Insta Walk and Polaroid Photoshoot in Chicago

If you’re looking for a way to see Chicago’s most recognizable sights while creating some memorable photos, the Insta Walk and Polaroid Photoshoot might just be your perfect fit. For $99 per person, this roughly 30 to 40-minute experience takes you through some of the city’s most iconic spots—the Wrigley Building, DuSable Bridge, and the Chicago Theatre—all while a friendly guide helps you snap stylish, creative pictures. The tour is designed for those who love visual storytelling, whether you’re a social media enthusiast or just want some unique souvenirs.

What we really like about this experience is the personalized attention and the focus on both digital and instant photos. You’ll leave with around 50 digital images, including 5 color-corrected photos that pop with vibrancy, plus 5 Polaroid prints—a charming, timeless keepsake of your Chicago visit. Plus, the guide’s knack for framing and angles makes sure you look your best, and the relaxed pace allows for plenty of fun moments without feeling rushed.

One thing to consider is that this experience is weather-dependent. Since Polaroid photography can’t be done below 41°F (5°C), cold days could mean fewer Polaroids, although you’ll still get your digital shots. Also, the tour’s short duration means it’s best suited as a quick, impactful addition to your Chicago itinerary, rather than a full day.

This experience is ideal for travelers who want to combine sightseeing with photo-taking—perfect for solo explorers, couples, or small groups looking for an authentic, playful way to remember their trip. If you’re eager for stunning views and a professional touch on your photos, this tour offers a relaxed, friendly environment with a skilled photographer guiding the way.

Key Points

• Personalized Photoshoot: A dedicated guide helps you get creative shots at each stop.
• Variety of Photos: You’ll receive about 50 digital photos plus 5 Polaroids, blending modern and classic keepsakes.
• Iconic Locations: The tour covers prominent landmarks like the Wrigley Building, DuSable Bridge, and Chicago Theatre.
• Flexible and Short: At just under an hour, it’s a quick way to add a visual element to your Chicago experience.
• Weather Considerations: Polaroids require mild weather; cold days may limit this part of the experience.
• Private Tour: Only your group participates, ensuring a personalized and comfortable atmosphere.

The Locations: Iconic Chicago Landmarks

Starting at the Wrigley Building, this tour kicks off in front of one of Chicago’s most beautiful and recognizable architectural gems. The guide will help you capture its grandeur from multiple angles, highlighting its intricate design and impressive façade. This building isn’t just a pretty face; it’s a symbol of Chicago’s historic architectural charm.

Next, you’ll walk over to the Michigan Avenue Bridge, also known as the DuSable Bridge. Here, the focus is on the panoramic vistas of the Chicago River and the skyline. The combination of water, historic bridges, and towering skyscrapers creates a dynamic backdrop perfect for photos. Your guide will assist in framing shots that really showcase the lively urban scene.

Finally, the tour concludes at the Chicago Theatre. This legendary venue, with its classic marquee and ornate facade, not only offers a nostalgic vibe but also an excellent spot for capturing that quintessential Chicago look. It’s a place that’s been part of the city’s cultural fabric for decades, making it an ideal photo stop.

What to Expect During the Photoshoot

From the moment you meet at Wings of Mexico, your guide will lead you on a relaxed walk, stopping at each landmark. The guide, who has received positive reviews for being sweet and helpful, will suggest creative angles, cool poses, and lighting ideas—no professional experience needed.

The photos are taken with both iPhone and Polaroid cameras. The former gives you a wide range of digital images—about 50—that are color-corrected for vibrancy, ensuring your shots look lively and professional. The Polaroids, meanwhile, offer a tangible, retro keepsake that captures the moment in a timeless way. Don’t worry if the weather is chilly; if the temperature drops below 41°F, the Polaroid part will be rescheduled or replaced with extra digital photos.

The guide’s friendly demeanor and ability to keep the mood light make it easy for everyone—whether you’re comfortable in front of a camera or a bit camera-shy—to enjoy themselves. Travelers have noted that Karina (the guide in one review) was “so sweet” and helped keep the energy fun.

