Romantic Things To Do In Chicago

It's hard to sum up all the romantic options Chicago has to offer but this curated list has something for every couple.  Whether you're seeking fun and adventure, want to explore the city or take a trip off the beaten path we have you covered. 

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Off The Beaten Path: Romantic Things to Do in Chicago 

Romantic Helicopter Tour

This one’s not so much off the beaten path but above it.  There’s nothing more romantic (or cooler) than dinner with your partner followed up by a nighttime helicopter tour of the city.   Enjoy the thrill and excitement of an intimate helicopter tour while you gaze upon the city in all its nocturnal glory.   See all of Chicago’s landmarks illuminated for a truly one of a kind view (and experience).  

source: here

Romantic Helicopter Tour | St. Jane Hotel Chicago
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Explore The West Loop

For those “in the know” the West Loop has some of the best foodie-friendly restaurants and authentic Chicago sights in all the city.  

Explore the West Loop and you’ll find…

City Skyline Chicago Hotels
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Visit Chinatown

Visiting Chinatown can be an experience in and of itself.  If you’re trying to make it romantic, which we’ll assume you are since you’re reading this, then you must check out the Tom (Ping) Memorial Park.  It’s absolutely stunning and sets the mood for a romantic stroll through carefully manicured gardens and exceptional Chinese architecture. 

About Ping Tom Memorial Park:

“Ping Tom Memorial Park’s 17.44-acre site was originally a Chicago and Western Indiana Railroad yard located along the edge of the South Branch of the Chicago River in the Armour Square Community. In 1998, the Chicago Park District began transforming the old rail yard into a beautiful rolling green space, taking full advantage of the impressive river views. Today, Ping Tom Memorial Park holds a children’s playground, community gathering areas and Chinese landscape design elements.”

src: https://www.chicagoparkdistrict.com/parks-facilities/tom-ping-memorial-park 

Chinatown Chicago
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Koval Distillery

This place has some history behind it, as Chicago’s oldest post prohibition distillery, and today it’s the go to spot for handcrafted spirits.  If you don’t like the hard stuff you might want to skip this one. Koval is renowned for their Whiskey and Gin.  They also distill hand crafted liqueurs and spirits.  They consider themselves the “Black Sheep of Whiskey Making” and they’re damn proud of it.  You can learn more on their site.

About Koval Distillery:

“Established in 2008, KOVAL produces organic whiskey, liqueurs and specialty spirits in Chicago’s first distillery since the mid-1800’s. Founders Robert and Sonat Birnecker, chose to leave their academic careers to bring the distilling traditions of Robert’s Austrian family to America. In making this decision, they vowed to make organic spirits from scratch (avoiding the common industry practice of purchasing and bottling pre-made spirits) and to change the way people understand whiskey by creating a new, signature style – using only the “heart” cut of the distillate – affording a brighter, cleaner take on whiskey.” 

src. https://www.koval-distillery.com/newsite/about-us 

Koval | Romantic Things to do in Chicago
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Art, Culture and Entertainment: Romantic Things to Do in Chicago

Looking Glass Theatre

What’s more romantic than a night out a the theatre?! Founded in 1988 by Northwestern University graduates, this theatre company is considered a nationwide leader in producing cutting edge plays.  They also give back to the community by working with aspiring actors and Chicago area youth and students.  Looking Glass Theatre won a Tony Award in 2011 for Outstanding Regional Theatre. With a constant stream of award winning shows you and your loved one can take it all in at this award winning theatre company. 

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Emporium Arcade Bar

This maybe isn’t as cultured as the theatre above, but we think it is just as romantic, and fun! Blast back in time and enjoy some competitive pacman (is that a thing?), classic arcade, pinball and table games. Foosball anyone? 

If you’re searching for a fun night out with your sweetheart and you enjoy arcade games or pinball, even a little bit, Emporium Arcade Bar is sure to fit the bill.  Where else can you play classic Mortal Kombat, Simpsons Arcade and Game of Thrones Pinball?  Also, they have a full bar and food available.  Their cocktail list looks tasty, but we’re really here for the video games.  It’s worth mentioning that outside food is allowed as their food menu is limited to bar snacks. 

Emporium Arcade Bar | Romantic Things to do in Chicago
Emporium Arcade Bar | Throwback Fun
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Adler Planetarium

We think it’s pretty romantic to gaze into the galaxy.  It’s also fun to learn something new with your loved one about space and our place in it.  The Adler Planetarium has everything a romantic evening needs.  Darkened room, check.  Glass of wine, check.  Looking into infinite space and traveling the cosmos together, check. There’s not much more that hasn’t already been said about the Adler Planetarium so we’ll leave it at this. 

