Things to Do in Chicago

Chicago, fondly known as the Windy City, is the third-largest city in the United States and one of the most dynamic urban destinations in the world. Perched on the edge of Lake Michigan, this bustling metropolis has become synonymous with towering skyscrapers, world-class museums, lively neighborhoods, legendary sports, and a culinary reputation that extends far beyond its deep-dish pizza. The city offers a rich tapestry of culture and history, from its rebirth after the Great Chicago Fire of 1871 to its role as a hub for jazz, blues, and architectural innovation.

Visitors are often amazed by the way Chicago balances its modern skyline with welcoming green spaces and how its neighborhoods each offer their own unique identity, from the artsy murals of Pilsen to the jazz clubs of Bronzeville. It is a city that celebrates diversity and creativity, drawing millions of visitors annually. If you are planning your next adventure, here is a comprehensive guide that highlights the best things to do in Chicago, along with insider tips to help you create unforgettable experiences.

Best Time to Visit Chicago

One of the key considerations when planning your trip to Chicago is timing. The city’s Midwestern climate offers stark seasonal changes, each bringing its own flavor to your journey.

• Spring (April to May 2025): This is a refreshing time to visit as the city’s parks and gardens burst into bloom. The weather is comfortable for exploring Millennium Park, strolling through the Riverwalk, or taking your first architectural boat cruise of the year. Seasonal festivals such as the Chicago Beer Classic bring crowds of enthusiasts together.
• Summer (June to August 2025): The heartbeat of the city comes alive in summer. Temperatures average between 75°F and 90°F, creating perfect conditions for rooftop bars, lakeside picnics, and iconic festivals. Expect events such as Lollapalooza, the Taste of Chicago, the Grant Park Music Festival, and neighborhood parades. Lake Michigan beaches are packed with sun seekers and water sports lovers. This season is vibrant but also busy, with higher hotel prices.
• Fall (September to November 2025): Arguably the best time to visit. Comfortable temperatures between 55°F and 75°F combine with spectacular fall foliage, especially in Lincoln Park and Jackson Park. The Chicago International Film Festival adds cultural richness to the city’s schedule, while foodies flock to restaurant weeks and Oktoberfest celebrations.
• Winter (December to March 2025): Winters are cold, snowy, and often harsh, with temperatures dipping below freezing. Yet for those who love a magical holiday atmosphere, this is a charming season. Ice skating at Millennium Park, holiday lights at Lincoln Park Zoo, and cozy indoor museums provide a different kind of warmth. Hotel rates also fall significantly during winter, making it budget-friendly.

2025 Insider Update: This year, the city is expanding its riverfront holiday market and adding a new art installation at Navy Pier, making both winter and summer even more appealing.

How to Reach Chicago

Chicago is one of the most connected cities in North America, offering multiple options for arrival, depending on your location and budget.

• By Air:
  • O’Hare International Airport (ORD): As one of the busiest airports in the world, O’Hare offers connections to virtually every major global city. International visitors often land here, and the CTA Blue Line provides direct access to downtown.
  • Midway International Airport (MDW) is smaller and often more convenient for domestic travel. Midway is popular for budget airlines like Southwest. It also connects to downtown via the CTA Orange Line.
• By Train: Amtrak’s Union Station serves as Chicago’s hub for train travel. Iconic routes such as the California Zephyr (to San Francisco) and Lake Shore Limited (to New York) begin and end here. The grand Beaux Arts architecture of the station is worth admiring even if you are not boarding a train.
• By Bus: Intercity bus operators such as Greyhound, FlixBus, and Megabus provide affordable access to Chicago from neighboring states and beyond. Buses usually arrive in downtown locations, making it easy to continue your journey.
• By Car: Chicago is at the center of America’s interstate system, accessible from I-90, I-94, and I-55. However, heavy traffic and high parking fees downtown make driving less convenient for visitors.

Estimated Trip Cost

Budgeting for your Chicago trip depends on your travel style.

• Flights:
  • Domestic round-trip fares: $150–$350.
  • International fares: $600–$1,000 (with prices higher in peak summer).
• Accommodation:
  • Budget hostels and hotels: $60–$120 per night.
  • Mid-range hotels: $150–$250 per night.
  • Luxury: $350 and above for five-star stays.
• Food and Drink:
  • Street eats and casual dining: $10–$20 per person.
  • Mid-range restaurants: $25–$50 per person.
  • Fine dining: $100+ per person for upscale experiences.
• Transportation:
  • CTA unlimited day pass: $5–$10.
  • Ride-share/taxis: $15–$30 per trip.
  • Bike rentals: $7–$15 per day via Divvy bikes.
• Attractions:
  • Museums: $20–$35 per ticket.
  • Chicago CityPASS (covers top museums and observatories): Around $134.
  • Free attractions: Millennium Park, Lincoln Park Zoo, Chicago Cultural Center.

