Chicago, the Windy City, is a bustling metropolis filled with rich history, vibrant culture, and diverse attractions.
As a first-time visitor, you’re in for an unforgettable experience.
Let’s dive into the essence of this remarkable city and explore the best things to do, from iconic landmarks to hidden gems, all easily accessible via public transportation.
A Brief History of Chicago
Chicago was incorporated as a city in 1837, rapidly growing due to its strategic location near the Great Lakes and the Mississippi River watershed.
It became a hub for railways and a major center for industry and commerce.
The Great Chicago Fire of 1871 was a turning point, leading to massive reconstruction and architectural innovations.
Today, Chicago is known for its impressive skyline, cultural diversity, and significant contributions to music, particularly jazz and blues.
Why Visit Chicago?
Chicago offers a unique blend of urban sophistication and Midwestern charm.
It’s a city where you can explore world-class museums, enjoy deep-dish pizza, stroll along beautiful lakefronts, and experience live music all in one day.
The city’s public transportation system, the CTA (Chicago Transit Authority), makes getting around convenient and affordable, ensuring you can maximize your visit even if time is limited.
Top 10 Must-See Chicago Attractions
Chicago is a city brimming with iconic attractions that every first-time visitor must experience.
From world-renowned museums to architectural marvels, these attractions offer a glimpse into the city’s rich cultural tapestry and dynamic history.
Each spot is easily accessible by public transportation, ensuring you can make the most of your visit.
Millennium Park
- Why Visit: Millennium Park is not just a park; it’s a cultural epicenter. Home to the iconic Cloud Gate sculpture, commonly known as “The Bean,” it offers stunning reflections of the city’s skyline.
The park also features the interactive Crown Fountain, the serene Lurie Garden, and the state-of-the-art Jay Pritzker Pavilion, which hosts free concerts and events.
- Cost: Free
- Getting There: Easily accessible by the ‘L’ train. Take the Red Line to the Lake station, then a short walk.
- From Hotels:
- Luxury Hotel – Four Seasons Hotel Chicago: 15-minute walk or 10 minutes on the Red Line from Chicago Station.
- Affordable Hotel – Cambria Hotel Chicago Loop: 10-minute walk.
- Economy Hotel – HI Chicago Hostel: 10-minute walk.
Art Institute of Chicago
- Why Visit: Renowned for its extensive collection of Impressionist and Post-Impressionist paintings, the Art Institute of Chicago is a treasure trove of art.
It houses iconic works such as Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.”
The museum also features ancient artifacts, modern art, and decorative arts.
- Cost: $25 for adults
- Getting There: Located near the Adams/Wabash station on the Brown, Green, Orange, Pink, and Purple Lines.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 15-minute walk or 10 minutes on the Orange Line from State/Lake.
- Affordable Hotel – Hampton Inn Majestic Chicago Theatre District: 10-minute walk.
- Economy Hotel – Congress Plaza Hotel: 5-minute walk.
Navy Pier
- Why Visit: Navy Pier is a vibrant entertainment destination on the shores of Lake Michigan.
It offers a variety of attractions, including restaurants, shops, theaters, museums, and the Centennial Wheel, which provides stunning views of the city and lake.
Navy Pier also hosts seasonal events, fireworks, and boat tours.
- Cost: Free entry, attractions vary in cost.
- Getting There: Accessible by bus; take the 2, 29, 65, 66, or 124 routes.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 25-minute walk or 15 minutes by bus (66 route).
- Affordable Hotel – AC Hotel by Marriott Chicago Downtown: 20-minute walk or 10 minutes by bus (29 route).
- Economy Hotel – Travelodge by Wyndham Downtown Chicago: 30 minutes by bus (2 route).
Shedd Aquarium
- Why Visit: One of the largest indoor aquariums in the world, the Shedd Aquarium is home to over 32,000 animals.
Visitors can explore exhibits like the Caribbean Reef, Amazon Rising, and the Oceanarium, which features beluga whales and dolphins.
The aquarium offers interactive experiences and daily aquatic shows.
