Looking for the best things to do in Chicago? Whether you’re after iconic landmarks like Millennium Park or unique local experiences, Chicago offers a diverse array of activities. The best overall pick is the Skydeck Chicago for breathtaking city views, while the Navy Pier provides family-friendly entertainment. Other standout options include exploring museums or enjoying outdoor recreation. The biggest tradeoffs involve balancing popular tourist spots with off-the-beaten-path adventures. Continue reading for a detailed breakdown of each top pick and how they suit different travelers.
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Key Takeaways
- The top-ranked options combine iconic sights with accessible experiences, making them suitable for most visitors.
- Many of the best attractions balance outdoor activities and indoor options, accommodating different weather conditions.
- Cost varies widely; some top picks are free or inexpensive, while others are premium experiences with higher price tags.
- The best picks tend to be centrally located or easily accessible via public transportation, saving time and effort.
- Visitor preferences differ: some prioritize cultural immersion, while others focus on scenic views or family-friendly fun.
| 111 Places in Chicago That You Must Not Miss |  | Best for Hidden Gems and Local Insights | Number of locations: 111 | Focus: Hidden gems and popular attractions | Intended audience: Travelers and locals | VIEW ON AMAZON | See Our Full Breakdown |
| The Ultimate Chicago Bucket List: 100 Unforgettable Things to Do, See, Eat & Experience |  | Best for Diverse Activities and Food Experiences | Number of activities: 100 | Focus: Attractions, food, experiences | Includes maps: No | VIEW ON AMAZON | See Our Full Breakdown |
| DK Top 10 Chicago: Top 10 Lists for Your Perfect Trip, Plus an All-Weather Folded Map |  | Best for Quick Planning and On-the-Go Navigation | Number of lists: 10 | Includes: All-weather folded map | Size: Compact | VIEW ON AMAZON | See Our Full Breakdown |
| 111 Places in Chicago That You Must Not Miss |  | Best for Diverse Interests and Hidden Gems | Number of locations: 111 | Focus: Interesting places and hidden gems | Includes maps: No | VIEW ON AMAZON | See Our Full Breakdown |
| Chicago Bucket List: The Complete Adventure Travel Guide to 150 Epic Destinations in the Windy City |  | Best for Extensive Exploration and Interactive Maps | Number of destinations: 150 | Includes: Interactive map | Focus: Famous and hidden sites | VIEW ON AMAZON | See Our Full Breakdown |
| Fodor’s Chicago (Full-color Travel Guide) |  | Best Overall for In-Depth Planning | Type: Full-color travel guide | Maps: Full-color maps included | Images: Color images throughout | VIEW ON AMAZON | See Our Full Breakdown |
| 100 Things to Do in Chicago Before You Die, Special Edition |  | Best for Unique Local Experiences | Type: Curated activity list | Number of activities: 100 | Content focus: Hidden gems and local favorites | VIEW ON AMAZON | See Our Full Breakdown |
| Fodor’s Chicago Travel Guide |  | Best for Detailed City Insights | Type: Printed city guide | Maps: Color maps included | Images: Color images | VIEW ON AMAZON | See Our Full Breakdown |
| 100 Things to Do in Chicago Before You Die |  | Best for Classic Tourist Experiences | Type: Curated activity list | Number of activities: 100 | Content focus: Top attractions and experiences | VIEW ON AMAZON | See Our Full Breakdown |
| Moon 52 Things to Do in Chicago: Local Spots, Outdoor Recreation, Getaways |  | Best for Outdoor and Local Spot Exploration | VIEW ON AMAZON | See Our Full Breakdown |
| things to do in chicago | Format | Focus |
|---|---|---|
| 111 Places in Chicago That You | Book | Hidden gems and popular attractions |
| The Ultimate Chicago Bucket Li | Book | Attractions, food, experiences |
| DK Top 10 Chicago: Top 10 List | — | Top highlights |
| 111 Places in Chicago That You | Book | Interesting places and hidden gems |
| Chicago Bucket List: The Compl | Book | Famous and hidden sites |
| Fodor’s Chicago | — | — |
| 100 Things to Do in Chicago Be | Printed book | — |
| Fodor’s Chicago Travel Guide | — | — |
| 100 Things to Do in Chicago Be | Printed book | — |
| Moon 52 Things to Do in Chicag | — | — |
More Details on Our Top Picks
111 Places in Chicago That You Must Not Miss
This book stands out for uncovering Chicago’s lesser-known spots alongside popular attractions, making it ideal for travelers who want an authentic experience beyond the typical tourist trail. Compared to DK Top 10 Chicago, which offers concise lists and practical maps, this guide provides a broader selection of off-the-beaten-path locations, though it lacks detailed descriptions or maps. It’s best for those who enjoy exploring at their own pace and discovering hidden corners, but it may fall short for visitors needing detailed directions or recent updates. Pros include a diverse list of unique places, suitability for both tourists and locals, and inclusion of hidden gems. Cons are the absence of detailed descriptions, limited maps, and possible outdated info.
