From boat cruises across the azure waters of Lake Michigan to picnics in Millennium Park and premier shopping on the Magnificent Mile, there is so much to see, do, and eat in the Second City.
Whether you’re a duo with your sights set on devouring every last Chi-town delicacy, or you’d rather sink your time into scoring scenic 360degree views of the lakefront. This urban oasis is a veritable playground for couples on the prowl.
Ignite your passion when you book an unforgettable romantic rendezvous in Chicago today!
Cool nights in Chi-town call for the coziest and most luxurious accommodations. Sleep in style with your significant other when you book any of our romantic Chicago Hotels.
Enjoy top amenities and upscale details such as hardwood flooring, plush lounge seating, marble-tiled bathrooms with luxury toiletries at the SOPHY hotel, or embrace boutique lodgings just minutes from Wrigley Park.
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Wherever you choose to relax with your dearest, reserve your stay with confidence knowing you are always guaranteed our lowest rates.
Most Romantic Restaurants
From five-course fine dining to street-style eats, the Chicago culinary scene is a thing of ever-evolving beauty. Share a sumptuous dinner for two in an amour filled atmosphere when you reserve a table at any of our favorite romantic restaurants in the Second City:
Some things never get old, including dinner with a view—feast both your eyes and your tummy when you dine at NoMi. Revel in epic views of Water Tower Place and Lake Michigan, thanks to their floor-to-ceiling windows.
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Savor Lobster Beignets, prime ribeye, and aubergine gratin before moving on to their heavenly affogato.
Virtue is often overrated, but not at chef Erick William’s seriously sexy restaurant.
Linger over southern American-inspired cuisine such as gumbo, glazed sweet potatoes, and shrimp served with buttered grits as you embrace the mood lighting and soulful playlist.
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Be sure to save room for their famous banana pudding served with classic ‘nilla wafers.
Do you go weak in the knees for anything, Austen? Embrace the British manor aesthetic with a dash of uptown swank at the Darling.
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For a fancy cocktail with a side of live performance, dine at the Library, or for a full sit-down experience, make a reservation at the Ballroom for libations such as the ‘fox & the hound’ and enjoy exquisitely hearty pub food.
Turn up the heat and the romance with a four-course fondue dinner at Geja’s. For over 50 years, this cafe has let couples dip, sear, and roast their way to epicurean enjoyment.
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Dunk bread into creamy Swiss Gruyere, and then choose from any combination of beef tenderloin, Australian lobster tail, white shrimp, fresh sea scallops, and boneless chicken breast.
Most Instagrammable Spots
Instagram husbands, wives, and partners relax! We’ve taken the guesswork out of compiling Chicago’s most scenic spots to bring you the most romantic couples' vacation pics yet:
Touristy, yes! But it doesn’t get more iconic than this reflective art structure in Millennium Park.
Willis Tower Skydeck
Feel light as air as you document the outstanding views and epic shots of this legendary tower thousands of feet in the air.
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‘Greetings from Chicago Mural’
Innovative street art abounds in the Windy City. Still, we have a soft spot for this mural located in Logan Square, which happens to be the first official on-the-road ‘postcard mural’ by NYC graffiti artist Victor Ving and Ohio-born photographer Lisa Beggs.
Michigan Avenue Bridge Viewpoint
Capture one of the city’s most recognizable vantage points on this picturesque bridge which perfectly frames the Chicago River and city skyline.
A bustling urban concrete jungle may not be what comes to mind when you picture a swoon-worthy sunset. Still, Chicago’s striking architecture and staggering skyscrapers provide a social media-worthy backdrop for some incredibly romantic sunset pics.
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Our top spots for sunsets in the Second City include:
City Parks & Sightseeing Tours
Shoreline Sightseeing Boat Tours
Ahoy Mate! Set sail for a day of high sea adventure with your first mate when you book any of the exclusive Shoreline Sightseeing Boat Tours.
A novel way to soak in the famous history, architecture, and culture of the Windy City, choose from three distinct cruise experiences to tour Chicago:
- Skyline Lake Tour - a quick 30-minute ride complete with live narration that showcases Chicago's colorful history and famous landmarks, including the John Hancock, the Tribune Tower, and Willis Tower, as well as Grant Park and Buckingham Fountain.
- Architecture River Tour from Michigan Avenue or Navy Avenue - a 40-minute comprehensive cruise tour focused on the area’s outstanding architecture and engineering.
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All tours include live narration, history, and fun facts regarding Chicago's role as the skyscraper's birthplace and modern architecture.
Chicago's Ultimate City Bike Tour
Pump those breaks, and pull on that helmet for an action-packed day of biking, sightseeing, and more on your Chicago's Ultimate Bike Tour.
Athletically inclined partners will appreciate the dual combination of Chicago’s most significant historic landmarks and locations married with physical activity.
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Stretch out those hammies as you and your boo embark on a 2.5 hour, 6-mile ride of the Windy City, including stops at:
- Museum Campus
- Cloud Gate (the Bean)
- Grant Park
- Buckingham Fountain
Novice bike riders are welcome as you will be going at a leisurely pace, with plenty of opportunities to stop for selfies and photo documentation.
