The Unofficial Guide: No FOMO Things to Do in Chicago!

Deep-dish pizza, pretty skyline views, insane architecture, rad street art culture, boating in the sun, awesome food: this is Windy City. The city’s bustling, but there’s unforgettable adventures waiting to sweep you away. Whether you’re planning a day trip nearby from Michigan or Wisconsin, or simply looking to add some serious sparkle to your Chicago visit, this is the ultimate rundown of the best things to do in Chicago. These are just a taste of the things you can find and book with ease on Dyvarcity – the passport to making every trip extraordinary!

1. See the City’s Incredible Architecture from a Giant Boat

Chicago with all its big, fancy buildings… such a pain to try to see all of it by foot! But who said you have to stay on land? Take a river cruise with the skyline and learn about the town, all from the comfort of a boat. 

What It Is: Get on the riverboat from either Navy Pier or Michigan Avenue. The boat will glide along the Chicago River, and your architecture guide will keep you entertained with all the juicy info (and drama)! Learn about Chicago’s rise from the Great Fire of 1871 and more. You’ll pass dozens of world-famous buildings by genius architects (like the Wrigley Building, John Hancock Center, and Willis Tower), learning about what’s so insane about their design and significance. Relax and see Windy City on water.

Why It’s Popular: This tour consistently ranks as a top Chicago must-do! You really can’t get the skyline views from street level. The live commentary turns buildings into real stories. With many tour times available throughout the day, efficiently cover lots of ground without tiring out, relax, and sightsee it all! 

Important Info:

• Duration: Tours are typically 60-90 minutes, depending on the season (60 minutes from Nov 11, 2024, through April 2025).
  
• Departure Points: Choose between Navy Pier or Michigan Avenue (confirm when booking).
  
• Amenities: All boats are equipped with full restrooms and a full bar for refreshments (drinks not included).
  
• Vessel Type: Note that vessel type (single-deck or multi-deck) cannot be guaranteed.
  
• Accessibility: Generally accessible for most travelers, and some tours are even dog-friendly! Wheelchair access is available from the Navy Pier dock only.
  
• Rescheduling: Tours can be rescheduled up to 24 hours prior to departure.
  

Tips for Travelers:

• Book in Advance: Especially during peak season or for sunset tours, spots fill up quickly!
  
• Dress for the Weather: Even on a sunny day, it can be breezy on the river, so bring a light jacket or layers.
  
• Charge Your Camera: The photo opportunities are endless – you’ll want to capture these iconic views!
  
• Arrive Early: Give yourself time to find your departure point, especially if using public transportation, and grab a good seat.
  
• Listen to Your Guide: The expert commentary is what truly elevates this tour, providing context and stories you’d otherwise miss.
  

2. With an Inflatable Boat & Chicago’s Skyline, Get Speedy!

Fly with the winds instead of getting swept away. With a rigid inflatable boat (aka RIB), this small-group boat tour puts you right on the water in a high-performance machine. This boat tour avoids the large crowd and is more thrilling with high speeds.

What It Is: All aboard the zippy secure US Navy-built RIB! For two hours, Lake Michigan is your adventure. Unlike larger, enclosed vessels, a RIB gets you closer to the water. Move dynamically and open-air. With a maximum of just six travelers, see Navy Pier, Soldier Field, Shedd Aquarium, Fort Dearborn, and downtown, including the Willis Tower and Tribune Tower. It’s safe, really fun, and has lots of photo opportunities— hold on tight!

Why It’s Popular: This tour stands out because it lets in less people. Enjoy views with nobody in the way. The RIB itself is a high-performance adventure boat that makes sightseeing even more exciting. Cover a wide area and get those “wow” photos. This tour is suitable for those who prefer an open-air, dynamic experience over a more traditional, enclosed cruise.

Important Info:

• Duration: Approximately 2 hours.
  
• Group Size: Limited to a maximum of 6 travelers for an intimate experience.
  
• Vessel Type: US Navy-built Rigid Inflatable Boat (RIB).
  
• Safety: Life jackets are provided and required.
  
• Accessibility: Not wheelchair accessible.
  
• Physical Considerations: Not recommended for travelers with back problems. Infants must sit on laps.
  
• Animals: Service animals are allowed.
  
• Location: Near public transportation for easy access.
  

Tips for Travelers:

• Dress for the Elements: Being in an open boat on Lake Michigan means you’ll feel the wind and sun more directly. Dress in layers, consider sunglasses, and perhaps a hat that won’t blow away!
  
• Be Ready to Zoom: The RIB offers a faster, more dynamic ride than a traditional boat – embrace the thrill!
  