Pros:- Provides a diverse list of unique Chicago attractions
- Great for both tourists and locals seeking authentic experiences
- Includes lesser-known hidden gems
Cons:- No detailed descriptions or maps provided
- May not include the most recent openings or changes
Best for: Travelers and locals eager to explore Chicago’s hidden treasures and authentic neighborhoods.
Not ideal for: Visitors seeking structured itineraries or comprehensive maps for navigating the city efficiently.
- Number of locations:111
- Focus:Hidden gems and popular attractions
- Intended audience:Travelers and locals
- Includes maps:No
- Updated recently:No
- Format:Book
Our verdict“This guide is perfect for explorers wanting to discover Chicago’s hidden side, but not for those seeking detailed navigation aid.”
The Ultimate Chicago Bucket List: 100 Unforgettable Things to Do, See, Eat & Experience
This book makes the list for offering a broad array of Chicago’s top sights, eats, and experiences, making it ideal for those wanting a comprehensive yet manageable overview. Unlike DK Top 10 Chicago, which favors quick top 10 lists and maps, this guide covers a wider spectrum of activities, including culinary adventures and cultural sights. It’s suited for travelers who want to maximize their trip with memorable experiences, but it can be overwhelming for visitors looking for a quick, focused plan. Pros include an extensive variety of attractions, inclusive of food and culture, and appeal to both visitors and locals. Cons are the lack of detailed descriptions and the potential for information overload.
Pros:- Extensive list of attractions and experiences
- Includes culinary, sightseeing, and unique activities
- Suitable for both visitors and locals
Cons:- No detailed descriptions or maps included
- Can be overwhelming for quick visits
Best for: Visitors and residents eager to experience Chicago’s best attractions, food, and hidden delights in one curated list.
Not ideal for: People seeking in-depth descriptions, reviews, or specific itineraries for a short trip.
- Number of activities:100
- Focus:Attractions, food, experiences
- Includes maps:No
- Target audience:Tourists and locals
- Format:Book
- Coverage:Sights, eats, activities
Our verdict“Ideal for those wanting a comprehensive, activity-rich overview of Chicago, but less so for quick or detailed planning.”
DK Top 10 Chicago: Top 10 Lists for Your Perfect Trip, Plus an All-Weather Folded Map
This guide excels at helping travelers quickly identify the top highlights of Chicago through concise top 10 lists, complemented by an all-weather folded map for easy navigation. Compared with 111 Places in Chicago, which emphasizes hidden gems, this option prioritizes quick, practical advice for travelers on a tight schedule or with limited time. Its compact size and included map make it well-suited for on-the-move exploration, but it offers less depth or unique insights into each site. Pros include concise recommendations, portable format, and practical maps. Cons are limited detail and no extensive descriptions or reviews.
Pros:- Concise top 10 lists for quick trip planning
- Includes an all-weather folded map for easy navigation
- Compact and portable for travelers
Cons:- Limited detailed information for in-depth exploration
- Lacks reviews or comprehensive descriptions
Best for: Short-term visitors and travelers who want quick, reliable suggestions with easy navigation tools.
Not ideal for: Visitors interested in in-depth exploration or discovering lesser-known spots beyond the top attractions.
- Number of lists:10
- Includes:All-weather folded map
- Size:Compact
- Target user:Quick planners and on-the-go visitors
- Focus:Top highlights
Our verdict“Best suited for travelers seeking quick, straightforward recommendations with practical maps for efficient touring.”
111 Places in Chicago That You Must Not Miss
This book mirrors the first entry but offers a slightly different selection of 111 must-see locations, making it ideal for those seeking a broad overview of Chicago’s interesting places, including hidden gems. Unlike DK Top 10 Chicago, which offers lists and maps, this guide emphasizes variety and discovery, though it shares the same limitation of lacking detailed descriptions or maps. It’s a good pick for travelers who prefer exploring at their own pace and enjoy uncovering lesser-known spots, but it may not satisfy those needing detailed directions or recent updates. Pros include a wide range of interesting locations and appeal to varied interests. Cons are the lack of detailed descriptions and potential outdated info.
Pros:- Provides a broad list of interesting places
- Great for varied interests, including hidden gems
- Suitable for both tourists and locals
Cons:- No detailed descriptions or maps
- May not reflect the most current openings
Best for: Visitors and locals wanting a broad, diverse list of Chicago’s interesting places, especially hidden gems.
Not ideal for: People needing detailed, step-by-step guides or recent updates on attractions.
- Number of locations:111
- Focus:Interesting places and hidden gems
- Includes maps:No
- Audience:Visitors and locals
- Format:Book
Our verdict“A solid choice for those wanting a wide-ranging list of Chicago’s diverse spots, but not for detailed planning.”
Chicago Bucket List: The Complete Adventure Travel Guide to 150 Epic Destinations in the Windy City
This comprehensive guide covers 150 destinations, blending iconic landmarks with hidden corners, and stands out for including an interactive map that enhances navigation. Compared to the other books, especially 111 Places in Chicago, which offer static lists, this guide’s interactive map makes it easier to plan visits efficiently. It’s ideal for travelers who want a thorough list that’s easy to navigate, but the lack of detailed descriptions or reviews limits its usefulness for those seeking deeper insights. It’s best for those who enjoy detailed itineraries and interactive tools to customize their exploration. Pros include extensive coverage, interactive mapping, and a mix of famous and hidden sites. Cons are the absence of detailed site descriptions and lack of user reviews.
Pros:- Covers 150 destinations, from landmarks to hidden spots
- Includes an interactive map for easy navigation
- Comprehensive and detailed list for thorough exploration
Cons:- No detailed descriptions or reviews for each site
- Price and ratings are not specified
Best for: Adventurous travelers who want a comprehensive, interactive exploration of Chicago’s attractions and hidden corners.
Not ideal for: Visitors who prefer guided tours, detailed descriptions, or curated itineraries with reviews.
- Number of destinations:150
- Includes:Interactive map
- Focus:Famous and hidden sites
- Target:Adventurous explorers
- Format:Book
- Coverage:Landmarks, hidden gems, corners
Our verdict“Perfect for travelers seeking a detailed, interactive exploration guide with a wide range of Chicago’s sights and secrets.”
Fodor’s Chicago (Full-color Travel Guide)
This comprehensive guide stands out for its detailed coverage of Chicago’s attractions, restaurants, and accommodations, making it ideal for travelers who want an all-in-one resource. Compared with Fodor’s Chicago Travel Guide, it offers more full-color maps and vibrant images that enhance navigation and visual appeal. However, the lack of specific publication updates could mean some information is outdated, which is a drawback for those relying on the latest tips. This pick makes the most sense for visitors seeking a thorough, visually engaging travel companion that covers every aspect of their trip, from major sights to hidden gems.
Pros:- Extensive coverage of attractions, restaurants, and hotels
- Full-color maps and vibrant images enhance navigation and experience
- Ideal for detailed trip planning and first-time visitors
Cons:- No specific edition or recent update details, risking outdated info
- Lacks digital format options for on-the-go access
Best for: Tourists planning a comprehensive trip who value detailed visuals and extensive information
Not ideal for: Frequent travelers or locals who need quick updates or off-the-beaten-path insights
- Type:Full-color travel guide
- Maps:Full-color maps included
- Images:Color images throughout
- Coverage:Attractions, restaurants, accommodations
- Edition:Print only
- Update info:No specific details
Our verdict“This guide is best suited for travelers who want an in-depth, visually rich resource to explore Chicago thoroughly.”
100 Things to Do in Chicago Before You Die, Special Edition
This curated list excels at highlighting Chicago’s most memorable activities, including hidden gems and local favorites, making it perfect for those seeking authentic experiences. Unlike 100 Things to Do in Chicago Before You Die, which provides a straightforward list, this special edition emphasizes unique and off-the-radar spots, adding a layer of discovery. The tradeoff is that it offers limited descriptions and minimal background, so it’s less helpful for in-depth planning or learning about each activity. This book makes the most sense for curious visitors and locals looking to add distinctive experiences to their Chicago adventures.
Pros:- Curated list of top and hidden activities in Chicago
- Great for discovering lesser-known spots
- Appeals to both visitors and locals craving authentic experiences
Cons:- Lacks detailed descriptions or reviews of each activity
- Limited content format, mostly lists without in-depth information
Best for: Adventurous travelers and locals eager to explore Chicago’s hidden gems
Not ideal for: First-time visitors needing detailed itineraries or background on attractions
- Type:Curated activity list
- Number of activities:100
- Content focus:Hidden gems and local favorites
- Intended audience:Locals and curious visitors
- Format:Printed book
- Update info:Not specified
Our verdict“This edition is ideal for explorers who want a curated, unique perspective on Chicago’s best-kept secrets.”
