Chicago’s skyline isn’t just a backdrop for photos; it’s a reason to grab your camera and start shooting. With its iconic architecture, lively neighborhoods, and world-class museums, Chicago offers more than just sightseeing—it’s a canvas for photographers at every level. Whether you want professional portraits, artistic street shots, or memorable selfies, the city’s diverse scenery makes it ideal for photography experiences that suit different styles and budgets.
From quick Insta walks to detailed private sessions, this guide covers the top nine photography tours that will help you capture Chicago in all its glory. Each offers a unique way to document your visit, whether you prefer casual strolls with Polaroid keepsakes or expert-guided shoots at famous landmarks. Ready your camera, and let’s explore the best options to turn your Chicago trip into a visual story.
1. Chicago Insta Walk with Digital and Polaroid Photoshoot
Starting from Millennium Park, this small group tour guides you through some of Chicago’s most photogenic landmarks. Your photographer guide will help you strike natural, flattering poses while capturing around 100 digital photos and five Polaroids to remember your trip. The tour balances professional-quality photo sessions with sightseeing, making it perfect for solo travelers, couples, or small groups who want high-quality images without the fuss of a full photoshoot.
What makes this tour stand out is the personalized attention from a guide who is both a photographer and a local. Guests rave about the friendly guide, Karina, who takes them to hidden spots and offers insights into the city’s history along the way. The tour’s value lies in the combination of professional photos, fun Polaroids, and the chance to explore popular and lesser-known locations. It’s ideal for travelers who want a quick, memorable, and Instagram-ready experience.
Bottom Line: With a high rating of 5.0/5 from 27 reviews, this tour offers excellent value and personalized service, perfect for those wanting quality souvenirs from their Chicago visit.
This creative Insta walk combines the use of both iPhone and Polaroid cameras to produce a variety of vibrant digital and timeless Polaroid images. In about 40 minutes, you’ll be guided through some of Chicago’s most photogenic spots, receiving about 50 digital photos and five Polaroids. The relaxed, no-posing vibe emphasizes natural, flattering shots, making it a great option for travelers who prefer candid captures over stiff poses.
What makes this experience unique is the use of different camera styles, creating a variety of visual effects. The guide helps you find the best angles while keeping the atmosphere fun and easygoing. It’s perfect for solo travelers or couples who want a quick, creative session that results in charming keepsakes.
Bottom Line: For around $150, this tour offers excellent value for high-quality, artistic photos in a short timeframe, with the bonus of Polaroid prints you’ll cherish.
3. Private Vacation Photography Session with Local Photographer in Chicago
This flytographer-style private session pairs you with a carefully selected local photographer to capture your most memorable moments. For about $325, your group of up to six people can enjoy a one-hour shoot at iconic Chicago locations, with the added benefit of insider tips on what to do and see.
The key advantage of this experience is the personalized service—the photographer works with you to find the best spots and angles, ensuring your photos are tailored to your style. Reviews highlight Lukas, who captured a variety of beautiful images along the Riverfront, making it clear that a professional’s eye makes a difference. These sessions are especially suited for honeymoons, family trips, or engagements.
Bottom Line: With high-quality photos and a flexible schedule, this experience is best for travelers seeking customized, professional images that truly reflect their vacation.
4. Instagram Photo Tour and Art Walk at The Art Institute in Chicago
This unique blend of museum visit and photoshoot takes you inside the Art Institute of Chicago, one of the world’s greatest art museums. The tour includes a walk through seven highlights, coupled with personalized photography around famous artworks and inside the museum itself. The experience lasts about 1 hour and 15 minutes, and your ticket includes museum admission.
What sets this tour apart is the opportunity to combine art appreciation with Instagram-ready shots. Ronaldo guides you through the museum’s most photogenic pieces, including works by Georgia O’Keeffe, Picasso, and Matisse, while also capturing your best angles in front of stunning art displays. It’s ideal for art lovers and those who want a cultural twist to their photos.
Guests praise Ronaldo’s skills, and the photos are described as “beyond incredible,” making this a well-rounded option for a cultural photo experience.
Bottom Line: This tour offers a rare chance to learn about world-class art while taking memorable photos, making it perfect for art enthusiasts and selfie lovers alike.
