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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

Free Cancellation
1 hour

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

Free Cancellation
1 hour to 1 hour 30 minutes

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

Chicago CityPASS®

9 days

Chicago Crime and Mob Bus Tour

Free Cancellation
1 hour 30 minutes to 2 hours

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

Free Cancellation
1 hour

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

Chicago Photo Walk to Bean and Landmarks

Free Cancellation
1 hour

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

Free Cancellation
4 hours

Price varies by group size

Likely to Sell Out

Make your Chicago trip unforgettable with a private photoshoot at the city’s most iconic locations. Your photographer customizes the route for your style and occasion—capture candid portraits by the Bean, Riverwalk, Wrigley Building, Millennium Park, and more. Solo adventurer, family, couple, or group—everyone’s welcomed! Choose a 30-minute or 1-hour shoot and receive 20–45 high-res, professionally edited photos delivered via a private online gallery within five days. Enjoy insider tips and authentic, natural photography from a top-rated team.

Private Vacation Photoshoot with Photographer in Chicago

Free Cancellation
1 hour

Price varies by group size

Discover the local shopping scene and its fashion DNA with a professional stylist as you embark on a personalized shopping circuit built to meet your style and wishes. Learn more about the art of styling your body features and take a figurative soft tour outside your comfort zone as your stylist pulls pieces for you to explore and try. Think of it as a mini style consultation followed by recommendations and a hands-on practice session during the shopping tour where you can ask any fashion and style-related questions. Throughout your shopping circuit and neighborhood's discovery, listen to fashion stories as told by your fashion savvy guide, and get a unique insight into the industry. Prior to your shopping tour, you will be sent a little shopping form to help personalize your experience. And following your fashion escapade, you will be sent a personal style summary of recommendations received by your stylist as well as some tour souvenir photos.

Chicago Local Fashion Designers Shopping Tour with a Stylist

3 hours

Price varies by group size

Comfortable Roundtrip Tour from your hotel in Chicago to Chicago Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Chicago Premium Outlets

Free Cancellation
5 to 6 hours

Price varies by group size

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

Free Cancellation
40 minutes

Comfortable Roundtrip Tour from your hotel in Chicago to Fashion Outlets of Chicago - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Chicago. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Chicago. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Chicago to Fashion Outlets of Chicago

Free Cancellation
5 hours

Price varies by group size

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

30 minutes

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

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

Attractions

Art Institute of Chicago

The red velvet seats and bohemian interior of the Chicago Theater.

Attractions

Chicago Theatre

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