• Protect Your Gear: If you’re bringing a camera or phone, ensure it’s secure or in a waterproof case, especially if there’s any spray.
  
• Hydrate: Even on cooler days, being on the water can be dehydrating.
  
• Book Ahead: With such a small group size, these unique tours often sell out quickly!
  

3. Tap Into Luxury and Privacy on a Sailboat Charter

Here’s another way to sail the waters: a private sailboat charter on Lake Michigan! Get on a private sailboat with a captain and an itinerary customized just for your group.

What It Is: You and up to five other guests will have exclusive use of the vessel. No crowds, no fixed routes – just your gang, a skilled captain, and the open waters. You’ll sail at your leisure and get uninterrupted views. You can even take a turn at the helm (under your captain’s guidance, of course). Entirely customizable, from the route to the music (thanks to a Bluetooth-enabled sound system), hop on in!

Why It’s Popular: The exclusivity and privacy here is unmatched by larger tours. This can be for romance, special occasions, or just fun– hey, it’s luxury! The customizable itinerary means you can do whatever you guys want, whether it’s soaking in the sun, enjoying skyline views, or even taking a refreshing dip in Lake Michigan (captain’s discretion and waivers apply for swimming on longer charters).

Important Info:

• Group Size: Exclusive to your private party, accommodating up to 6 guests.
  
• Customization: Fully customizable itinerary to suit your interests.
  
• Amenities: Bluetooth-enabled device for music, full bar (bring your own alcohol, within state law – no glass containers except secure wine/champagne bottles).
  
• Captain Included: Your experienced captain is provided for the duration of the tour.
  
• Key Prohibitions: Strictly NO SMOKING, no weapons, and no animals (service animals are not mentioned as an exception for this specific tour, so assume no animals).
  
• Behavior: Appropriate behavior is expected; inappropriate behavior may lead to early termination of the charter.
  
• Food & Drink: Food and beverages are permitted on deck, but please clean up after yourselves and take trash with you to avoid cleaning fees.
  
• Swimming: May be permitted on charters of 3 hours or longer, at the captain’s discretion, and requires a signed waiver. Not allowed after the sunset sail departure time.
  
• Seasickness: If you experience seasickness, you must remain on deck. Cleaning fees apply for vomiting below deck.
  
• Galley/Sinks: The onboard stove and sinks are not for customer use or waste disposal.
  

Tips for Travelers:

• Plan Your Perfect Route: Since it’s customizable, chat with your captain beforehand about what you’d love to see or experience.
  
• Curate Your Playlist: Bring your favorite tunes to set the mood on the water!
  
• Pack Smart: Remember no glass containers! Opt for cans or plastic bottles for drinks, and bring your own plastic cups.
  
• Discuss Swimming: If swimming is important to you, inquire about the possibility beforehand, especially noting the 3-hour minimum and captain’s discretion.
  
• Dress Comfortably: Layers are always a good idea on Lake Michigan, even on a sunny day.
  
• Be Mindful of Rules: Pay close attention to the specific prohibitions (smoking, weapons, animals) and behavioral expectations to ensure a smooth and enjoyable experience for everyone.
  

4. Paddle, Paddle! Milwaukee River Kayak Rentals

While Chicago brags about all its grand architecture, Milwaukee offers a more humble urban river experience. Breweries and restaurants dot the area. Why battle traffic when you can paddle through the city? It’s much less stressful. Grab a kayak and explore the Milwaukee River your way!

What It Is: Pick up your kayak from Brew City Kayak in Milwaukee’s Harbor District. After a quick safety briefing and map review (with life vests included), you’ll launch directly into the Milwaukee River. You have up to four hours to paddle upstream through downtown, gliding past big shots like the Hoan Bridge, the Bronze Fonz, and other highlights. This rental gives you the freedom to explore at your pace, stop wherever you like, and even bring along a cooler with your own snacks and drinks.

Why It’s Popular: This kayak rental is a hit because it has more freedom and flexibility. Unlike a guided tour, you pick your own pace, choosing exactly how much time you spend on the water or exploring the attractions riverside. With more independence, those solo and even groups wanting an adventure without rush will like this. There’s also on-site free parking and you can bring your own cooler.

Important Info:

• Location: Brew City Kayak (820 S. Water St.) in Milwaukee’s Harbor District, shared with popular spots like Boone and Crockett, Taco Moto, and Hawthorne Coffee Roasters.
  
• Parking: Free parking available on-site.
  
• Duration: Up to 4 hours of rental time.
  
• Inclusions: Kayak, life vest, safety instructions, and a map of the river.
  
• Accessibility: Wheelchair accessible.
  
• Group Size: Maximum of 20 travelers (though you’re kayaking independently).
  
