Chicago Itinerary - Three Days in Chicago for First Timers
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Explore Chicago in three days with this packed itinerary! Visit top attractions, iconic landmarks, local eats, museums, and unique spots across the city.
Getting Around Chicago
Chicago’s public transportation system is easy to navigate, with a network of buses and elevated trains, known locally as “the L,” that will get you almost anywhere you need to go. The L is especially useful for visiting major landmarks like the Loop, Museum Campus, and neighborhoods like Wicker Park and Lincoln Park. You’ll also find many options within walking distance in downtown Chicago. While it might be tempting to rent a car, driving in the city can be challenging with traffic, limited parking, and pricey garage fees. Opt for a Ventra card, which allows easy transfers between buses and trains, or consider using rideshares for quicker trips to farther destinations.
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Day 1: Exploring the Loop, Millennium Park, and the Magnificent Mile
Day 1 of this three-day Chicago itinerary covers iconic spots like the Art Institute, Millennium Park, and the Magnificent Mile. From world-class art to deep-dish pizza, this day introduces you to the city’s top attractions and classic Chicago experiences.
The Art Institute of Chicago
Map: Google Maps
Website: Link
Cost: Adults: $32; Seniors (65+), Students, Teens (14-17): $26; Kids (under 14): Free
Start your visit with a classic Chicago landmark, the Art Institute of Chicago. Known for its world-renowned collection, this museum houses iconic works like Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, and a vast impressionist collection. Its Modern Wing features contemporary art, with beautiful views over Millennium Park. The institute’s collection spans ancient to modern art and includes everything from sculptures to textiles. Plan to spend at least a few hours here to fully appreciate the diverse exhibits, including the museum’s famous Thorne Miniature Rooms, which showcase incredibly detailed replicas of historical interiors.
Millennium Park and Cloud Gate
Map: Google Maps
Website: Link
Cost: Free!
Next, head to Millennium Park to see Cloud Gate, Chicago’s most famous public sculpture. More popularly known as The Bean, this reflective artwork by Anish Kapoor mirrors the skyline and creates some truly unique photo opportunities. Beyond The Bean, Millennium Park features the Crown Fountain, a playful digital fountain that showcases faces of Chicago locals. In the summer, the Jay Pritzker Pavilion hosts free concerts, and you’ll find art installations throughout the year. Grab a coffee nearby and take some time to explore the Lurie Garden, an urban green space within the park that’s perfect for getting a break from the city buzz.
Chicago Riverwalk
Map: Google Maps
Website: Link
Cost: Free!
The Chicago Riverwalk is a bustling waterfront area lined with cafes, public art, and open-air seating along the river. As you stroll along, you’ll see landmarks like the Marina City Towers and hear the hum of passing water taxis. Stop by City Winery or Tiny Tapp for a drink, or rent a kayak if you want to experience the river firsthand. The Riverwalk is a great place to learn about Chicago’s architectural history, with views of the city’s most iconic skyscrapers, from the Wrigley Building to the Tribune Tower.
Magnificent Mile
Map: Google Maps
Website: Link
Cost: Free to browse, shops vary
Head north along the Magnificent Mile, Chicago’s most famous shopping district, where you’ll find everything from high-end boutiques to flagship stores. Stop by the iconic Water Tower, one of the few structures to survive the Great Chicago Fire, or explore the high-end shops at 900 North Michigan. The Magnificent Mile is also home to top department stores and landmarks like the John Hancock Center, where you can go up to 360 CHICAGO Observation Deck for panoramic city views.
Navy Pier
Map: Google Maps
Website: Link
Cost: Free to browse, shops vary
Finish the afternoon with a visit to the icon of the city, Navy Pier. The historic pier was built in the early 1900s. Over the years it has served many purposes including a training facility for the US Navy, a shipping port, a jail, and even a university. These days it’s home to some of the city’s top attractions including the massive Centennial Wheel, a Ferris wheel with amazing views of the city and Lake Michigan shoreline. There are also numerous unique shops and restaurants to experience. Sports fanatics should check out Harry Caray’s Tavern, a restaurant and sports bar named for the famous broadcaster.
Dinner at Lou Malnati’s Pizzeria
Map: Google Maps
Website: Link
Cost: Varies, approx. $15-$25 per person
No trip to Chicago is complete without deep-dish pizza, and Lou Malnati’s is a classic. Known for its buttery crust and rich layers of cheese and tomato sauce, this iconic dish is best shared with friends. Lou Malnati’s offers various toppings, but the “Malnati Chicago Classic” with sausage, extra cheese, and butter crust is a crowd-pleaser. The pizzeria has locations across the city, so you’re never far from a slice of this indulgent Chicago favorite.
Day 2: Museum Campus and South Loop
Day 2 in our three-day Chicago itinerary takes you to the Museum Campus for a day with dinosaurs at the Field Museum, underwater wonders at Shedd Aquarium, and celestial views at Adler Planetarium. The evening wraps up with live jazz in the historic South Loop.
Field Museum
Map: Google Maps
Website: Link
Cost: Adults $30; Students: $27; Kids (3-11); $23; Under 3: Free. (Discounts for Chicago and Illinois residents)
Spend your morning at the Field Museum, home to the world’s largest and most complete T. rex fossil, SUE. Beyond dinosaurs, the museum offers exhibitions on ancient Egypt, Native American cultures, and even a hall dedicated to gems and minerals. Interactive exhibits make the Field Museum enjoyable for visitors of all ages, and you could easily spend several hours here. Don’t miss the impressive Pawnee Earth Lodge, a full-scale replica that offers insight into the life of the Plains Indians.
