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Romantic Things to Do in Chicago

Romantic Things to Do in Chicago

Chicago is a city with style and verve, and its beautiful parks, picturesque waterways, and vertiginous heights all make the perfect backdrop to a romantic excursion. From 2-passenger helicopter flights to Lake Michigan cruises and after-dark speakeasy visits, here’s how to enjoy a special trip to Chicago with your significant other.

Cruise Lake Michigan at Sunset

Lake Michigan is almost oceanic in scope, and a night out on the water is a classic Chicago experience. Book an early evening tour to watch the sun descend over the iconic Chicago skyline, and enjoy a romantic moment out on the deck. Alternatively, a dinner cruise—complete with gourmet dishes and flutes of sparkling wine—is the perfect way to toast a special occasion.

Enjoy a Couple’s Photo Shoot in Millennium Park

Visit one of the Windy City’s most in-demand sightseeing destinations—and enjoy a special way to record your memories for posterity—when you book a couple’s photo shoot. Explore the greenery and public artworks of Millennium Park, admire the perspective on the Loop’s gleaming skyscrapers, and see the famous Cloud Gate sculpture by Anish Kapoor—better known as “The Bean.” Your very own photographer will be present to show you the sights and capture your romantic moments.

Sip Cocktails in the City’s Speakeasies

During its Prohibition-era heyday, Chicago was filled with speakeasies (not to mention infamous gangsters the likes of Al Capone). Today, that legacy lives on in the city’s plethora of top-notch cocktail haunts (which, today, are thankfully free of bathtub gin). Book a speakeasy tour for a dose of history and to discover a number of cozy, candlelit drinking dens with your significant other.

Book a Private Helicopter Tour

Few views of Chicago can compare with the ones afforded by a helicopter—and taking to the air on a freewheeling journey above the skyscrapers is one of the city’s most popular romantic experiences. Book a private flight for a particularly intimate experience, and enjoy an indulgent accompaniment in the form of Champagne and chocolates.

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7 Tours and Activities | All Chicago Tours

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Millennium Park Photo Shoot and Walking Tour

Millennium Park Photo Shoot and Walking Tour

star-5
On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.
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  • 1 to 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Museum Campus Photo Shoot and Walking Tour

Museum Campus Photo Shoot and Walking Tour

star-5
Enjoy a private portrait session with your own professional photographer during this VIP shoot in Chicago. Discover top landmarks in the city as you follow a photogenic, pre-planned route, with backdrops such as the Adler Planetarium, the Field Museum, and the Shedd Aquarium. Then, receive a digital portrait gallery of edited images within just one to two days.
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  • 1 hour
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Odyssey Chicago River Dinner Cruise

Odyssey Chicago River Dinner Cruise

star-3.5
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
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  • 3 hours
  • Taking safety measures
From
$169.86
From
$169.86
Taking safety measures

Private Photo Session with a Local Photographer in Chicago

Private Photo Session with a Local Photographer in Chicago

Want to capture your amazing honeymoon? Family vacation while the kids are still little? Your perfect couples retreat from everyday busy life? A solo trip without asking strangers to take pictures of you? Stop searching, we got you here! We are the largest network of local vacation photographers in the world! Besides Chicago, we operate in over 700 destinations worldwide! We always make sure that every special moment of each client is captured well. We believe in our service and quality of our photos so much that we even offer a 100% money back satisfaction guarantee for your photo shoot. Which means, if you don’t like the result of your photo shoot, you can contact us within 7 days and claim your money back! So what are you waiting for? Become one of our hundreds of happy customers by treating yourself to this special experience! Your family and friends will love the result too!
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  • 30 minutes
From
$270.18
per group
From
$270.18
per group