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Discover Chicago with a fun, personalized Insta Walk featuring professional digital and Polaroid photos, guided by an expert. Book for $169 per person.
Experience the ultimate way to capture Chicago’s vibrant scenery and iconic landmarks with the Chicago Insta Walk with Digital and Polaroid Photoshoot. Priced at $169 per person, this approximately 1-hour tour is perfect for those looking to combine sightseeing with professional photo memories. The tour departs from the Shake Shack at Chicago Athletic Association, in the heart of downtown Chicago, and accommodates small groups of up to 8 travelers for a personalized experience.
What makes this tour stand out is the professional photography involved, ensuring that visitors leave with about 100 digital photos and five Polaroid prints, capturing the city’s most photogenic spots. The expert guide and photographer leads the way, sharing insights into Chicago’s sights while helping you stand out in every shot. While the group size is limited for quality, travelers should note that good weather is necessary for Polaroids, and booking in advance (around 39 days ahead) is recommended due to high demand.


This tour kicks off at the Shake Shack located at 12 S Michigan Ave inside the Chicago Athletic Association. It’s a central and convenient spot, near public transportation options, making it easy to reach. The meeting point is straightforward, and the tour ends back at the same location, simplifying logistics.
The small group size of up to 8 people ensures that every participant receives personalized attention. The guide doubles as the photographer, so you get expertly captured images through digital and Polaroid formats. Travelers should arrive prepared for a lively, engaging experience that mixes sightseeing with photography tips.
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The tour’s route highlights some of Chicago’s most photogenic locations. It starts with rooftop views of Millennium Park and the famous Cloud Gate, known as “The Bean,” giving stunning urban backdrops immediately. The guide then takes you to Chicago Theater, a site with vibrant history and a lively atmosphere.
Crossing DuSable Bridge offers scenic river views and city skyline snapshots that are perfect for social media. The tour culminates at the Wrigley Building, an architectural icon with its distinctive design, providing a great photo opportunity. Every location is selected for its visual appeal, making your collection of photos truly pop.

The key feature of this experience is the combination of professional digital and Polaroid photos. You receive about 100 digital shots, with 10 color-corrected images, ensuring you have high-quality images for sharing or printing. The Polaroids provide a nostalgic, physical souvenir, with five prints included, processed in safe temperatures (above 41°F/5°C).
The guide’s expertise shines in choosing the best angles and spots, including some less obvious locations that often go unnoticed by typical travelers. The photos are not just taken but are artistically composed, with the guide offering insights into best lighting and framing, resulting in beautiful shots.

Based on reviews, the guide, often named Karina, is praised for her friendly attitude and photography skills. She offers city insights, historical tidbits, and tips for striking photos. Her ability to identify hidden or overlooked photo spots elevates the experience, especially for solo travelers or those new to Chicago.
Participants appreciate the personalized attention and the expert eye she brings to every shot. Her knowledge of Chicago’s architecture and landmarks adds depth to the tour, making it both informative and visually rewarding.

The tour is most popular when booked around 39 days in advance, reflecting high demand. It requires good weather for Polaroid pictures, with cancellation possible if weather conditions are poor, or the option to reschedule.
The activity is suitable for most travelers, with service animals allowed and close proximity to public transportation. The duration of approximately 1 hour makes it a quick but impactful experience. Travelers should be prepared for walking and standing, but the route is manageable for most levels.

For $169, the experience combines professional photography, sightseeing, and tangible souvenirs in one package. The small group size ensures quality interaction and personalized shots, making it a worthwhile investment for those wanting memorable photos of Chicago.
The inclusion of digital files and Polaroids makes this tour stand out among typical city tours, providing both digital archives and physical keepsakes. It’s especially recommended for solo travelers, couples, or small groups eager to capture Chicago’s iconic sights in style.

This tour offers a fun, efficient, and visually rewarding way to explore Chicago’s top landmarks. The expert guidance and photography skills produce beautiful images that guests cherish long after the tour ends. It’s a great choice for anyone looking to combine sightseeing with professional-quality photos.
While weather conditions can impact Polaroid prints, the digital photos and the personalized experience remain strong selling points. The small group size and high praise in reviews reinforce its reputation as a top-rated photography and sightseeing tour.
“Karina was amazing and very friendly. Since I was a solo- traveler, it was like having a friend and discovering hidden photo spots within the city….”

What is included in the tour price?
You receive a photography session, about 100 digital shots, 10 color-corrected photos, and 5 Polaroid prints.
Where does the tour start and end?
The tour begins and ends at Shake Shack, 12 S Michigan Ave, inside the Chicago Athletic Association.
How long does the tour last?
The activity runs for approximately 1 hour, making it a quick yet comprehensive experience.
Is this suitable for solo travelers?
Yes, the small group size and friendly guide make it ideal for solo travelers seeking memorable photos.
Can I book this tour in advance?
Absolutely. Booking around 39 days ahead is recommended due to high demand.
What if the weather is bad?
The tour requires good weather for Polaroids. If canceled due to poor weather, travelers can reschedule or get a full refund.
Are service animals allowed?
Yes, service animals are permitted on this tour.
Can I bring creative or bright outfits?
Yes, bright, creative looks are encouraged to make your photos stand out.
Is the tour accessible for most travelers?
Most travelers can participate, with accommodations for those comfortable with walking and standing.
What makes this tour unique?
The combination of beautiful city landmarks, personalized photography, and the chance to take home both digital and physical photos makes this experience truly special.