Chicago Travel Guide for First-Time Visitors: Top Attractions, Hotels, and Tips
Chicago, the “Windy City,” is one of the most dynamic and diverse cities in the United States. Situated on the shores of Lake Michigan, this Midwest metropolis is known for its stunning architecture, world-class museums, vibrant food scene, and deep-rooted cultural history. If you're visiting Chicago for the first time, this guide will help you explore the Chicago city's must-see attractions, find the right accommodations, and navigate the city like a pro.
Top Attractions in Chicago
1. Millennium Park and Cloud Gate
No visit to Chicago is complete without a selfie at “The Bean.” Officially named Cloud Gate, this iconic stainless-steel sculpture is the centerpiece of Millennium Park. The park itself is a vibrant green space offering art installations, gardens, and the Jay Pritzker Pavilion where live music events often take place.
2. Art Institute of Chicago
Home to over 300,000 works of art, the Art Institute is one of the oldest and most prestigious museums in the country. From Monet and Van Gogh to modern and contemporary artists, the collection is impressive and suitable for art lovers of all kinds.
3. Navy Pier
This 3,300-foot-long pier on Lake Michigan is filled with attractions including the Centennial Wheel, Chicago Children’s Museum, and numerous restaurants and shops. It's an ideal destination for families and those looking to enjoy lakeside views and entertainment.
4. Willis Tower Skydeck
Once the tallest building in the world, the Willis Tower offers breathtaking views of the city from its 103rd-floor Skydeck. Don’t miss “The Ledge”—glass boxes that extend outside the building, offering a thrilling view straight down.
5. Museum Campus
Located along the lakefront, Chicago’s Museum Campus is home to the Field Museum (natural history), Shedd Aquarium, and Adler Planetarium. It's perfect for spending a full day immersed in science, nature, and space.
6. Magnificent Mile
Stretching along Michigan Avenue, the Magnificent Mile is a shopper’s paradise. You'll find everything from luxury boutiques and department stores to popular chains. It’s also dotted with historic buildings and top-rated restaurants.
7. Lincoln Park and Zoo
Just north of downtown, Lincoln Park offers a more relaxed, neighborhood vibe. The Lincoln Park Zoo is one of the oldest in the country and is free to the public, making it a great stop for budget-conscious travelers.
Where to Stay: Top Hotel Recommendations
Chicago offers a wide variety of accommodations to suit different budgets and preferences. Here are a few popular choices:
1. Luxury: The Peninsula Chicago
Located just off the Magnificent Mile, The Peninsula is known for its world-class service, spacious rooms, and a rooftop spa. It’s perfect for travelers looking for a high-end experience in the heart of the city.
2. Mid-Range: Hotel Lincoln
Situated near Lincoln Park, this boutique hotel offers comfortable, stylish rooms with a touch of vintage flair. It’s ideal for visitors who want to stay outside the hustle and bustle but still close to the action.
3. Budget-Friendly: Freehand Chicago
This trendy hostel-hotel hybrid offers shared and private rooms, a hip cocktail bar, and a communal atmosphere. Located in River North, it’s a solid option for solo travelers and young tourists.
4. Family-Friendly: Embassy Suites Downtown
With spacious two-room suites, complimentary breakfast, and a convenient location near the Riverwalk, this is a favorite among families traveling with children.
Getting Around the City
Chicago is a large but highly navigable city with several convenient transportation options:
CTA (Chicago Transit Authority): The “L” trains and buses are the most cost-effective way to get around. A Ventra card allows easy access to both systems.
Walking: Many attractions in downtown Chicago are within walking distance.
Divvy Bikes: Bike-sharing is popular during warmer months and great for short trips.
Taxis & Rideshares: Readily available and easy to use through apps like Uber and Lyft.
Water Taxis: A scenic way to move between attractions near the river and lake.
Pro tip: Avoid renting a car unless you plan to explore the suburbs. Parking in downtown Chicago can be expensive and difficult to find.
Food and Dining: What to Eat in Chicago
Chicago’s food scene is legendary. From Michelin-starred restaurants to beloved local diners, there’s something for everyone.
Deep-Dish Pizza: Lou Malnati’s, Giordano’s, and Pequod’s are among the top places to try this cheesy, tomato-packed pizza.
Chicago-Style Hot Dogs: A must-try. These all-beef franks come topped with mustard, onions, relish, tomato slices, a pickle spear, sport peppers, and celery salt—on a poppy seed bun. No ketchup allowed!
Italian Beef Sandwiches: A savory, juicy sandwich best enjoyed at places like Portillo’s or Al’s Beef.
International Cuisine: Chicago has vibrant neighborhoods like Chinatown, Pilsen (Mexican), and Greektown with amazing authentic food.
Fine Dining: For something special, book a table at Alinea, one of the best restaurants in the world.
Tips for First-Time Visitors
1. Pack for the Weather
Chicago weather can be unpredictable. Summers are hot and humid, while winters are bitterly cold. Spring and fall are pleasant but vary, so bring layers.
2. Plan Your Museum Visits
Some museums offer free admission on certain days for Illinois residents. If you’re not local, consider getting a CityPASS to save on admission fees.
3. Be Mindful of Time Zones
Chicago is in the Central Time Zone. If you're traveling from the East or West Coast, adjust your schedule accordingly.
4. Tipping Etiquette
Like most of the U.S., tipping is standard. Aim to tip 15–20% at restaurants and a couple of dollars for bellhops, housekeeping, and cab drivers.
5. Stay Safe
Downtown and the tourist areas are generally safe, but like in any big city, stay alert, especially at night or in less-populated neighborhoods.
Bonus: Off-the-Beaten-Path Experiences
If you’ve got extra time or want to explore beyond the main sights, consider:
Chicago Architecture Boat Tour: A relaxing and educational way to see the city’s skyline and learn about its rich architectural history.
The 606 Trail: An elevated bike and walking trail offering art installations and great views.
Andersonville and Logan Square: Trendy neighborhoods with cool cafes, independent shops, and local flavor.
Garfield Park Conservatory: A beautiful (and free!) indoor botanical garden on the West Side.
Final Thoughts
Chicago is a city that blends history, culture, and modern innovation. Whether you’re marveling at the skyline from the Willis Tower, eating your way through neighborhoods, or relaxing by the lake, there's something to captivate every kind of traveler. With this guide in hand, you’ll be well-equipped to enjoy the best that Chicago has to offer on your first trip.
For more information on planning your trip, be sure to check out the following resources:
Safe travels and enjoy your visit to the Windy City!
