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Dorchester Center, MA 02124

Book a private 1-hour Chicago photo session with a local photographer for $325, capturing your memories at iconic spots with high-resolution images.

This private vacation photography experience in Chicago offers a unique way to create lifelong keepsakes of your trip. Priced at $325 per group (up to 6 people), this session provides about 1 hour of personalized photography led by a local, hand-picked professional photographer. The tour is booked on average 31 days in advance, making it accessible for travelers planning ahead. The session includes 15 to 60 high-resolution digital photographs delivered within 5 days, giving you stunning images to cherish forever.
What makes this experience stand out is the personalized approach and the opportunity to explore Chicago’s most iconic locations. Whether you’re celebrating an engagement, family trip, or just want high-quality photos, this tour offers a tailored, private alternative to selfies. With over 10,000 five-star reviews, Flytographer has established itself as the leading provider of vacation photography across six continents.
However, keep in mind that this is a short, 1-hour session, so it’s best suited for those who want quick, high-quality photos rather than a lengthy shoot. Also, the meeting point is in Chicago city center, and additional costs might apply if you choose locations outside the designated routes or need transportation. This experience is perfect for small groups eager to capture their Chicago adventure with professional guidance.

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This experience pairs you with a local photographer who is skilled in capturing stunning, natural-looking photos against Chicago’s most famous backdrops. The photographer is hand-picked by Flytographer, ensuring quality and professionalism. Once booked, you’ll be contacted within 24 hours to confirm your meeting time and location, making planning straightforward.
The meeting point is in Chicago, close to public transportation, making it easy to reach the start location. The session ends back at the initial meeting point, with no additional transportation required. The private nature of the session ensures a relaxed atmosphere, allowing for genuine moments and candid shots.
Choose from several favorite routes such as the Chicago Riverwalk, Millennium Park, North Avenue Beach, or Lincoln Park. Each location offers a distinct vibe: the Riverwalk features stunning cityscape views, Millennium Park provides the famous Cloud Gate sculpture, North Avenue Beach offers sandy backgrounds with Lake Michigan, and Lincoln Park combines greenery with skyline views.
You can also opt for a custom route, giving you flexibility to include any special spots or areas meaningful to your group. The photographer guides you through the best angles and moments, ensuring your photos highlight Chicago’s most photogenic spots.

The 1-hour session is designed to be relaxed yet efficient, with a focus on capturing natural, high-quality images. The friendly photographer provides guidance on poses and locations but also encourages candid moments. The photos are for personal use, with options for commercial use available for an additional fee.
Once the shoot concludes, you will receive an online gallery with your images within 5 days. The package includes 15 to 60 images, depending on the chosen option, all in high resolution, perfect for sharing or printing.
This experience is suitable for individuals, couples, families, or small groups, with the maximum group size of 6. Service animals are allowed, and most travelers can participate, provided they can stand or walk for the duration.

Booking is simple: the experience is most often booked 31 days in advance, indicating its popularity for planned trips. The experience offers a free cancellation policy, allowing full refunds if canceled 24 hours before the scheduled shoot. Changes or cancellations less than 24 hours in advance cannot be accommodated, so it’s best to plan ahead.
Customer service teams assist in planning the details, making sure your shoot fits your schedule and expectations. The price includes all taxes and fees, with no hidden costs, ensuring transparent pricing.
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This private session appeals most to visitors who want professional, high-quality photos without the hassle of self-timing or crowds. It’s particularly suitable for honeymoons, engagements, romantic getaways, family trips, or multi-generational vacations. Small groups and individuals who value authentic images in Chicago’s most scenic spots** will find this experience rewarding.
It’s also an excellent choice for those who want a personalized, flexible photography experience, as the photographer can help craft a route that highlights your favorite Chicago sights or special moments.

The Chicago private vacation photography session offers a convenient, professional way to document your trip. The local photographer’s tips and guidance ensure you get stunning images in the city’s most iconic locations, all within a short, 1-hour window. The high-resolution photos delivered within 5 days become a treasured souvenir.
While the session is relatively brief, its personalized nature and quality of images make it a compelling choice for small groups seeking timeless keepsakes. The flexible routes and easy booking process add to its appeal, especially for those eager to capture their Chicago experience authentically.
This tour is less about extensive sightseeing and more about creating professional-quality photos with minimal effort, perfect for busy travelers or those celebrating a special occasion. The free cancellation policy and straightforward logistics further enhance its convenience.
“First timers in Chicago and our photographer Lukas was the best. Lukas took a variety of pictures at several locations along the River front. Than…”

What is included in the price of $325?
The package covers a private photo shoot with a professional photographer, online gallery, and 15 to 60 high-resolution digital photographs. All taxes, fees, and handling charges are included.
How far in advance should I book?
Most bookings are made about 31 days before the scheduled session, ensuring availability and planning time.
Where does the meeting take place?
The experience starts in Chicago, with the meeting point in the city center, accessible via public transportation.
Can I customize the route?
Yes, you can select from favorite routes like the Riverwalk, Millennium Park, North Avenue Beach, or Lincoln Park, or suggest a custom route.
Are children and service animals allowed?
Yes, most travelers can participate, and service animals are permitted.
Will I receive my photos quickly?
Images are delivered within 5 days after the shoot, providing plenty of time to prepare prints or share online.
Is this experience suitable for large groups?
The maximum group size is 6 people, making it ideal for small families, couples, or friends.
Can I cancel if my plans change?
Yes, full refunds are available if canceled 24 hours before the session; late cancellations are non-refundable.
Are additional costs involved?
The price includes all taxes and fees. Extra charges may apply if you want commercial rights or if location entrance fees apply for certain spots.
What if I want proposal photography?
Proposal photography is not included with this package but can be arranged separately.
Is transportation to the locations necessary?
The tour is designed to be accessible, with near public transportation, but travelers are responsible for their own transportation if visiting locations outside the default routes.
Who is the experience provider?
The service is provided by Flytographer, renowned for their global vacation photography expertise.
This private Chicago photo session delivers beautiful, high-quality memories with minimal effort, making it a smart choice for those wanting to preserve their trip in stunning images.