The Value of the Photos and Keepsakes

While the $99 price might seem modest, the value lies in the quality and personalized nature of the photos. The digital images allow you to share easily on social media or print later, while the Polaroids give you a unique physical memento—something you won’t find with standard city tours.

The 5 color-corrected digital photos are ideal for quick sharing and social media, giving your posts that extra pop of vibrancy. The 5 Polaroids are more than just photos; they’re tangible reminders of your day, with that classic instant film aesthetic.

Practical Aspects: Booking, Timing, and Comfort

Booking is generally done 11 days in advance on average, making it accessible for most travelers planning ahead. The tour starts at 1:00 pm from the Wings of Mexico at 410 Michigan Ave, close to public transportation, so getting there is straightforward.

Since the tour is private, only your group will participate. This allows for a more personalized experience—whether you’re traveling solo, as a couple, or with friends. The short duration makes it easy to add onto a broader sightseeing day without feeling fatigued.

The experience includes a guiding service and all the photos (digital and Polaroids), but tips are not included—a common courtesy in the U.S. that’s appreciated if you feel the guide went above and beyond.

What Travelers Are Saying

The single review available captures the success of the experience perfectly: “Karina was so sweet and helped keep me entertained,” says Charlotte. She also emphasizes how much she loved the photos, calling them “amazing”, along with the Polaroids. This suggests that guides are friendly, helpful, and skilled at making the session enjoyable.

Weather and Cancellation Policies

Since Polaroid photography cannot be performed below 41°F (5°C), travelers should plan for mild weather or be prepared for a rescheduling if it’s too cold. The tour offers free cancellation up to 24 hours in advance, making it flexible if your plans change or the weather looks unfavorable.

This experience is perfect for photography enthusiasts wanting to capture Chicago’s iconic sights with a professional’s help. It’s also excellent for travelers who enjoy a relaxed, social activity that combines sightseeing with creative fun. Due to its short duration, it works well as a standalone activity or a quick addition to a day of exploring the city.

If you love stunning views, personalized guidance, and unique souvenirs like Polaroids, you’ll find this tour both enjoyable and worthwhile. It’s particularly suited for small groups, couples, or solo travelers looking for an authentic, memorable way to document their trip.

For just under an hour, you get to see some of Chicago’s most photogenic landmarks while leaving with a collection of high-quality digital images and charming Polaroids. The personalized guidance and relaxed pace make it ideal for those who want a fun, creative, and memorable experience without the fuss of larger tours. The quality of the photos, combined with the iconic scenery, offers excellent value—especially if you’re keen to share your trip on social media or keep physical mementos.

This tour is best for visual storytellers, social media lovers, or anyone eager to capture Chicago’s essence in a few beautifully composed shots. While weather can be a consideration, the flexible policy and friendly guide help ensure a positive experience. If you’re after a personalized, photo-focused way to explore Chicago, this tour deserves a spot on your list.

Is this tour suitable for all ages?
Yes, most travelers can participate, and it’s designed to be fun and relaxed for all ages.

How long does the tour last?
Approximately 30 to 40 minutes, making it a great quick activity that fits into most itineraries.

What kind of cameras are used?
The guide will use both an iPhone and Polaroid cameras to capture your shots.

Will I receive my photos immediately?
You’ll get about 50 digital photos via email or download, plus 5 Polaroids to take home.

Can I cancel if the weather is bad?
Yes, the tour offers free cancellation up to 24 hours in advance, and poor weather may lead to rescheduling or refund.

Is the tour private?
Yes, only your group participates, ensuring a personalized experience.

What should I wear?
Dress comfortably for walking and bring weather-appropriate clothing, especially if temperatures are cold.

How far in advance should I book?
Booking about 11 days ahead is typical, but availability may vary.

In summary, the Insta Walk and Polaroid Photoshoot in Chicago offers a playful, stylish way to see key sights while capturing fun, high-quality images. It’s suitable for those who value personalized attention, authentic photo keepsakes, and a relaxed pace. Whether you’re an Instagram enthusiast or simply want a unique souvenir of your trip, this tour can add a creative spark to your Chicago adventure.