Average Daily Budget:

• Budget traveler: $90–$120
• Mid-range traveler: $200–$300
• Luxury traveler: $500

Millennium Park and Cloud Gate

The city’s most famous gathering spot, Millennium Park, is where locals and tourists converge. The Bean, officially called Cloud Gate, reflects Chicago’s skyline in stunning ways, making it one of the most photographed spots in the city. Free concerts and open-air yoga sessions add to the experience.

Navy Pier

This historic pier is filled with family-friendly attractions. From the Centennial Wheel offering sweeping views to fireworks shows in summer, Navy Pier is a must-visit. Restaurants, live theater, and art exhibitions add to its appeal.

The Art Institute of Chicago

An essential stop for art lovers, this museum boasts over 300,000 artworks, including Grant Wood’s American Gothic and Monet’s Water Lilies. The modern wing is particularly impressive.

Willis Tower and Skydeck

Formerly the tallest building in the world, Willis Tower remains iconic. The Skydeck’s glass “Ledge” extends four feet outside the building, giving thrill-seekers an unforgettable view.

Chicago Riverwalk and Architecture Tour

The Chicago River is framed by architectural masterpieces. A boat cruise here introduces you to landmark buildings designed by legendary architects such as Mies van der Rohe and Jeanne Gang.

Lincoln Park Zoo

Dating back to the 1860s, this free zoo houses species from around the globe. It is one of the few major zoos in the U.S. without an entry fee.

Museum of Science and Industry

One of the largest science museums in the world, with exhibits like a U-505 German submarine and interactive displays for children and adults alike.

Sports Experiences

Chicago’s sports culture is legendary. Catch a Cubs game at historic Wrigley Field, see the Bulls at the United Center, or watch the Bears in NFL action at Soldier Field.

Hidden Gems

• Garfield Park Conservatory: One of the most beautiful indoor gardens in the country.
• Chicago Cultural Center: Free rotating exhibits and a jaw-dropping Tiffany glass dome.
• Andersonville: A neighborhood known for boutique shopping, Swedish heritage, and cozy cafes.
• Bronzeville: Rich in African American history, filled with jazz clubs and heritage sites.

Accommodation Options

• Budget: Freehand Chicago, HI Chicago Hostel.
• Mid-range: Hotel Lincoln, The Robey.
• Luxury: The Langham Chicago, Four Seasons Hotel Chicago, and Waldorf Astoria.

Local Food & Cuisine

• Deep-Dish Pizza: Giordano’s, Lou Malnati’s, and Pequod’s.
• Chicago-Style Hot Dog: Classic stands like Portillo’s keep this tradition alive.
• Italian Beef Sandwich: A local staple found at Al’s Beef.
• Fine Dining: Alinea, a three-Michelin-star restaurant, is globally celebrated.
• Ethnic Cuisine: Chinatown, Greektown, and Little Italy offer authentic experiences.

Travel Tips & Safety Advice

• Dress in layers; Chicago’s weather is unpredictable.
• Purchase a CTA pass to save on transportation.
• Avoid driving downtown to sidestep high parking fees.
  Stick to well-lit, busy areas at night.
• Be respectful of cultural diversity, and remember to tip appropriately (15–20%).

Itinerary Suggestions

3-Day Plan

• Day 1: Millennium Park, The Art Institute, Riverwalk.
• Day 2: Navy Pier, Willis Tower, Magnificent Mile.
• Day 3: Lincoln Park Zoo, Wrigley Field, Chicago-style dining tour.

5-Day Plan

Add the Museum of Science and Industry, Pilsen murals, jazz clubs, and Garfield Park Conservatory.

7-Day Plan

Include Andersonville, Oak Street Beach, Second City comedy shows, and a day trip to Evanston.

Final Thoughts

Chicago is a city of contrasts, blending architectural brilliance with natural beauty, historic traditions with modern creativity, and local neighborhoods with global culture. Whether you are savoring deep-dish pizza in a family-owned pizzeria, gazing at impressionist art, or dancing to live blues music, every moment in Chicago is infused with character and energy. It is a city that does not just welcome visitors; it makes them feel like part of its story.

FAQs

What is the best month to visit Chicago in 2025?

May, June, September, and October provide the best balance of weather and events.

How many days do I need?

Three days cover highlights, while five to seven days allow deeper exploration.

What food is essential to try?

Deep-dish pizza, Chicago hot dogs, and Italian beef are iconic staples.

Is Chicago expensive?

Costs vary, but smart planning with passes and free attractions makes it affordable.

Is public transportation reliable?

Yes, the CTA system covers most tourist attractions efficiently.