Chicago, the third-largest city in the US, boasts a captivating blend of modern architecture and rich history. Its nickname, “The Windy City,” likely originates from the strong winds funneling off Lake Michigan. While the etymology of “Chicago” itself stems from a Native American word meaning “stinky onion,” the city’s true character is defined by its iconic skyscrapers, stunning churches, and world-class museums. While expensive, budget-conscious travel is entirely possible.

Chicago city skyline.

Along the Chicago River.

This guide provides a comprehensive overview of planning your first trip to Chicago, covering transportation, ideal travel times, accommodation options, must-see attractions, and exciting activities.

The Cloud Gate (“The Bean”) at Millennium Park.

Chicago’s vibrant cultural landscape includes diverse ethnicities, cuisines, shopping, and expansive park systems. Shopaholics will love the Magnificent Mile, while architecture enthusiasts can marvel at iconic structures like the Willis Tower, Aqua Tower, Tribune Tower, 875 North Michigan Avenue (formerly the John Hancock Center), and the Chicago Water Tower, showcasing a beautiful mix of architectural styles.

The Magnificent Mile.

Aqua Tower.

Chicago: A City Overview

Chicago skyline from Lincoln Park Zoo.

Located on the shores of Lake Michigan in Illinois, Chicago boasts a sprawling metropolitan area. Covering 606.1 square kilometers (with a metropolitan area of 28,120 km²), it houses over 2.6 million residents (the metropolitan area’s population exceeding 9.5 million in 2021). Its significance in American history dates back to the post-Civil War era, when it rapidly grew and rebuilt after the Great Chicago Fire of 1871. This devastating fire, which killed over 300 and destroyed 18,000 buildings, resulted in significant changes to building codes and urban planning.

A Chicago street scene.

Cable car offering Chicago skyline views.

A Chicago theater.

Founded in 1837, Chicago’s strategic location on Lake Michigan, combined with its pivotal role as a major railway hub connecting the East and West coasts, fueled its growth as a significant center for meatpacking and distribution worldwide.

Chicago skyline at dusk.

Best Time to Visit Chicago

Chicago 360 Observatory.

April and May offer pleasant weather and fewer crowds, making them ideal for exploring the city. June through August is festival season, with events like the Chicago Pride Parade and the Chicago Blues Festival drawing large crowds. September and October provide beautiful autumn foliage perfect for hiking and outdoor activities. November through March are ideal for winter activities.

A Chicago River cruise.

Chicago Blues Festival.

This multifaceted city offers diverse experiences throughout the year, appealing to various interests and preferences.

Getting Around Chicago: A Traveler’s Guide

Chicago, a Midwestern US city, boasts two major international airports: O’Hare (ORD) and Midway (MDW). Flights from various international locations, including Vietnam, are readily available through airlines like Korean Air, China Airlines, Cathay Pacific, and American Airlines, with fares generally ranging from $525 to $1200, depending on the travel season and airline.

Airport Transportation

From O’Hare (ORD) to Downtown: Located approximately 18.1 miles from the city center, O’Hare offers convenient access via the CTA Blue Line ‘L’ train. This cost-effective option takes about 21 minutes and costs $5 per ride. Follow the “CTA Trains” or “Trains to the City” signage within the airport terminals. More information on CTA.

From Midway (MDW) to Downtown: Midway Airport, situated about 11.6 miles from the city center, provides access to the Orange Line train. This line connects the southwest side of Chicago to the downtown Loop area, with a travel time of 20-25 minutes and a fare of $2.50 or less per ride. More information on CTA.

Taxis, ride-sharing services (Uber/Lyft), and rental cars also offer transportation to downtown Chicago. See the fare comparison chart below.

Exploring Chicago: Transportation Options

Exploring Chicago offers diverse transportation choices. The Chicago Transit Authority (CTA) operates the extensive “L” train system (elevated train), providing 24/7 service across 102.8 miles (165.4 km) with eight lines. It’s the fourth largest rapid transit system in the US. Taxis, water taxis, and ride-sharing services (Uber, Lyft) are also readily available. For a budget-friendly, immersive experience, walking or cycling are excellent options, especially for shorter distances. However, parking can be challenging in the congested city center.

