Chicago for couples: the most romantic things to do

If you're planning a romantic getaway in Chicago, you can consider these date ideas. Sunset cruises are the best romantic activities to enjoy in this city.

Are you thinking of treating your partner to a romantic city break in Chicago? This list of the top things to do in Chicago for couple might just help you choose.

Lots of partners enjoy taking cruises on Lake Michigan or the Chicago River to soak up the tranquil waters and excellent views. You can also take a speedboat tour, should extra adrenaline float your boat.

Those in the mood for romance might also appreciate night tours around the city. Chicago is well-lit at night, so you will experience beautiful views of the major city landmarks.

And, of course, many Chicago date ideas are centered around food. The city is associated with many famous foods, including deep-dish pizza and brownies. What could be more romantic than sharing a carb coma?

Read on for couples' activities and more.


1. Watch the panoramic sunset with the Big Bus night tour

Experience Chicago sunsets on the Big Bus night tour. This will give you gorgeous views of the Navy Pier, the Magnificent Mile, and several other attractions of Chicago. You will also get to admire the dazzling lights of the Chicago River from the open-top tour bus.

Best time to go:

Spring and summer are the best months to see the Chicago sunset. The skies will be clearer, and reflections on Lake Michigan will create a spectacular sight. If you're able to take a vacation in spring or fall, you may see the famous Chicagohenge.


2. Take a 60-minute speedboat tour on Lake Michigan

There's nothing more romantic than a cruise with colorful fireworks shows. On Wednesdays and Saturdays, you can treat your partner to a speedboat cruise on Lake Michigan. The cruise gives you the best views of the Navy Pier fireworks, an experience that has been ranked among the best fireworks shows in the country. Aside from watching the fireworks on Navy Pier, you will get to see the impressive Chicago skyline.

Best time to go:

This experience runs from Memorial Day weekend through Labor Day weekend. If you don't like large crowds, you shouldn't go on special days like July 4th.


3. Take your love to new heights at the Willis Tower Skydeck

With the Willis Tower Skydeck and Ledge Ticket, you can go up the tallest building in Chicago. The Skydeck is guaranteed to be memorable. On the Skydeck, you can get views spanning over 50 miles and multiple states. Make sure you go up to the 103rd floor and step onto The Ledge to get vertical views of the city below. The Ledge will give you a rush of adrenaline, given that it is a glass balcony hanging over the edge of the building.

Best time to go:

Aim at arriving just when the tower opens or after 5:00 PM as the crowds will be fewer.


4. Grab a table for two at historic Chicago speakeasy bars

The 1920s were the heyday of bootleggers in Chicago. Speakeasy bars were established in these years and have become fascinating historical landmarks in the city. You can spend an evening with your partner in these bars and relive the glamor of the Prohibition Era in this speakeasy cocktail VIP tour. The guide will take you through secret entrances that were used by gangsters like Al Capone.

Best time to go:

The best time to visit speakeasy bars is after sunset. The bars will be quite lively at these hours.


5. Sail Lake Michigan or the Chicago River for the most romantic moments

A romantic vacation wouldn't be complete without a date on a cruise. On this Wine and Cheese Thursday Evening Cruise, you will get to savor wine as you look over the Chicago skyline. You can also choose to take beers and a BBQ instead of cheese. The open-air decks will give you access to a refreshing breeze from the water. If the weather isn't great, you can opt for the climate-controlled interiors of the cruise ship.

Best time to go:

You should take this cruise on a warm or sunny day.


6. Explore Chicago attractions on a night tour

The Chicago Small-Group Night Tour with Skydeck & Skyline Cruise is great for a relaxing evening. This experience covers many romantic activities in Chicago, as well as the top attractions of the city. You will witness the Buckingham Fountain light and music show, the Chicago Bean, and Willis Tower. To end the night, you will take a cruise in the moonlight.

Best time to go:

This is one of the best Chicago couples' activities for a weekend.


7. Have a bite of famous Chicago foods

Chicago has culinary tours for every taste. Some of the foods you can sample in this guided walking tour include Chicago-style hotdogs, Italian beef sandwiches, and deep-dish pizzas. You also have to taste brownies as they were invented in this city. As a walking tour, this experience will take you through major landmarks like the Wrigley Building.

Best time to go:

Chicago date ideas involving long walks are best for cooler seasons. You should especially avoid taking this tour in July since the temperatures can be very high.


8. Get a bird's eye view of Chicago in a helicopter tour

Enjoy an intimate and thrilling 45-minute flight on this private helicopter tour. This bucket-list experience will give you panoramic views of Lake Michigan, as well as other famous buildings in the city. Your pilot will offer live commentary throughout the flight.

Best time to go:

In the summertime, you will enjoy extra thrill since the doors can be off for the tour.


9. Get 360-degree views of the city at the 360 Chicago Observation Deck

The 360 Chicago Observation Deck offers magnificent views of the city. Depending on the weather, you may even be able to see up to 4 different states. Adrenaline junkies will also appreciate the thrilling high-speed elevator ride. This is definitely one of the most romantic activities to strengthen the bond between you and your partner.

Best time to go:

You should pick a day with clear skies as this will let you watch the sunset.


10. Go for a romantic sunset date on a Lake Michigan cruise

Serene cruises on the tranquil waters of Lake Michigan are great for romantic dates. The only thing that can make such anniversary ideas better is a breathtaking sunset. The Lake Michigan sunset cruise will mostly be silent and won't have a lot of narration from the guide. You can spend the time toasting the evening with a glass of wine or cocktail as you take in the amazing sights.

Best time to go:

The best time to view sunsets in Chicago is in spring or summer.


11. Enjoy excellent views of the Navy Pier fireworks

One of the best romantic things to do in Chicago is to watch the Navy Pier fireworks. You will get the best views of these fireworks displays on the Chicago Fireworks Cruise, a 45-minute kid-friendly tour that goes over the Chicago River. You can also opt for a 2-hour cruise over Lake Michigan and enjoy views of the Chicago Skyline.

Best time to go:

This cruise runs biweekly from Memorial Day to Labor Day.


12. Take a romantic stroll at Promontory Point

Promontory Point is a must-visit spot for lovebirds traveling in Chicago. It is known for being the place where Obama and Michelle had their first kiss. This spot offers a perfect escape from the busy Chicago streets, and you can stroll slowly as you snap selfies with your partner. Make sure you turn your phone to 'do not disturb' mode and give all your attention to nature and your partner. Promontory Point offers spectacular views of the Skyline and is the perfect place for a picnic and other romantic activities.

Best time to go:

Pick a warm day with clear skies to get the best sunset views.


What are the most romantic activities to do in Chicago?

The most romantic activities to do in Chicago include taking cruises, watching the Navy Pier fireworks, and watching the sunset.

What are some offbeat romantic things to do in Chicago?

If you're looking for offbeat romantic activities, you should consider taking a speedboat ride on Lake Michigan. You can also view the city from the 360 Chicago Observation Deck.

What are the most romantic spots to watch the sunset in Chicago?

Promontory Point is considered the most romantic spot to watch the Chicago sunset. You can view the Chicago sunset on a bus night tour or cruise.

What are some romantic day trips from Chicago?

During the day, you can take a helicopter tour or food walking tour. There are also guided tours of movie sets in the suburbs and some great lake trips and river cruises that offer meals and drinks.

What are the best places to take romantic photos in Chicago?

The best places to take romantic photos include Promontory Point, Millennium Park, the Skydeck at the Willis Tower, and the Chicago Riverwalk.