• Weather Dependent: Activities may be canceled due to inclement weather.
  

Tips for Travelers:

• Dress Smart: You might get a little wet, so dress comfortably and consider bringing a change of clothes. Dress for the weather, and a hat and sunscreen are highly recommended.
  
• Stay Hydrated: Bring plenty of water, especially on warmer days.
  
• Pack a Cooler: Take advantage of the kayak’s cooler-holding capacity for snacks and drinks to enjoy on the water.
  
• Plan Your Route: While it’s self-paced, having a rough idea of what you want to see or where you might stop (like a riverside brewery) can enhance your experience.
  
• Allow Return Time: If you paddle all the way upstream, allow about 1.5 hours to comfortably paddle back to the launch point.
  

5. The Donut Walk: Diet Starts… Later!

The Loop neighborhood’s hiding something… the tastiest donuts ever! Go to local favorite dessert spots that most people never find.

What It Is: Join your donut-obsessed guide for a morning. Explore the sugary part of town. This walking tour takes you to the city’s top donut bakeries, like Doughnut Vault, Firecakes Donuts, Stan’s Donuts & Coffee, and Do-Rite Donuts & Chicken (specific stops may vary). All donut tastings are included in the tour cost, and you’ll get to try a variety of glazed, cake, cream-filled, and some more unusual options – be sure to come hungry! Along the way, you’ll also pass by Chicago landmarks.

Why It’s Popular: Donuts, obviously! But this tour is also great for exploring the downtown Loop area and sightseeing. But the allure of irresistible donuts is the big show. Enjoy enough samples to feel like a very sweet meal. There’s options for various dietary needs (vegan, gluten-, and nut-free are often available upon request). Let your sweet tooth win on your Chicago trip for a day!

Important Info:

• Duration: Approximately 2 hours.
  
• Group Size: Maximum of 20 travelers, ensuring a manageable and engaging group experience.
  
• Tastings Included: All donut samples are included in the tour price.
  
• Dietary Needs: Vegan, gluten-, and nut-free options are often available upon request – please advise your specific dietary requirements at the time of booking.
  
• Accessibility: Wheelchair and stroller accessible, including transportation and surfaces. Service animals are allowed.
  
• Location: The tour takes place in Chicago’s downtown Loop neighborhood, near public transportation for easy access.
  
• Guarantee: The tour offers a 100% Money Back Guarantee if you don’t have a good time.
  

Tips for Travelers:

• Come Hungry: Seriously, there are plenty of samples! Don’t eat a big breakfast beforehand.
  
• Wear Comfy Shoes: It’s a walking tour, so be prepared to stroll through the Loop.
  
• Book in Advance: Especially for weekend tours, spots can fill up quickly.
  
• Request Dietary Accommodations Early: If you have specific dietary needs, make sure to communicate them when you book.
  
• Explore More: The tour finishes near Michigan and Erie Avenue, a great spot to continue exploring Chicago’s attractions.
  

6. The Ultimate Foodie Deep Dive: Plus Architecture & History Walking Tour

So what if you really want to experience the food, architecture, and learn some history of Chicago? This tour has got you covered! Dive into iconic Chicago meals, beautiful buildings, and learn about rich history for half a day. The real Chicago isn’t just the popular tourist spots. If you wanna be an insider, come on in.

What It Is: Passionate local experts will lead this small-group tour, capped at just 12 guests. Learn about Chicago’s legendary past and stunning present, and expect to sample dishes like deep-dish pizza, a real Chicago style hot dog, and Italian beef. Between bites, you’ll explore different sights, including the Riverwalk, Magnificent Mile, the Pedway, and the Millennium Park (home of “The Bean”). From the Great Fire of 1871 to the Prohibition era and the immigrant heritage, discover it all.

Why It’s Popular: This tour is really comprehensive. Those who love history, architecture, culture, and food should come. You’ll be well taken care of with lots of attention because of the small group size. Don’t be afraid to ask questions! Make new friends and meet new people in your group. This tour is also run by a certified B Corp, great for travelers looking for ethical and responsible tourism.

Important Info:

• Duration: Approximately half a day (exact length not specified, but typically 3-4 hours).
  
• Group Size: Maximum of 12 travelers.
  
• Food Included: Sufficient bites and samples for a full lunch (options and portions vary seasonally).
  
• Walking Distance: Covers between 4.8 to 6.4 km (3-4 miles), suitable for most fitness levels.
  
• Accessibility: Wheelchair and stroller accessible, including transportation and surfaces. Service animals allowed.
  
• Child-Friendly: Children under 6 are permitted to join free of charge.
  