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Public Transportation Details

Buses: Chicago’s extensive bus network provides affordable and convenient transportation throughout the city, including specialized services for individuals with disabilities.

Water Taxis: A unique sightseeing and transportation option, Chicago’s water taxis offer a cost-effective way to explore popular attractions along the Chicago River. Chicago Water Taxi Website

Bikes: The Divvy bike-sharing system offers a convenient and healthy way to explore the city, particularly for shorter distances. Walking is another excellent option. Divvy Bikes Website

Chicago Highlights: Millennium Park

Millennium Park, a sprawling 24.5-acre (99,000 m²) urban oasis, features a large performance stage with state-of-the-art sound and lighting, accommodating up to 11,000 people. Its striking sculptures and Crown Fountain are iconic Chicago landmarks. Beyond the impressive architecture and performances, the park offers a relaxing green space in the heart of the city.

  • Address: 201 E Randolph St, Chicago, IL 60602, USA
  • Opening Date: July 16, 2004
  • Access: Millennium Station (Washington/Wabash and South Shore Line)

Chicago’s Top Attractions: A Tourist’s Guide

Chicago boasts a vibrant mix of iconic landmarks, world-class museums, and exciting entertainment venues. This guide highlights some must-see destinations:

Cloud Gate (“The Bean”)

Millennium Park’s Cloud Gate, nicknamed “The Bean,” is an iconic Chicago symbol. Designed by Anish Kapoor, this 110-ton stainless steel sculpture reflects the city’s skyline and sky, creating a mesmerizing visual experience. Its smooth, curved form, inspired by liquid mercury, is a popular photo opportunity.

Navy Pier

Once a U.S. Navy base, Navy Pier is now a bustling entertainment hub. This expansive pier features numerous restaurants, bars, shops, theaters, and attractions, including the iconic Centennial Wheel offering stunning lake views. Visitors can enjoy various shows (like those at the Pepsi Skyline stage), boat tours on the Chicago River, or simply stroll along the pier’s lively atmosphere.

Navy Pier Centennial Wheel Chicago

  • Address: 600 E Grand Ave, Chicago, IL 60611, United States
  • Area: 14 ha
  • Year Built: 1916
  • Hours: 10 AM – 12 AM (Seasonal variations apply; check for specific times and ticket requirements).

The Art Institute of Chicago

Located in Grant Park, this renowned museum houses a world-class collection of over 300,000 works spanning various eras and cultures. The Art Institute of Chicago consistently hosts acclaimed exhibitions, making it a must-visit for art enthusiasts.

  • Address: 111 S Michigan Ave, Chicago, IL 60603, United States
  • Hours: 11 AM – 6 PM (Tuesdays); Wednesdays: Closed

Chicago Museums: A Diverse Collection

Chicago’s museum scene is incredibly rich and diverse. Beyond the Art Institute, several other prominent museums offer unique experiences:

  • Field Museum: Famous for Sue, the largest and most complete Tyrannosaurus Rex fossil ever discovered.
  • Museum of Science and Industry: Features interactive exhibits covering a broad range of scientific and technological advancements.
  • Chicago History Museum: Showcases the city’s rich and multifaceted history.

While these institutions often have substantial entrance fees, they frequently offer free admission days and discounted tickets, making them accessible to a wider audience.

Shedd Aquarium

Established in 1930, the Shedd Aquarium remains one of the world’s largest indoor aquariums. It offers an extensive display of marine life, featuring over 32,000 animals representing approximately 1,500 species, including whales, dolphins, and sea lions. The aquarium is renowned for its detailed exhibits and informative displays.

  • Address: 1200 S Lake Shore Dr, Chicago, IL 60605, United States
  • Hours: 9 AM – 5 PM
  • Total Tank Volume: 5 million US gallons (19,000 m3)
  • Admission: $39.95 (adult); $29.95 (child under 11)

Chicago Water Tower

The Chicago Water Tower, a striking Gothic Revival structure built in 1869, stands as one of the oldest water towers in the United States. This 115-foot tall landmark miraculously survived the Great Chicago Fire of 1871, which consumed surrounding buildings. Today, it houses the City Gallery in the Historic Water Tower, showcasing works by renowned photographers and artists.

