Chicago Date Ideas: Romantic Things to Do in Chicago for Couples

The most romantic things to do in Chicago for couples. Whether planning a weekend getaway in the city with your significant other or looking for unique Chicago date night ideas, these are the best activities to enjoy in Chicago with your partner.

Romantic Things to Do in Chicago for Couples

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Listen to Music at an Intimate Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. You can find the full list of current candlelight concerts in Chicago here.

Live Jazz & Dinner for Two

Have dinner for two with craft cocktails while listening to live music at Le Piano (6970 N Glenwood), a cozy, elegant, and romantic venue.

Take a Helicopter Tour

If you are able to splurge, one of the best ways to see Chicago is from a helicopter tour.

Take an Architecture River Cruise

An architecture river cruise is a must on any Chicago bucket list. In addition to cruises throughout the day, there are also architecture river cruises at night for couples on a date night.

Take a Lake Cruise

If you enjoy being on the water, a lake cruise is also a fun activity at night. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. If your time is short, you can do a combination river and lake cruise.

Watch Free Summer Fireworks on Wednesday and Saturday nights

Navy Pier puts on a free fireworks show every Wednesday (9:00 pm- 9:10 pm) and Saturday night (10:00 pm- 10:10 pm) between Memorial Day weekend and Labor Day.

While you can watch the fireworks from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.

Another great option for watching the fireworks is on a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.

Relax on the Riverwalk

The Chicago Riverwalk, located along the south bank of the Chicago River from Lake Michigan to west of Franklin Street, is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars and other places to sit and relax along the way. You can find a map of attractions on the Riverwalk here.

Watch Digital Art at Art on theMart

Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown twice every night. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Enjoy the Views from 360 Chicago

360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has an observatory with great panoramic views of Chicago. The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. Click here to buy a skip the line ticket). You can also visit BAR 94 which has a full 360-degree view of Chicago.

If you prefer to enjoy the same views over a meal or a drink, there is an upscale restaurant on the 95th floor named the The Signature Room at the 95th, and a bar on the 96th floor called The Signature Lounge at the 96th which are open late in the evening.

Ride the Ferris Wheel at Navy Pier

Navy Pier has several fun outdoor activities at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).

Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises:

Watch the Water Displays at Buckingham Fountain

Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. When the water is turned on, it produces a major water display with a center jet shoots water to a height of 150 feet into the air.

Couples should visit Buckingham Fountain at night when a light and music display accompanies the water display.

Visit the new Chicago: Museum of Ice Cream

Chicago’s newest attraction, Museum of Ice Cream is opening this month. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles.

Where: Tribune Tower, 435 North Michigan Ave, Chicago, IL 60611

Cost: You can see full prices and purchase tickets in advance here.

Experience the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières featured in Emily in Paris (one of my favorite travel shows on Netflix), the popular Immersive Van Gogh Exhibit is a massive indoor digital presentation of Vincent Van Gogh’s artwork.

Couples can also book date night packages which include access to a private Juliet balcony, chocolate truffles, champagne and a handcrafted floral arrangement.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago

Cost:  Tickets start at $39.99 plus fees for off peak times. You can see full prices and purchase tickets in advance here.

Look for Street Art

Another fun activity for couples is walking around the city looking for street art.

One of the most famous murals in Chicago is Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Listen to Free Outdoor Music Concerts

One of the best things for couples to do in Chicago in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

Grant Park Music Festival runs on Wednesdays, Fridays and Saturdays from June 15 -August 20, 2022.

Millennium Park Summer Music Series runs on Mondays & Thursdays from June 20–August 18, 2022.

Watch Free Movies in the Park

There are several places you can watch free outdoor movies in Chicago.

You can also watch free movies outside every Tuesday evening from July 12–August 30, 2022 at Millennium Park on the state-of- the-art, 40-foot LED screen. You can find the full schedule for the Millennium Park Summer Film Series here.

Navy Pier has free movies on Monday evenings (6:30PM – 9:00pm) from July 18 to August 29, 2022.

Chicago Park District is showing over 100 movies at neighborhood parks as part of the Movies in the Parks from June 15 to August 27, 2022.

Watch Movies on a Rooftop

Want to watch movies on a rooftop against the backdrop of the Chicago skyline? Rooftop Cinema Club is a high end outdoor movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including loveseats. Guests can also order drinks and snacks.

Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St in Fulton Market) and tickets range from $20–$30.

Walk the Lakefront Trail

What is more romantic than a walk on the beach? Couples can walk along the Lakefront Trail, a paved path on a 18-mile-long stretch along Lake Michigan.

There are numerous beaches along the way if you want to stop for a picnic on the beach. Don’t forget to pack your beach essentials!