Chicago is a vibrant, architectural powerhouse known for its stunning skyline, deep-dish pizza, and rich cultural history along the shores of Lake Michigan. The best time to visit is during the late spring or early fall, when the weather is mild and the city's extensive park system is in full bloom.
Top Things to Do in Chicago
Tap an attraction to look it up on TripAdvisor.
Getting Around Chicago
From the Airport
Train. The CTA Blue Line 'L' train runs directly from O'Hare International Airport to downtown for approximately $5.00. Rideshare. Uber and Lyft are widely available at both O'Hare and Midway airports with designated pickup zones outside the terminals.
Once You're There
Metro. The CTA 'L' train system is the most efficient way to navigate the city, with the Red and Blue lines covering most major tourist hubs. Rideshare. Uber and Lyft are the standard for point-to-point travel, especially at night or when heading to neighborhoods not served by the train. Walking. The downtown area, specifically the Loop and River North, is highly walkable and best explored on foot to appreciate the architecture.
Where to Stay in Chicago
Hotel picks for Chicago are coming soon. In the meantime, search directly, pre-filled with your dates:
Where to Eat in Chicago
Au Cheval★ 4.7 (13,113)800 W Randolph St, Chicago, IL 60607, USARenowned for serving what is widely considered the best cheeseburger in the country, often with a significant wait time.
Girl & The Goat★ 4.7 (8,492)809 W Randolph St, Chicago, IL 60607, USAChef Stephanie Izard’s flagship restaurant offers bold, globally-inspired small plates in a bustling West Loop atmosphere.
Bavette's Bar & Boeuf★ 4.7 (4,207)218 W Kinzie St, Chicago, IL 60654, USAA moody, speakeasy-style steakhouse that delivers perfectly prepared cuts in an incredibly intimate and classic setting.
The Purple Pig★ 4.6 (7,512)444 N Michigan Ave Upper Level, Chicago, IL 60611, USALocated on the Magnificent Mile, this spot specializes in exceptional Mediterranean-influenced small plates and house-cured meats.
Alinea★ 4.6 (3,044)1723 N Halsted St, Chicago, IL 60614, USAExperience world-class molecular gastronomy that consistently ranks as one of the best dining experiences on the planet.
Garrett Popcorn Shops★ 4.5 (2,779)835 N Michigan Ave, Chicago, IL 60611, USAGrab the iconic Garrett Mix, a signature blend of cheddar and caramel popcorn that is a mandatory Chicago snack.
Spiaggia★ 4.5 (564)980 N Michigan Ave Ste 1, Chicago, IL 60611, USAOffering high-end Italian cuisine with spectacular views overlooking the northern end of Michigan Avenue.
Portillo's Hot Dogs★ 4.4 (24,916)100 W Ontario St, Chicago, IL 60610, USAA local institution where you must order the classic Chicago-style hot dog with everything on it, including neon green relish.
Lou Malnati's Pizzeria★ 4.4 (13,524)439 N Wells St, Chicago, IL 60654, USAThis is the quintessential spot to try authentic Chicago-style deep-dish pizza with a famous buttery crust.
Rick Bayless' Frontera Grill★ 4.4 (3,460)445 N Clark St, Chicago, IL 60654, USAThis landmark restaurant serves elevated, authentic Mexican cuisine that highlights regional ingredients from the Midwest.
Tours & Activities
Bookable through Viator.
3 Days in Chicago
Iconic Architecture & Downtown Parks
Morning. Start your Chicago adventure at Millennium Park, arriving early to get a clear photo of Cloud Gate before the crowds descend. Wander through the serene Lurie Garden, which offers a beautiful contrast to the towering skyscrapers surrounding the park. From there, walk north toward the Chicago Cultural Center to admire the world's largest Tiffany stained-glass dome. It is free to enter and provides a quiet moment of awe before the busy afternoon. Finish your morning by walking a few blocks over to the Chicago Riverwalk to watch the architecture tour boats pass by.
Afternoon. After grabbing a quick bite, head toward the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend at least three hours here exploring the Impressionist collection and the iconic Grant Wood painting, American Gothic. Once you have had your fill of art, walk over to the Willis Tower to ascend to the Skydeck. Stepping out onto 'The Ledge'—a glass balcony extending four feet out from the 103rd floor—is a rite of passage for every first-time visitor. Be sure to book your tickets online in advance to skip the long ticket counter lines.
Evening. As the sun begins to set, make your way to the Chicago Riverwalk for a cocktail at City Winery. The atmosphere here is electric as the city lights begin to twinkle against the water. Walk along the river toward the Michigan Avenue Bridge for the best vantage point of the Wrigley Building and the Tribune Tower illuminated at night. End your evening with a classic deep-dish pizza experience at a nearby local favorite. It is the perfect way to cap off a day of exploring the heart of the city.
Magnificent Mile & Lakefront Views
Morning. Begin your day on the Magnificent Mile, the famous stretch of Michigan Avenue lined with high-end shops and historical landmarks. Start at the historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871. Walk across the street to the John Hancock Center and head up to 360 Chicago for a panoramic view of the city and the lake. If you are feeling adventurous, try the 'Tilt' experience for an angled view of the streets below. Afterward, stroll through the nearby Palmolive Building to admire its stunning Art Deco architecture.
Afternoon. Head toward the lakefront and spend your afternoon at Navy Pier, Chicago's most visited tourist attraction. Take a ride on the Centennial Wheel for a bird's-eye view of the shoreline and the expansive Lake Michigan. Wander through the indoor Crystal Gardens to escape the wind if it gets chilly, then walk along the pier to see the various street performers and small shops. If you have time, consider booking a short lake cruise from the pier to see the skyline from the water. It provides a unique perspective that you simply cannot get from land.
Evening. Travel north to the Gold Coast neighborhood for a more sophisticated evening vibe. Walk along the tree-lined streets to see the historic mansions before heading to a high-end steakhouse for dinner. The area is known for its upscale dining and vibrant nightlife, making it the perfect place to relax after a long day of sightseeing. If you still have energy, stop by a local jazz club to hear some of the city's legendary blues and jazz musicians. It is the quintessential Chicago way to end the day.
Culture, Sports & Local Neighborhoods
Morning. Take the 'L' train south to the Hyde Park neighborhood to visit the Museum of Science and Industry. This massive museum is housed in the only remaining building from the 1893 World's Fair and is home to a captured WWII German submarine. Spend your morning exploring the interactive exhibits, especially the coal mine simulation and the space exploration hall. Afterward, walk through the nearby University of Chicago campus to see the stunning Gothic-style architecture of the Rockefeller Memorial Chapel. It is a peaceful and intellectual side of the city that is often overlooked by first-time visitors.
Afternoon. Head back toward the city center and make your way to Wrigleyville to see the legendary Wrigley Field. Even if there isn't a game, you can take a walking tour of the stadium to learn about the history of the Chicago Cubs. Walk around the perimeter to see the ivy-covered walls and the famous marquee that has welcomed fans for over a century. Grab a hot dog at a local stand nearby to get the full ballpark experience. Afterward, explore the surrounding bars and restaurants that make this neighborhood so lively during baseball season.
Evening. Finish your trip in the West Loop, Chicago's premier dining destination. This former industrial area is now home to the trendiest restaurants in the city, centered around Randolph Street. Start with a cocktail at a speakeasy-style bar before settling in for a world-class meal at one of the neighborhood's celebrated spots. The atmosphere is energetic and modern, reflecting the city's growth and culinary innovation. It is the perfect place to reflect on your three-day journey through the Windy City.