Chicago is the perfect city for a romantic escape. We’ve partnered with Kirsten Maxwell of Kids Are A Trip to share her favorite date night ideas in a city known for its fine dining, beautiful architecture, and charming spots made for two.

Looking for romance in the Windy City? One doesn’t have to look very far in a city filled with award winning restaurants, top notch attractions, and an abundance of natural beauty. Whether the city is bundled up for the winter, or embracing the summer sun, it’s the perfect destination for strolling arm and arm, seeing the sights, and savoring quiet moments together. Here are some of the best romantic date ideas in Chicago.

Make a reservation at a top restaurant

Chicago is home to over 40 James Beard award winning chefs, and the most outstanding restaurant of 2016, Alinea. Start there and if you can’t get a reservation (which is quite possible), don’t be disappointed as there are many other fabulous choices in the city for a special night out. Les Nomades is a cozy French restaurant that exudes elegance. Bavette’s Bar and Bouef is the place to go for a steakhouse meal that is anything but traditional. Piccolo Sogno features exceptional Italian cuisine with an extensive wine menu. La Sirena Clandestina is one of those hidden spots (the name means “hidden mermaid”) serving Latin fare at candlelit tables. Any of these restaurants are perfect for date night.


Photo credit: Choose Chicago

Splurge for a room at a deluxe hotel

The Peninsula, Four Seasons, Langham, Fairmont Chicago, Park Hyatt, and Waldorf Astoria Chicago all fit the bill when it comes to luxurious escapes that ooze romance. Order breakfast in bed (especially at Park Hyatt where the food comes from NoMI Kitchen, one of the best hotel restaurants in the world) and book his and hers spa appointments. The spa at The Peninsula is spread over two floors of the hotel and has plenty of options for couples. The Fairmont has a champagne candlelight couples massage that sounds indulgent and relaxing all at the same time. The Four Seasons offers a private Skylight Swim where guests have private access to the hotel pool, champagne, and canapés. One thing is for sure, any of these properties are perfect for romance.


Photo credit: Four Seasons Chicago

Head out on the water

One of the best ways to see Chicago is to head out on the water, either Lake Michigan or the Chicago River. There are several ways to accomplish this, some are more romantic than others. Several companies offer sunset dinner cruises, others offer architectural tours of the city, and during the summer there are boats that go out on Lake Michigan to see the fireworks over Navy Pier. Most of these are group tours, but if money is not an object, there are private tours available on chartered boats. It’s a beautiful view of the Chicago skyline and a perspective one doesn’t see every day.


A view of the city from the water can’t be beat!
Photo credit: Choose Chicago


Take a carriage ride through the city

Ever imagine what it would be like to jaunt through the city in a horse drawn carriage? Several companies offer tours of the downtown area, allowing couples to experience the city at a slower pace. Carriages tend to pick up downtown by the Water Tower near Michigan Avenue, with rates that vary depending on the length of the ride. For couples looking for a fairy tale adventure, this could be a dream come true.

Catch the sunset from a building with a view

Head to the John Hancock Building where you can take an elevator to the 94th floor and enjoy views of four states and Lake Michigan on a clear day. 360 Chicago offers cocktails to toast the end of the day while enjoying a romantic view. On the 95th floor you can make reservations for dinner in the Signature Room, or head up to the 96th floor to the Signature Lounge if you want to spend more time enjoying the sights. Other options for terrific sunset views include: The Willis Tower Skydeck or Everest Restaurant on the 40th floor of the Chicago Stock Exchange. Any of these will give you beautiful views as long as the weather is good.


The views from above can’t be beat! Photo credit: Kirsten Maxwell

Enjoy a night out at the theater

Chicago has a vibrant theater scene with Broadway shows, musicals, plays, and comedies offered almost every night of the week. Grab a bite to eat at a nearby restaurant such as: Petterino’s, Catch 35, and Atwood. All are good choices for a quick meal beforehand in the theater district. The performances are all top notch and some of the older venues are truly stunning.

Pack a picnic, head to the park, and soak in some culture

Of course this is not something to plan for the middle of winter, but in the summer the city hosts their summer music series at Jay Pritzker Pavilion. Grab provisions for a picnic, head to Millennium Park, enjoy your meal and the concert. When you’re finished head over to the Art Institute of Chicago where you can spend the evening enjoying some of the world’s great masterpieces before retiring for the evening.


Photo credit: Choose Chicago

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