- Cost: $39.95 for adults
- Getting There: Take the Red Line to Roosevelt, then a 15-minute walk or transfer to bus 146.
- From Hotels:
- Luxury Hotel – Waldorf Astoria Chicago: 35 minutes by Red Line from Clark/Division to Roosevelt.
- Affordable Hotel – Holiday Inn Chicago Mart Plaza River North: 25 minutes by Brown Line from Merchandise Mart to Roosevelt.
- Economy Hotel – Best Western Grant Park Hotel: 10-minute walk.
Field Museum
- Why Visit: The Field Museum is a must-visit for history buffs and natural science enthusiasts.
It houses Sue, the largest and most complete T. rex skeleton ever discovered.
Other highlights include the Ancient Egypt exhibit, the Grainger Hall of Gems, and the evolving planet exhibit, which explores the history of life on Earth.
- Cost: $25 for adults
- Getting There: Take the Red Line to Roosevelt, then a 10-minute walk or transfer to bus 146.
- From Hotels:
- Luxury Hotel – The Ritz-Carlton, Chicago: 35 minutes by Red Line from Chicago to Roosevelt.
- Affordable Hotel – Hotel Blake: 20-minute walk.
- Economy Hotel – Chicago Parthenon Hostel: 30 minutes by Blue Line from UIC-Halsted to Jackson, transfer to Red Line to Roosevelt.
Willis Tower Skydeck
- Why Visit: Experience breathtaking views from the 103rd floor of the Willis Tower, including the glass-floored Ledge, which extends four feet outside the building.
On a clear day, you can see up to four states from the Skydeck. It’s an exhilarating way to see the city from above.
- Cost: $30 for adults
- Getting There: Accessible via the Quincy/Wells station on the Brown, Orange, Pink, and Purple Lines.
- From Hotels:
- Luxury Hotel – Trump International Hotel & Tower Chicago: 20 minutes by Brown Line from Merchandise Mart to Quincy.
- Affordable Hotel – Residence Inn by Marriott Chicago Downtown/Loop: 5-minute walk.
- Economy Hotel – The Chicago Parthenon Hostel: 20-minute walk.
Museum of Science and Industry
- Why Visit: The Museum of Science and Industry is one of the largest science museums in the world.
It features interactive exhibits such as the U-505 submarine, a full-size replica of a coal mine, and a model train that crosses a giant, intricate layout.
The museum also hosts temporary exhibitions on a variety of scientific topics.
- Cost: $21.95 for adults
- Getting There: Take the Metra Electric Line from Millennium Station to 55th-56th-57th Street station.
- From Hotels:
- Luxury Hotel – Park Hyatt Chicago: 45 minutes by Red Line from Chicago to Roosevelt, transfer to Metra Electric Line.
- Affordable Hotel – The Buckingham Hotel: 30 minutes by Metra Electric Line from Van Buren Street.
- Economy Hotel – HI Chicago Hostel: 35 minutes by Red Line from Harrison to Roosevelt, transfer to Metra Electric Line.
Chicago Riverwalk
- Why Visit: The Chicago Riverwalk is a scenic walking path along the Chicago River, offering restaurants, bars, boat tours, and public art. It’s a great place to relax, enjoy a meal, and watch the boats go by. The Riverwalk is also home to several events and festivals throughout the year.
- Cost: Free
- Getting There: Easily accessible from various points along the river.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 5-minute walk.
- Affordable Hotel – Club Quarters Hotel, Wacker at Michigan: 5-minute walk.
- Economy Hotel – St. Jane Chicago: 10-minute walk.
Lincoln Park Zoo
- Why Visit: One of the oldest zoos in North America, Lincoln Park Zoo offers free admission and features a wide variety of animals.
It’s located in the beautiful Lincoln Park, which also has gardens, a conservatory, and scenic walking paths.
The zoo offers educational programs and seasonal events.
- Cost: Free
- Getting There: Take the Brown or Purple Line to Armitage, then a 15-minute walk.
- From Hotels:
- Luxury Hotel – Four Seasons Hotel Chicago: 20-minute walk.
- Affordable Hotel – Hotel Versey Days Inn by Wyndham Chicago: 15-minute walk.
