Top Chicago Photo Shoots

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.

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

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.

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.

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!

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.

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.

Getting quality photos at Chicago's key landmarks independently means relying on other visitors for help or missing the angles and timing that make the difference between a snapshot and a usable portrait. This private shoot covers locations including the Bean, Riverwalk, and Wrigley Building, with a photographer who customizes the route to suit your group.

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

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.