From deep dish pizza to the White Sox, to jazz music and sleek contemporary architecture, Chicago is a city of many talents. If art and architecture are your thing, you won’t know where to look in this exciting city. Public art peppers the streets, the art museums are world class, and the high-rise skyline is wall-to-wall iconic, from the gleaming Willis Tower to the stainless steel ‘head-dress’ of the Frank Gehry designed Pritzker Pavilion. 

Food lovers will be in heaven in the Windy City. With a range of global eats, from hot and spicy Italian beef sandwiches to the Chicago hot dog, an elasticated waistband is an essential. Chicago knocks it out of the park when it comes to pro sports too, with a team for every season. Whether you’re a football fan, or you’d rather be in the bleachers, experience the excitement first hand in one of the city’s stadiums, or in pretty much any neighborhood bar. 

It’s the perfect destination for couples. With everything from big city glitz to low-key, candle-lit restaurants, and super-fun, date-night activities, you’re sure to fall in love with Chicago.

Food Tour

Originally invented in the 1940s, the Chicago deep-dish pizza is an Italian American version of the classic dish. More like a savory layer cake than a Neapolitan-style thin crust, the Chicago pizza pie is at least an inch thick, with layers of mozzarella and chunky tomato sauce. A Chicago born and raised icon, it’s delicious, inventive, and seriously indulgent. This 3-hour group pizza tour takes you to four of the city’s best pizzerias on the ‘Dough Force One’, where you’ll sample everything from deep-dish and stuffed, to coal oven and tavern style. Make sure you wear your eating pants!

Featured Experience: Pizza Tasting Tour of Chicago - From $80

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Flying Lesson

Head to Chicago Executive Airport and meet your certified flight instructor before they show you the ropes of flying your own light aircraft. Then it’s time to climb into the pilot’s seat and take to the skies! You’ll help with taxiing down the runway and take off, and once the Cessna is in the air, you’ll take control and carry out a number of airborne manoeuvres, doing everything that a qualified pilot would do! Your experience lasts around 1.5 hours, with 30 – 40 minutes of flight time. It’s the thrill of a lifetime, and the kind of couples’ experience that you’ll be reminiscing about together for years to come.

Featured Experience: Chicago First Flight Lesson - From $169

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Chicago Symphony Orchestra

One of the three most acclaimed orchestras in the US, the Chicago Symphony Orchestra is a giant on the international music scene. Renowned for its rich tone, talented conductors and stellar guest artists it’s a precise, world class ensemble that performs over 100 concerts every year. The ensemble is resident at Orchestra Hall in Chicago, a grand Georgian building designed by the pioneering architect Daniel Burnham. Tickets to see the orchestra in action in their home venue would be a memorable experience gift for any couple, or a dream night out for you and your other half.

Featured Experience: Chicago Symphony Orchestra Tickets

Dinner Cruise

Dress to impress for an evening of dinner, drinks and dancing aboard the Odyssey of Chicago. With three tiers, an elegant dining room, and a built-in dancefloor, it’s a dream venue for a night in the city with your partner. Meet the captain and crew before enjoying a mouth-watering three-course meal, paired with a selection of prize-winning wines. Then head out onto the deck for a cocktail with views of the city skyline from the Willis Tower to the John Hancock Centre. Round the night off by grabbing your partner by the hand and strutting your stuff together on the dancefloor.

Featured Experience: Gourmet Chicago Dinner Cruise For Two - From $470

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Centennial Wheel

Chicago is the home of the Ferris Wheel with the very first ever wheel opening to a rapturous reception in the World’s Fair of 1893. In 2016, almost 110 years after the original wheel was demolished, a new Ferris Wheel was opened on the Navy Pier. Measuring 196 feet in height, the Centennial Wheel is an iconic fixture on the city skyline and offers unparalleled vistas of the city and Lake Michigan from its high-tech, glass gondolas.  A ride on the wheel is a must for any couple visiting the city or locals looking for a romantic experience with a view.

Featured Experience: Ride Glass Bottom Gondola on the Centennial Wheel - From $99

Haunted City Tour

Hold your loved one close as you experience Chicago’s spookiest places. ‘Weird Chicago’ is a whistles top tour of the city’s most chilling and ghastly spots. Choose from four different ghoulish guided tours, from a haunted histories experience and a gangsters and guns adventure to a true crime tour. Learn about the notorious ‘Murder Castle’, hear terrifying tales of the Lip-Stick Killer, and follow in the footsteps of the infamous serial killer, John Wayne Gacy. It’s a mix of ghosts, gangsters and true crime that’ll keep you both awake at night!

Featured Experience: Weird Chicago Tour - From $43

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Bike Tour

Chicago’s Lakefront Trail is an 18-mile paved path on the Lake Michigan shoreline. With the lake’s blue waters to one side and verdant parks and city skyline on the other, it’s one of the most scenic routes in the city and there’s no more romantic way to explore it than on a bicycle made for two! Hop on your comfy ride with your co-captain and pedal your way along the front, taking in the beautiful scenery, stopping for refreshments at the seasonal snack shacks, and kicking back on the beach or in one of the many city parks that are linked by the trail.

Featured Experience: Chicago Lakefront Bike Trail

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Chicago is a dream destination for a couple and packed with activities to do as a pair. It’s also a fantastic place for couples’ experience gifts, for weddings, anniversaries or special birthdays. Check out our full range of Chicago experience gifts.