Romantic things to do in Chicago

Here’s our pick of the most romantic things to do in Chicago

Chicago oozes romance, with its big-city bravado and picturesque gardens and grounds. Couples can make the most of the city’s most impressive sights by heading up to a secluded rooftop bar, or stick to ground level (or should that be water level?) by taking a sunset river kayaking tour down the Chicago River. There’s also dreamy neighbourhoods and scenic pier points to choose from, as well as the classic date-night options – ice-skating or ferris wheel rides, anyone? Whatever your vibe is, you’ll be tempted by this selection of romantic things to do in Chicago.

  1. Head up to a rooftop bar
  2. Explore the Crystal Gardens at Navy Pier
  3. Hit up a beachfront restaurant (yes, really)
  4. Lace up your skates in Millenium Park
  5. Explore Boystown
  6. Go kayaking down the Chicago River

In collaboration with
Rough Guides

1. Head up to a rooftop bar

You can appreciate some of the finest views Chicago has to offer at one of the city’s many rooftop bars. The city is the birthplace of the skyscraper, after all! Whatever vibe you and your partner are after, you’ll find it here. Either keep to yourselves with secluded, garden-style options, or clink to good company at livelier patio bars. These aren’t just summertime options, though; many rooftop bars offer covered protection, which is made all the more atmospheric with the addition of twinkling fairy lights, candles and more. Get ready to swoon over Chicago!

Best for: Admiring the views.

Don’t forget: Bring a camera!

2. Explore the Crystal Gardens at Navy Pier

Take the time to explore the Crystal Gardens at Navy Pier, a great option for couples thanks to its perfect date-night options. Enjoy the incredible views of Lake Michigan from the Botanical Garden, which inside houses 80 palm trees, verdant foliage and sprinkling fountains. Spanning six storeys within a glass atrium, a touch of romance is added with its hanging fairy lights. After you’ve explored the Botanic Garden, head over to Pier Park. Here, you can take a spin on an amusement ride or two or head out on a boat excursion.

Best for: Those looking for multiple activities.

Don’t forget: Go for a spin on the Ferris Wheel for even more unique views over Lake Michigan.

3. Hit up a beachfront restaurant (yes, really)

When you think of Chicago, you probably don’t think of beaches. So you’ll be pleasantly surprised to learn that there’s miles of shoreline here, thanks to its lakeside proximity to Lake Michigan. There’s loads of beaches to hang out from, whether you want to give water sports a go or simply check out some lakeside attractions. But for a romantic experience with your partner, head to 12th Street Beach where you can enjoy spectacular views, or dine at a swanky beachfront restaurant at one of the chic options on North Avenue Beach.

Best for: Beach bums.

Don’t forget: Head to Montrose Beach if you’re a dog lover.

4. Lace up your skates in Millenium Park

There’s no missing the Millenium Park during your Chicago holidays; it’s a popular spot with locals and visitors alike, thanks to its wealth of sights, attractions and events. In fact, you could probably make a date out of most things to do here – there’s the tranquil Lurie Garden, happening Jay Pritzker Pavilion, arty Boeing Galleries – but ice-skating is the best way to soak up the romance. You can’t go wrong with this classic couples activity, which is held in Maggie Daley Park (just cross the pedestrian bridge). This is one of the best romantic things to do in Chicago, as you get to skate through the scenic outdoor space.

Best for: Those wanting to keep active!

Don’t forget: You can amp it up a notch with rock climbing, also held in Maggie Daley Park.

5. Explore Boystown

The LGBTQ-centered Boystown is home to the city’s annual Pride Parade, but outside of this major event it makes for one of the most romantic places to visit in Chicago. With plenty of cool bars and cafes to check out, one of the best things to do here is to take the Legacy Walk. You can book onto a private tour, or simply read the placards that explain more about various LGBTQ icons, from Harvey Milk to Frida Kahlo.

Best for: LGBTQ history.

Don’t forget: Head down to the nearby lakefront for a scenic stroll.

6. Go kayaking down the Chicago River

The Chicago Riverwalk is undoubtedly the setting for some of the most romantic things to do in the city. Take your pick from a sundowner tipple from one of the chic bars on the riverfront patio, board a scenic architecture-themed boat tour or while away the evening on a glitzy River dinner cruise. Our top pick, though, has to be a kayaking trip; paddle the calm waters down the Chicago River while taking in the Riverwalk, historic bridges and iconic buildings.

Best for: Those wanting to mix sightseeing with action.

Don’t forget: Book onto a sunset tour for a romantic hue.

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