Chicago Luxury Flying Dress Photoshoot: A Stylish Spin on City Photography

If you’re after a unique way to capture your visit to Chicago, this Luxury Flying Dress Photoshoot might just be the perfect fit. While I haven’t personally done this experience, the reviews, details, and photos paint a pretty appealing picture. Imagine yourself dressed in a vibrant red or green flowing gown, striking poses against Chicago’s iconic architecture, with a professional photographer helping you look your best. It’s less about a typical tourist snap and more about creating a personal work of art, a memorable souvenir that’s both fun and elegant.
What we really like about this experience is its combination of glamour and the city’s unmistakable vibe—plus, the fact that it’s private, so you get personalized attention. The dresses themselves look stunning, and the photographer’s expertise promises flattering angles and lighting. But, since it’s a tailored, photoshoot experience, it’s not a walk-in attraction—you’ll want to plan ahead and be willing to spend about 1.5 to 2 hours on it. This isn’t a quick selfie session; it’s an opportunity to feel like a model in one of America’s most photogenic cities.
One thing to keep in mind is that transportation costs are not included, and printed photos aren’t part of the package. So, if you’re after physical prints rather than digital images, you might need to arrange that separately. This experience is best suited for those who enjoy a bit of glamour, want high-quality images, and love the idea of blending fashion with cityscape backgrounds. It’s particularly appealing if you’re celebrating a special occasion or just want to do something memorable and different during your Chicago trip.
You can check availability for your dates here:Key Points

- Personalized Experience: It’s a private photoshoot with a professional photographer, which means tailored attention and guidance.
- Stunning Dresses Included: You can choose between a vibrant red or green flowing gown, styled in various ways for different looks.
- Quick Turnaround: Expect 30 digital photos delivered via a convenient online gallery within 2 days.
- Flexible Styling: The dresses are “one size fits all” and can be styled as halter neck, cross front, or one shoulder, so you can pick what feels best.
- Ideal for Special Moments: Perfect if you’re celebrating something or just want to feel glamorous against Chicago’s landmarks.
- Extra Costs: Transportation isn’t included, and printed photos are optional and not part of the package.
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A Close Look at the Experience

The Setting and Meeting Point
The shoot begins at The Chicago Theatre, a location that immediately sets a glamorous tone. Meeting here makes sense since it’s iconic and central, allowing the photos to effortlessly incorporate Chicago’s signature architecture. The exact meeting time and details are confirmed after booking, giving you some flexibility, but it’s good to be punctual.
The Dresses: Style and Fit
The included dresses are designed to be “transformer dresses,” meaning they can be styled in multiple ways—halter, cross front, or one shoulder. This flexibility allows you to customize your look and ensures that you’ll find a style that makes you feel confident. Just remember to bring appropriate undergarments, like strapless bras if needed, based on your preferred style.
More Great Tours NearbyThe Photoshoot: What to Expect
Over the course of around 1.5 to 2 hours, you’ll work with a photographer who’s experienced in making people look their best. We loved the comments from reviews praising the friendly and professional attitude of Elena Badea, the photographer. She’s praised for her punctuality, helpfulness, and her ability to create a comfortable environment—important factors if you’re camera-shy or nervous.
During the shoot, you’ll be moving around on foot, taking advantage of Chicago’s vibrant scenery, while Elena guides you on poses and angles. It’s a relaxed but focused process, designed to make you feel both comfortable and confident. Since the photographer helps with pose suggestions and lighting, you don’t need to be a model to get great shots.
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The Photos: Quality and Delivery
After the session, you’ll receive a link to an online gallery with 30 carefully edited digital images within 2 days. This fast turnaround means you can share your photos quickly—ideal if you’re tight on time or want to post about your trip while it’s fresh. Several reviews specifically mention that the photos turned out “amazing,” with some friends even thinking they looked Vogue-worthy.
Price and Value
At $400 per person, this experience might seem on the higher side for a short photo session. But when you consider that it includes a gorgeous dress, a professional photographer, and digital images you can keep forever, it offers good value—especially if you love the idea of styled, high-quality photos that stand out from typical city snapshots. Keep in mind, extras like printed photos or transportation are not included, so budget accordingly if those are important to you.
Reviews: What Others Are Saying
The glowing reviews reinforce that this is a well-run, enjoyable activity. Erica described the photographer as “approachable, friendly, and professional,” while Anne raved about the quality of her photos, mentioning how she attracted a lot of attention while in her dress—a sign that this shoot really makes you feel special. Another reviewer called Elena “very nice,” noting how she coordinated everything in advance, which helped ease any nerves.
Pros and Cons
Pros:
– Private, personalized experience
– Stunning, versatile dresses included
– Quick delivery of high-quality digital images
– Friendly, professional photographer
– Beautiful cityscape backdrop for memorable photos
Cons:
– Transportation costs aren’t included (plan to arrange your own travel)
– No printed photos unless you organize that separately
– The price may be steep for some, especially if you’re only after casual shots
Who Is This Tour Best For?

This experience suits travelers looking to add a touch of glamour to their Chicago trip. It’s ideal if you want professional-quality photos that go beyond typical tourist shots, especially if you enjoy fashion and style. It’s also great for special occasions—anniversaries, birthdays, or just because—you want a memorable and high-end keepsake. While families can enjoy it too, it’s most suited to those comfortable in front of a camera and eager to try something different.
If you’re someone who appreciates detailed, well-composed photos, and doesn’t mind the extra cost for a luxurious souvenir, this is a fun way to see Chicago through a different lens.
FAQs

Is transportation included in the package?
No, transportation isn’t included. You’ll meet at The Chicago Theatre, and it’s up to you to arrange your travel to and from the meeting point.
How long does the photoshoot last?
The session lasts between 1.5 to 2 hours, including time spent walking between locations and getting your photos taken.
Are there options for different dress styles?
Yes, the dresses are transformer-style, allowing you to style them as halter neck, cross front, or one shoulder, depending on your preference.
When will I receive my photos?
You’ll get a link to an online gallery with 30 photos within 2 days of your session.
Can I get printed photos?
Printed photos are not included in the package. You can, however, organize prints separately if you wish.
Is this experience suitable for children or families?
While suitable for anyone comfortable in front of the camera, this experience is designed as a private, fashion-focused photoshoot. Not specifically tailored for children or large family groups, but small groups or individuals will enjoy it most.
Chicago Luxury Flying Dress Photoshoot
Final Thoughts

All in all, the Chicago Luxury Flying Dress Photoshoot offers a polished, stylish way to capture your time in the Windy City. It combines a glamorous aesthetic with Chicago’s architectural charm, resulting in memorable images that are much more than your average holiday snaps. Whether you’re celebrating something special or just want to indulge in a bit of luxury, this experience delivers both fun and fantastic photos.
If you’re into fashion, love a bit of pampering, and want high-quality keepsakes of your trip, this photoshoot could be just the thing. It’s not the most budget-friendly option, but for those who value professional guidance and striking images, it’s an investment in memories you’ll cherish long after your visit.
In summary, this experience is best for style-minded travelers seeking tailored, high-quality photos in a private setting, with the gorgeous backdrop of Chicago’s iconic skyline. It’s a chic way to turn your trip into an artful story—one frame at a time.
You can check availability for your dates here:More Photography Tours in Chicago
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