- Economy Hotel – Inn at Lincoln Park: 20-minute walk.
Adler Planetarium
- Why Visit: America’s first planetarium, the Adler Planetarium offers exhibits and shows about space and astronomy.
Visitors can explore the solar system, learn about the history of astronomy, and experience immersive sky shows in the Grainger Sky Theater.
- Cost: $19 for adults
- Getting There: Take the Red Line to Roosevelt, then a 15-minute walk or transfer to bus 146.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 35 minutes by Red Line from Chicago to Roosevelt.
- Affordable Hotel – Hampton Inn Majestic Chicago Theatre District: 25 minutes by Red Line from Monroe to Roosevelt.
- Economy Hotel – HI Chicago Hostel: 20-minute walk.
Lesser-Known but Memorable Attractions
For those looking to explore beyond the typical tourist spots, Chicago offers a plethora of lesser-known yet equally fascinating attractions.
These hidden gems provide unique insights into the city’s diverse cultural landscape and are perfect for those seeking a more intimate experience of Chicago.
Garfield Park Conservatory
- Why Visit: A stunning indoor garden with a variety of plant species, the Garfield Park Conservatory is often referred to as “landscape art under glass.”
It features several rooms with different climates and plant types, from lush tropical palms to arid desert plants.
It’s a peaceful retreat from the bustling city.
- Cost: Free
- Getting There: Take the Green Line to Conservatory-Central Park Drive.
- From Hotels:
- Luxury Hotel – The Ritz-Carlton, Chicago: 40 minutes by Red Line from Chicago to Ashland, transfer to Green Line.
- Affordable Hotel – Hotel Chicago West Loop: 25 minutes by Green Line from Ashland.
- Economy Hotel – Freehand Chicago: 35 minutes by Blue Line from Grand to Ashland, transfer to Green Line.
Chicago History Museum
- Why Visit: Discover the history of Chicago through interactive exhibits that cover the city’s past from its founding to the present day.
The museum features a replica of the first L train, dioramas of the Great Chicago Fire, and exhibits on the city’s cultural and political history.
It’s an educational and engaging experience for all ages.
- Cost: $19 for adults
- Getting There: Take the Brown Line to Sedgwick, then a 10-minute walk.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 20 minutes by Brown Line from State/Lake to Sedgwick.
- Affordable Hotel – Best Western River North Hotel: 15-minute walk.
- Economy Hotel – HI Chicago Hostel: 35 minutes by Brown Line from Harold Washington Library to Sedgwick.
Museum of Contemporary Art
- Why Visit: The Museum of Contemporary Art showcases cutting-edge art and offers a platform for innovative artists.
The museum’s collection includes works by notable contemporary artists such as Jeff Koons and Cindy Sherman.
In addition to its exhibits, the museum hosts performances, film screenings, and educational programs.
- Cost: $15 for adults
- Getting There: Take the Red Line to Chicago, then a 10-minute walk.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 5-minute walk.
- Affordable Hotel – Homewood Suites by Hilton Chicago Downtown/Magnificent Mile: 5-minute walk.
- Economy Hotel – The Whitehall Hotel: 5-minute walk.
Pilsen Murals
- Why Visit: Explore vibrant street art in the Pilsen neighborhood, where colorful murals adorn buildings and tell stories of the community’s rich cultural heritage.
Pilsen is known for its strong Mexican-American influence, and the murals reflect themes of social justice, cultural pride, and local history.
It’s a visually stunning and culturally enriching experience.
- Cost: Free
- Getting There: Take the Pink Line to 18th.
- From Hotels:
- Luxury Hotel – The Ritz-Carlton, Chicago: 35 minutes by Red Line from Chicago to Lake, transfer to Pink Line.
- Affordable Hotel – Chicago South Loop Hotel: 20 minutes by bus 18 from Michigan & 24th Place.
- Economy Hotel – Chinatown Hotel: 20 minutes by Red Line from Cermak-Chinatown to Lake, transfer to Pink Line.
Chicago Cultural Center
- Why Visit: The Chicago Cultural Center offers free art exhibitions, performances, and cultural events in a stunning historic building.
