Top Chicago Honeymoon Experiences

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.

Discover Chicago in a fun new way—and combine your sightseeing with a lively scavenger hunt—on this two-in-one excursion. With your smartphone in hand, set off at a time that works best for you on this self-led tour. Prompted by the game, explore the Windy City's vibrant Loop neighborhood. You'll spot historic buildings, famous streets, and other local landmarks along the way, all while your party solves clues and challenges.

Do you have what it takes to solve puzzles, figure out clues, and flee your escape room—all in just 60 minutes? Find out when you book a Chicago escape room experience. Pick from five themed rooms: The California-themed Gold Rush; Special Ops: Mysterious Market, where you play secret agents; Prison Break, where you escape from a warden; the extraterrestrial-themed Mission: Mars; and the Heist, where you track down an art thief.

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).

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.