5 Exciting Ideas for a Date Night in Chicago

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Written By Aaron Smith

Rev. Aaron Smith enjoys sharing insights from over 10 years of wedding officiating experience.

If you’re planning a date night in Chicago, you’ve come to the right place. Chicago is known for plenty of things, such as the Cubs and the Bears, the summers and the winters, the concerts, and the lakeshore. Anyone who has lived in Chicago for a significant amount of time will tell you that despite its challenges, Chicago is an amazing city. One of its best features is the romantic side of it. There are enough date night ideas in Chicago as anywhere. Let’s explore one of the best reasons to visit this incredible place and share some favorite stops for your upcoming date night

date night in chicago
5 Exciting Ideas for a Date Night in Chicago 2 date night in chicago

1) Date Night in Chicago: The Art Institute of Chicago

This museum is located on Michigan Avenue and is home to more than 200,000 pieces of art. It was founded in 1879 by businessman Henry Clay Frick. He wanted to create a collection of paintings from around the world. Today, the Art Institute is considered one of the most important museums in the United States. You can find many famous works here, including “The Scream” by Edvard Munch and “The Birth of Venus” by Sandro Botticelli.

2) Navy Pier 

Located at Lake Michigan, this pier offers visitors a chance to enjoy rides, games, food, shopping, and much more. In addition to all the fun activities available, Navy Pier hosts several events throughout the year. These include festivals, concerts, fireworks displays, and other special events.

3) Millennium Park

This park is another popular attraction in downtown Chicago. With over 100 sculptures, fountains, and public areas, Millennium Park offers something for everyone. Many enjoy taking pictures with statues like ‘Cloud Gate’ or listening to music while walking through the park.

4) The Magnificent Mile

Home to the World-Famous Water Tower, The Magnificent Mile is a tourist destination in Chicago offering fine dining, luxury stores, and unique shops.

5) The Willis Tower (formerly Sears Tower)

The Willis Tower is commonly referred to as the tallest building in America. Standing at 1,730 feet tall, the tower contains several restaurants, offices, condos, and lounges. On top of the main structure is an observatory where guests can purchase tickets to access the upper viewing deck, which is open daily.

More Ideas

Take a Helicopter Tour

Chicago is well known for its beautiful parks and gardens. Take a helicopter tour and see them all! For just $50 per person, you’ll get to see the city from above and experience wind currents, clouds, and sunsets. No matter what neighborhood you choose, there is sure to be a heliport near you.

Visit Lincoln Park Zoo

One of the oldest zoos in North America, Lincoln Park Zoo is home to over 2,200 animals representing 350 species. Some of the highlights of the zoo include: the Great Cats exhibit; the Polar Bear Plunge pool; the Children’s Zoo; and the African Journey.

Enjoy a Show at Cadillac Palace Theatre

Cadillac Palace Theatre is located in the heart of the theater district on State Street in Chicago. Since opening its doors in 1927, the palace has hosted stars like Frank Sinatra, Judy Garland, and Michael Jackson. Today, it continues to host Broadway shows, musical acts, comedians, and family shows.

Dine at Alinea

Alinea is located within the Drake Hotel in Chicago and serves modern American cuisine using locally sourced ingredients. Diners rave about the tasting menus offered here, especially the ones prepared by chef Grant Achatz.

A Lakeshore Bike Ride

Bike along the lakefront trail in Chicago and take in breathtaking views of Lake Michigan. Rent bikes from Pedal Power Bikes, a bike shop located in Chicago’s Old Town. They offer rentals for every skill level.

Best Chicago Restaurant Neighborhoods

Whether you want to dine at a fancy restaurant, casual eatery, or somewhere in between, Chicago has it all. Check out our list of the best Chicago restaurants, including reviews and ratings.

Chef Art Smith’s Reunion



Publican Quality Bread

Loaf Lounge

Perennial Virant

Odd Duck



Wicker Park Cheeserie

Taqueria La Tortilleria

Equinox Fitness Club

Saucebox Social House

Lincoln Hall

Roti Chai

Navy Pier

Millennium Park

Willis Tower

Magnificent Mile

Lake View

Back Bay

River North

West Loop

East Loop

North Center

South Loop

West Side

Central West Side

Central East Side

Central South Side

Central North Side

As you can see, there is no shortage of excellent restaurants in Chicago, from River North to Lincoln Park to Logan Square to Hyde Park. For that reason, you want to be sure to get your reservation in with plenty of time to spare, especially for special events. 

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