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Chicago, United States of America - Things to Do in Chicago

Things to Do in Chicago

Chicago, United States of America - Complete Travel Guide

Chicago, the Windy City, stands as one of America's greatest urban destinations, where world-class architecture meets deep-dish pizza and blues music echoes through the streets. This dynamic metropolis on Lake Michigan's shores boasts an impressive skyline punctuated by architectural marvels, from the Willis Tower to Frank Lloyd Wright masterpieces, while its cultural scene rivals any major city with renowned museums, theaters, and music venues. Beyond its iconic attractions, Chicago pulses with authentic neighborhood character, from the trendy boutiques of Wicker Park to the historic charm of Lincoln Park. The city's culinary landscape extends far beyond its famous pizza and hot dogs, encompassing innovative fine dining, diverse ethnic cuisines, and a thriving craft beer scene. Whether you're admiring public art in Millennium Park, catching a Cubs game at Wrigley Field, or exploring world-class museums along the lakefront, Chicago offers an perfect blend of Midwestern warmth and metropolitan sophistication.

Top Things to Do in Chicago

Architectural Boat Tour

Cruise along the Chicago River to witness the city's stunning architectural legacy from a unique water-level perspective. These guided tours showcase over 40 notable buildings including the Willis Tower, Tribune Tower, and Marina City while expert guides share fascinating stories about the architects and history behind each structure.

Booking Tip: Tours run April through November with tickets ranging from $40-60. Book morning or early afternoon tours for the best lighting and photography opportunities. Chicago Architecture Foundation tours are considered the gold standard.

Millennium Park and Cloud Gate

Explore Chicago's crown jewel public space featuring the iconic reflective Cloud Gate sculpture (affectionately called 'The Bean') and the stunning Crown Fountain. The park also hosts free concerts at the Jay Pritzker Pavilion during summer months and offers beautiful views of the city skyline.

Booking Tip: The park is free to visit year-round, but arrive early morning or late afternoon to avoid crowds around Cloud Gate. Summer concerts are free but arrive 1-2 hours early for good seating.

Art Institute of Chicago

Discover one of the world's premier art museums housing an incredible collection of Impressionist and Post-Impressionist masterpieces, including works by Monet, Renoir, and Van Gogh. The museum also features extensive American art, contemporary pieces, and rotating special exhibitions that draw visitors from around the globe.

Booking Tip: General admission costs around $30-35 for adults. Purchase tickets online in advance to skip lines, and consider visiting on weekday mornings for smaller crowds. Chicago residents get discounted admission with ID.

Deep Dish Pizza Experience

Indulge in Chicago's most famous culinary creation at legendary establishments like Lou Malnati's, Giordano's, or Pequod's. These thick-crust pizza pies are loaded with cheese, toppings, and chunky tomato sauce, representing a uniquely Chicago dining experience that's part meal, part cultural immersion.

Booking Tip: Deep dish pizza takes 30-45 minutes to prepare, so call ahead or be prepared to wait. Expect to pay $15-25 for a medium pizza. Many places don't take reservations, so visit during off-peak hours.

Lincoln Park Zoo and Lakefront

Visit one of America's last free major zoos, home to over 1,000 animals in beautifully landscaped grounds. After exploring the zoo, stroll along the adjacent lakefront trail offering stunning views of Lake Michigan and the Chicago skyline, perfect for jogging, cycling, or simply relaxing by the water.

Booking Tip: The zoo is completely free year-round, though parking costs $40-50 on weekends. Visit weekday mornings for the most active animals and smallest crowds. The lakefront trail extends for miles in both directions.

Getting There

Chicago is easily accessible via two major airports: O'Hare International Airport (ORD), one of the world's busiest hubs located 17 miles northwest of downtown, and Midway International Airport (MDW), smaller but closer at 10 miles southwest. The city serves as a major rail hub with Amtrak's Union Station connecting to destinations across the country, while extensive interstate highways including I-90, I-94, and I-55 provide excellent road access. The Blue Line train connects O'Hare directly to downtown in about 45 minutes for $5, while the Orange Line serves Midway, making airport transfers both convenient and affordable.

Getting Around

Chicago's comprehensive public transportation system, operated by the CTA, includes eight 'L' train lines and extensive bus routes that efficiently connect all major neighborhoods and attractions. A 1-day CTA pass costs $20 and covers unlimited rides on both trains and buses, while individual rides are $2.50-3.25. The city is also very walkable, especially in the downtown Loop area and along the lakefront, while ride-sharing services like Uber and Lyft are readily available. For longer stays, Divvy bike-share stations throughout the city offer an eco-friendly way to explore, with day passes starting at $15.

Where to Stay

The Loop (Downtown)
River North
Magnificent Mile
Lincoln Park
Wicker Park/Bucktown
South Loop

Food & Dining

Chicago's culinary scene extends far beyond deep-dish pizza, encompassing everything from Michelin-starred fine dining to authentic ethnic neighborhoods and innovative food halls. The city excels in steakhouses, with legendary spots like Gibsons and RPM Steak, while areas like Chinatown, Little Village, and Devon Avenue offer authentic international cuisines. Don't miss Chicago-style hot dogs (never with ketchup!), Italian beef sandwiches, and the growing craft brewery scene in neighborhoods like Logan Square and Pilsen. Food halls like Revival Food Hall and Time Out Market provide excellent opportunities to sample multiple local vendors in one location.

Top-Rated Restaurants in United States

Highly-rated dining options based on Google reviews (4.5+ stars, 100+ reviews)

Peppermill and Fireside Lounge

4.5 /5
(19043 reviews) 2
bar night_club

Moonshine Grill

4.6 /5
(7161 reviews) 2
bar

The Southern Gentleman

4.8 /5
(4877 reviews) 2

The Guenther House

4.5 /5
(4678 reviews) 2

Canlis

4.6 /5
(2800 reviews) 4
bar

Whiskey Bird

4.8 /5
(2525 reviews) 2

When to Visit

The ideal time to visit Chicago is late spring through early fall (May through October) when temperatures are comfortable and outdoor activities, festivals, and lakefront attractions are in full swing. Summer months (June-August) offer the warmest weather and most events but also bring crowds and higher hotel rates. Spring (April-May) and fall (September-October) provide pleasant weather with fewer tourists and beautiful seasonal changes, especially along the lakefront. Winter can be harsh with temperatures often below freezing and strong winds off Lake Michigan, but holiday decorations, indoor attractions, and lower hotel rates make it appealing for budget-conscious travelers who don't mind bundling up.

Insider Tips

Many of Chicago's best attractions are free, including Lincoln Park Zoo, Millennium Park, the lakefront trail, and numerous festivals throughout the summer
The Chicago CityPASS offers significant savings if you plan to visit multiple major attractions like Skydeck, Art Institute, and Shedd Aquarium
Avoid driving in downtown Chicago if possible - parking is expensive ($25-40/day) and traffic can be heavy, while public transportation efficiently connects all major areas

Explore Activities in Chicago