The center’s architecture alone is worth the visit, featuring beautiful stained-glass domes and intricate mosaics.
It’s a great place to enjoy free cultural programming and explore local and international art.
- Cost: Free
- Getting There: Located near the Randolph/Wabash station on the Brown, Green, Orange, Pink, and Purple Lines.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 10-minute walk.
- Affordable Hotel – AC Hotel by Marriott Chicago Downtown: 15-minute walk.
- Economy Hotel – HI Chicago Hostel: 15-minute walk.
Oz Park
- Why Visit: Themed around “The Wizard of Oz,” Oz Park features statues of beloved characters from the classic story, including Dorothy, Toto, the Tin Man, the Scarecrow, and the Cowardly Lion.
The park also has playgrounds, sports fields, and a lovely garden, making it a great spot for families and fans of the Oz series.
- Cost: Free
- Getting There: Take the Brown or Purple Line to Armitage, then a 10-minute walk.
- From Hotels:
- Luxury Hotel – Waldorf Astoria Chicago: 25-minute walk or 15 minutes by Brown Line from Chicago to Armitage.
- Affordable Hotel – The Willows Hotel: 20-minute walk.
- Economy Hotel – Inn at Lincoln Park: 15-minute walk.
The 606
- Why Visit: An elevated trail for walking, running, and biking, The 606 features public art installations and connects several neighborhoods along the old Bloomingdale Line railroad.
It’s a unique way to explore the city and enjoy outdoor activities, with plenty of entry points and scenic views along the way.
- Cost: Free
- Getting There: Take the Blue Line to Damen.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 35 minutes by Blue Line from Chicago to Damen.
- Affordable Hotel – Holiday Jones: 10-minute walk.
- Economy Hotel – Freehand Chicago: 30 minutes by Blue Line from Grand to Damen.
Chicago Architecture Center
- Why Visit: Learn about Chicago’s architectural history through exhibits and tours at the Chicago Architecture Center.
The center offers a comprehensive look at the city’s renowned architecture, with scale models, interactive exhibits, and guided tours that highlight Chicago’s iconic buildings and design innovations.
- Cost: $14 for adults
- Getting There: Located near the Michigan/Wacker stop on several bus routes.
- From Hotels:
- Luxury Hotel – Trump International Hotel & Tower Chicago: 5-minute walk.
- Affordable Hotel – Club Quarters Hotel, Wacker at Michigan: 5-minute walk.
- Economy Hotel – St. Jane Chicago: 10-minute walk.
The Rookery Building
- Why Visit: The Rookery Building is a historic landmark known for its stunning lobby designed by Frank Lloyd Wright.
The building is a masterpiece of Chicago School architecture and offers tours that delve into its architectural significance and history.
It’s a must-see for architecture enthusiasts.
- Cost: Free to visit lobby, tours available for a fee
- Getting There: Located near the Quincy/Wells station on the Brown, Orange, Pink, and Purple Lines.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 15-minute walk.
- Affordable Hotel – The Buckingham Hotel: 5-minute walk.
- Economy Hotel – HI Chicago Hostel: 15-minute walk.
Promontory Point
- Why Visit: Promontory Point is a scenic spot in Burnham Park offering stunning views of the Chicago skyline and Lake Michigan.
It’s a popular spot for picnics, swimming, and enjoying the outdoors.
The Point’s unique limestone steps provide access to the lake, making it a tranquil and picturesque destination.
- Cost: Free
- Getting There: Take the Metra Electric Line from Millennium Station to 51st/53rd Street.
- From Hotels:
- Luxury Hotel – Park Hyatt Chicago: 45 minutes by Red Line from Chicago to Roosevelt, transfer to Metra Electric Line.
- Affordable Hotel – The Buckingham Hotel: 30 minutes by Metra Electric Line from Van Buren Street.
- Economy Hotel – HI Chicago Hostel: 35 minutes by Red Line from Harrison to Roosevelt, transfer to Metra Electric Line.
