Private Chicago Highlights Photography Session
Visitors to Chicago who want to capture fantastic vacation photos shouldn’t settle for smartphone selfies when you can book a professional photographer. With this photo shoot experience, simply meet your photographer-guide and enjoy a session with iconic Chicago landmarks as your backdrop.
Photo shooting spots in Chicago:
Millennium Park (including Cloud Gate)
Willis Tower Skydeck
Chicago Riverwalk
Navy Pier
North Avenue Beach
The Magnificent Mile
Wicker Park
Lincoln Park
Rooftop Chicago (extra charge may apply depending on the venue)
Capture your most memorable moments during this private photo shoot. Return from your trip with beautiful, high-quality vacation photos — the best souvenir you can take home.
PLEASE NOTE:
This photo shoot package covers only one location from the list. Adding more locations will increase the package fee.
The service fee mentioned is per person.
This is not a group price.
Please specify your preferred location from the list when making your booking.
Duration: 1 hr 30 min
- Free cancellation
- Private tour
Private 2-Hour Walking Tour: Chicago Loop Interior Architecture
Make the best of your visit to Chicago and explore the interiors of the emblematic Loop of Chicago downtown with a private licensed guide.
You will enjoy a private tour and discover the hidden architectural treasures of Chicago with a local expert.
Here are some examples of what you will enjoy:
- Chicago Loop, Chicago
- Chicago Cultural Center
- Untitled by Picasso,
- Block 37,
- Marshall Field's Wholesale Store,
This is a private tour just for your group.
Duration: 2 hours
- Private tour
The Art Institute in Chicago Highlights Tour & Photoshoot
Discover the Art Institute in a unique way that blends art, storytelling, and photography. After a warm welcome, we'll head inside with tickets included & begin an immersive journey through the galleries.
Together, we'll explore the museum's most celebrated highlights, featuring masterpieces by Monet, Picasso, Van Gogh, Dalí, Warhol, Hopper, and more. I'll share fascinating stories that bring the art and its creators to life, revealing the hidden meanings and personal histories behind.
Along the way, I'll capture beautiful, candid photographs at the best photo spots. Using your phone or my iPhone 14 Pro, I'll guide you with simple posing tips and angles to ensure you receive stunning, professional-quality images perfect for memories or social media.
Anyone looking for more than just a museum visit, you'll leave with gallery-worthy images plus knowledge that transforms how you experience art—an unforgettable blend of photography, storytelling, & culture.
Looking forward to hosting you!
Duration: 1 hr 15 min
- Free cancellation
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Chicago Chinatown: Dragon Kings Puzzle Adventure
The year is 1375, and a devastating drought grips China. The Emperor sends you, his Imperial Advisor, to find the four Dragon Kings, rulers of weather and water. Armed with a scroll of clues, your search leads through Chicago's Chinatown.
Solve 12 challenges across Chinatown's landmarks: decode ciphers at the Nine Dragon Wall, consult jade peacocks at the Pui Tak Center, crack zodiac riddles among twelve animal statues, and follow dragon claw prints to Ping Tom Memorial Park on the Chicago River.
Download the Questo app, activate your quest with the booking code, and start at Chinatown Square Plaza. No guide, no schedule, explore at your own pace.
Discover stories most visitors walk past: a 100,000-piece mosaic shipped from China, an FBI casino raid inside a landmark building, a feng shui library, and the dumpling shop on every Chicago food list.
Perfect for couples, friends, or families exploring Chicago beyond the Loop. About 1 hour, 12 stops through Chinatown.
Duration: 48 min – 1 hr 18 min
- Free cancellation
- Private tour
Shameless TV Show Location Tour
Experience the ultimate Private Shameless TV Location Tour with the convenience of hotel pick and drop-off, allowing you to sit back, relax and enjoy the ride while exploring Chicago's iconic filming locations.
Tour Highlights:
- Visit the exterior of Gallagher House (Private Residence)
- Visit the exterior of Sheila's House (Private Residence)
- Visit the exterior of Kelvin & Veronica's House (Private Residence)
- Explore Millennium Park and take a photo in front of the famous
"Bean" Sculpture, a popular Chicago Landmark.
- Explore the Chicago Cultural Center renowned for its stunning architecture, including the world's largest Tiffany stained-glass dome.
This tour offers a unique blend of Shameless fandom and Chicago exploration, while prioritizing respect for private residences and local communities.
Duration: 2 hours
- Free cancellation
Iconic Photoshoot in Chicago
Capture your Chicago adventure with a professional photoshoot at the city’s most famous landmarks. Perfect for solo travelers, couples, or friends — no posing experience needed!
We’ll visit: The Bean, Chicago Theatre, Riverwalk, Millennium Park & colorful street art spots.
You will receive:
• 100 high-resolution edited photos
• Natural posing guidance
• Optional outfit changes
• Insider local tips for dining & exploring
Come as you are — I’ll take care of the angles, lighting & magic!