• Dietary Needs: Can accommodate vegetarian options; advise in advance. Cannot accommodate other food allergies or dietary preferences.
  
• Weather: Tours run rain, shine, or snow – dress accordingly.
  

Tips for Travelers:

• Come Hungry (Again!): You’ll be enjoying a generous amount of food, so save room.
  
• Wear Comfortable Shoes: You’ll be covering a good amount of ground on foot.
  
• Dress for Any Weather: Chicago weather can be unpredictable, so layers are always a good idea, and be prepared for rain or shine.
  
• Ask Questions: With a small group and expert guides, it’s a great opportunity to dig deeper into Chicago’s stories.
  
• Notify for Vegetarian: If you are vegetarian, be sure to inform the tour operator when booking.
  

7. Taste, Explore, and Kayak in Downtown!

This is another walking food/sightseeing tour, but here’s what makes it special: it includes a free 2-hour bike or kayak rental! Feast on deep-dish pizza, Chicago hot dogs, and brownies, and explore landmarks like Millennium Park.

What It Is: Loop the Loop with your guide, kicking off with an introduction to Chicago’s history, then dive into the essential foods. A bubbling, cheesy deep-dish pizza awaits. Savor a Chicago hot dog at a timeless stand like Max’s Take Out. Taste the original brownie! Pass by Michigan Avenue, spots like the Wrigley Building, and the start of Route 66. Enjoy the free 2-hour bike or kayak rental to use within three days of your tour!

Why It’s Popular: Generous food tastings + a guided city walk + bike/kayak = fun exploration from every angle! Cover key landmarks, enjoy Chicago’s flavors, and get adventurous. The tour is highly rated, having received TripAdvisor’s highest-level Traveler’s Choice Award each year since 2002!

Important Info:

• Duration: Walking tour duration not specified, but covers an easy 1.5 miles (2.4 km).
  
• Food Included: All food tastings (deep-dish pizza, hot dogs, brownies) are included and equal a generous meal.
  
• Start Points: Morning tours start at Lou Malnati’s Pizzeria; evening tours start at Gino’s East.
  
• Bonus Rental: Includes a FREE 2-hour bike or kayak rental.
  
  • Usage: Must be used within +/- 3 days of your tour booking.
    
  • Bike Rental Location: Bobby’s Bike Hike World Headquarters (540 N. Lake Shore Drive), open year-round (excluding major holidays).
    
  • Kayak Rental Location: Ohio Street Beach, Bobby’s Kayak (550 E. Grand Avenue), open mid-May to mid-October, weather dependent.
    
  • Exclusions: Not available for Saturday bike/kayak rentals between Memorial Day weekend and Labor Day.
    
• Accessibility: Wheelchair and stroller accessible, near public transportation, with accessible transportation and surfaces.
  
• Dietary Needs: Can accommodate vegetarians or those who don’t eat beef or pork. Cannot cater for gluten-free (limited options) or vegan (extremely limited options) diets. Please advise when booking and follow up with an email.
  
• Optional Upgrade: VIP Adult Beverage upgrade (3 samples) available for an extra cost.
  
• Weather: Operates in all weather conditions – dress appropriately.
  

Tips for Travelers:

• Come Hungry! This tour provides enough food to be considered a full meal.
  
• Plan Your Rental: Make sure to coordinate your free bike or kayak rental within the eligible time frame (within 3 days of your tour) and note the seasonal/weekend exclusions for the rentals.
  
• Dress Comfortably: Wear good walking shoes for the 1.5-mile stroll.
  
• Be Mindful of Diet: If you have dietary restrictions beyond vegetarianism, this might not be the best food tour option for you. If vegetarian, notify the operator when booking.
  
• Enjoy the Perks: Take advantage of the exclusive VIP access to locations mentioned by the tour operator.
  

8. Taste the Asia Living in Chicago on a Chinatown Food Tour!

If you love Asian cuisine, you need to head to Chicago’s Chinatown! Meet a small-group and explore Chinatown’s food with a walking tour. Your guide will take you to the awesome spots and make sure you try the best eats.

What It Is: Begin at the heart of Chinatown, and let your guide lead you through the history of this unique neighborhood with its array of Chinese cuisine. From savory dim sum dumplings to flavorful Xi’an noodles, you’ll find food representing various regions of China. Explore the aesthetic streets, pass through the new Chinatown Square development, and browse markets. Become a part of this lively community!

Why It’s Popular: This is a full-on cultural experience. Taste the best genuinely authentic Chinese cuisine. With the small group size of 15 travelers, you’ll meet people also interested in Chinese cuisine and culture— so don’t be afraid to make new friends! Often overlooked by mainstream tourism, if you’re a foodie and culture nerd, don’t let that make you miss out.