Shedd Aquarium
Map: Google Maps
Website: Link
Cost: Adults: $36.95 & Up; Kids (3-11): $27.70 & Up (price varies daily, discounts for Chicago residents).
Located nearby, the Shedd Aquarium is home to over 32,000 animals and offers interactive exhibits like Stingray Touch. Explore ecosystems from the Amazon to the Pacific Ocean, and watch a variety of aquatic shows featuring beluga whales, sea otters, and dolphins. The aquarium’s Caribbean Reef exhibit is a 360-degree tank showcasing vibrant fish, sea turtles, and rays. For an unforgettable experience, check out their penguin encounters, where you can meet these charming animals up close.
Adler Planetarium
Map: Google Maps
Website: Link
Cost: Adults: $32; Kids (3-11): $20
The Adler Planetarium offers a chance to journey through space with interactive exhibits and stunning shows. Learn about the history of astronomy, from ancient tools to the most advanced telescopes. The planetarium’s “Sky Theater” takes visitors on immersive journeys through the galaxy, showcasing everything from black holes to the planets of our solar system. The view of the Chicago skyline from the planetarium is also a highlight, providing a fantastic photo opportunity.
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Evening: Jazz Showcase
Map: Google Maps
Website: Link
Cost: Ticket Prices Vary
For a classic Chicago evening, spend the night at Jazz Showcase in the South Loop. Established in 1947, this historic jazz club features live performances by local musicians and renowned jazz artists. The intimate venue is great for enjoying the music up close, and it’s a wonderful way to experience Chicago’s vibrant jazz scene. With shows every evening, Jazz Showcase offers a mix of styles, from traditional jazz to modern interpretations.
Check out our other posts about things to see and do in Chicago or Illinois!
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Day 3: Wicker Park and Lincoln Park
Day 3 of this three-day Chicago itinerary explores vibrant neighborhoods like Wicker Park and Lincoln Park, featuring scenic trails, the free Lincoln Park Zoo, and the Chicago History Museum. End the day with an unforgettable meal at Girl & the Goat, one of Chicago’s most celebrated restaurants, or a fun dinner at Wilde’s followed by some drinks in Boystown.
The 606 Trail
Map: Google Maps
Website: Link
Cost: Free
Start your morning with a visit to The 606, an elevated urban trail built on a former railway line. Stretching 2.7 miles, this path connects four neighborhoods and is popular with cyclists, joggers, and walkers alike. You’ll see murals, sculptures, and gardens along the way, giving you a taste of Chicago’s art scene. The 606 is a unique way to explore Wicker Park and Bucktown, two vibrant neighborhoods known for their cafes and boutiques.
Lincoln Park Zoo
Map: Google Maps
Website: Link
Cost: Free!
Head north to Lincoln Park Zoo, one of the oldest free zoos in the country. Here you’ll find everything from big cats to penguins, all in beautifully landscaped habitats. The zoo’s Regenstein African Journey offers up-close views of rhinos, hippos, and giraffes, while the Kovler Seal Pool features sea lions swimming right at eye level. Lincoln Park Zoo is a great spot for families and offers an escape into nature right in the heart of the city. Plus it’s free!
Chicago History Museum
Map: Google Maps
Website: Link
Cost: Adults: $19; Seniors (65+), Students (age 19-22): $17; Kids (18 & Under): Free
Dive into Chicago’s past at the Chicago History Museum, where you can explore exhibits on the Great Chicago Fire, the city’s industrial boom, and Chicago’s role in shaping music, sports, and politics. Interactive displays and multimedia exhibits make history engaging and accessible. Don’t miss the museum’s vintage L car, where you can step into a piece of Chicago’s transit history.
Dinner at Girl & the Goat
Map: Google Maps
Website: Link
Cost: Varies, $20-$40 per dish
End your Chicago adventure with dinner at Girl & the Goat, one of the city’s most acclaimed restaurants. Helmed by chef Stephanie Izard, the menu features globally inspired small plates, with standouts like the wood-fired sea bass, roasted oysters, and goat empanadas. The restaurant’s inventive flavors and chic, lively atmosphere make it a fantastic choice for a final meal in Chicago.
or Dinner at Wilde Bar & Restaurant
Map: Google Maps
Website: Link
Cost: Varies, $20-$40 per dish
If you’re looking for a great meal at a lower price point, Wilde Bar & Restaurant is another great option. The restaurant is named for the Irish poet and playwright Oscar Wilde. Wilde’s Irish heritage inspires many of the menu items including the Irish Whiskey glazed burger and the Shepard’s Pie. The literary theming of the interior is also a nod to Mr. Wilde. It’s a great place to go if your evening plans include some of the LGBTQ+ bars on nearby Halsted St.
Best Places to Stay in Chicago
For first-timers, staying in neighborhoods like River North, the Loop, or Lincoln Park offers easy access to the city’s main attractions. The Chicago Athletic Association Hotel in the Loop offers stylish accommodations with historic charm, while The Robey in Wicker Park combines modern design with great neighborhood views. For a more luxurious stay, consider the Waldorf Astoria in the Gold Coast, just steps away from upscale shopping and dining.
Best Things To Do in Chicago, Illinois
The Art Institute of Chicago
Millennium Park and Cloud Gate
Chicago Riverwalk
Magnificent Mile
Navy Pier
Lou Malnati’s Pizzeria
Field Museum
Shedd Aquarium
Adler Planetarium
Jazz Showcase
The 606 Trail
Lincoln Park Zoo
Chicago History Museum
Girl & the Goat
Wilde Bar & Restaurant
