Explore Chicago
Like a Local
Plan your perfect Chicago trip with this customizable 3-day itinerary featuring top attractions and local favorites.
Your Complete Chicago Companion
Everything you need for an unforgettable 3-day adventure in one interactive template
Day-by-Day Planner
A perfectly balanced 3-day itinerary with morning to evening activities
Interactive Maps
Optimized routes with all attractions, restaurants and viewpoints mapped out
Budget Breakdown
Transparent cost estimates for every budget level with money-saving tips
Local Secrets
Hidden gems and insider tips you won't find in standard guidebooks
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Customize Your Trip
Personalize days, add your own stops, adjust timing to suit your pace
Share & Collaborate
Plan together with travel companions in real-time
Chicago Attractions
Discover iconic landmarks and hidden gems all included in your itinerary
The Art Institute of Chicago
The Art Institute of Chicago is a world-renowned museum boasting an impressive collection of art spa...
Wrigley Field
Wrigley Field, the iconic home of the Chicago Cubs, offers a nostalgic journey into the heart of bas...
Frank Lloyd Wright Home & Studio
Step into the genius of Frank Lloyd Wright at his Home & Studio in Chicago, where architectural inno...
Lincoln Park Conservatory
Nestled within Chicago's vibrant Lincoln Park, the Lincoln Park Conservatory is a verdant oasis offe...
Your Guide to Chicago
Chicago, known as the Windy City, is a vibrant metropolis that beautifully blends history, culture, and modernity. Nestled on the shores of Lake Michigan, this city is renowned for its stunning architecture, world-class museums, diverse culinary scene, and lively sports culture. Visitors can immerse themselves in the rich history at the Field Museum, enjoy the architectural marvels at the Frank Lloyd Wright Home & Studio, and take in a game at the iconic Wrigley Field. Art enthusiasts will be captivated by the extensive collections at The Art Institute of Chicago, and nature lovers can find tranquility in the lush greenery of the Lincoln Park and Garfield Park Conservatories. With its bustling theater district, diverse neighborhoods, and a skyline that is second to none, Chicago offers an unforgettable experience for every kind of traveler.
Best Time to Visit
The best time to visit Chicago is from late spring to early fall (May to September) when the weather is most pleasant.
Getting Around
Chicago offers a comprehensive public transportation system, making it easy for visitors to navigate the city.
Local Insider Tips
Chicago’s weather can be unpredictable, so it’s essential to dress in layers and be prepared for sudden changes, especially if you're visiting in spring or fall.
Your Day-by-Day Itinerary
We've planned everything - from must-see attractions to local dining spots
Day 1
Morning
- Shree Ganesh Temple of Chicago - Regal Foundation90 min•$
- The Art Institute of Chicago120 min•$$$
- + 1 more activities
Afternoon
- Frank Lloyd Wright Home & Studio90 min•$$
- Lincoln Park Conservatory90 min•Free
- + 1 more activities
Evening
- Frank Lloyd Wright Home & Studio90 min•$$
Day 2
Morning
- Holy Name Cathedral60 min•Free
- Field Museum180 min•$$$
- + 1 more activities
Afternoon
- 875 North Michigan Avenue90 min•$$
- Cloud Gate45 min•Free
- + 1 more activities
Evening
- Lincoln Park Conservatory90 min•Free
Day 3
Morning
- Chicago Cultural Center90 min•Free
- National Museum of Mexican Art90 min•$
- + 1 more activities
Afternoon
- Peggy Notebaert Nature Museum90 min•$
- Frederick C. Robie House90 min•$$
- + 1 more activities
Evening
- Garfield Park Conservatory90 min•$
Where to Stay in Chicago
Our guide includes the best neighborhoods and accommodation options for every budget
The Loop
$$$-$$$$The Loop is Chicago's bustling downtown area, home to iconic landmarks like Millennium Park, the Art Institute of Chicago, and the Willis Tower. It's ideal for visitors who want to be in the heart of the city's business and cultural district.
River North
$$-$$$River North is known for its vibrant nightlife, art galleries, and dining scene. This trendy neighborhood offers a mix of upscale hotels and boutique accommodations, making it perfect for travelers looking to experience Chicago's lively atmosphere.