Duration: 1 hour
- Free cancellation
- Private tour
Chicago Highlights Private Walking Tour with a Guide
Immerse yourself in Chicago's architectural heritage on an exclusive walking tour, delving into the city's iconic structures and Art Deco gems. Begin your intimate journey by marveling at the grandeur of the Wrigley Building, followed by a step into the opulence of the Palmer House Hilton lobby.
Admire the sleek lines of the Carbide and Carbon Building, a testament to Art Deco elegance, before appreciating the historic significance of the Reliance Building. Conclude your architectural odyssey with a visit to the exquisite Chicago Cultural Center, a masterpiece of design and culture. Throughout the tour, your knowledgeable guide illuminates Chicago's rich history and architectural evolution, weaving captivating stories that offer insight into the city's vibrant past and enduring legacy.
Duration: 2 hours
- Free cancellation
- Private tour
Private Transfer Chicago Airport to Chicago by Luxury Car or SUV
Why spend your precious time waiting in long shuttle or taxi lines? Avoid the language barrier and currency exchange. Travel in style from Chicago O'Hare Airport ORD or Chicago Midway Airport to your Hotel in Chicago by private vehicle and reach your final destination relaxed and refreshed.
Duration: 45 min
- Free cancellation
- Private tour
2 hr Single Guided Kayaking Tour near Chicago
Come see the beautiful Starved Rock Area as we wander through towering St. Peters sandstone bluffs with Bald Eagles soaring overhead. Great American Pelicans populate this area along with blue herons, turtles and more. Our tour guides will educate and entertain you as you paddle through an American lotus flower field on the water. Your 2 hour adventure begins with a land based lesson and safety briefing and then we venture out on the water for a trip you will never forget. We now allow your furry friends on our tours!(in tandem kayaks only for a fee)
Duration: 2 hours
- Free cancellation
Chicago O`Hare Airport (ORD) to Chicago hotel/address - Arrival Private Transfer
Book your Private Arrival Transfer from Chicago O`Hare Airport (ORD) to Chicago hotel or address.
Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer.
Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination.
• Meeting with a Nameplate
• We track your Flight
• Door-to-door Service
• No Hidden Charges
• Clean cars & Professional drivers
Duration: 35 min
- Free cancellation
- Private tour
Chicago Airport Transfer: Chicago to O'Hare Airport in Luxury SUV
Exceptional Luxury SUV Chauffeur Services - When it comes to luxurious and reliable airport transfers, look no further than our elite private SUV chauffeur service. We take pride in delivering the pinnacle of sophistication and professionalism in the industry.
Unparalleled Reliability - Count on us for punctual and seamless airport transfers that reflect the utmost reliability. We understand the value of your time and ensure you reach your destination without a hitch.
Elite Chauffeurs - Our chauffeurs are not just drivers; they are the epitome of professionalism. With years of experience and a commitment to exceeding your expectations, they embody the best in the business.
Up-to-date Luxury Vehicles - Travel in style and comfort with our meticulously maintained fleet of modern luxury SUVs. From the latest models to the most advanced amenities, we ensure your journey is nothing short of exceptional.
Duration: 30 min – 1 hour
- Free cancellation
- Private tour
Chicago Scavenger Hunt Adventure
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment!
Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
Duration: 2 hours
- Free cancellation
Chicago Full-Day Walking Food Tour with Free Bike or Kayak Rental
Get ready for the most complete adventure the city has to offer—an immersive Full Day Chicago Food Tour and Walking Tour that blends Chicago’s legendary flavors with its most iconic landmarks. Savor Chicago Pizza, Hot Dogs, Italian Beef, Garrett’s Chicago Mix Popcorn, and the original Palmer House Brownie, or elevate your day with our VIP craft beer upgrade. This unforgettable Chicago in a Day Tour explores Millennium Park, the Chicago Riverwalk, Michigan Avenue, Cloud Gate, Chicago Theater, and more, guided by true local experts. Enjoy a 5-hour journey through culture and cuisine, plus a FREE 2-hour bike or kayak rental to continue the adventure along Lake Michigan. Recently honored among the “Top 10 Food Tours in America” (USA Today) and “Top 20 Food Tours in the World” (TripAdvisor), this award-winning Culinary Tour is one of the top Things to do in Chicago. Don’t miss the most delicious, scenic Full Day Food Tour in Chicago—all in one extraordinary day.
Duration: 5 hours
- Free cancellation
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Airport Transfer: O'Hare Airport ORD to Chicago by Luxury SUV
Your safety is our crew’s biggest priority. Before your journey even begins, your driver completely disinfects the vehicle and places free hand sanitizer in the back seat. One of our professionally-trained drivers will greet you with a name sign in the arrivals terminal of the airport, will offer to assist with luggage and guide you to your vehicle. Your driver will open and close the door for you, and for your safety, guests are only permitted to ride in the back seat. We’re here to ensure you arrive at your destination feeling healthy, happy, and ready to take on the day.
Duration: 30 min
- Free cancellation
- Private tour
Chicago Walking Tour: Modern Architecture
Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future.
If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Duration: 1 hr 30 min
- Free cancellation
Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)
Discover authentic Italian cooking in Chicago during this pasta-making class hosted through Cozymeal. Limited to just 8 guests, this immersive workshop showcases the art of crafting fresh pasta dough and creating a full three-course menu.