Important Info:

• Group Size: Maximum of 15 travelers, for an intimate experience.
  
• Food Included: A generous array of tastings adding up to a hearty lunch.
  
• Dietary Needs: Can accommodate vegetarians or those who don’t eat beef or pork. Vegan (limited options) or gluten-free (extremely limited options) diets cannot be fully catered for. Advise specific requirements at booking and email reservations@bobbysbikehike.com to confirm.
  
• Optional Upgrade: VIP Adult Beverage upgrade (3 samples) available on arrival for ages 21+.
  
• Accessibility: Wheelchair and stroller accessible, near public transportation, with accessible transportation and surfaces. Service animals allowed.
  
• Weather: Operates in all weather conditions – dress appropriately.
  
• Minimum Numbers: Tour may be subject to cancellation if minimum guest requirements are not met (alternative or full refund offered).
  
• Accolades: TripAdvisor has rated this tour its highest-level Traveler’s Choice Award each year since 2002.
  

Tips for Travelers:

• Come Hungry, you’ll be sampling a lot of delicious food that collectively makes for a full meal.
  
• Inform Dietary Needs Early: If you’re vegetarian or have beef/pork restrictions, be sure to note this when booking and follow up with an email to ensure accommodations.
  
• Explore Further: The tour concludes at Chiu Quon Bakery, leaving you perfectly placed to continue exploring Chinatown’s unique shops and atmosphere independently.
  
• Wear Comfy Shoes: It’s a walking tour, so be prepared for a pleasant stroll through the neighborhood.
  

9. Say Hi to Ghosts & Grub: Chicago’s Haunted Pub Tour

Having fun feeling your spine-tingling after dark. Haunted pub tours will open the eerie door of chilling legends. If that sounds like a fun night out, take this tour to explore the city’s spooky past while enjoying drinks at haunted bars!

What It Is: Walk into the dark of Chicago’s ghostly history. Your guide’s totally  from the 1920s by the way, just so you know. They’ll lead the mile-long journey through the city. Forgotten cemeteries, lingering spirits, and the dark secrets will open the gates of Chicago’s haunted past. The tour includes stops at three different bars,  so grab a drink (at your own risk) come ‘round to listen to the haunted lore.

Why It’s Popular: Let nightlife turn to mystery with entertainment and local lore. The costumed guide to the theatre. Hear tales of Chicago’s haunted past come alive, maybe to haunt you. No promises. Stop at actual pubs, get loose, social, and have fun.

Important Info:

• Duration: Not specified, but includes a mile-long walk and three bar stops.
  
• Age Restriction: Minimum age is 21 years due to the pub stops.
  
• Drinks: Drinks at the bars are at your own expense and not included in the tour cost.
  
• Starting Point: Tour begins inside Glascott’s Saloon (2158 N Halsted). Look for your costumed guide.
  
• Group Size: Maximum of 12 travelers, ensuring a personal experience.
  
• Booking: Minimum of 2 adults required to book.
  
• Physical Fitness: Travelers should have a moderate physical fitness level for the walking portion.
  
• Accessibility: Not wheelchair accessible.
  
• Weather: Operates in all weather conditions – please dress appropriately.
  

Tips for Travelers:

• Budget for Drinks: Remember to factor in the cost of your drinks at the pubs.
  
• Wear Comfortable Shoes: You’ll be walking about a mile, so comfortable footwear is a must.
  
• Dress for the Weather: Since it operates in all conditions, layers or rain gear might be necessary depending on the forecast.
  
• Bring Your Curiosity: Your guide has fascinating stories to tell, so be ready to listen and learn about Chicago’s darker history.
  
• Embrace the Theme: The costumed guide sets a fun tone – lean into the spooky atmosphere!
  

10. This Barrel Bus Want To Take You Out For Beer

You’re a true connoisseur, so let me introduce you to Chicago’s booming craft beer scene! Get behind the scenes of the best breweries in town. Your ride? A Prohibition-style barrel bus!

What It Is: Chicago’s craft beer landscape will be unraveled by your guide. Meet your captain at the River North area and hop aboard a barrel bus from the Prohibition era. You’ll visit up to three unique Chicago breweries, each with its own special qualities and brewing approach. At each stop, you’ll go on behind-the-scenes production facility tours, learning the science and artistry behind the brewing process. And most importantly, you’ll enjoy plenty of beer samples throughout the tour, 45-55 ounces total!

