well-traveled areas like downtown, the lakefront, and popular neighborhoods. Like any big city, it’s wise to stay alert, avoid wandering alone late at night in unfamiliar areas, and keep valuables secure.
3. How many days should I spend in Chicago?
For a first trip, 3 to 4 days is enough to see the highlights—Millennium Park, the museums, the Riverwalk, and a few neighborhoods. If you want to explore at a slower pace and enjoy food tours or day trips, plan for 5 to 6 days.
4. Is it better to use public transit or rent a car in Chicago?
Public transit is the better choice. Chicago’s “L” trains and buses connect you to most attractions affordably and quickly. Parking downtown is expensive, and traffic can be frustrating. A car is only useful if you’re planning day trips outside the city.
5. What food is Chicago famous for besides deep-dish pizza?
Locals love Italian beef sandwiches, Chicago-style hot dogs, thin-crust tavern pizza, and Garrett Mix popcorn (a sweet-and-savory popcorn blend). You’ll also find incredible international cuisine in neighborhoods like Chinatown, Greektown, and Pilsen.
6. Do I need to book tickets in advance for Chicago attractions?
Yes, especially for popular attractions like Willis Tower Skydeck, 360 Chicago, and architecture boat tours. Booking ahead saves time and ensures you get your preferred time slot. Museums also offer advance ticketing for quicker entry.
7. Can I walk between Chicago’s main attractions?
Many downtown attractions are walkable—Millennium Park, the Art Institute, Navy Pier, and the Riverwalk are all close together. However, for farther spots like Wrigley Field or Museum of Science and Industry, you’ll need public transit or a rideshare.
8. Why is Chicago called the “Windy City”?
Although Chicago is breezy because of Lake Michigan, the nickname originally came from the city’s “windy” politicians in the late 19th century. Today, visitors notice both meanings—the strong lakefront winds and the historic nickname.
9. Are there free things to do in Chicago?
Yes! Locals recommend free attractions like Millennium Park, Lincoln Park Zoo, Navy Pier’s outdoor spaces, the Chicago Riverwalk, and the Cultural Center. These are perfect for budget-friendly exploring without sacrificing fun.
10. What should I avoid as a first-time visitor?
Avoid only eating deep-dish pizza, skipping neighborhoods beyond downtown, and trying to see too many museums in one day. Also, don’t put ketchup on your Chicago hot dog—it’s a local no-no!