Magnificent Mile
$$$-$$$$Magnificent Mile is Chicago's premier shopping district, lined with luxury stores, restaurants, and hotels. It’s a great area for those who love shopping and want to stay in an upscale, lively environment.
Recommended Properties
The Langham, Chicago
$$$$The Loop
The Langham, Chicago offers luxurious accommodations with stunning views of the city skyline and the Chicago River. Located in The Loop, it's within walking distance to major attractions like Millennium Park and the Art Institute of Chicago.
The Godfrey Hotel Chicago
$$River North
The Godfrey Hotel Chicago is a chic, modern hotel located in River North. It features a rooftop bar with panoramic city views, stylish rooms, and is close to the area's vibrant nightlife and dining scene.
The Peninsula Chicago
$$$$Magnificent Mile
The Peninsula Chicago offers world-class luxury and service in the heart of the Magnificent Mile. With spacious rooms, a rooftop spa, and a prime location near high-end shopping and attractions, it's a top choice for discerning travelers.
Accommodation Insider Tip
Book accommodations 3-4 months in advance for the best rates, especially during peak tourist season. Many hotels offer free cancellation up to 24-48 hours before your stay, so you can always change plans later.
Budget Your Trip
Plan your finances with our transparent cost breakdown for every budget level
Budget Traveler
Perfect for frugal adventurers
Accommodation | $30-70 per night in hostels or budget hotels |
Food | $15-30 per day with meals from food trucks or inexpensive cafes |
Transportation | $10-15 using public transport |
Activities | $10-25 for affordable or free attractions |
Mid-Range
Comfort without breaking the bank
Accommodation | $100-200 per night in 3-4 star hotels |
Food | $40-70 per day with meals at mid-range restaurants |
Transportation | $15-25 using public transport and occasional taxis |
Activities | $30-60 for a mix of paid attractions and tours |
Luxury
Premium experience all the way
Accommodation | $300+ per night in 5-star hotels |
Food | $100+ per day with meals at high-end restaurants |
Transportation | $40+ using taxis or private car services |
Activities | $100+ for premium experiences and tours |
Money-Saving Tips
Weather-Proof Your Trip
Alternative plans for every situation so your trip is perfect no matter what
Rainy Day Plan
Art Institute of Chicago
One of the oldest and largest art museums in the U.S., featuring an extensive collection of Impressionist and Post-Impressionist works.
Museum of Science and Industry
A fascinating museum with interactive exhibits on everything from space exploration to the human body.
Chicago Cultural Center
A beautiful venue offering free art exhibits, concerts, and cultural events.
Family-Friendly Plan
Lincoln Park Zoo
A free zoo with a wide variety of animals, a farm-in-zoo, and children’s programs.
Shedd Aquarium
An indoor public aquarium housing over 32,000 animals, offering immersive exhibits and interactive shows.
Chicago Children's Museum
An engaging museum offering hands-on exhibits and activities for children of all ages.
Essential Travel Resources
Everything you need for a smooth and enjoyable Chicago experience
Useful Apps
Ventra
An app for purchasing and managing fares for Chicago’s public transportation system.
Chicago Travel Guide
A comprehensive guide to Chicago’s attractions, restaurants, and events.
ParkChicago
An app for finding and paying for parking in the city.
Useful Websites
Choose Chicago
The official tourism site for Chicago, offering comprehensive visitor information.
Chicago Transit Authority
Information on Chicago’s public transportation system, including routes, schedules, and fares.
Safety Tips
Be aware of your surroundings, especially in crowded areas and on public transportation.
Keep your valuables secure and avoid displaying them in public.
Stay in well-lit, busy areas, especially at night.
Use reputable transportation options, such as registered taxis or ride-sharing services.
Follow local news and weather updates, particularly during extreme weather conditions.
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About This Template
This 3-day Chicago itinerary template is designed by local experts and experienced travelers to give you the perfect balanced experience.
Why Chicago
- Stunning landmarks and views
- Diverse food scene and culture
- Mix of urban and natural attractions
Best Times to Visit
The best time to visit Chicago is from late spring to early fall (May to September) when the weather is most pleasant.
Seasonal note: Year-round, best April-October
More Resources
© 2025 Travel Guides. All information is provided for planning purposes only.