More about the Adler Planetarium: 

“The Adler Planetarium connects people to the universe and each other. Whether it is introducing a guest to the Ring Nebula, a neighborhood school to a community partner, a research team to a network of citizen scientists, or one staff member to another, the Adler’s focus on meaningful connections dates back nearly a century.

Today, the museum hosts more than half a million visitors each year and reaches millions more through youth STEAM programs, neighborhood skywatching events, online citizen science, and other outreach projects. With the Adler’s support, people of all ages, backgrounds, and abilities gain the confidence to explore their universe together and return to their communities ready to think critically and creatively about any challenge that comes their way.”

Alder Planetarium | St. Jane Hotel Chicago
Enjoy Stargazing at Alder Planetarium
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RM Champagne Salon

Champagne lovers unite! If you love a glass of bubbly you’re in luck! Champagne connoisseurs, head to the West Loop for this decadent 1,500 sq. ft. space nestled in a secret cobblestone alley. It’s something you have to see to believe (and truly appreciate). RM Champagne’s fine selection of estate-grown wines and specialty champagne is sure to please anyone (wine lovers included)

Travel Caution: This place has a LONG waitlist! You’ll want to plan ahead.

QUICK TIP: Call our concierge at 312-345-1000 to make a reservation before you arrive.

Champagne Salon Romantic Date Ideas
IMG SRC: RM Champagne Salon
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Historic Hotel Tour

If you’re already staying at St. Jane​ you can skip this one!

You’re staying in a historic hotel (The Carbide and Carbon Building​).

If you’re not staying at our Magnificent Mile hotel head over to the Intercontinental Hotel for a tour. Like our hotel, this tour allows you to step back into the Roaring Twenties with prohibition-era decor and art deco inspiration throughout.

Intercontinental Hotel
Img: InterContinental Chicago Magnificent Mile | Like St. Jane Hotel Chicago this Historic Hotel is a throwback to the splendor of the roaring 20's.
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Thalia Hall

A beautiful historic landmark nestled in Chicago’s Pilsen neighborhood boasting a beer inspired restaurant, punch cocktail bar and a public hall.  Built by John Dusek with the intention of bringing the arts of Bohemia to Chicago.  Modeled after the Prague opera house and completed in 1892, Thalia Hall, remains largely untouched in all of it’s original splendor.  

About Their Venues

Thalia Hall

“Thalia Hall was built by John Dusek with the hopes of bringing arts and entertainment from Bohemia to play for his bohemian neighbors.  Architects Faber & Pagel, who modeled the hall after the Prague opera house, completed the public hall in 1892.  For over 7 decades the Hall was a beacon of the neighborhood community.  Thalia existed as one of the most ornate theaters of its times.  This opulence, which differentiated it from more traditional interior theaters, was granted landmark status in 1985.  The hall was used not only to house a multitude of entertainment over the years, but was also used as a central meeting spot for the neighborhood.  In 1915, the hall was used to draft a bill paving the way for bohemian statehood and the birth of Czechoslovakia in 1918.  Closed to the Public in the 1960’s, Thalia Hall has remained virtually untouched until the end of 2013, when we first began working on it.  Our goal is to restore Thalia to its original charm and character, to breath life into this community treasure, and to bring a wide array of music, community, and artistic events to the neighborhood it serves.”

Punch House

“Punch House is located in the basement of Thalia Hall. It’s a bar inspired by the history and manufacture of this original communal beverage. Punch was originated by British merchant sailors in the middle 17th century.  Borrowing techniques from the Far East to extend rum rations, these punches allowed for an all-day drink with mitigated effect. The term ‘Punch’ is borrowed from the Hindi word ‘Panch’ (meaning five), referring to strong, weak, bitter, sour, and sweet, the five flavors balanced in a batch of proper punch. Punch House will offer classic and contemporary punches by the glass, carafe and bowl.  A ‘Not Punch’ cocktail category will contain concise offerings of beer, wine, and sipping rum to supplement the Punch Program welcoming imbibers of all types.”

The Tack Room

“In 1890’s every Czech tavern owner didn’t have a piano bar but they all had a carriage house. John Dusek’s Thalia Hall was no different. In a forgotten about corner of the property, in a space that once housed Dusek’s horses, we have assembled a cozy cocktail bar. With a simple and curated cocktail menu, a view of Pilsen and patio seating, and a well-loved piano that has been patiently waiting to be played, it’s the kind of place you’ll stay all night: Tack Room, our last (maybe) addition to the Thalia Hall property. Nights will find our pianist banging out familiar favorites to be enjoyed by all. Let us know if you would like to sing along – we certainly encourage it.”

Thalia Hall
IMG SRC. Thalia Hall
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St. Jane Hotel
230 N. Michigan Ave.
Chicago, IL 60601


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