Off the Beaten Path Attractions
For those looking to explore beyond the typical tourist spots, Chicago offers a plethora of lesser-known yet equally fascinating attractions.
These hidden gems provide unique insights into the city’s diverse cultural landscape and are perfect for those seeking a more intimate experience of Chicago.
Baha’i House of Worship
- Why Visit: One of only eight continental Baha’i temples in the world, the Baha’i House of Worship is known for its stunning architecture and serene gardens.
The intricate lace-like exterior and tranquil interior provide a peaceful retreat.
It’s a beautiful and spiritually enriching place to visit.
- Cost: Free
- Getting There: Take the Purple Line to Linden, then a 15-minute walk.
- From Hotels:
- Luxury Hotel – The Ritz-Carlton, Chicago: 45 minutes by Red Line from Chicago to Howard, transfer to Purple Line.
- Affordable Hotel – Hampton Inn Chicago North-Loyola Station: 30 minutes by Purple Line from Loyola to Linden.
- Economy Hotel – Freehand Chicago: 50 minutes by Red Line from Grand to Howard, transfer to Purple Line.
Pullman National Monument
- Why Visit: The Pullman National Monument is a historic neighborhood showcasing the early industrial community and labor history of the Pullman Company.
Visitors can explore preserved buildings, including the Pullman Factory and Hotel Florence, and learn about the significance of the Pullman Strike of 1894.
- Cost: Free
- Getting There: Take the Metra Electric Line from Millennium Station to 111th Street.
- From Hotels:
- Luxury Hotel – Waldorf Astoria Chicago: 45 minutes by Red Line from Chicago to 95th/Dan Ryan, transfer to Metra Electric Line.
- Affordable Hotel – The Buckingham Hotel: 30 minutes by Metra Electric Line from Van Buren Street.
- Economy Hotel – Chinatown Hotel: 35 minutes by Red Line from Cermak-Chinatown to 95th/Dan Ryan, transfer to Metra Electric Line.
National Museum of Mexican Art
- Why Visit: Located in the vibrant Pilsen neighborhood, the National Museum of Mexican Art showcases Mexican, Latino, and Chicano culture and art.
The museum’s extensive collection includes folk art, textiles, prints, and paintings, highlighting the rich cultural heritage of the Mexican community.
- Cost: Free
- Getting There: Take the Pink Line to 18th.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 35 minutes by Pink Line from State/Lake.
- Affordable Hotel – Hotel Chicago West Loop: 20 minutes by Pink Line from Ashland.
- Economy Hotel – HI Chicago Hostel: 30 minutes by Pink Line from Harold Washington Library.
Oriental Institute Museum
- Why Visit: The Oriental Institute Museum at the University of Chicago features ancient Near Eastern artifacts, including statues, pottery, and manuscripts.
Highlights include the massive statue of King Tutankhamun and the Persian gallery.
It’s an educational and fascinating journey through ancient history.
- Cost: $10 suggested donation
- Getting There: Take the Green Line to Garfield, then a bus transfer.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 50 minutes by Red Line from Chicago to Garfield, transfer to bus 55.
- Affordable Hotel – Chicago South Loop Hotel: 30 minutes by bus 29 and bus 55.
- Economy Hotel – HI Chicago Hostel: 40 minutes by Red Line from Harrison to Garfield, transfer to bus 55.
Smart Museum of Art
- Why Visit: The Smart Museum of Art at the University of Chicago features a diverse collection of art from different periods and cultures.
Highlights include contemporary art, European paintings, and Asian sculptures.
The museum also hosts rotating exhibitions and educational programs.
- Cost: Free
- Getting There: Take the Green Line to Garfield, then a bus transfer.
- From Hotels:
- Luxury Hotel – Four Seasons Hotel Chicago: 50 minutes by Red Line from Chicago to Garfield, transfer to bus 55.
- Affordable Hotel – Hyatt Place Chicago-South/University Medical Center: 10-minute walk.
- Economy Hotel – Chicago Parthenon Hostel: 45 minutes by Red Line from UIC-Halsted to Garfield, transfer to bus 55.
Hull House Museum
- Why Visit: The Hull House Museum is the former home of social reformer Jane Addams and serves as a testament to her work in social justice and community development.