The menu you will prepare includes:
- Starter: Bruschetta with ripe tomatoes and basil on crisp bread
- Main course: Handcrafted gnocchi with tomato-basil sauce
- Dessert: Classic tiramisù with mascarpone and espresso-soaked ladyfingers
With personalized instruction from your pasta chef, this small-group class combines hands-on practice with flavorful dining. Guests are welcome to bring wine or beer to enjoy with their freshly made meal.
Duration: 2 hr 30 min
- Likely to sell out
Chicago, Cloud Gate, Grant Park Full-Day City Tour
Discover Chicago, a vibrant city set along the shores of Lake Michigan, known for its world-class architecture, iconic skyline, and rich cultural scene. As the third-largest city in the United States, Chicago offers a perfect blend of modern innovation and historic charm.
Visit Millennium Park and admire the famous Cloud Gate, where the city’s skyline reflects in a unique and unforgettable way. Enjoy stunning views at 360 Chicago or explore architectural wonders along the Chicago River. Take in the beauty of Buckingham Fountain, one of the largest fountains in the world, and immerse yourself in art at the renowned Art Institute of Chicago. With its striking landmarks, scenic waterfront, and diverse culinary experiences, Chicago is a must-visit destination for travelers seeking both culture and city charm.
Duration: 8–10 hours
- Free cancellation
Canoe/Kayak Day Tour of Mississippi Wildlife & Fish Refuge
The Mississippi backwaters in this area is an untouched natural habitat. No other canoe/kayak rental company will put you into the heart of this wonderland. Take a day tour or overnight camping trip on the river. The sound of nature will calm you. Stop and listen. Visit an island with a sandy beach. Thousands of lily pads bloom huge yellow flowers in late summer. Large flocks of water fowl stop by in spring and fall. Turtles are common sights. Tall trees grow on numerous islands.
Max capacity of canoe (people): 695 lbs.
Max capacity of canoe (total weight including equipment): 775 lbs.
Max wt. of individual person in canoe: 250 lbs.
Max number of people in canoe: 5 persons
Max capacity of both Pelican kayaks: 225 lbs
Mac capacity of both Quest kayaks: 275 lbs
We have one canoe and four kayaks so we can accommodate up to 9 people (within weight limits).
Duration: 2–4 hours
- Free cancellation
Private Vacation Photoshoot with Photographer in Chicago
⭐ Top-Rated Vacation Photoshoots 2025
We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip.
In Chicago, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here.
We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.
Duration: 1 hour
- Free cancellation
- Private tour
Luxury SUV Airport Transfer: Downtown Chicago to O'Hare/Midway
After booking, please message us through Viator with: (1) your flight number for airport pickups, (2) your exact pickup time, and (3) your full drop-off address. You can also add these in the Special Requirements box at checkout.
Experience a seamless and stylish journey from downtown Chicago to either O'Hare (ORD) or Midway (MDW) airports with our premier SUV transfer service. Our luxury SUVs offer ample space for up to 6 passengers and 4 suitcases, ensuring a comfortable and relaxing ride for business travelers and families alike. Enjoy the privacy and professionalism of a dedicated chauffeur who guarantees punctuality and a stress-free travel experience. Book your transfer today and arrive at the airport relaxed and on time.
Duration: 45 min – 1 hr 30 min
- Free cancellation
- Private tour
Private Cultural Walking Tour in Chicago with Lakefront Landmarks
This private cultural walking tour in Chicago presents the city’s architectural heritage and lakefront legacy. You will begin in Millennium Park, where public art reflects modern civic expression. What defines Chicago’s identity as a center of American innovation? Cloud Gate offers a striking reflection of skyline and sky. The DuSable Bridge stands as an engineering achievement tied to the city’s growth. Along the waterfront, Navy Pier reveals Chicago’s connection to commerce and recreation. This route connects cultural landmarks with the story of a city shaped by industry and design. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.
Duration: 2 hours
- Free cancellation
- Private tour
Chicago Architecture Walking Tour: What's New
Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment.
What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments.
As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.
Duration: 1 hr 30 min
- Free cancellation
Private Cairo Airport Transfer (Pickup or Drop-off Service)
What sets us apart:
• Private, modern, air-conditioned vehicles
• Professional, friendly, English-speaking drivers
• Flight tracking & 60-minute waiting time included
• Meet & greet with name sign at arrivals hall
• Complimentary bottled water
• 24/7 reliable service with no hidden fees
Duration: 1 min
- Free cancellation
- Private tour
Private Wicker Park and Bucktown Walking Tour
This is your chance to tour the coolest of Chicago's 77 neighborhoods alongside a funny, knowledgeable local guide. You've done the Loop; now it's time to see a whole different side of the city.
The tour has 2 options:
Wicker Park and Bucktown - faster pace, 2.5 miles of walking.
Wicker Park only - slower pace, 1.5 miles of walking
Duration: 2 hr 30 min
- Free cancellation
- Private tour