Chicago is a city that practically begs to be photographed. With its striking skyline, historic architecture, and lively neighborhoods, it offers endless opportunities for memorable images. Whether you’re after classic cityscape shots or fun, candid portraits, Chicago’s photography experiences are second to none. We’re particularly fond of tours that combine professional guidance with creative freedom—like the Chicago Insta Walk with Digital and Polaroid Photoshoot, which offers a personalized glimpse of the city through both modern and vintage lenses. This tour’s promise of about 100 digital photos and five Polaroids makes it a fantastic way to capture the city’s essence in a few fun, relaxed hours.
For travelers who want a more private or upscale experience, options like the Chicago Luxury Flying Dress Photoshoot or the Private Vacation Photography Session provide personalized, stylish options that turn your visit into a true photo art piece. Want to blend culture and creativity? The Art Institute Photo Walk combines museum highlights with an Instagram-friendly photoshoot inside one of the world’s top art museums. Each experience offers a different flavor of Chicago’s visual appeal, helping you go beyond the standard tourist snapshots.
1. Chicago Insta Walk with Digital and Polaroid Photoshoot
Starting from the iconic Millennium Park, this tour is designed for those who want to capture professional quality photos of their visit. Led by an expert guide, you’ll visit some of Chicago’s most photogenic landmarks—think city skylines, hidden alleyways, and unique vantage points. The guide not only takes the photos but also offers tips on angles and lighting, ensuring your images stand out. At the end of the hour, you’ll walk away with about 100 digital photos and five Polaroids, perfect keepsakes.
What makes this trip special is its small group setting, which guarantees personalized attention. Reviewers praise Karina’s friendly approach and her knack for discovering lesser-known spots while still capturing the classic Chicago skyline. One reviewer called her “an amazing photographer who knew the best angles and shared fascinating city facts,” and many appreciate the Polaroids’ nostalgic charm. The tour is ideal for solo travelers, couples, or small groups wanting a professional and fun experience. The price of $169 offers excellent value considering the quality and quantity of photos received.
Bottom Line: This is a well-rounded, personalized photo tour perfect for travelers who want professional shots in a short time with the added fun of instant Polaroids.
2. Shared Jungle Dreams Insta-Walk Photoshoot
At around 40 minutes, this tour keeps it quick and creative, perfect for those with a tight schedule or looking for a casual, fun experience. The guide uses both iPhone and Polaroid cameras to give a variety of styles and textures, from vibrant digital images to timeless Polaroids. The relaxed atmosphere means no stiff poses—just natural, flattering shots guided by your photographer.
You’ll receive approximately 50 digital photos, five polished Polaroids, and five more Polaroids with a unique color correction. The tour focuses on the downtown core, with stops at the Wrigley Building, Michigan Avenue Bridge, and the Chicago Theatre—some of the city’s most recognizable sights. Guests consistently mention how friendly and approachable the guide is, making the photo-taking process enjoyable. The cost of $150 is reasonable for such a personalized, quick experience, especially for travelers who want a quick, memorable set of photos.
Bottom Line: A short, friendly tour that balances digital and instant photography, suitable for those wanting a quick but quality snapshot collection.
3. Chicago Luxury Flying Dress Photoshoot
Imagine feeling like a fashion model amid Chicago’s skyline—this private, 1.5-2 hour photoshoot makes it possible with a stunning flying dress included. You’ll wear a flowing gown in red or green, styled in multiple ways, while your photographer captures glamorous, high-fashion shots in some of Chicago’s most photogenic locations.
This experience is tailored for those who want more glamour and exclusivity. The guide helps with posing and composition, ensuring you look your best. You’ll come away with 30 professionally edited digital photos, perfect for social media or framing. The private setting and stunning gowns make this a memorable experience, ideal for special occasions like anniversaries or just a desire to feel extraordinary. The $400 price tag reflects the luxury and personalized attention, making it a worthwhile indulgence for anyone craving a high-end fashion shoot.
Bottom Line: For those wanting a glamorous, private photoshoot with a striking dress, this is the top choice—ideal for a special celebration or a unique keepsake.
4. Private Vacation Photography Session with Local Photographer in Chicago
This customizable, one-hour photoshoot connects you with a local professional photographer who knows Chicago inside out. It’s suitable for honeymoons, family trips, engagements, or romantic getaways, offering a personal touch that captures your trip’s essence. Your photographer will suggest the best spots—be it Millennium Park, the riverfront, or lesser-known corners—based on your interests.
The $325 fee covers up to six people, making it an excellent value for groups or families. One reviewer praised Lukas for taking a variety of pictures along the riverfront, highlighting the flexibility and personalized service. The online gallery allows quick sharing and easy access to high-quality images. This experience is best for travelers who prefer tailored sessions with a local expert guiding the process.
Bottom Line: Ideal for travelers seeking a personalized, high-quality collection of vacation photos with a local insider’s knowledge.
5. Instagram Photo Tour and Art Walk at The Art Institute in Chicago
This tour combines art appreciation and social media in one experience. Inside Chicago’s renowned Art Institute, you’ll visit seven highlights and learn about artworks and artists like Georgia O’Keefe, Picasso, and Matisse, while you also have a dedicated photoshoot. The guide shares stories and insights, making the visit educational and visually engaging.
The highlight is the interior photoshoot in front of famous artworks, perfect for Instagram or personal collections. The tour lasts about 1 hour 15 minutes, with the price of $94 including the museum entrance fee. Reviewers praise Ronaldo’s enthusiasm and the quality of photos, calling it a “must-do for art lovers who want great photos without the hassle of organizing it alone.” It’s great for solo travelers, couples, or groups who love art and want a creative, cultural experience.
Bottom Line: Perfect for art aficionados and social media enthusiasts wanting a blend of museum exploration and a fun photoshoot.
$94.00 per person
6. Insta Walk and Polaroid Photoshoot in Chicago
This 30-40 minute stroll covers three iconic locations: the Wrigley Building, Michigan Avenue Bridge, and the Chicago Theatre. Your guide uses both iPhone and Polaroid cameras for a variety of stylish, creative shots. The approach is relaxed, and you’ll walk away with about 50 digital photos, five Polaroids, and a set of color-corrected images.
Guests love the friendly guide, Karina, for her patience and eye for detail. The tour’s compact length makes it ideal for travelers seeking a quick yet quality photo session. The $99 price is particularly attractive considering the locations and personalized service.
Bottom Line: A brief but fun Instagram-worthy walk that’s perfect for travelers wanting a snapshot of Chicago’s most photogenic spots.
$99.00 per person
7. Private Professional Vacation Photoshoot in Chicago
This flexible experience offers either a 30-minute or 1-hour private photoshoot, with a professional photographer capturing your best moments at Chicago landmarks. The 20, 45, or 60 professionally edited portraits are tailored to your needs, whether for social media, prints, or gifts.
The $264.82 price reflects the premium quality and customization. The guide works with your schedule, and within four days, you receive high-resolution photos. It’s ideal for travelers who want a personalized, high-end keepsake of their trip or special occasion.
Bottom Line: A flexible, upscale option for travelers who value professional, tailored photos and quick delivery.
$264.82 per person
8. 1 Hour Photoshoot in Chicago
This experience targets those who want to capture iconic Chicago scenes like Millennium Park, Cloud Gate (“the Bean”), Chicago Theater, and the Riverwalk. Your own photographer guides you through the most photogenic spots in a relaxed one-hour session.
While reviews are not yet available, the focus on famous locations makes this a solid choice for travelers wanting professional images in prime spots. The $179 price positions it as a mid-range option suitable for those who want quick, high-quality photos without the extra frills.
Bottom Line: Great for travelers who want to check off the classic Chicago landmarks with professional guidance.
$179.00 per person
9. Private Photo Session with a Local Photographer in Chicago
This flexible, group-oriented experience offers three packages: 20, 35, or 60 photos depending on the session length—30, 60, or 100 minutes. Your photographer works with you to select the best locations and style, providing professionally edited photos within four working days.
Suitable for solo travelers, couples, or groups, this experience is perfect for those who want customized, professional shots with a local’s touch. The cost is competitive for a personalized service, especially considering the quick turnaround and high-quality images.
Bottom Line: Excellent for those seeking tailored, professional photos with flexible timing and group options.
$289.40 per group (up to 4)
How to Choose Your Perfect Chicago Photography Experience
Picking the right tour hinges on your budget, schedule, and what kind of photos you want. If a quick, fun, and creative walk appeals, the Insta Walk and Polaroid Photoshoot offers great value. For a glamorous, private session, the Flying Dress Photoshoot combines luxury with style, ideal for special occasions. Want a personalized tour with insider tips? The Private Vacation Photography Session is your best bet.
For art and culture lovers, the Art Institute Photo Walk provides a perfect blend of education and aesthetics. Budget travelers might prefer the Chicago Insta Walk, which delivers high-quality photos at a reasonable price in a short time.
Remember to consider the duration, group size, and what photos you want to keep as memories. Booking early is wise, especially for popular times or upscale experiences.
Final Thoughts
Chicago offers a wide array of photography experiences suited to every taste and budget. For those seeking a personalized, professional touch, options like the Private Vacation Photoshoot or the Glamorous Flying Dress Photoshoot shine. If you prefer a fun, quick snapshot of the city’s most iconic sights, the Insta Walk and Polaroid Photoshoot or the Chicago Insta Walk are excellent choices.
No matter your style or budget, these tours make it easy to walk away with beautiful, professionally-taken photos that truly reflect your Chicago experience. Book early, especially for popular times, to ensure you secure your spot—your camera (or phone) will thank you.