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Private Chicago Highlights Photography Session

Visitors to Chicago who want to capture fantastic vacation photos shouldn’t settle for smartphone selfies when you can book a professional photographer. With this photo shoot experience, simply meet your photographer-guide and enjoy a session with iconic Chicago landmarks as your backdrop. Photo shooting spots in Chicago: Millennium Park (including Cloud Gate) Willis Tower Skydeck Chicago Riverwalk Navy Pier North Avenue Beach The Magnificent Mile Wicker Park Lincoln Park Rooftop Chicago (extra charge may apply depending on the venue) Capture your most memorable moments during this private photo shoot. Return from your trip with beautiful, high-quality vacation photos — the best souvenir you can take home. PLEASE NOTE: This photo shoot package covers only one location from the list. Adding more locations will increase the package fee. The service fee mentioned is per person. This is not a group price. Please specify your preferred location from the list when making your booking.

Private Chicago Highlights Photography Session

1 hour 30 minutesFree Cancellation

Private Photo Session with a Local Photographer in Chicago

Don’t rely on strangers or selfies to capture your vacation memories—with this private photoshoot experience, you’ll walk away from your Chicago getaway with professional photos to commemorate your experience. For solo travelers, the 30-minute Bronze Package offers 20 edited, hi-res photos; the 60-minute Silver Package is ideal for couples, and offers 35 photos; and the 100-minute Gold Package is perfect for larger groups, and offers 60 photos.

Private Photo Session with a Local Photographer in Chicago

Private Photography Session with Local Photographer in Chicago

Flytographer Private Vacation Photo Shoot Connect with a local hand-picked professional photographer in Chicago and capture your most memorable moments during this private photo shoot. Get insider tips on the best things to do in Chicago, including where to eat & what to see from your vacation photographer. Return from your trip with beautiful, high-quality vacation photos — the best souvenir ever. We specialize in: - honeymoons - family trips - engagements - anniversaries - romantic getaways - multi-generational trips - babymoons - solo travellers - and just because! With over 10,000 5-star reviews, Flytographer is the global leader in vacation photography and has captured over 3 million memories for travellers across six continents. We’ve been featured across A-list media, including Conde Nast Traveler, Oprah, Forbes, Travel + Leisure, New York Times, BRIDES, Martha Stewart Weddings, InStyle Magazine, Elle, Buzzfeed, Refinery29, Huffington Post, & many more.

Private Photography Session with Local Photographer in Chicago

1 hourFree Cancellation

Professional Photo Shoot in Chicago

Capture the highlights of your Windy City visit—and walk away with professionally taken portraits—on this private photo shoot experience. Meet your guide at a time and place that work best for you; you can also select your preferred duration and number of photos. Then, get ready to strike a pose: your guide will take a number of photos, and chronicle your special moments. See Windy City highlights as you go

Professional Photo Shoot in Chicago

4 hoursFree Cancellation

Price varies by group size

Iconic Photoshoot in Chicago

Capture your Chicago adventure with a professional photoshoot at the city’s most famous landmarks. Perfect for solo travelers, couples, or friends — no posing experience needed! We’ll visit: The Bean, Chicago Theatre, Riverwalk, Millennium Park & colorful street art spots. You will receive: • 100 high-resolution edited photos • Natural posing guidance • Optional outfit changes • Insider local tips for dining & exploring Come as you are — I’ll take care of the angles, lighting & magic!

Iconic Photoshoot in Chicago

1 hourFree Cancellation

Photo Shoot in Chicago’s Urban Jungle Garden

Enjoy a private photoshoot in Chicago’s beautiful urban jungle at the Lincoln Park Conservatory. During this 40-minute session, I’ll help you feel confident and relaxed while taking high-quality photos using iPhone, optimized for social media. You’ll receive about 50 digital photos, including 5 professionally edited images, delivered via a private online gallery. Please download your photos within 14 days after receiving access, as the gallery link will expire.

Photo Shoot in Chicago’s Urban Jungle Garden

40 minutesFree Cancellation

Private Vacation Photoshoot with Photographer in Chicago

Private Vacation Photoshoot with Photographer in Chicago

1 hourFree Cancellation

Price varies by group size

Chicago Architecture River Cruise

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

Likely to Sell Out

Private Chicago Photography Class for Stunning City Shots

Chicago has architecture that stops you in your tracks, a lakefront that stretches to the horizon and neighborhoods full of color and character. With instruction tailored entirely to your group of 2 to 4, you'll quickly get to grips with the skills that separate memorable images from forgettable ones: light, composition, exposure and framing, whether you're on a smartphone or a digital camera. No rushed theory, no generic advice. Just hands-on coaching at your own pace. Then it's out into the city itself. On a guided photo walk through urban landmarks and open lakefront scenes, your instructor will be right there with you, helping you read the light and find the correct frame. Leave with sharper instincts, full control of your device and a collection of images that finally do Chicago justice. Perfect for groups of friends, couples or families, whether you're visiting for the first time or you've lived here for years and never quite managed to capture it the way you imagined.

Private Chicago Photography Class for Stunning City Shots

2 hoursFree Cancellation

Top Attractions in Chicago

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Entrance to Chicago Riverwalk surrounded by skyscrapers, Chicago

Attractions

Chicago Riverwalk

The Magnificent Mile in Chicago on a warm spring day.

Attractions

The Magnificent Mile

A woman exploring the view from the Skydeck Chicago at Willis Tower.

Attractions

Skydeck Chicago at Willis Tower (Sears Tower)

The statue of a lion at the entrance to Art Institute of Chicago, USA

Attractions

Art Institute of Chicago

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