Why It’s Popular: Taste wonderfully made beer, learn about it, and have fun, all without the hassle of driving (don’t think you could with all that in your system anyway). The Prohibition barrel bus is a fun, wacky experience. Explore local breweries that you might not find on your own, and learn a lot during the production tours. Sample a wide variety of craft beers. Perfect for a fun trip with friends and family over 21, experience a vital part of Chicago’s beer culture.

Important Info:

• Duration: Half-day tour.
  
• Age Restriction: Minimum age is 21 years – government-issued photo ID required.
  
• Inclusions: 45-55 ounces of craft beer samples, professional guide, live commentary, and transport by climate-controlled barrel bus.
  
• Departure: Choose between morning and afternoon departure times from a convenient River North location.
  
• Footwear: Closed-toe shoes are required for entry into the production facility tour at one of the breweries.
  
• Accessibility: Not wheelchair accessible.
  
• Minimum Numbers: This experience has a minimum number of travelers required to operate; if not met, an alternative time or full refund will be offered.
  
• Group Size: Maximum of 36 travelers.
  

Tips for Travelers:

• Bring Your ID: Absolutely essential, as this is a 21+ tour.
  
• Wear Closed-Toe Shoes: This is a firm requirement for the production facility tour.
  
• Hydrate: You’ll be sampling a fair amount of beer, so remember to drink water between stops.
  
• Eat Beforehand: While there are samples, this is not a meal tour, so plan to eat before or after.
  
• Ask Questions: The guides are professional and knowledgeable, so take advantage of the behind-the-scenes access to learn more about brewing!
  

11. More Donuts, The West Loop is a Delight Sweet Walk!

This is for those with a case of serious sweet tooth syndrome. The cure? Get your vaccine at Chicago’s hottest food neighborhoods, with an indulgent donut walking tour through the West Loop! Top specialty bakeries and unique donut styles are calling you, ready to treat your case.

What It Is: Meet your guide in Chicago’s trendy West Loop neighborhood, a hotspot known for its “Restaurant Row.” From your starting point near the Morgan Street Green and Pink Line stations (convenient for day-trippers using public transport), your walking tour takes you to four of the city’s top donut bakeries. Sample a diverse array of donuts, each with different styles and traditions. As you move between stops like Do-Rite Donuts, Voodoo Doughnuts, and others (including those featuring Doughnut Vault treats or coffee from Sawada Coffee), wander through the busy West Loop and learn about Chicago’s dining.

Why It’s Popular: With the focus on the West Loop, a neighborhood renowned for its top tier restaurants, this tour gives a glimpse into Chicago’s cutting-edge culinary world. It’s a dream for donut fans because of the generous array of samples from top-tier, specialty bakeries. Get in a pleasant walk, about 1.5 miles,  to finish your donut exploration.

Important Info:

• Duration: Approximately 2 hours (estimated based on walking distance and stops).
  
• Starting Point: Do-Rite Donuts (181 N Morgan Street) in the West Loop.
  
• Ending Point: Sawada Coffee (112 N Green St), conveniently connected to Green Street Smoked Meats if you’re craving savory after sweet.
  
• Tastings Included: Four different donuts, each from a top bakery.
  
• Walking Distance: Covers an easy 1.5 miles (2.4 km), suitable for most fitness levels (not recommended for those who cannot walk and stand for 2 hours).
  
• Accessibility: Wheelchair and stroller accessible, near public transportation, with accessible surfaces. Service animals allowed.
  
• Group Size: Maximum of 20 travelers.
  

Tips for Travelers:

• Come Hungry (Seriously!): You’ll be enjoying four generous donut samples, so pace yourself.
  
• Use Public Transport: The tour starts right next to Green and Pink Line stations, making it easy to access.
  
• Explore More: The tour ends in the heart of the West Loop, leaving you perfectly situated to explore more of “Restaurant Row” or grab some BBQ at Green Street Smoked Meats!
  
• Comfortable Shoes: While it’s an “easy” walk, it’s still 1.5 miles, so comfy footwear is key.
  

12. Pedal Through Chicago’s & Get Active

Enjoy the sun, zip through the city, see landmarks, and move your body with the breeze in your hair. This bike tour is a fantastic way to explore places like Museum Campus, beautiful parks, and grand monuments with easy-going bike paths.

What It Is: Grab a bike and follow your professional guide along Chicago’s waterfront. Cycle through famous areas, learn about Chicago’s history and culture. You’ll circle the majestic Buckingham Fountain, discover the stories behind public art, parks, and museums, and be able to get lots of great pictures! This is a fun and safe way to sightsee for families and most fitness levels.

Why It’s Popular: Explore, get active, and sightsee! The entirely bike-path route makes is relaxed and safe, great for many riders. With bikes provided, pick them up and return them on this hassle-free experience.

