Chicago, affectionately known as the Windy City, captivates first-time visitors with its stunning architecture, world-class museums, beautiful lakefront, and celebrated food scene. Visiting Chicago for the first time? From the iconic skyline views to cultural landmarks, this comprehensive guide will help you navigate the best of the city of Chicago's tourist information.
Best Time To Visit Chicago
Chicago experiences four distinct seasons, each offering a unique atmosphere for visitors. The best time to visit Chicago depends on your tolerance for weather extremes and what activities you hope to enjoy during your stay in the Windy City.
Seasonal Highlights for Visitors
Summer (June-August) brings warm temperatures averaging 73°F-84°F, perfect for exploring outdoor attractions and enjoying the city's many festivals. This peak tourist season features events like Taste of Chicago, Lollapalooza, and spectacular fireworks at Navy Pier. While summer offers ideal weather for sightseeing, expect larger crowds and higher accommodation rates.
Fall (September-November) treats visitors to stunning foliage and comfortable temperatures between 50°F-70°F. The city becomes less crowded after Labor Day, making autumn an excellent time for those seeking a balance between pleasant weather and fewer tourists. Chicago's cultural calendar remains lively with events like the Chicago International Film Festival and Open House Chicago.
Winter (December-February) transforms Chicago into a winter wonderland, though temperatures frequently drop below freezing. Despite the cold, this season has its charms with festive holiday decorations, ice skating at Millennium Park, and the magnificent Christkindlmarket. Budget-conscious travelers will find the most affordable hotel rates during this period.
Spring (March-May) offers gradually warming temperatures and blooming gardens throughout the city. While early spring can be unpredictable with occasional rain showers, May brings comfortable conditions ideal for outdoor activities. Spring visitors enjoy fewer crowds than summer tourists while witnessing the city's reawakening.
Top Attractions To Explore and Best Times to Visit
Chicago's world-class attractions offer something for every interest, and Chicago CityPASS® tickets provide an excellent way to experience the city's highlights while saving on admission costs. Here's what to see and when to visit for the optimal experience.
Art Institute of Chicago
The Art Institute of Chicago houses one of the world's finest art collections, featuring works from ancient civilizations to contemporary masterpieces. Highlights include an impressive Impressionist collection and the iconic "American Gothic" painting. Allow at least 3-4 hours to appreciate this cultural treasure.
Best Time To Visit: Thursday evenings provide extended hours with a more relaxed atmosphere, perfect for appreciating the masterpieces without the usual crowds.
Skydeck Chicago
At the Skydeck Chicago, visitors can step onto The Ledge — glass balconies extending four feet outside the 103rd floor of Willis Tower, offering heart-stopping views 1,353 feet above the city streets. On clear days, visibility extends to four states.
Best Time To Visit: For spectacular sunset views, arrive at least 90 minutes before sunset. While this coincides with peak visiting hours, the extra planning ensures you'll experience this breathtaking perspective without excessive waiting.
Field Museum
The Field Museum invites exploration of natural history through impressive exhibits, including SUE, the world's most complete Tyrannosaurus rex fossil. Interactive displays engage visitors of all ages in scientific discovery through millions of specimens and artifacts.
Best Time To Visit: Weekday mornings (Tuesday through Thursday) typically offer the lightest crowds. Arriving 30 minutes before opening time means you'll be among the first to enter, giving you unobstructed views of popular exhibits.
Shedd Aquarium
Shedd Aquarium brings the aquatic world to life with Caribbean coral reefs, Amazon flooded forests, and Great Lakes exhibits among its diverse habitats, housing more than 32,000 animals. The oceanarium's dolphin presentations showcase these intelligent mammals' natural behaviors.
Best Time To Visit: Like the Field Museum, weekday mornings offer the best experience with smaller crowds. Check the schedule for dolphin presentations upon arrival and plan your visit accordingly.
Griffin Museum of Science and Industry
The Griffin Museum of Science and Industry, housed in the former Palace of Fine Arts from the 1893 World's Columbian Exposition, offers hands-on exhibits ranging from a coal mine to a German U-boat captured during World War II. Its interactive approach makes complex scientific concepts accessible to visitors of all ages.
Best Time To Visit: This expansive museum tends to be less crowded on weekday afternoons, allowing for more hands-on interaction with the exhibits without competing with school groups that often visit in the mornings.
360 CHICAGO Observation Deck
For magnificent city views from a different perspective, 360 CHICAGO Observation Deck offers panoramic vistas from 1,000 feet above the Magnificent Mile. Thrill-seekers can experience TILT, a moving platform that extends outward at an angle over Michigan Avenue.