5. Insta Walk and Polaroid Photoshoot in Chicago
This short and sweet 30 to 40-minute walk covers three iconic locations: the Wrigley Building, the Michigan Avenue Bridge, and the Chicago Theatre. Your guide, Karina, helps you find the best angles and lighting while capturing about 50 digital photos (with five color-corrected) and five Polaroids.
The tour’s charm lies in its casual, friendly approach—no stiff poses, just fun photos during a quick stroll through downtown. Many reviewers love the Polaroids as a keepsake, and the guide’s friendly attitude makes it feel like a personalized experience.
Bottom Line: For travelers seeking a quick, affordable way to get striking photos of Chicago’s downtown, this tour offers a memorable experience at a reasonable price.
6. Private Professional Vacation Photoshoot in Chicago
This more comprehensive private experience allows you to choose either a 30-minute or 1-hour session with a professional photographer. Starting outside the Wrigley Building, you’ll explore different landmarks and receive 20 to 45 high-quality, professionally edited portraits depending on your chosen package.
The flexibility of start times makes it easy to fit into your schedule, and the focus on personalized, top-notch images makes it ideal for romantic couples or families wanting to commemorate their trip with a polished souvenir. Reviews highlight the quality of images and the friendly guides.
Bottom Line: For those who want a more tailored, in-depth photoshoot, this experience delivers professional images that capture your Chicago adventure beautifully.
7. 2 Hour Magnificent Chicago Tour with Photos and Popcorn
At just $35 per person, this 2-hour group tour blends sightseeing, storytelling, and on-the-go photography. Guided by a local, you’ll visit key landmarks like Navy Pier, the Battle of Fort Dearborn, and Michigan Avenue, all while enjoying popcorn and learning about Chicago’s history.
Your tour guide takes professional photos during the trip, giving you a collection afterward—perfect if you want a fun, casual way to see the city through a lens. Reviewers appreciate Angelo’s knowledge and the opportunity to capture beautiful shots while relaxing.
Bottom Line: If you’re on a budget and want a combination of sightseeing, storytelling, and photos, this tour hits the mark.
8. 1 Hour Photoshoot in Chicago
This standard one-hour session covers the most iconic downtown Chicago sights, such as Millennium Park, Cloud Gate (“the Bean”), and the Chicago Riverwalk. Your personal photographer guides you between locations, ensuring you get the perfect shot at each.
While there are no reviews, the focus on popular landmarks and personal photography makes it ideal for travelers who want professional images of their time in Chicago. The fixed itinerary guarantees you hit the city’s best spots.
Bottom Line: Perfect for visitors who want timed, professional photographs at Chicago’s top sights without fuss.
9. Private Photo Session with a Local Photographer in Chicago
This up to 4-person private package offers 30-minute or 60-minute options, with 20 to 60 edited photos. The photographer works with you to choose your preferred landmarks and backgrounds, providing tailored, high-res images within four days.
Ideal for small groups or couples, this experience offers flexibility in timing and location, making it easy to fit into your schedule. The focus on professional editing ensures your photos look polished. Since there are no reviews yet, it’s best for travelers who prioritize customization and quality.
Bottom Line: If you want a quick, private, and customizable photoshoot with professional results, this experience provides a great solution.
How to Choose the Best Photography Experience in Chicago
When deciding which tour suits you best, consider your budget, time available, and whether you prefer guided group experiences or private sessions. For budget-friendly options, the 2 Hour Magnificent Chicago Tour offers a fun, affordable way to see the city and get photos. If you want a more personalized experience with professional portraits, the Private Vacation Photography Session or Private Photo Session give you tailored results.
For a quick, stylish shoot with a creative flair, the Insta Walk and Polaroid Photoshoot or Insta Walk with Digital and Polaroid Photoshoot are excellent choices. Lastly, if you’re passionate about art and culture, the Art Institute tour combines museum highlights with great photo opportunities.
Booking early, especially for private sessions, ensures you secure your preferred time and location. Think about what kind of memories you want to take home and pick the experience that best matches your style and budget.
To sum it up, Chicago offers a rich variety of visual memory-making options. If you want professional portraits, consider the private sessions or the Insta walks. For casual sightseeing combined with photography, the group tours deliver fun at a budget-friendly price. Whether you’re after art-filled photos or stunning skyline shots, there’s an experience to help you turn your trip into a collection of vibrant, lasting images. Act early to lock in your spot, and get ready to see Chicago through a fresh lens.