22 romantic things to do in Chicago
Written by Alison Lynwood

22 romantic things to do in Chicago

Crank the heat up on your next date with these fun and romantic activities.

Believe it or not, Chicago is brimming with romance, even in the coldest months. Aside from keeping each other warm, there are tons of romantic things to do in Chicago. When we're looking to elevate date night, we take dips in thermal baths, explore the city's many lush green spaces, attend laugh-out-loud shows and dine at the most romantic restaurants. Some of the best things to do in Chicago can also be a perfect bonding experience. So whether you're going on a first date or just looking to liven up a Saturday, these romantic things to do in Chicago should do the trick.

1. Have a romantic and intimate dinner

There’s no shortage of romantic restaurants in Chicago to wine and dine your partner at. You’ll find dimly lit spots, fondue feasts, rooms with beautiful views and many more intimate options. They all know how to set the mood so that couples can have a lovely and unforgettable experience. The food’s obviously stellar, too, featuring everything from French and Italian cuisine to dry-aged steaks.

2. Spend the night at a romantic hotel

Planning a romantic weekend away doesn't mean that you have to leave town. In fact, there are so many romantic hotels in Chicago that you probably don't even need to hop in the car. They boast luxurious amenities, in-room dining from some of the best restaurants in Chicago and jaw-dropping views—everything you need to set the mood. A deep tub and fluffy robes don't hurt either. Pack your overnight bag and prepare for a night away at the most romantic hotels in Chicago.

3. Hold hands at the Maggie Daley Park Skating Ribbon

If you don't mind sharing the ice with a few kiddos, dust off your ice skates (or rent a pair onsite) and hit the winding rink at Maggie Daley Park in the heart of downtown Chicago. Hold your honey's hand as you make your way around the circular path set against skyline views. Don't forget: you'll need to plan ahead and make a reservation online if you want to get on the ice.

4. Take a dip at Aire Ancient Baths

Breathing new life into the ancient tradition of Greek and Roman bath houses, Aire Ancient Baths is a singular spa experience that can be enjoyed solo or with a partner. Book a couples massage or body treatment and make time to explore the spa's different baths, which vary from ice-cold to steaming hot.

5. Have a laugh at a comedy club

One of the quickest ways to win someone’s heart is to make them laugh. Which is why a show at any of Chicago’s top comedy clubs is always a good idea. Our favorite spots include Zanies and the Second City, where you can watch sketches, improv performances and stand-up routines from some of the best local talents.

6. Watch the sunset in style

Chicago is home to some of the tallest buildings in the world so why not take full advantage of them? Climb more than 1,000 feet above ground to CloudBar at 360 Chicago or the Signature Lounge and watch the sunset from the city’s highest points. Pair the stunning views with a cocktail to really enhance the experience.

Written by

Alison Lynwood

Alison Lynwood

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