75 Fun Vacation Activities to Include in Your Chicago Itinerary

Planning a vacation is exciting! There are so many vacation activities to include in a Chicago itinerary and countless numbers to choose from.

To create an awesome trip though, it’s essential to ensure your itinerary includes a variety of experiences.

Whether you enjoy outdoor adventures, cultural experiences, or simply prefer to relax on the beach, we have some incredible ideas for you to consider that will help you make the most of your time away.

Keep this list handy for your next Chicago or other destination. It is a great guide for how to make an itinerary.

Now, let’s explore some of the best vacation activities to include in your Chicago itinerary, so sit back, relax, and enjoy the read.

Vacation Activities to Include in a Chicago Itinerary

Hiking and Nature Exploration

Things to Do in Advance

1. Research local hiking trails and nature reserves.
2. Make a packing list that includes appropriate footwear and clothing.
3. Plan for the weather, including bringing rain gear if necessary.
4. Pack snacks and water for longer hikes.

Ideas for Hiking and Nature Exploration in Chicago

• Chicago Lakefront Trail
• Bloomington 606 Trail
• Starved Rock State Park
• Peggy Notebaert Nature Museum
• Lincoln Park Zoo

Cultural and Historical Tours

Things to Do in Advance

1. Research local cultural and historical attractions, such as museums or historic landmarks.
2. Check tour schedules and book in advance if possible.
3. Find a knowledgeable tour guide who can provide additional context and insight.
4. Consider taking a walking tour to get exercise while sightseeing.

Ideas for Cultural and Historical Tours in Chicago

• African American Heritage Tour of Chicago
• Chicago Walking Tour: Historic Treasures of Chicago
• Chicago Crime and Mob Tour
• Chicago History Museum

Food and Drink Experiences

Things to Do in Advance

1. Research local restaurants and bars that offer unique cuisine, drinks, or dining experiences.
2. Make reservations in advance, especially for popular spots.
3. Try a few local specialties and branch out from typical fare.
4. Take a cooking or mixology class to learn new skills and techniques.

Ideas for Food and Drink Experiences in Chicago

• Original Walking Food Experience in Chicago with Tastings
• Chicago West Loop Pizza Crawl
• Taste of Chinatown Food Walking Tour
• Nutella Cafe
• Alinea

Adventure Activities

Beach and Water Activities

Things to Do in Advance

1. Research local beaches, lakes, or other bodies of water for swimming, kayaking, or surfing.
2. Check for any water conditions, advisories, and beach restrictions.
3. Bring sunscreen, towels, and water-resistant items.
4. Consider taking a boat tour or fishing trip.

Ideas for Beach and Water Activities in Chicago

• North Avenue Beach
• Oak Street Beach
• Kayak Lake Michigan
• Lakefront Fireworks Cruise

Art and Culture Events

Things to Do in Advance

1. Research local art galleries, theaters, or concerts.
2. Check schedules and purchase tickets in advance if necessary.
3. Dress appropriately for the event.
4. Bring a camera to capture memories.

Ideas for Art and Culture Events in Chicago

• Chicago Cultural Center
• Chicago Architecture Center
• The Art Institute of Chicago
• Field Museum of Natural History

Wellness and Relaxation

Things to Do in Advance

1. Research local spas, hot springs, or yoga studios.
2. Book appointments in advance.
3. Bring comfortable clothing and a book to read.
4. Consider incorporating mindfulness or meditation practices.

Ideas for Wellness and Relaxation in Chicago

• Waldorf Astoria Spa
• Kohler Waters Spa at Lincoln Park
• Aire Ancient Baths
• Chuan Spa

Sports and Recreation

Things to Do in Advance

1. Research local sports teams or recreational leagues.
2. Check schedules and purchase tickets in advance.
3. Bring appropriate gear and clothing.
4. Consider trying a new sport or activity, like axe throwing or a batting cage.

Ideas for Sports and Recreation in Chicago

• See a game at a local University
• Plan a trip to see a Cubs Game
• Bad Axe Throwing 
• Chicago Sports Museum

Shopping and Markets

Things to Do in Advance

1. Research local markets or shopping districts.
2. Check hours and days of operation.
3. Bring a shopping list and budget.
4. Consider trying local artisanal goods or handicrafts.

Ideas for Shopping and Markets in Chicago

• Magnificent Mile (The Shops at North Bridge, 900 North, Water Tower Place)
• Block 37
• Fashion Outlets of Chicago
• Randolph Street Market
• Maxwell Street Market
• Daley Plaza 
• Chicago Farmer’s Markets (various neighborhoods)

Photography and Sightseeing

Things to Do in Advance

1. Research local landmarks, vistas, or viewpoints.
2. Check for any necessary permits or access restrictions.
3. Bring a camera or smartphone with good photo capabilities.
4. Consider taking a guided tour or using a photography app to enhance your skills.

Ideas for Photography and Sightseeing in Chicago

• Chicago Architectural Cruise
• Baha’i Temple
• Cloud Gate | Millenium Park
• The Wrigley Building
• DuSable Bridge | Marina City | Chicago Riverwalk
• Historic Water Tower
• The Chicago Theater
• Famous Buildings in Chicago

Family Activities

Things to Do in Advance

1. Research family-friendly activities and attractions.
2. Check for any age or height restrictions.
3. Bring necessary gear such as strollers or baby carriers and confirm there are no restrictions.
4. Consider incorporating educational activities or games.

 Ideas for Family Activities in Chicago

• Chicago’s Chinatown
• Millenium Park
• Navy Pier
• Chicago Walking Tours
• The Big Bus Tour

Nightlife and Entertainment

Things to Do in Advance

1. Research local bars, nightclubs, or theaters.
2. Check hours of operation and dress codes.
3. Bring identification.
4. Consider trying local music or performances.

Ideas for Nightlife and Entertainment in Chicago

• Comedy Clubs – Zanies | The Second City | The Comedy Bar
• Buddy Guy’s Legend | Kingston Mines
• Howl at the Moon
• Tao Chicago
• Three Dots and a Dash
• Cindy’s Rooftop
• Chicago Riverwalk – The Northman Beer and Cider Garden | City Winery

Educational Activities

Things to Do in Advance

1. Research local educational institutions or workshops.
2. Check for any necessary prerequisites or prerequisites.
3. Prepare to take notes or participate in discussions.
4. Consider incorporating new knowledge into your itinerary.

Ideas for Educational Activities in Chicago

• Adler Planetarium
• American Writers Museum
• Chicago Children’s Museum
• Museum of Science and Industry

Relaxing Activities

Things to Do in Advance

1. Research local activities such as meditation, a park or conservatory for meditation, or a quaint coffee house.
2. Choose activities that align with your interests and values.
3. Allow ample time for rest.
4. Plan for meals and snacks.

Ideas for Relaxing Activities in Chicago

• Lincoln Park Conservatory | Alfred Caldwell Lily Pool
• Garfield Park Conservatory
• The Art Institute of Chicago South Garden
• Nature Boardwalk at Lincoln Park Zoo
• Chicago Botanic Garden
• Humboldt Park Garden

FAQs on Vacation Activities to Include in Your Itinerary

By checking hours of operation, location, and booking in advance, and allowing ample time for each activity, you can make the most of your visit.

Final Thoughts on Vacation Activities to Include in Your Chicago Itinerary

Planning vacation activities to include in your Chicago itinerary should span a range of categories. This is key to having a memorable and unique vacation experience.

Use our guide to mix and match experiences that appeal to you most. In these articles, you’ll find more useful information to help plan your visit to Chicago.