Fodor’s Chicago Travel Guide
This guide offers thorough insights into Chicago’s attractions, restaurants, and hotels, similar to Fodor’s Chicago (Full-color Travel Guide), but with a more practical focus on local tips and updated travel advice. Its strength lies in providing current recommendations, yet it lacks the vibrant visuals of the full-color guide, which can make exploration less engaging visually. It also doesn’t include a digital version, limiting convenience for on-the-go use. This guide makes the most sense for travelers who want a reliable, detailed resource that balances comprehensive information and practical tips, especially if they prefer printed materials over visual-heavy guides.
Pros:- Comprehensive, updated city insights
- Useful local tips and recommendations
- Good balance of attractions, dining, and accommodations
Cons:- No digital or app version available
- Limited coverage of lesser-known or offbeat sites
Best for: Travelers seeking detailed, current insights and practical recommendations
Not ideal for: Visitors who prefer visual navigation and interactive digital content
- Type:Printed city guide
- Maps:Color maps included
- Images:Color images
- Coverage:Attractions, restaurants, hotels
- Edition:Updated edition
- Digital:Not included
Our verdict“This guide is well-suited for travelers who prioritize detailed, up-to-date information for planning their Chicago visit.”
100 Things to Do in Chicago Before You Die
This list provides a solid selection of Chicago’s must-see attractions and activities, making it a good pick for both tourists and locals seeking a curated experience. Compared with the 100 Things to Do in Chicago Before You Die, Special Edition, it offers a broader appeal, but with fewer unique or hidden options. The limited details on each activity mean it’s less useful for detailed planning but great for quick inspiration. This book is best for those who want a straightforward list of essential Chicago experiences without the need for extensive background or descriptions.
Pros:- Concise, curated list of Chicago’s key attractions
- Suitable for both tourists and locals
- Offers practical tips for exploring popular spots
Cons:- Limited details or descriptions of activities
- No specifications or in-depth content
Best for: Tourists wanting a quick, curated list of Chicago’s top attractions
Not ideal for: Visitors seeking unique or offbeat experiences or detailed itineraries
- Type:Curated activity list
- Number of activities:100
- Content focus:Top attractions and experiences
- Audience:Tourists and locals
- Format:Printed book
- Update info:Not specified
Our verdict“This list is perfect for visitors who want a quick, reliable set of Chicago’s essential experiences without extra frills.”
Moon 52 Things to Do in Chicago: Local Spots, Outdoor Recreation, Getaways
This guide shines in offering a curated selection of outdoor activities, local spots, and short getaways, making it especially meaningful for those looking to explore Chicago’s outdoor scene or nearby escapes. Unlike the more extensive lists in 100 Things to Do in Chicago Before You Die, this book emphasizes outdoor recreation and local experiences, which could be limiting for visitors seeking indoor attractions or cultural sites. The absence of detailed specifications and reviews might make it less reliable for planning, but its focused approach makes it excellent for outdoor lovers and those wanting a relaxed, active exploration of the city and its surroundings.
Pros:- Curated list of outdoor activities and local spots
- Includes getaway ideas for nearby escapes
- Ideal for outdoor lovers and relaxed explorers
Cons:- Limited to outdoor and local spots, missing cultural options
- No detailed specs or reviews available
Best for: Outdoor enthusiasts and locals interested in local spots and short trips
Not ideal for: Visitors primarily seeking indoor activities, museums, or cultural experiences
Our verdict“This guide is best for outdoor adventurers and locals wanting to explore Chicago’s outdoor scene and nearby getaways.”
How We Picked
To determine the best products for this roundup, I evaluated each based on popularity, variety, accessibility, and overall visitor experience. I considered how well each option captures the essence of Chicago, whether it offers unique or iconic experiences, and how suitable it is for different types of travelers. The ranking reflects a balance between must-see landmarks, local hidden gems, and practical considerations like location and cost. I also looked for options that provide good value and appeal to a broad audience, ensuring that each pick has a clear role in a well-rounded itinerary.| things to do in chicago | Focus | Format |
|---|---|---|
| 111 Places in Chicago That You | Hidden gems and popular attractions | Book |
| The Ultimate Chicago Bucket Li | Attractions, food, experiences | Book |
| DK Top 10 Chicago: Top 10 List | Top highlights | — |
| 111 Places in Chicago That You | Interesting places and hidden gems | Book |
| Chicago Bucket List: The Compl | Famous and hidden sites | Book |
| Fodor’s Chicago | — | — |
| 100 Things to Do in Chicago Be | — | Printed book |
| Fodor’s Chicago Travel Guide | — | — |
| 100 Things to Do in Chicago Be | — | Printed book |
| Moon 52 Things to Do in Chicag | — | — |
Factors to Consider When Choosing Things To Do In Chicago
When choosing activities in Chicago, it’s important to consider your personal interests, budget, and the type of experience you seek. Some attractions are ideal for first-time visitors, while others cater to locals or adventure seekers. Weather can also influence your choices, so planning for indoor and outdoor options is smart. Additionally, proximity to your accommodation saves travel time, and understanding ticket costs upfront helps manage your budget. Keep these factors in mind to craft a memorable and hassle-free visit.Interest and Experience Type
Consider whether you want to see iconic sights, explore cultural institutions, enjoy outdoor activities, or indulge in local cuisine. Your preferences will guide you toward the most rewarding experiences. For example, history buffs might prioritize museums or historic neighborhoods, while families may prefer amusement parks or boat tours. Matching activities to your interests ensures your trip feels personalized and satisfying.
Budget and Cost
Chicago offers options across a wide price spectrum. Free attractions like Millennium Park and Lincoln Park are great for budget travelers, while premium experiences like sky-high observation decks come with a higher price tag. Planning your budget in advance helps avoid surprises and allows you to allocate funds toward experiences that matter most to you.
Weather and Seasonal Considerations
Chicago’s weather can vary dramatically, with cold winters and hot summers. Indoor attractions like museums or theaters are ideal for winter visits, while outdoor activities shine in milder weather. Check seasonal events or festivals that might influence your plans, and always have backup options in case of weather changes.
Location and Accessibility
Select activities that are conveniently located near your accommodation or easily reachable via public transit. This saves travel time and reduces stress, especially if you’re on a tight schedule. Many top attractions are clustered downtown, making it simple to combine multiple experiences in a day.
Crowds and Popularity
Some attractions, like Navy Pier or the Skydeck, draw large crowds, which can impact your experience. Visiting during off-peak hours or choosing lesser-known spots can provide a more relaxed visit. Balance popular sights with hidden gems to enjoy a richer, less hectic experience.
Frequently Asked Questions
What is the best time of year to visit Chicago for outdoor activities?
The best time for outdoor activities in Chicago is late spring through early fall, typically from May to September. During these months, the weather is generally mild and warm, making outdoor festivals, parks, and boat tours much more enjoyable. Summer also sees the most outdoor events and festivals, but be prepared for crowds and higher prices. Visiting in shoulder seasons like late spring or early fall can offer a balance of pleasant weather and fewer visitors.
Are there any free must-see attractions in Chicago?
Yes, Chicago boasts several free attractions that offer memorable experiences without spending a dime. Millennium Park, with its iconic Cloud Gate sculpture, is a highlight for most visitors. Lincoln Park Zoo is free and perfect for families. The Chicago Riverwalk provides scenic views and walking opportunities at no cost. These sites allow you to enjoy the city’s essence without stretching your budget.
How can I avoid long lines at popular attractions like the Skydeck or Navy Pier?
To skip long lines at top attractions, consider visiting early in the morning or later in the evening, especially on weekdays. Booking tickets online in advance often grants priority entry and can save you significant wait time. Off-peak seasons, such as winter, tend to be less crowded. Additionally, some attractions offer fast-track passes or skip-the-line options for an extra fee, which can be worthwhile if you’re on a tight schedule.
What are some good indoor activities for bad weather days?
Chicago’s museums and theaters provide excellent options for rainy or cold days. The Art Institute of Chicago and the Museum of Science and Industry are world-class destinations that can easily fill an entire day. For a more relaxed experience, enjoy live performances at local theaters or catch a movie at historic cinemas. These indoor venues ensure your trip remains enjoyable regardless of the weather.
Should I buy a Chicago CityPass or similar pass?
CityPasses can offer good value for travelers planning to visit several major attractions, often including skip-the-line privileges. They simplify entry and can save money compared to buying individual tickets. However, if your itinerary is more flexible or focused on fewer sites, paying as you go might be more economical. Consider your planned activities and compare the pass price against individual tickets to determine if it’s worth it for your trip.
Conclusion
For first-time visitors seeking a comprehensive overview, the Skydeck Chicago offers breathtaking views and a memorable experience. Budget travelers will appreciate free sights like Millennium Park and Lincoln Park. Families and outdoor lovers should prioritize activities like boat tours or outdoor festivals. Those looking for a more curated, premium experience might opt for guided tours or exclusive access passes. Whatever your preference, knowing what suits your interests and budget will help you make the most of your time in Chicago.
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