Important Info:

• Distance: Covers approximately 9 miles (14.5 km) on bike paths.
  
• Inclusions: Bike rental and a professional guide.
  
• Group Size: Maximum of 15 travelers.
  
• Age/Fitness: Appropriate for most ages and fitness levels. However, children must be strong, capable riders and able to bike for 9 miles.
  
• Accessibility: Not wheelchair accessible.
  
• Weather: Operates rain or shine – please dress appropriately. If extreme weather forces cancellation, alternatives or a full refund will be offered.
  
• Minimum Numbers: This tour has a minimum number of travelers required to operate; if not met, an alternative or full refund will be offered.
  

Tips for Travelers:

• Dress Appropriately: Since it operates rain or shine, check the forecast and dress in layers.
  
• Hydrate: Bring water to stay hydrated during your ride.
  
• Sun Protection: Wear sunscreen and possibly a hat, especially on sunny days.
  
• Charge Your Camera: The scenic views and iconic landmarks provide endless photo opportunities.
  
• Listen to Your Guide: The guides are experts who bring the city’s history and culture to life.
  

13. Canvas of the City: Chicago Street Art Exploration

The street art is another level in Chicago. It’s raw, vibrant, creative, and urban. Explore some of its hippest neighborhoods and art in the city in a street art tour.

What It Is: Grab a coffee or pastry with your art-expert guide at Goddess and Grocer. See murals, graffiti, public art installations, and hip neighborhoods– your guide will tell you about artists, the stories behind the artworks, and the cultural significance of this evolving urban canvas.

Why It’s Popular: Get a fresh and raw look of Chicago from beyond the road-most-taken tourist routes into neighborhoods bustling with creativity and local life. For those who appreciate contemporary art, love unique photo opportunities, experience the pulse of Chicago’s cultural underground.

Important Info:

• Duration: Approximately 2 hours (based on 2 miles of walking).
  
• Group Size: Maximum of 20 travelers, allowing for a focused experience.
  
• Meeting Point: Upstairs dining room of Goddess and Grocer (look for your guide in an Offbeat Street Art Tour t-shirt).
  
• Ending Point: Logan 11 (2230 N California Ave), a spot for craft cocktails, beers, and food.
  
• Physical Activity: Travelers should be healthy enough to walk 2 miles in 2 hours.
  
• Accessibility: Not wheelchair accessible.
  
• Animals: Service animals are allowed.
  
• Transportation: Near public transportation for easy access.
  

Tips for Travelers:

• Wear Comfy Shoes: You’ll be walking for about two hours, so supportive footwear is essential.
  
• Charge Your Camera/Phone: The street art is incredibly photogenic, offering fantastic opportunities for unique shots.
  
• Ask for Recommendations: Your guide is an expert on the area – don’t hesitate to ask for tips on food, drinks, or other places to explore in the neighborhood after the tour.
  
• Embrace the Offbeat: This tour is designed to show you a different side of Chicago, so come with an open mind and a spirit of discovery!
  

14. You’re the Artist: Get Hands-On With Graffiti at an Urban Art Workshop

Activate your creations with urban art in a hands-on workshop, learning the secrets of graffiti and street art, practicing different techniques, and bringing a  masterpiece home.

What It Is: Head to Studio W.I.P. in Chicago’s Uptown neighborhood to the urban art workshops that welcome everyone, no matter their skill level. Meet local guest artists who will guide you through various street art techniques, from precise stenciling to splashy spray-painting. Bring out creativity and self-expression as you experiment with different styles. By the end of this 90-minute session, you’ll have a mini-canvas of your own artwork to keep for yourself! Feel free to bring your own drinks along to sip while you paint.

Why It’s Popular: This workshop is a hands-on creative outlet, directly engage with Chicago’s famous street art culture instead of just observing it. Distinct from traditional tours, get creative, colorful, passionate, and maybe a little dirty. Create your own art piece to keepsake.

Important Info:

• Duration: 90-minute interactive session.
  
• Location: Studio W.I.P. (1047 W. Lawrence Ave.) in Chicago’s Uptown neighborhood.
  
• Skill Level: Open to participants of all skill and experience levels.
  
• Inclusions: All necessary materials are provided, including a mini-canvas to take home.
  
• Drinks: You’re welcome to bring your own drinks of choice.
  
• Accessibility: Wheelchair and stroller accessible, near public transportation, with accessible transportation and surfaces. Service animals allowed.
  
• Group Size: Maximum of 30 travelers.
  

Tips for Travelers:

• Dress Comfortably: You’ll be moving and potentially getting a little paint on you (though usually minor), so wear clothes you don’t mind getting creative in.
  