Best Time To Visit: Weekday evenings offer breathtaking twilight views of the cityscape with fewer visitors. Witness the magical transformation as thousands of lights illuminate the Chicago skyline, creating a perfect photo opportunity.
Getting Around Chicago
Chicago boasts one of America's most comprehensive public transportation systems, making it remarkably easy to navigate without a car.
Public Transportation Options
The Chicago Transit Authority (CTA) operates an extensive network of trains and buses covering virtually every part of the city. The "L" train system, named for its elevated tracks in many areas, features color-coded lines connecting downtown with outlying neighborhoods and both airports.
Metra commuter trains serve Chicago's suburbs with reliable service and comfortable cars. For water-based transportation, seasonal water taxis offer scenic routes between major attractions along the lakefront and the Chicago River during warmer months.
Rideshare services like Uber and Lyft operate throughout Chicago, providing convenient door-to-door service when public transportation might not be ideal. The city's DIVVY bike-sharing program offers another flexible option for shorter trips.
Navigating the CTA System
First-time visitors should consider purchasing a Ventra Card, Chicago's reloadable transit card that's usable on all CTA trains and buses. These can be purchased at airport stations, Ventra vending machines at all train stations, or select retail locations throughout the city.
When riding the "L," remember that trains are identified by their terminal destination and color. Downtown stations serve multiple lines, so confirm you're boarding the correct color line heading in your desired direction.
For efficient travel between major attractions, the Red and Blue Lines operate 24/7, while other lines maintain regular hours from early morning until midnight or later. Downtown Chicago's Loop area serves as the hub of the transit system, with connections to all train lines.
To maximize your transit experience, download the Ventra app for real-time arrival information and route planning. Consider a multi-day pass if you'll be making several trips daily.
Bike Rentals and Cycling Paths
Chicago has embraced cycling culture with over 200 miles of bike lanes and paths. The DIVVY bike-sharing system offers convenient short-term rentals with stations throughout the city. Simply use the DIVVY app to locate and unlock bikes, then return them to any station when finished.
The crown jewel of Chicago's cycling infrastructure is the 18.5-mile Lakefront Trail, offering uninterrupted scenic views of Lake Michigan, beaches, and the city skyline. This path connects many major attractions, including the Museum Campus, Navy Pier, and Lincoln Park.
For a less congested route, the 606 Trail (also called the Bloomingdale Trail) provides an elevated path through northwest neighborhoods, while the North Branch Trail offers a nature-focused ride along the Chicago River.
Many bike rental companies offer guided tours highlighting architectural landmarks, historic neighborhoods, or culinary hotspots for those wanting a more structured experience.
Walking Tips for Visitors
Chicago's downtown area is remarkably walkable, with a grid-based street system making navigation straightforward. State Street and Madison Street serve as the zero points for address numbering, with eight blocks roughly equaling one mile.
The Chicago Riverwalk provides a scenic pedestrian path along the Chicago River, connecting many downtown attractions without crossing streets. For longer distances, the underground Pedway system offers climate-controlled walkways connecting buildings throughout the Loop, particularly useful during extreme weather.
When exploring beyond downtown, be mindful that neighborhoods can change character quickly. Research your route beforehand and consider using public transportation for longer distances between areas of interest.
Practical Tips for First-Time Visitors
Making the most of your Chicago visit requires some insider knowledge to navigate the city like a local.
Safety Tips for Exploring the City
Chicago, like any major city, requires common-sense precautions while exploring. Stay aware of your surroundings, especially when using public transportation or visiting unfamiliar neighborhoods. The CTA system is generally safe, particularly during daylight hours and in tourist-heavy areas.
Downtown areas frequented by tourists maintain a strong police presence, particularly around major attractions and shopping districts. When using the "L" train after dark, ride in the first car near the conductor for added security.
Keep valuable items secure, and avoid displaying expensive electronics or jewelry conspicuously. If using a backpack in crowded areas, consider wearing it front-facing to deter pickpockets.
For emergency assistance, dial 911. For non-emergency police matters, call 311, Chicago's city services number that can also provide information about city regulations and services.
Best Neighborhoods To Stay In
The Loop offers convenient access to major attractions, transportation hubs, and business districts. Hotels here provide prime locations for first-time visitors wanting to maximize sightseeing opportunities without extensive travel time.
River North places you amid Chicago's renowned dining scene, with hundreds of restaurants ranging from casual eateries to fine dining establishments. This neighborhood also provides easy access to the Magnificent Mile shopping district.