  • Address: 806 N Michigan Ave, Chicago, IL 60611, United States
  • Hours: 10 AM – 7 PM
  • Architectural Style: Gothic Revival

This overview provides a starting point for exploring Chicago’s diverse attractions. Further research will be beneficial in planning your itinerary, including checking hours of operation, ticket prices, and any special events.

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Must-See Chicago Attractions: A Tourist’s Guide

Visiting Chicago without experiencing its iconic landmarks is a missed opportunity. Let’s explore some of the city’s highlights:

Willis Tower (formerly Sears Tower)

For 25 years, the Willis Tower, reaching 1,451 feet (442 meters) to its antenna tip, held the title of the world’s tallest building. It remains the tallest steel-structured building in the United States. Its distinctive black-clad architecture dominates the Chicago skyline. The Skydeck, located on the 103rd floor, offers breathtaking panoramic views of the city. Nighttime visits are particularly captivating, showcasing Chicago’s dazzling cityscape. This popular tourist destination attracts over two million visitors annually.

The Skydeck Chicago provides unparalleled views.

  • Address: 233 S Wacker Dr, Chicago, IL 60606, United States
  • Construction Started: 1970
  • Skydeck Ticket Price: Adults (12+): $26.00-$30.00; Youth (3-11): $14.00-$18.00; Children under 3: Free

Maximizing Your Chicago Experience: CityPASS and Other Options

To optimize your Chicago sightseeing budget, consider purchasing a CityPASS. This all-inclusive pass provides skip-the-line access to numerous attractions, including the Shedd Aquarium, the Field Museum, and Skydeck Chicago. It also offers a choice between the Adler Planetarium or the Art Institute of Chicago, and between the Museum of Science and Industry or the 360 Chicago Observation Deck.

Alternatively, explore the Go Chicago All-Inclusive Pass and Go Chicago Explorer Pass for potentially even greater flexibility and value.

Frederick C. Robie House

This architectural masterpiece, designed by Frank Lloyd Wright and completed in 1909, exemplifies the Prairie School style. It’s a significant contribution to Chicago’s architectural legacy and a must-see for architecture enthusiasts.

  • Address: 5757 S Woodlawn Ave, Chicago, IL 60637, United States
  • Opened: 1909
  • Hours: 10AM–3PM (Closed Tuesdays and Wednesdays)
  • Admission: $18 USD (adult); discounts available for students, seniors, military personnel, and children.

Lake Michigan: Chicago’s Natural Wonder

Lake Michigan, one of the five Great Lakes, acts as a natural climate regulator for Chicago, moderating temperatures throughout the year. Its stunning waterfront offers picturesque views, particularly enhanced by air shows held in August.

Movable Bridges: A Unique Chicago Feature

Chicago’s history is reflected in its numerous movable bridges—though their number has decreased from 56 to approximately 38 due to urban development. These bridges represent a fascinating aspect of the city’s infrastructure and history.

Magnificent Churches: Architectural Gems

Chicago boasts a rich collection of architecturally stunning churches, some featuring remarkably tall bell towers. Notably, several claim to have the tallest bell towers globally. Amongst many noteworthy examples are St. Josaphat Parish, St. Adalbert’s Catholic Church, St. Mary of the Angels, and the St. Nicholas Ukrainian Catholic Cathedral (representing Byzantine architectural influence).

Grant Park and Buckingham Fountain: Urban Oasis

Grant Park, often called Chicago’s “front yard,” is a sprawling 319-acre park, beloved by residents and tourists alike. At its heart lies the Buckingham Fountain, one of the world’s largest fountains—inspired by the Latona Fountain at the Palace of Versailles. Its 133 jets create a mesmerizing water display, reaching heights up to 150 feet (46 meters), every 20 minutes (April-October). In winter, it’s illuminated with festive lights.

  • Address: 301 S Columbus Dr, Chicago, IL 60605, United States

The Magnificent Mile: Chicago’s Premier Shopping Destination

The Magnificent Mile, a stretch of Michigan Avenue, is renowned for its upscale shopping. Over 450 stores, from high-end boutiques like Gucci and Hermes to flagship stores of brands such as Nike and Apple, line this iconic avenue. Beyond retail therapy, the Magnificent Mile boasts high-rise buildings, supermarkets, and numerous restaurants offering diverse culinary experiences. The area also houses the Museum of Contemporary Art Chicago and several luxury hotels, solidifying its status as a key Chicago attraction.