• Bring Your Drink: If you want a specific beverage, remember to bring it along to enjoy during the workshop.
  
• Embrace Your Creativity: Don’t be afraid to experiment! The instructors are there to guide you, not judge.
  
• Plan Post-Workshop: The Uptown neighborhood is vibrant, so consider exploring local restaurants or bars after your creative session.
  

15. Chilling Dive into History: The Medieval Torture Museum

Humanity’s darker chapters are not closed. With advance tickets to Chicago’s Medieval Torture Museum, if you’re a fan of horror or are fascinated by history’s more gruesome side, step inside. This museum looks at medieval justice– it’s an interesting view back through history.

What It Is: With hundreds of realistic examples of torture, interrogation, restraint, and execution devices, you’ll find detailed wax sculptures depicting both executioners and their victims, bringing the macabre history in front of your eyes. The museum is big, like 6,000 square feet big. Your visit includes an audio guide of medieval practices, and a ghost-hunting app— enjoy eerie discovery. Look into a terrifying, yet historically significant, period.

Why It’s Popular: Unconventional, this attraction is quite thrilling. There’s a wealth of information in a uniquely visual and interactive way. If you like horror movies, history, or the darkness of human nature, you’ll get it (if you don’t, maybe this isn’t your kind of fun). Booking in advance guarantees your admission, with the audio guide and ghost-hunting app setting your museum trip apart.

Important Info:

• Location: Chicago.
  
• Exhibition Size: Covers 6,000 sq. ft.
  
• Inclusions: Advance tickets, audio guide, and ghost-hunting app.
  
• Age Recommendation: Not recommended for children under 18 without an adult.
  
• Child Admission: Children under 10 are admitted free with a dedicated adult (1 adult per 1 child).
  
• Accessibility: Wheelchair and stroller accessible, including transportation and surfaces. Service animals are allowed.
  
• Transportation: Located near public transportation.
  

Tips for Travelers:

• Book Ahead: Secure your tickets in advance for guaranteed admission and a smooth visit.
  
• Come Prepared: This museum deals with mature and potentially disturbing content, so be aware before visiting, especially if you’re sensitive.
  
• Utilize the Tech: Make the most of the audio guide for in-depth information and try out the ghost-hunting app for an extra layer of interactive creepiness!
  
• Consider Your Company: This might be a better experience for adults or older teens rather than young children, given the graphic nature.
  

16. Laugh, But Don’t Get Lost in the Illusions at Trickery’s BYOB Magic Show

For your next night out, get a few giggles in. Trickery’s BYOB Magic Show wants you to sit back, sip your favorite drinks, and enjoy the magic performance!

What It Is: Let your mind bend to illusions and tricks with a one hour show. Did I mention it’s BYOB? Bring your fave drinks, cups and bottle openers are provided! Arrive a few minutes before curtain time to snag the best general admission seats, settle in, let the magician guide the night.

Why It’s Popular: Trickery’s BYOB Magic Show has a unique BYOB policy, and is great for adults looking for a fun, shorter activity at night. Booking your tickets in advance is highly recommended to guarantee your entry.

Important Info:

• Location: Near the SE corner of Halsted and Cornelia, across from Elixir Cocktail Lounge.
  
• Show Length: Approximately one hour.
  
• BYOB: Bring your own beverages; cups and bottle openers are available.
  
• Seating: General admission. Doors open 30 minutes before showtime.
  
• Age Recommendation: Intended for adult enjoyment; not recommended for guests younger than 12 years of age.
  
• Accessibility: Not wheelchair accessible.
  
• Group Size: Maximum of 36 travelers.
  
• Transportation: Located near public transportation.
  

Tips for Travelers:

• Arrive Early: Since seating is general admission, arriving a few minutes before the doors open (15 minutes before showtime) will help you get better seats.
  
• Plan Your Drinks: Decide what you’d like to sip during the show and bring it along.
  
• Book Ahead: This is a popular show, so buying your tickets in advance is key to securing your preferred date and time.
  
• Combine Your Night: Given the shorter runtime, it’s easy to pair this magic show with dinner or other evening activities in the vibrant neighborhood.
  

Where to Next?

Whether you’re soaring through skies, unleashing the artist within, savoring delicious local eats, or unraveling history, we hope this whirlwind tour of unique experiences has sparked your wanderlust.

Just so you know, this is just the tip of the iceberg. To turn these inspiring ideas into more adventures, head over to Dyvarcity. With the seamless booking platform, you can effortlessly discover and book even more thrilling, fun, and unique experiences – not just in Chicago, but around the globe. Dyvarcity doesn’t just help book your next adventure – its mission is to transform moments outside into days truly lived!