For a more relaxed atmosphere with tree-lined streets and local character, consider Lincoln Park or Lakeview. These neighborhoods offer lower hotel rates while maintaining good public transportation connections to downtown attractions.
Families might appreciate the Museum Campus area near Soldier Field, with proximity to the Field Museum, Shedd Aquarium, and Adler Planetarium. This location offers peaceful lake views away from downtown congestion while remaining accessible via short bus rides.
Budget-Friendly Options
Chicago offers numerous free attractions perfect for budget-conscious travelers. Millennium Park showcases public art, including the famous Cloud Gate sculpture (The Bean) reflecting the city skyline in its polished surface. Free concerts and events frequently take place at the Jay Pritzker Pavilion, particularly during the summer months.
The Chicago Riverwalk provides a scenic pedestrian path along the Chicago River with public seating areas, restaurants, and impressive views of architectural landmarks. Walking this 1.25-mile path costs nothing but offers million-dollar perspectives of the city.
Grant Park, known as "Chicago's front yard," encompasses 319 acres of green space, including Buckingham Fountain — one of the world's largest fountains. During summer evenings, the fountain features spectacular light and water displays synchronized to music.
For cultural enrichment without cost, many museums offer free admission days throughout the year. The Chicago Cultural Center hosts free exhibitions, performances, and lectures in a beautiful Beaux-Arts building featuring the world's largest Tiffany glass dome.
Weather and What To Pack
Chicago's weather can be unpredictable, sometimes experiencing significant temperature changes within a single day. Layered clothing provides flexibility, regardless of the season.
Summer visitors should pack lightweight, breathable clothing and a light jacket for cooler evenings or air-conditioned indoor spaces. Comfortable walking shoes, sunscreen, and sunglasses are essential for extended outdoor exploration.
Fall and spring travelers benefit from medium-weight layers that can be added or removed as temperatures fluctuate. A waterproof jacket or umbrella prepares you for unexpected rain showers common during these transitional seasons.
Winter demands serious cold-weather gear like a heavy insulated coat, hat, gloves, scarf, and waterproof boots. Thermal underwear provides additional comfort when exploring outdoor attractions during frigid conditions.
Year-round, comfortable walking shoes remain the most important item for Chicago visitors, as you'll likely cover significant distances on foot even when using public transportation between destinations.
Food and Dining Near Major Attractions
Chicago's culinary scene offers distinctive local specialties and international cuisine options, many conveniently located near major attractions.
Near the Art Institute and Millennium Park, The Gage offers upscale comfort food in a historic building, while Cindy's Rooftop provides American cuisine with spectacular views across Michigan Avenue. For quick bites, Goddess and the Baker serves excellent coffee and sandwiches perfect for a mid-sightseeing refuel.
The Museum Campus area near the Field Museum and Shedd Aquarium offers fewer immediate dining options, making Kim and Carlo's Hot Dog Stand a popular choice for quick, affordable meals. For sit-down service, Acadia offers fine dining nearby, while Eleven City Diner provides family-friendly comfort food within walking distance.
Near Willis Tower and the Skydeck, visitors can enjoy classic Chicago deep-dish pizza at Lou Malnati's or Giordano's, both offering the quintessential Chicago pizza experience. The French Market food hall provides multiple quick-service options in an indoor marketplace setting.
The Museum of Science and Industry area connects to Hyde Park's diverse dining scene. Medici on 57th serves classic American fare in a bohemian setting, while Virtue Restaurant offers refined Southern cuisine worthy of its national acclaim.
For authentic Chicago-style hot dogs (never with ketchup!), Portillo's locations throughout the city offer this local specialty, featuring all-beef franks topped with yellow mustard, green relish, chopped onions, tomato wedges, pickle spear, sport peppers, and a dash of celery salt on a poppy-seed bun.
Maximize Your Chicago Experience With CityPASS® Tickets
Make your first Chicago visit memorable and affordable with Chicago CityPASS® tickets. These curated ticket packages offer significant savings on admission to Chicago's top attractions while providing the flexibility to explore at your own pace.
Beyond substantial cost savings — up to compared to combined individual admission prices — CityPASS® tickets offer convenience by eliminating the need to purchase separate tickets at each venue. The tickets remain valid for nine consecutive days, starting with your first attraction visit, allowing ample time to explore without rushing between destinations.
Whether you're in Chicago for a weekend getaway or an extended vacation, CityPASS® tickets provide an excellent foundation for discovering what makes this magnificent city so beloved by visitors and locals alike.
Chicago Lodging
To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you: