Chicago is a city that has it all—stunning architecture, world-class museums, beautiful parks, and food that will make your taste buds dance. Whether you’re here for a long weekend or planning a short getaway, spending 3 days in Chicago is the perfect way to experience its charm. From the bustling downtown streets to the peaceful green spaces along Lake Michigan, there’s something for everyone to enjoy.
🏠 Where to Stay in Chicago
- 💎 Luxury Hotel: Four Seasons Chicago
- ✨ 5-Star: Trump International Tower Chicago
- 🏨 4-Star: ACME Chicago
- 🛏️ 3-Star: Inn and Suites Chicago Downtown River North
- 💸 Cheap: Arlington House International Hostel
- 🏢 Apartament: Sentral Michigan Avenue
- 👨👩👧👦 For Families: Royal Sonesta Chicago Riverfront
- 🏩 For Couples: Staypineapple The Loop
In this guide, I’ll take you through a 3-day itinerary that covers the best things to do in Chicago. You’ll visit iconic landmarks like Millennium Park and Willis Tower, explore vibrant neighborhoods, and taste some of the city’s most famous dishes. By the end of your trip, you’ll see why Chicago is one of the most exciting cities in the world!
💁 Best Guided Tours in Chicago
- Chicago Architecture River Cruise from € 125 (⭐4.5/5)
- Chicago River Architecture Tour from € 125 (⭐4.5/5)
- Gangsters and Ghosts Tour in Chicago from € 125 (⭐4.5/5)
- Chicago Crime and Mob Tour from € 125 (⭐4.5/5)
- Chicago Food Tour: Pizza, Beer, Brownies, and Hot Dogs from € 125 (⭐4.5/5)
3 Days in Chicago: Itinerary Overview
- Day 1 🌆 Classic Chicago: Start your trip with stunning views from the Skydeck at Willis Tower. Stroll through Millennium Park to see Cloud Gate (The Bean) and visit the Art Institute of Chicago. In the evening, enjoy deep-dish pizza at Giordano’s and take an Architecture River Cruise to see the city lights.
- Day 2 🎨 Museums & Culture: Visit the Field Museum and Shedd Aquarium in Museum Campus. Relax in Grant Park or walk along the Chicago Riverwalk. Spend your evening in the West Loop, sampling local cuisine and craft cocktails at trendy restaurants.
- Day 3 🚢 Neighborhoods & Hidden Gems: Explore Lincoln Park, including the zoo and conservatory. Wander through Wicker Park for boutique shopping and street art, then head to Pilsen for authentic Mexican food. End your trip with dinner at a rooftop restaurant overlooking the skyline.
Day 1: Iconic Downtown
Morning: Skydeck Chicago
Skyline Thrills: Starting my 3-day Chicago itinerary at Skydeck Chicago was unforgettable. Standing on “The Ledge,” a glass box 103 floors above the city, gave me stunning views of the Chicago skyline and Lake Michigan—it felt like floating in mid-air.
Interactive Displays: Beyond the breathtaking views, the Skydeck offers interactive exhibits that highlight Chicago’s history and architecture. I spent time exploring displays about the Great Chicago Fire of 1871 and how it shaped the city’s skyline, as well as a fascinating timeline of Willis Tower’s construction. These exhibits added depth to the experience and made me appreciate the city even more.
Practical Tip: Tickets range from $30–44 USD depending on the time slot, and booking online saves time. If you’re planning a long weekend, the Chicago CityPASS is a great way to bundle attractions like this and save money.
Skydeck Chicago at Willis Tower – Check availability of tickets
Midday: Millennium Park
Park Strolls: Millennium Park is one of Chicago’s most destinations, and it didn’t disappoint. I took photos at Cloud Gate (The Bean), cooled off near Crown Fountain, and wandered through Lurie Garden, all while soaking in the vibrant energy of the city.
Seasonal Highlights: During the summer months, Millennium Park comes alive with free events like the Summer Music Series and Film Series at the Jay Pritzker Pavilion. I was lucky enough to catch a live jazz performance on the Great Lawn, surrounded by the stunning Chicago skyline—it was the perfect blend of music and scenery.
Must-See Spots in Millennium Park:
- Cloud Gate (The Bean): Reflects the city skyline beautifully for memorable photos.
- Crown Fountain: An interactive art installation with water features that’s fun for everyone.
- BP Pedestrian Bridge: Offers panoramic views of Millennium Park and beyond.
Best Activities
Chicago Food, Architecture, and History Tour: Join the Chicago Food, Architecture, and History Tour for a unique experience that combines delicious local cuisine with fascinating insights into the city’s rich history. You’ll explore neighborhoods while tasting famous Chicago hot dogs, deep-dish pizza, and more, making it a perfect way to immerse yourself in the culture of this vibrant city!
Lunch: Grab a Bite Nearby
Taste Local: For lunch, I opted for a classic Chicago dog from a nearby stand along the Riverwalk. The combination of mustard, relish, onions, pickles, and sport peppers on a poppy seed bun was a true taste of Chicago.
Options Nearby: If you’re in the mood for something different, Millennium Hall also features Napolita Pizzeria for authentic Neapolitan-style pizzas baked in imported Italian ovens. Alternatively, Casa Bonita Cantina serves up fresh Mexican fare with homemade guacamole and their famous “Perfect Margarita.” Both options are fantastic for a quick yet flavorful lunch.
Afternoon: Architecture River Cruise
River Adventures: Taking an Architecture River Cruise was hands down one of the highlights of my Chicago trip. You’ll get to see over 40 iconic buildings, including the Wrigley Building and Tribune Tower, while learning about the Great Chicago Fire of 1871 and how it shaped the city’s skyline.
| Attraction | Adult Price (USD) | Child Price (USD) |
|---|---|---|
| Skydeck Chicago | $30–44 | $22–36 |
| Architecture River Cruise | $45 | $20 |
Pro Tip: Book a cruise with the Chicago Architecture Center (CAC) for $45 USD (€43.75) to enjoy narration by expert docents who provide deeper insights into each building’s history and design. For a unique experience, opt for an evening cruise where you’ll see the buildings illuminated against the night sky—it’s magical!
Best Activities
Chicago Architecture River Cruise: Experience the Chicago Architecture River Cruise for a unique perspective on the city’s stunning skyline. This informative tour takes you past over 40 buildings, including the Wrigley Building and Tribune Tower, while highlighting Chicago’s rich architectural history.
Evening: Navy Pier
Pier Fun: I wrapped up my day at Navy Pier, one of Chicago’s most vibrant attractions. After dinner with views of Lake Michigan, I rode the Centennial Wheel for peaceful nighttime views of the city skyline—it was the perfect way to end my first day in Chicago.
Nighttime Highlights: Navy Pier truly comes alive after sunset with its lively entertainment options. I caught a live music performance at the Miller Lite Beer Garden, where local bands played against the backdrop of the shimmering lake.
Practical Tip: The Ferris wheel costs $20 USD per ticket; booking online can help you skip lines during busy evenings. Navy Pier also features seasonal events like fireworks shows or live music performances—check schedules in advance!
Top Things to Do at Navy Pier:
- Centennial Wheel Ride: Offers panoramic views of Lake Michigan and downtown Chicago.
- Outdoor Dining Options: Enjoy fresh seafood or classic American dishes by the lakefront.
- Shops & Entertainment: Explore boutiques or catch a live performance at the pier’s theater.
Best Activities
Flyover Chicago: Experience the thrill of Flyover Chicago, a breathtaking ride that takes you above the city’s major landmarks. This immersive experience combines stunning visuals and storytelling, allowing you to see the Windy City from a unique perspective.
Navy Pier Centennial Wheel – Check availability of tickets
Practical Tips for Day 1:
- Transportation: Get a 3-day CTA Ventra Pass ($20 USD) for unlimited rides on buses and trains—it’s convenient and affordable.
- Weather Prep: Always bring layers; even in summer, Chicago’s lake breeze can catch you off guard.
- Dining Tip: Avoid eating at touristy spots near major attractions—venture out for local favorites instead!
Day 2: Exploring Chicago’s Culture and Waterfront
Morning: Museum Campus
Cultural Wonders: I started my second day in Chicago at Museum Campus, a hub for some of the city’s most iconic attractions. The Field Museum was my choice, and seeing Sue the T-Rex up close was incredible—it’s one of the largest and most complete T-Rex skeletons in the world.
Immersive Exhibits: One exhibit that truly stood out was Inside Ancient Egypt. Walking through a recreated burial chamber with 23 human mummies and 30 animal mummies felt like stepping back in time. The hieroglyph-covered walls and a 4,000-year-old royal boat made it one of the most fascinating displays I’ve ever seen.
Unique Finds: Another highlight was The Griffin Halls of Evolving Planet, which explores life on Earth from single-celled organisms to modern humans. You’ll see fossils from Illinois’ state fossil, the Tully Monster, and learn about mass extinctions that shaped our planet’s history. It’s an awe-inspiring way to understand evolution and our place in nature.
Best Activities
- Field Museum of Natural History Admission: Visit the Field Museum of Natural History for an incredible journey through time and nature. Explore fascinating exhibits, including Sue, the largest and most complete T-Rex skeleton ever discovered, and learn about ancient cultures and ecosystems from around the world.
- 25 Hours Chicago's Lakefront Segway Tour: Experience Chicago in a fun and unique way with the 25 Hours Lakefront Segway Tour. Glide along the scenic lakefront paths while enjoying stunning views of Lake Michigan and the city’s skyline.
Field Museum of Natural History – Check availability of tickets
Midday: Grant Park and Buckingham Fountain
Urban Oasis: After the museum, I took a relaxing walk through Grant Park, often called “Chicago’s Front Yard.” Buckingham Fountain was a highlight, with its impressive water displays and views of Lake Michigan creating a perfect backdrop.
Heads-Up: Exploring Grant Park is completely free, which makes it a great addition to any weekend in Chicago itinerary. I grabbed a quick snack from a nearby food truck and found a shaded bench to take in the scenery.
Must-See Spots in Grant Park:
- Buckingham Fountain: A stunning centerpiece with hourly water shows.
- Maggie Daley Park: A fun spot for families with climbing walls and playgrounds.
Best Activities
Chicago City Minibus Tour: This is a fantastic way to visit Chicago and see its iconic landmarks in a short amount of time. This tour takes you through the heart of the city, where you’ll find famous sites like Millennium Park and the Art Institute, making it ideal for anyone looking to maximize their experience during a long weekend in Chicago.
Afternoon: Chicago Riverwalk
Riverfront Vibes: Walking along the Chicago Riverwalk was one of my favorite parts of the day. The path along the river offers incredible views of the city’s architecture, and I even stopped at a café for coffee while watching boats pass by.
Hidden Treasures: One unique stop was the McCormick Bridgehouse & Chicago River Museum, a five-story space that celebrates the city’s famous movable bridges. For just $8 USD (€7.77), I climbed to the top and was rewarded with panoramic views of the river and skyline, while learning about Chicago’s history as a waterway hub.
| Activity | Price (USD) |
|---|---|
| Kayak Rental | $20–$40 per hour |
| Guided Walking Tour | $30–$50 |
| Dining at Riverwalk Cafés | $15–$30 per meal |
Pro Tip: If you want a unique perspective of the Windy City, take a boat tour along the river. It’s an amazing way to see the city while learning about its famous architecture from expert guides.
Evening: Magnificent Mile
Shop and Dine: To end my second day in Chicago, I headed to Magnificent Mile, where luxury shops, historic landmarks, and lively restaurants line Michigan Avenue. I spent some time window-shopping before sitting down for dinner at one of the many restaurants offering classic Chicago food like deep-dish pizza.
Architectural Marvels: Don’t miss landmarks like Tribune Tower or Wrigley Building as you explore this vibrant area. For an unforgettable view of the city at night, visit 360 CHICAGO Observation Deck in the John Hancock Center—it’s breathtaking!
Top Things to Do on Magnificent Mile:
- 360 CHICAGO Observation Deck: Offers panoramic views of Lake Michigan and beyond.
- Shopping Stops: From high-end boutiques to local shops, there’s something for everyone here.
- Historic Landmarks: Admire architectural gems like Tribune Tower and Wrigley Building.
360 CHICAGO Observation Deck – Check availability of tickets
Day 3: A Relaxing Finale in Chicago
Morning: Lincoln Park
Nature Escape: I began my final day in Chicago with a walk through Lincoln Park, the perfect place to enjoy some tranquility amidst the bustling city. The Lincoln Park Zoo, one of the oldest free zoos in the U.S., was a highlight, where you’ll see everything from snow leopards to penguins.
Recommendation: Don’t miss the Lincoln Park Conservatory nearby, which features exotic plants and flowers in a historic greenhouse. For a peaceful moment, take a stroll around the Alfred Caldwell Lily Pool and admire its serene beauty.
Top Spots to Explore in Lincoln Park:
- Lincoln Park Zoo: Free entry and home to nearly 200 species.
- Lincoln Park Conservatory: A lush indoor botanical garden.
- South Pond Nature Walk: Offers stunning views of the Chicago skyline and Lake Michigan.
Family Spot: Another unique spot in Lincoln Park is Oz Park, where you’ll find life-sized statues of characters from The Wizard of Oz. Walking through the park, I stumbled upon sculptures of Dorothy and Toto, the Tin Man, and the Cowardly Lion—all set against beautifully landscaped gardens. It’s a fun stop for families or anyone who loves a bit of whimsy.
Best Activities
Bobby's Bike Hike Chicago Lakefront Neighborhoods Tour: This engaging experience is a great way to explore the city while enjoying the fresh air and scenic views, making it a perfect addition to your 3-day Chicago itinerary. You’ll ride through iconic areas, including Old Town and Lincoln Park, and discover the local culture while having fun!
Midday: Art Institute of Chicago
Art Haven: The Art Institute of Chicago was a highlight of my trip, and stepping inside felt like entering a world of creativity and inspiration. With over 300,000 artworks, I was excited to explore everything from ancient artifacts to modern masterpieces.
Iconic Pieces: I was particularly drawn to Grant Wood’s American Gothic and Seurat’s A Sunday on La Grande Jatte, both of which are even more striking in person. The museum’s extensive Impressionist collection took my breath away, showcasing works that I’ve admired in books for years.
Art Institute of Chicago Fast Pass – Check availability of tickets
Afternoon: Museum of Science and Industry
Interactive Fun: For my afternoon, I visited the Museum of Science and Industry, one of the largest science museums in the Western Hemisphere. Highlights included standing inside a 40-foot tornado at the Science Storms exhibit and exploring the U-505 Submarine, a real German U-boat from World War II.
Must-See Exhibits
- U-505 Submarine: The only German U-boat on display in the U.S., offering a fascinating glimpse into World War II history.
- Science Storms: Interactive exhibits where you can experience tornados, tsunamis, and avalanches up close.
- Numbers in Nature Mirror Maze: A fun and educational maze that explores mathematical patterns found in nature.
Evening: Navy Pier Farewell
Lakeside Farewell: To wrap up my weekend in Chicago, I returned to Navy Pier for one last dose of lakeside fun. I enjoyed dinner at Riva Crabhouse, where fresh seafood and views of Lake Michigan made for a memorable final meal.
Heads-Up: If you’re visiting during summer, Navy Pier often hosts fireworks displays on Wednesday and Saturday nights—check the schedule for an unforgettable send-off! Don’t forget to take one last ride on the Centennial Wheel for breathtaking nighttime views of the city skyline.
Best Activities
Chicago Fireworks Cruise: Experience the Chicago Fireworks Cruise for a spectacular view of the city’s skyline and stunning fireworks displays over Lake Michigan. This tour is a fantastic way to end your day in the city, offering a perfect blend of relaxation and excitement while you enjoy the vibrant atmosphere of Chicago.
Day 3 Cost Breakdown
| Expense Category | Activity/Item | Estimated Cost (USD) | Estimated Cost (EUR) |
|---|---|---|---|
| Attractions | Museum of Science and Industry | $21 | €20.42 |
| Lincoln Park Zoo (Free Entry) | $0 | €0 | |
| Art Institute of Chicago | $30 | €25 | |
| Lincoln Park Conservatory (Free Entry) | $0 | €0 | |
| Meals | Breakfast, Lunch, and Dinner | $50 | €48.63 |
| Transportation | CTA Ventra Pass (Day 3 portion) | $20 | €19.45 |
| Miscellaneous | Snacks, Drinks, Souvenirs | $15 | €14.59 |
| Total | $106 | €103.09 |
Practical Tips for Your Weekend in Chicago
Getting Around Chicago
Efficient Transit: Chicago’s public transportation system, operated by the CTA, is one of the best ways to navigate the city. The “L” train connects major Chicago attractions like the Art Institute of Chicago, Willis Tower, and Lincoln Park Zoo. A 3-day unlimited Ventra Pass costs $15 USD (€14.58) and covers both buses and trains, making it a cost-effective option for your 3-day Chicago itinerary.
Insider Advice: Download the Ventra app to check schedules and reload your pass on the go. Avoid driving downtown during peak hours (7–9 AM and 3–7 PM) as parking can cost up to $45 USD (€43.65) per day in central areas like the Loop or Magnificent Mile.
Dining in Chicago
Foodie Favorites: Chicago is a haven for food lovers, offering everything from Michelin-starred dining to iconic street food. Don’t leave without trying a deep-dish pizza at Lou Malnati’s or a classic Chicago-style hot dog at Portillo’s. For fine dining, restaurants like Boka in Lincoln Park or Girl & the Goat in the West Loop are highly recommended.
Must-Try Foods in Chicago:
- Deep-Dish Pizza: Thick crust with layers of cheese and chunky tomato sauce.
- Italian Beef Sandwich: Juicy beef served on a roll, often dipped in au jus sauce.
- Chicago-Style Hot Dog: Topped with mustard, relish, onions, tomatoes, and sport peppers—never ketchup!
Booking Attractions
Plan Ahead: Many popular attractions like Skydeck Chicago at Willis Tower and the Art Institute of Chicago encourage online reservations to skip long lines. Tickets for Skydeck cost $30 USD (€29.17), while entry to the Art Institute is $25 USD (€24.31).
Smart Bundles: If you’re spending 3 days in Chicago, the Chicago CityPASS is a fantastic way to save money and time. For $139 USD (€134.70), it includes admission to five must-see attractions like Shedd Aquarium, Skydeck Chicago, and the Field Museum, plus your choice of three others such as the Art Institute of Chicago or 360 CHICAGO Observation Deck.
| CityPASS Attractions | Regular Price (USD/EUR) | Included with CityPASS |
|---|---|---|
| Shedd Aquarium | $58.65 / €56.97 | ✔ |
| Skydeck Chicago | $61 / €59.30 | ✔ |
| Field Museum | $43 / €41.72 | ✔ |
| 360 CHICAGO | $50 / €48.50 | Optional |
| Art Institute | $40 / €38.80 | Optional |
Neighborhood Highlights
Explore Beyond Downtown: While downtown is packed with iconic landmarks, neighborhoods like Wicker Park and Logan Square offer unique vibes with trendy cafés, street art, and boutique shopping. Hyde Park is home to the Museum of Science and Industry and beautiful green spaces along Lake Michigan’s shore.
Local Pointer: Take a guided food or architecture tour to get an insider’s perspective on these vibrant areas. Walking tours typically cost around $30–$50 USD (€29–€48).
Seasonal Considerations
Weather Prep: Winters can be harsh in the Windy City, so pack warm layers if visiting between November and March. Summers are perfect for outdoor activities like walking along the river or biking by Lake Michigan on the Lakeshore Trail.
Unique Experience: Don’t miss seasonal highlights like summer fireworks at Navy Pier or ice skating at Millennium Park during winter months—it’s a magical way to see the city! By following these practical tips, you’ll make the most of your trip to the Windy City while staying within budget!
❓ FAQ
What is the perfect 3 days in Chicago itinerary?
A perfect 3 days in Chicago includes iconic landmarks, cultural attractions, and local food. Start with the Skydeck at Willis Tower, walk along the Chicago Riverwalk, and take a river cruise. On Day 2, explore Museum Campus with stops at Shedd Aquarium and the Field Museum, then visit Millennium Park. End Day 3 with Lincoln Zoo, shopping on the Magnificent Mile, and Navy Pier for a relaxing evening.
What are the must-see attractions in Chicago?
Must-see Chicago attractions include Skydeck Chicago for skyline views, the Art Institute of Chicago for world-famous art, and Millennium Park for Cloud Gate (The Bean). Museum Campus is a highlight with its natural history museum and aquarium. Navy Pier is another top destination in Chicago for dining and entertainment.
How do I get around Chicago during my trip?
Getting around Chicago is easy with the CTA Ventra Pass ($20 USD/€19.45) for unlimited bus and train rides. The “L” train connects major attractions like Millennium Park. Walking along the Chicago River or taking a hop-on-hop-off bus is a great way to see as much as possible without worrying about parking fees downtown.
What are some iconic foods to try in Chicago?
Chicago is famous for its deep-dish pizza from spots like Lou Malnati’s, classic hot dogs from Portillo’s, and Italian beef sandwiches at Al’s Beef. These dishes are a must-try during your trip to Chicago and offer a true taste of the city’s culinary culture.
What are some unique activities for my trip to Chicago?
For something unique, visit Oz Park in Lincoln Park or catch a show at the historic Chicago Theatre. Nature lovers can enjoy South Pond Nature Walk or take a tour of Lake Michigan by kayak for stunning views of the city of Chicago from the water.
Is 3 days enough time to explore Chicago?
Three days in Chicago is enough to experience its famous attractions and vibrant neighborhoods if you plan carefully. A well-organized 3-day itinerary lets you see landmarks like Skydeck Chicago and enjoy local gems like Alfred Caldwell Lily Pool while leaving time to savor iconic food like deep-dish pizza or hot dogs.