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Chicago River: Architectural Wonders and Affordable Water Transportation

The Chicago River offers stunning views of the city’s impressive architecture. While architectural boat tours are available (expect to pay around $20 per person), a more budget-friendly alternative is the water taxi service running between Michigan Avenue and Chinatown. This provides an equally scenic experience, allowing you to admire the buildings from the water and easily access some of Chicago’s best restaurants.

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Kayaking on Chicago River. | chicago blog

Lincoln Park Zoo: A Free and Engaging Urban Oasis

Located amidst lagoons and mature forests, the Lincoln Park Zoo is a free, world-class zoo offering close encounters with diverse wildlife. Established in 1868, it’s one of the oldest zoos in the United States and a popular destination for recreation, education, and conservation efforts. Its tranquil setting provides a welcome escape from the city’s bustle.

| secretchicago.com

Lincoln Park Zoo

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  • Address: 2001 N Clark St, Chicago, IL 60614, United States
  • Hours: 10AM–5PM

Chicago’s Culinary Scene: From Deep Dish to Jibaritos

Chicago boasts a renowned culinary scene, with dining experiences ranging from affordable street food to high-end restaurants (expect to pay $85-$150+ per meal at top establishments). Here are some must-try dishes:

Chicago-Style Deep Dish Pizza: A Chicago Icon

Chicago-style deep-dish pizza, particularly the deep-dish variety, is a city staple. Baked in a deep pan, it’s characterized by its high, buttery crust, ample cheese, and chunky tomato sauce.

Deep-dish pizza | chicago travel blog

Jibarito Sandwiches: A Puerto Rican Delight

The jibarito, a Puerto Rican sandwich made with fried green plantains instead of bread, is a popular Chicago food. Typically filled with meat, cheese, lettuce, and tomato, it’s a delicious and unique culinary experience.

Must-eat in Chicago.

Chicago-Style Hot Dogs: A Street Food Classic

Chicago-style hot dogs are a quintessential street food, served on a steamed bun with yellow mustard, chopped onions, sweet pickle relish, sport peppers, a dill pickle spear, tomato wedges, and celery salt.

Chicago Cocktails: A Toast to the Windy City

Chicago’s nightlife offers a wide array of bars and pubs. For a taste of local drinks, try the Chicago Fizz Cocktail (rum, ruby port, egg white, soda) or the Chicago Cocktail (brandy-based with champagne).

Chicago Fizz Cocktail

The Chicago Cocktail

Chicago Travel Guide: Accommodation and Activities

Planning a trip to Chicago? This guide offers advice on finding affordable accommodation and suggests exciting activities.

Budget travelers should avoid hotels in the city center, particularly on the Magnificent Mile, due to high prices. Consider staying in neighborhoods like Lakeview, Lincoln Park, or Bucktown, or opt for hotels further from the city center but conveniently located near major transportation routes for easy access to attractions.

| choosechicago.com

Recommended Hotels:

This list provides a range of hotel options, categorized by price and star rating. Remember to check current rates on booking sites.

Sofitel Chicago Magnificent Mile

Shared Artist Loft Own Private Room

Chicago Tours and Activities:

Consider these options for enhancing your Chicago experience:

  • CityPASS: Provides access to multiple attractions at a discounted rate. (Klook)
  • Go Chicago Card (All-Inclusive or Explorer Pass): Offers flexibility in choosing attractions. (Klook)
  • 360 Chicago Observation Deck: Stunning city views. (Klook)
  • Architecture River Cruise: Explore Chicago’s iconic architecture from the water. (Klook)
  • Museum Visits: The Art Institute of Chicago and The Field Museum offer diverse exhibits. (Klook)
  • Big Bus Hop-On Hop-Off Tours: Convenient sightseeing. (Klook)
  • Segway Tours: A fun and unique way to explore. (Klook)
  • Airport Transfers: Pre-booked transportation for a smooth arrival and departure. (Klook)
  • Other Tours: Explore options for Broadway shows, North Chicago excursions, and combination tours. (Klook)

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For more detailed information on things to do and places to visit in Chicago, explore these resources: Klook Chicago Activities and Visit Famous Places US Guide.

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