If a warm weather escape just isn’t possible – or maybe you don’t want to go to the beach – why not warm things up when it’s freezing outside with a little bit of city romance? A quick weekend trip or for a longer stay, Chicago can help you amp up the romance and leave the everyday behind with all it has to offer.  Here are a few ways to help you plan the perfect romantic city getaway.


A spa retreat is great for one person, but it’s even better for two! The spa at Waldorf Astoria Chicago is the perfect romantic oasis in the heart of Chicago. The full-service spa combines both traditional and modern services for the ultimate in relaxation. Get a couples massage where you are whisked away to one of the private spa suites designed for two. Finish your evening with a bottle of champagne and some of the most beautiful architecture in the city.

If the spa isn’t your thing, perhaps a romantic package at The Drake Hotel is perfect for you. Enjoy a bottle of champagne in your room to get your evening started and start the day in luxury with an in-room dining experience.


Whether you are grabbing a quick lunch on the way to see a show or you want an award-winning dining experience, Chicago’s local restaurant scene doesn’t disappoint. One of the best ways to experience the food that Chicago has to offer is Chicago Restaurant Week. This 17-day event runs between January and February of every year and is the largest celebration of its kind in the United States. Plan your romantic city escape around delicious culinary destinations all with prix fixe menus for you to choose from.

Eat your way through Chicago at Potter’s Chicago Burger Bar. With a full menu of burgers celebrating the city’s favourite neighbourhoods, there is a burger for every taste. There are nine different burgers to choose from so you can make it a regular lunch date during your stay in Chicago and never eat the same one twice. Top it off with a milkshake for two and recreate the classic two straws, one milkshake (if you are ok sharing!).

When it comes to food, you should always listen to the locals, and the locals love Stephanie Izard and her famed Girl & the Goat. One of five of her restaurants, Girl & the Goat offers bold flavors and craft beers & cocktails in a cozy, West Loop setting. The restaurant is known for everything from it’s wood oven roasted pig face to warm, savory breads. If you know you’ll be visiting Chicago, make your reservation in advance, it’s still a popular place to dine and books up fast.

The Hilton Chicago is right in the heart of the city and steps away from countless favourite Chicago restaurants. And after a romantic dinner for two, you can snuggle up near the fireplace in the hotel to warm up and watch the world go by on the bustling streets of Chicago.


Every city has its own culture and flair. Take in a show, an iconic attraction, or simply enjoy the breathtaking views of the city skylines – all with a romantic twist for the perfect romantic city break.

While Chicago has a vibrant and unique theatre scene all year round, Chicago Theatre Week often offers theatre tickets at discounted prices. With more than 100 productions to choose from, a pair of theatre tickets is a perfect date night to get you inside and out of the cold.

If you want to get out for a bit of fresh air, visit Chicago’s Millennium Park, which features an ice rink through March. Stay at any Chicagoland Hilton hotel and get 2 pairs of free skates when you show your Hilton confirmation email for that day.

If you are looking to experience a can’t-miss iconic attraction that helps to define Chicago’s skyline, go for a romantic ride in Navy Pier’s Centennial Wheel. The fully enclosed gondolas are heated so you can enjoy a snuggle and incredible views of Chicago and Lake Michigan from heights of 200 feet in the cold winter weather. Also at Navy Pier, enjoy a relaxing cruise to take in the beautiful city skyline, or check out a show at leading international theatre company Chicago Shakespeare Theatre. Why not plan a full day date at Navy Pier?

While Chicago has so many opportunities to view the city skyline, the 360 Observation Deck and Skydeck Chicago are the two best views in the city. 360 Observation Deck towers above Chicago at 1000 feet and has an inviting bar where you can enjoy a local brew or a cocktail while you split your loving gaze between your partner and the beauty of the city. Through April, you can show your Hilton key card for a Complimentary TILT ticket or free drink upgrade at BAR94, see site for details. Skydeck Chicago is located in Willis Tower, one of the tallest building in the Western Hemisphere with glass boxes located at 1,353 feet up that extend 4 feet out over the city. They even have a date night package with options for VIP dining before and after the facilities officially close. With a 7-table maximum, this is a truly memorable way to experience Chicago.

It may be cold outside, but that doesn’t mean you need to feel cold. Warm up with a romantic Chicago city break!

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