Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience a glamorous photoshoot in Chicago with a stunning flying dress, professional photographer, and quick online gallery—perfect for memorable moments.

The Chicago Luxury Flying Dress Photoshoot offers a unique way to turn your visit into a striking piece of art. For $400 per person, you receive a 1.5 to 2-hour private photoshoot that includes the rental of a vibrant flying dress and 30 digital photos. The tour departs from the iconic Chicago Theatre, creating an ideal setting to combine city views with high-fashion glamour.
This experience is perfect for those who want to feel like a model and capture memorable moments amid Chicago’s stunning architecture. With friendly, professional guides and a quick turnaround, this photoshoot stands out as a fun, stylish activity that adds a personal touch to your trip. Keep in mind, it’s a private group experience, and transportation is not included, so plan accordingly.
You can check availability for your dates here:
Want to capture memories? We've looked into these other photo experiences in Chicago

The photoshoot begins at The Chicago Theatre, a landmark in Chicago’s downtown district. This spot provides a lively backdrop that complements the vibrant flying dress and offers plenty of great angles for photos. The location’s historic architecture and energetic atmosphere help set the tone for a fun and glamorous session.
Once on site, you’ll meet your photographer, who is experienced in guiding poses and capturing flattering shots. The meeting at this well-known venue also makes it easy for friends and family to cheer you on or take photos from afar. The location’s centrality ensures easy access from most downtown hotels or attractions.

The flying dresses are designed to be “one size fits all” transformer gowns. These dresses can be styled in multiple ways—halter neck, cross front, or one shoulder—allowing you to choose your preferred look.
The bright red or green dresses are made to create stunning ripples of color against Chicago’s architecture and skyline. The dresses are designed to be flowing and elegant, perfect for movement during the photoshoot. To get the best results, you should bring suitable undergarments, such as a strapless or halter-top bra, depending on your chosen style.
The versatility of these dresses allows for different fashion expressions within the same photoshoot, adding variety to your digital gallery. The dresses’ “transformer” nature makes them accessible for all body types, enhancing your comfort and confidence.

Guided by a talented photographer, you’ll quickly feel at ease as they help you with poses and angles. Their expertise ensures your features are highlighted with flattering lighting and creative composition.
They are also attentive to capturing the perfect shot, making the session enjoyable rather than rushed. The photographer’s guidance is especially helpful for those unfamiliar with posing or camera tricks, resulting in photos that look polished and natural.
Within 2 days, you’ll receive a link via email to an online gallery with 30 high-quality digital photos. This quick turnaround means you can easily share your favorite shots with friends and family, or post them on social media.
More Great Tours Nearby
This photoshoot uniquely combines the vibrant ripples of color from the flying dress with Chicago’s iconic skyline and architecture. The city’s lively backdrop enhances the visual impact of each shot, whether you’re standing in front of towering skyscrapers or against the historic theaters.
The photographer skillfully captures this contrast, making your photos both modern and timeless. The movement of the dress against Chicago’s skyline creates dynamic compositions, adding an artistic flair to your personal gallery.

The activity is a private group experience, ensuring personalized attention from the photographer. The meeting point is set at The Chicago Theatre, a convenient and recognizable location for visitors. After confirmation, the exact time and date will be arranged.
The photo session includes walking between locations, taking around 1 hour within the overall 1.5 to 2-hour experience. Since transportation isn’t included, participants should arrive ready to walk around the area comfortably. The experience is available in the morning, afternoon, or evening, offering flexibility for your schedule.

The $400 price covers the dress rental, professional photography, and digital gallery. While printed photos are not included, the digital images are easily shareable and high quality.
Flexibility is available with the Reserve & Pay Later option, allowing you to book now and pay closer to the date. You can also cancel up to 24 hours in advance for a full refund, making this a low-risk activity to add to your Chicago itinerary.

This experience offers a combination of fashion, fun, and cityscape photography, making it more than just a typical photoshoot. The vibrant flying dresses add a unique element that elevates your images beyond standard city photos.
The professional guidance helps you look your best, whether you’re posing confidently or playfully twirling in your dress. The quick delivery of digital images makes it easy to share your moments instantly, perfect for social media or special keepsakes.
The private setting ensures your session feels personal, and the friendly guides speak multiple languages, including English, Romanian, and Spanish, for added comfort.

This activity appeals to fashion enthusiasts, social media lovers, or anyone wanting a glamorous keepsake of their trip. It’s especially suitable for those who enjoy stylish photos or want to experience something different during their visit.
It’s also ideal for celebrations such as birthdays or anniversaries, thanks to the fun and stylish nature of the dress and photography. Since the session is private, it guarantees a relaxed environment for your personal or romantic photos.
The Chicago Luxury Flying Dress Photoshoot offers a stylish, fun, and customizable way to capture your time in Chicago. The vibrant dresses, professional photographer, and iconic city backdrop create images that are both modern and elegant.
While transportation isn’t included, the central location at The Chicago Theatre makes it accessible and convenient. The quick delivery of digital photos means you can share your stunning images almost immediately. This experience suits travelers looking for a personalized, fashionable activity that turns their trip into a visual masterpiece.
How much does the photoshoot cost?
The total price is $400 per person, which includes dress rental, a 1-hour photography session, and 30 digital photos.
Where does the activity start?
The meeting point is at The Chicago Theatre in downtown Chicago.
What dresses are available?
You can choose between a bright red or green flowing gown, styled in multiple ways such as halter neck, cross front, or one shoulder.
How long does the photoshoot last?
The total experience lasts 1.5 to 2 hours, including walking between locations and the photo session.
Can I get printed photos?
No, printed photos are not included; you will receive digital photos via an online gallery.
What languages are spoken by the guides?
Guides speak English, Romanian, and Spanish.
Is transportation included?
No, transportation between locations is on foot, so comfortable walking shoes are recommended.
What if I need to cancel?
You can cancel up to 24 hours in advance for a full refund.
How quickly will I receive my photos?
Your 30 digital photos are sent via email within 2 days of the session.
Is this experience suitable for all body types?
Yes, the dresses are “one size fits all” transformer gowns, designed to be styled in multiple ways and accommodate various body types comfortably.