When it’s date night in Chicago, you and your partner are spoiled for choice. A city like Chicago offers just about any experience you can dream of, including those that are prime for romance. Add these 10 romantic activities in Chicago to your date night to-do list.
Enjoy a Couple’s Retreat at Chuan Spa
Photo by engin akyurt on UnsplashTreat yourselves to a luxurious spa day at Chuan Spa, where Eastern wellness meets urban elegance. Indulge in massages, facials, or even a private couple's suite, all designed to leave you both feeling recharged and rejuvenated. Book a room at the hotel and make a whole weekend of your time together.
Take a Sunset Cruise on Lake Michigan
Photo by Victoria Elliott on UnsplashThe two of you on a boat, cruising Lake Michigan as the sun dips below Chicago’s skyline, painting the sky in stunning colors — there isn’t much that can top it. A cruise with local charter company Wendella Boats is an incredibly romantic way to enjoy each other’s company while taking in the city's skyline from a fresh, breathtaking angle.
Hear the Chicago Symphony Orchestra
en.m.wikipedia.orgLet the music of the night carry your relationship to new heights. With world-class musicians in a historic venue, the Chicago Symphony Orchestra will sweep you both off your feet, creating memories in a setting filled with elegance and romance.
Ride the Centennial Wheel
www.rawpixel.comFrom 200 feet up, the illuminated city stretches out around you, perfect for a cozy, shared moment with some of the best views Chicago has to offer. It’s located on the famous Navy Pier, which has tons of other date night activities like dining, shopping, and amusements.
Tour the Magnificent Mile
Photo by Engin Yapici on UnsplashTake a leisurely stroll along the Magnificent Mile, home to Chicago’s high-end shops, landmark buildings, and charming side streets. This is a great first date spot since it’s free and gives you both the chance to get to know each other as you explore, talk, and just roll with the day. Get the perfect blend of sightseeing and shopping, with plenty of chic cafés and restaurants for a cozy break.
Stroll the Riverwalk
commons.wikimedia.orgChicago’s Riverwalk offers a charming setting for a couple’s walk along the water. Grab a drink or a snack at a riverside café, relax by the water, and enjoy people-watching or taking in some art installations along the way. In the summer, there are also opportunities for kayaking in the area.
Snuggle Up at the Celeste Rooftop Patio
For an intimate and stylish night out, head to Celeste's rooftop patio. This trendy spot offers chic decor, stunning city views, and a romantic ambiance perfect for sharing cocktails under the stars. It’s open year round and in all weather, thanks to its retractable glass roof.
See the City on a Helicopter Tour
Photo by Pedro Lastra on UnsplashOffering tours in the sky since 2003, Chicago Aerial Tours gives you a whole new way to explore the Windy City. You’ll fly over the skyline and along the lake, getting jaw-dropping views of the city that are sure to spark a little extra excitement.
Grab Dinner at Boka
Boka is one of Chicago’s most acclaimed restaurants, ideal for a romantic dinner date. The ambiance is warm and sophisticated, and the food is incredible — seasonal, beautifully presented, and perfectly paired with a top-notch wine list. And for extra special occasions, they also offer private dining.
Take a Cooking Class at The Chopping Block
a person cutting a lime on a cutting boardPhoto by Anju Ravindranath on UnsplashWhy not spice things up with a cooking class? The Chopping Block offers a fun, hands-on date night where you can learn new skills together and then enjoy the delicious meal you’ve created as a team. It’s a complete date night experience, from the food to the music to the ambiance.
Highlights of Chicago’s Best Couple Activities
- Relax and recharge with luxurious massages, facials, and private couple's suites at this urban oasis. Make it a romantic weekend by booking a hotel stay.
- Enjoy a romantic cruise with stunning sunset views of Chicago's skyline aboard Wendella Boats.
- Experience world-class music in an elegant setting that creates unforgettable memories.
- Share cozy moments with breathtaking views of the illuminated city from 200 feet above at Navy Pier.
- Stroll through high-end shops, charming side streets, and landmark buildings, perfect for a casual yet romantic outing.
- Take a scenic walk along the water, relax at riverside cafés, or enjoy art installations and kayaking during summer.
- Sip cocktails under the stars at this trendy rooftop spot with stunning city views and a romantic atmosphere year-round.
- Explore Chicago from above with breathtaking aerial views of the skyline and lake for an exhilarating experience.
- Savor a romantic dinner at this acclaimed restaurant with seasonal dishes, a warm ambiance, and exceptional wine pairings.
- Spice up your date night by cooking a meal together and enjoying it in a fun, hands-on environment.
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