10 Ideas for Couple Looking to Explore Chicago

10 Ideas for Couple Looking to Explore Chicago

If it’s your first time in the city, you may find yourself falling even more in love with your significant other because of these ideas.  

Couples can learn about art, history or even get outdoors to take in the beautiful views of the Windy City together.

These are just a few ideas for couples looking to enjoy the Windy City together. Hopefully, this list will provide some great suggestions to try out in order to keep your relationship strong and healthy.

The Art Institute of Chicago

While the Art Institute of Chicago is full of various sculptures and paintings, one can’t forget that it also offers many rooms where those in love can curl up on a bench or old chair with a good book to read together. 

You can also decide to play a game in these rooms. If you’d like to play with your significant other, click now to read more about some of the games you can play as a couple. 

In addition, the museum has an extensive library as well as exhibits from other museums around the world.

Garfield Park Conservatory

As the name suggests, the popular Garfield Park conservatory is located near Garfield Park, making it easily accessible by the CTA Green Line.  

The conservatory has various plants and flowers that are on display throughout the year for couples looking to get away from their everyday lives to experience something beautiful together.  

Couples can sit in one of the various corners of the conservatory with a blanket to take in the majestic beauty that it offers.

The Magnificent Mile

The Magnificent Mile is a stretch on North Michigan Avenue immediately east of the Chicago River. 

It includes numerous upscale shops as well as many popular restaurants to stop for some appetizers or dinner.  

For those looking not to dine but still want to experience some fun stores, The Mag Mile offers several prime lounging examples from American Girl Place to Apple.

Chicago Architecture Foundation Tours

Although somewhat expensive, one can’t argue against the fact that these tours are often quite popular.  

The architecture foundation offers several tours of various buildings throughout downtown Chicago, including famous landmarks such as the John Hancock Center or The Rookery.  

While on tour, couples can talk about how it looks like, what they’ve done in the past, or discuss how they’ve grown.

360 Chicago Observation Deck

Located on the 94th floor of the Aon Center, one can find 360 Chicago. It’s considered the highest observation deck in the Western Hemisphere and it offers some fantastic views of downtown Chicago.  

While there are some great locations for couples to take pictures of the skyline together, nothing beats being up on the top of a tall building where one can look out over the entire city.

The Bristol

Built-in 1927, this bar has become a prominent location for those looking to enjoy nice drinks with good food.  

It’s located on the North Side of Chicago just off the intersection of Lincoln Avenue and Clark Street.  The Bristol is known for being both classy as well as comfortable at the same time.

If you’re looking for where to laugh before visiting the bar, you can check out Chicago comedy spotlights for the upcoming events.

Tour Michigan Avenue by horse and carriage

One can’t forget that there are many tour activities where one could enjoy the Windy City with their significant other.  

For example, it’s possible to take a horse and carriage down Navy Pier, which is located on the far North Side of Chicago in Streeterville.  

As with all things in life, this tour provides both a taste of the area as well as a unique opportunity for those looking to add a little something extra into their life.

Set sail across Lake Michigan

Since the Great Lakes are one of Michigan’s best resources, Set Sail is an experience unlike any other.  

It’s known as the only company to offer overnight sails on Lake Michigan due to how they guarantee customers will catch a breathtaking sunrise or sunset on their trip.  

While on the ship, guests are able to enjoy live music as well as different activities such as kayaking or paddleboarding.  For those wanting to take their relationship to the next level, this is one romantic experience that shouldn’t be missed.

Watch a Broadway show at Chicago Theatre

Located in the Loop, Chicago Theatre is one of the most prestigious venues for watching a Broadway show.  

From classics such as Wicked or Les Miserables to newer pieces like Hamilton, there’s something at this theater for everyone.  

For those looking to experience some culture together, this venue is perfect given its beautiful architecture and history.

Tour Chicago by helicopter

One of the most romantic things to do in Chicago is to take a helicopter ride around the city.  

From beginning to end, Tour Chicago Helicopter offers an exciting trip that includes some fantastic views of downtown Chicago. 

Not only does this company provide a personalized experience, but it also offers tours for those with respiratory problems.


Couples in Chicago have a wide range of interesting things to do when they’re looking for something different to try out.  

While an ideal date may be dinner and a movie, there’s definitely nothing wrong with venturing off the beaten path every once in a while.  

One can find many opportunities in the Windy City to explore fresh ideas and have a great time.

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