21 Most Romantic Things to Do in Chicago For Valentine's Day

We do live in a pretty romantic city!

January 23, 2019

Valentine's Day is all about romance. When else are you going to swoop your significant other off their feet?

Thankfully, we live in one of the most romantic cities in the world -- #8 according to Instacart Romance Index

Related: 14 Most Instagram-Worthy Places in Chicago

It's impossible not to fall in love while strolling by the lake with the skyline gleaming behind you. 

The city offers plenty of romantic offerings in the city, so check out our suggestions and plan the most romantic date night of your life this Valentine's Day! 


Around The City

1. You Spin Me Right Round

Take in the sights of the city aboard the Centennial Wheel, which offers 360-degree views of Chicago in enclosed gondolas that are perfect for snuggling. 

“Hay que intentar hacer el bien cada vez que uno pueda. Las vueltas que da la vida no se pueden adivinar”. - Se acerca la hora de regresar y quiero darte gracias Dios, por la sorpresa que me tenías reservada. - #NavyPier | #Chicago | #Shooting - Fotografía: @ncphoto555 --

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2. Take a Valentine's Day Cruise

Take your romance to the water aboard Chicago's cruise lines. Odyssey is offering a few Valentine's Day Cruises -- a Riverfront Cruise, a Lakefront Cruise and a Brunch Cruise -- while Spirit Cruises is offering a Valentine's Day cruise complete with a dinner buffet and dancing with a live DJ. 

Cruise time! #odysseycruisechicago #happynewyear2018 #letthefunbegin #chicago #navypierchicago

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3. Snuggle Up in an Igloo

The Godfrey and City Winery aren't letting the cold weather stop the romance. You can take in the views of the city in a heated, transparent igloo. Each igloo seats up to six. Enjoy a delicious menu of shareable small plats and some wintery-themed drinks. I'd argue there isn't anything a more romantic setting in this city. Be sure to make a reservation in advance! 

See the coming snow in the comfort and warmth of a #vip igloo! #GodfreyStyle #WinterWonderland

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4. Rooftop drinks at Cindy's on Michigan Ave

Some of the best views of the city can be found at Cindy's on Michigan Ave. Stop by for the drinks, stay for the cozy atmosphere. 

Making the last #SundayFunday of 2018 count ✨--✨ Please note we'll be closed for a private event on New Year's Eve – our last seating tomorrow will be 2PM. --: @hilauren

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Something Sweet 

1. Satisfy your sweet tooth! 

Head over to Margie’s Candies, a mainstay in Bucktown, and share a banana split together.

Baby it's cold outside, but the thought of Margie's Candies is sure to warm your thoughts! Why not plan on bringing that special someone here for Valentine's Day? Our selection of fine chocolates and ice cream can't be beat!

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Pamper & Relax

1. Escape from Reality at Aire Ancient Baths 

You've never experienced a spa quite like Aire Ancient Baths, set in a 1900s factory and boasting Roman and Greek architecture. There are many options to choose from including candlelit thermal baths, aromatherapy steam rooms and massages. For a steep price of $500, you can get the most indulgent Valentine's Day experience by soaking in "the antioxidant properties of the Spanish Ribera del Duero red grapes in this special and unforgettable journey designed for two." While you're enjoying yourself, you can dine on Wine and a cheese board. You may also opt for The Sweetheart Ritual package

Do you have your gifts ready? Right in time for a virtual gift box. Visit link in bio... let the magic begin #holidaygifts #experience #beaire #giftsomethingmagical

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2. Cozy up by the fireplace at Chief O’Neils 

Chief O'Neils, a British-style pub decked out in Irish decor and offering a traditional menu which includes Guinness-inspired treats. Grab a pint, some fish and chips or Guinness Cheddar soup, and cozy up by the fire for the evening. 



Romantic Dinner Options

1. Eat on the River

Dine on Italian and steak while overlooking the river view at Gibson’s on the River. Be sure to surprise your love with a dessert with a chocolate sign that says “I Love You” in chocolate by calling in advance or whispering to your waiter as you “head to the bathroom."

Snow days aren’t so bad after all. --: @chicagofoodauthority #GibsonsItalia

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2. Views + Dinner at the Signature Lounge

Nothing says Chicago and romance quite like the Signature Lounge atop the John Hancock Center. Drinks and dinner with your significant other as you're taking in the view of the city from the 96th floor is indescribable, which is why it's the "signature" thing to do on Valentine's Day. Just be aware -- everyone around you is going to be getting engaged! If you are interested, be sure to make reservations ahead of time. 