The museum offers exhibits and programs that explore the history of social reform movements and the impact of Hull House on the community.
- Cost: Free
- Getting There: Take the Blue Line to UIC-Halsted.
- From Hotels:
- Luxury Hotel – Trump International Hotel & Tower Chicago: 30 minutes by Blue Line from Clark/Lake to UIC-Halsted.
- Affordable Hotel – Holiday Inn & Suites Chicago-Downtown: 10-minute walk.
- Economy Hotel – HI Chicago Hostel: 25 minutes by Blue Line from Jackson to UIC-Halsted.
Lillstreet Art Center
- Why Visit: The Lillstreet Art Center is a community art center offering classes, workshops, and galleries.
Visitors can explore exhibitions of local artists, participate in hands-on art-making, and shop for unique handmade items in the gift shop.
It’s a creative and inspiring place to visit.
- Cost: Free entry, classes vary in cost.
- Getting There: Take the Brown Line to Montrose.
- From Hotels:
- Luxury Hotel – The Langham, Chicago: 35 minutes by Brown Line from State/Lake to Montrose.
- Affordable Hotel – The Willows Hotel: 25 minutes by bus 152.
- Economy Hotel – Freehand Chicago: 30 minutes by Brown Line from Merchandise Mart to Montrose.
Glessner House Museum
- Why Visit: The Glessner House Museum is a historic 19th-century home that showcases the rich history and architectural heritage of Prairie Avenue.
The house, designed by architect Henry Hobson Richardson, offers guided tours that delve into its unique design and the life of the Glessner family.
- Cost: $15 for adults
- Getting There: Take the Red Line to Cermak-Chinatown, then a 10-minute walk.
- From Hotels:
- Luxury Hotel – The Ritz-Carlton, Chicago: 30 minutes by Red Line from Chicago to Cermak-Chinatown.
- Affordable Hotel – Chicago South Loop Hotel: 20-minute walk.
- Economy Hotel – Chinatown Hotel: 10-minute walk.
Chicago Maritime Museum
- Why Visit: The Chicago Maritime Museum explores the city’s maritime history through fascinating exhibits.
Visitors can learn about the importance of the Great Lakes, the Chicago River, and the city’s shipping industry.
The museum offers a unique perspective on Chicago’s development and its connection to waterways.
- Cost: $10 for adults
- Getting There: Take the Orange Line to Ashland.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 35 minutes by Orange Line from State/Lake to Ashland.
- Affordable Hotel – Holiday Inn & Suites Chicago-Downtown: 25 minutes by Orange Line from Quincy to Ashland.
- Economy Hotel – HI Chicago Hostel: 30 minutes by Orange Line from Harold Washington Library to Ashland.
Beverly Arts Center
- Why Visit: The Beverly Arts Center offers a variety of arts programming, including theater performances, art exhibitions, and classes.
It’s located in the historic Beverly neighborhood and provides a vibrant community space for artistic expression.
The center hosts events and activities for all ages.
- Cost: Free entry, event costs vary.
- Getting There: Take the Rock Island District Line from LaSalle Street Station to 103rd Street/Washington Heights.
- From Hotels:
- Luxury Hotel – The Peninsula Chicago: 45 minutes by Red Line from Chicago to 95th/Dan Ryan, transfer to Rock Island District Line.
- Affordable Hotel – The Buckingham Hotel: 40 minutes by Rock Island District Line from LaSalle Street Station.
- Economy Hotel – HI Chicago Hostel: 45 minutes by Red Line from Harrison to 95th/Dan Ryan, transfer to Rock Island District Line.
Immerse Yourself In Chicago
Chicago is a city that offers an array of experiences, from iconic landmarks to lesser-known gems, all conveniently accessible via its extensive public transportation system.
Whether you’re marveling at the architectural wonders, exploring world-class museums, or discovering hidden treasures, Chicago promises a memorable visit that captures the heart and soul of this vibrant metropolis.
So pack your bags, grab your Chicago City Pass, and get ready to explore all that this incredible city has to offer.