We made it to the weekend! Treat yourself to food, cocktails & views on the 96th floor! --: @sladja.purkovic #signatureroom

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3. A Little Fondue Never Hurt Nobody

Is there anything more romantic than chocolate dipped strawberries, marshmallows or various meats, veggies and seafood alongside a delicious cheese fondue. You can both and a romantic atmosphere at Geja's Cafe in Lincoln Park or at the Melting Pot

Grab your fondue fork and take a dip! --: @brittanyreichwein • • • • • #chicagorestaurants #lincolnpark #chicago #fondue #datenight #romantic #wine #mondaymotivation #foodie #lincolnpark #gejascafe #chicagofoodie #eeeats #nomz

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4. Go to Italy

Well, Eataly. The Italian mega-market and upscale food court is located in River North and boasts seventeen restaurants and cafes. While you're there, shop around and enjoy some imported beers and wine. Or check out the latest pop-up concept, BAITA, an Alpine-themed restaurant that screams "hygge" with holiday decor, blankets, and fireplaces. The menu includes ski-lodge approved bites like pillowy gnocchi, melted raclette cheese  and Roman-style pizza.

This winter, it's wood-fired Neapolitan style pizza > fireplaces. ---- #myEatalyChicago - - - EAT: Have you tried our Neapolitan-style pizza? For our classic recipe, we've teamed up with the experts at Rossopomodoro, a Napoli-based pizza company, to bring you traditional Neapolitan pizza. Creamy mozzarella, charred yet elastic crust, and sweet San Marzano tomatoes make for a pizza so delicious you will be singing along with our vibrant Neapolitan pizzaioli (pizza makers). @rossonyc

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Have A Little Fun

1. Recreate Your First Date

Just because you've been together forever doesn't mean you have to lose the romance. Recreate what you did the first time you went out. Did you meet at a coffee shop? Did you grab dinner at a local joint? Did you catch a movie? Reignite the spark! Bonus points if you even dress the same way you did on your first date... if you even remember you wore. 


2. Cooking Class

Do something out-of-the-box this Valentine's Day — take a cooking class at The Chopping Block. You won't regret the memories you make and you definitely won't regret the delicious meal you whip up together. You might even learn some useful skills for the kitchen! 

The ultimate family bonding experience is an old fashioned throw down in the kitchen. See how @pageandplateblog planned a friendly #cooking competition for the holidays in today's blog (link in profile). Are you ready to put your family, friends or colleagues to the test? #thechoppingblock

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3. Put Your Heads Together at an Escape Room

Escape Room's are all the rage these days. They force you to bond and work together. Check out The Escape Game Chicago in River North! 

That face when you escape with 0:01 on the clock! ⏱--

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Get a Little Hipster

1. MoneyGun, MoneyGun, MoneyGun

Grab drinks at MoneyGun in the West Loop. It's a speakeasy-type bar nestled inside fo an unassuming building and a restaurant.

ICYMI, @britishgq named us one of the coolest things to do in Chicago! That’s pretty high praise, if we do say so ourselves. Head to our Facebook page for the article, and to 660 W. Lake Street for the drinks.

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2. Au Cheval

Love is eating the best burger in the city together. Grab dinner and drinks at Au Cheval in the West Loop. It has a diner vibe, but they also play music "reel-to-reel."

Leadership opportunities available at www.hogsalt.com/jobs/

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Grab Some Libations

1. Get Lost in Paradise

Escape to a tropical destination over drinks at Lost Lake on Diversey.

Leadership opportunities available at www.hogsalt.com/jobs/

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2. The Language of Love

Get serenaded by a mariachi singer and guitar player at Maria’s Mexican Restaurant on Harlem while sipping killer margaritas and eating fajitas. 


3. Sip on Some Wine

Chill out in an intimate setting at Angelo's Wine Bar for pizza and wine flights.

Restaurant week starts today! Make your reservations. . . . #angeloswinebar #resturantweek #cocktails #wine #chicago #chicagoeats #bestfoodchicago #chicagowinebar #food #instafood #foodie #bar #foodandwine #draaaaanks #eeeeeats #checkpleasepics #vscocam #huffposttaste #goodeatschicago #fabfoodchicago #chicagofoodscene #zagat #imbibe #imbibegram #cocktailparty #eaterchicago #redeyechicago #chicagopulse #chicagopizza

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Hang Out at Home! 

1. Cook a Cute Dinner with Heart Shaped Pasta

WorldMarket sells adorable heart-shaped pasta that could pair really well with lobster and greens.

Look at this super cute #ValentinesDay pasta! I ❤️ @worldmarket ! #WorldMarket

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Under that cream sauce is the #ValentinesDay heart-shaped pasta from @worldmarket I was so excited about! It paired well w/the lobster, green beans, white wine & #HarryPotter on the TV lol #GreatestGirlfriendEver

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2. Unleash Your Inner Bartender

Get crafty by whipping up a signature love potion (or a few) for you and bae. Check out this list and make whatever your little heart desires!