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Night Crime Tours
Take back the night with your very own partner in crime on one of the sultry after-dark Night Crime Tours.
Ideal for gruesome twosomes who love a touch of macabre and danger, this 2.5-hour adults-only tour takes you on a wild ride through Chicago’s seedy underbelly.
Climb aboard your luxury bus and prepare for an eventful evening of visiting infamous crime scenes, historic bars, and untold photo opportunities.
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Set foot on the same hallowed ground as the St Valentine's Day Massacre, The Biograph Theater, Holy Name Cathedral, and Cook County Criminal Court House, as well as Chicago neighborhoods made famous by their crime.
Lap up true stories about the most devilish and devious criminals of all like John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, and Al Capone, all while participating in a fun crime quiz and interactive live commentary.
Ice Skating in Maggie Daley Park
Gliding around a sparkling ice ribbon hand in mittened hand with your loved one while soaking in the striking Chi-town cityscape. Is there anything more romantic than couples ice skating in Chicago?
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Spend a few hours in a veritable winter wonderland when you make reservations for ice skating in Maggie Daley Park.
Lace up those skates and show off your best moves when you speed around this stunning path that is twice the length of a traditional ice skating rink.
This year’s skating season promises to be especially sweet as the ribbon will be adorned by artwork inspired by Van Gogh’s seminal works of ‘Sunflowers’ and ‘Starry Night.’
Warm up with a rich cup of cocoa post skating session, and be sure to take a few cute couples selfies and cross this romantic adventure of your Chicago winter bucket list!
Art, Architecture, and Museums
360 Chicago Observation Deck
Hold tight to your honey’s hand as you both marvel in awe at the jaw-dropping views offered up over 1,000 ft in the air.
Challenge that fear of heights and experience a thrill like no other when you travel to the 94th floor of the John Hancock Center on your 360 Chicago Observation Deck visit.
A ‘must do’ for any daring duo, the 360 Chicago Observation Deck is the only place to observe panoramic views of Chicago, Lake Michigan, and four neighboring states.
Level up the romance of this award-winning view by sharing a cocktail with your companion at the Observation Deck’s bar & cafe or testing your mettle on TILT- Chicago’s highest thrill ride.
Be sure to budget time to take in all interactive and immersive exhibits on both the concourse level and 94th floor that detail Chicago’s history, architecture, and long-standing culturally diverse neighborhoods.
Art Institute of Chicago
If the secret of art is love, it stands to reason that an enchanting afternoon gazing at masterpieces of yore is a recipe for amorous affection.
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Titillate your turtle dove with the pure power and passion of artistic visionaries when you spend a day at the Art Institute of Chicago.
Gaze at such seminal works as Pablo Picasso’s “The Old Guitarist” and Grant Wood’s “American Gothic” and more modern pieces from pop-focused Roy Lichtenstein.
This acclaimed museum is consistently ranked as one of the world’s best and features over 300,000 works of art from across the centuries and around the world. So whether your tastes run classic to post-modern, the Art Institute of Chicago has something for everyone.
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
Not all art is found in museums! Stray off the traditional path and intrigue your lover with a non-conventional art tour when you unearth the underground world of Chicago’s street art.
Your Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals is the ideal foray into the expansive street art community and scene.
Strap on those walking shoes, and begin your 2-hour sojourn led by your local experienced art guide.
Pay close attention as they impart essential in-depth commentary and insight on the street art movement, its history, and specific artists.
Enjoy stealthy stops at:
- Wicker Park - home to many murals and local pieces of street art.
- The 606 - a unique urban corridor.
- Ipsento 606 - a sneaky tour surprise may be in store for you here!
- Logan Square Chicago - observe even more celebrated urban art here.
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Famous Tastes of Chicago Food Tour
Chi-town food is the stuff of legends. From deep-dish pizza to Italian beef sandwiches, there are many midwestern delicacies to try.
Delight your fellow foodie-loving fanatic with the best treats of the Windy City when you reserve a spot on the Famous Tastes of Chicago Food Tour.
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A veritable smorgasbord of mouth-watering eats, culture, and history, this intimate 3-hour food-focused tour will take you on an unbelievable epicurean escapade featuring everything from specialty food shops to over 80-year-old restaurants.
Much on six samples of quintessential Chicago dishes and enjoy visits to:
- Pizano's Pizza & Pasta
- Goddess and the Baker, Wabash
- Chicago Kernel Gourmet Popcorn
- Fannie May Chocolates
- Billy Goat Tavern
- The Berghoff
Chicago Favorites Food and Walking Tour
Squeeze in those steps and those delicious samples when you and your sugar pie hightail it all over Chicago for some iconic eats.
Your 2.5 hour Chicago Favorites Food & Walking Tour is a fun-filled way to taste the flavors that made Chi-town famous.
Trade romantic bites of gooey deep dish pizza, moist chocolatey brownies, and sips of refreshing craft beer as you walk 1.5 miles through Chicago's most well-known neighborhoods, downtown hot spots, and historical sights.
Keep your ears and mouths open, as your affable and hilarious guide will have you in stitches with their offbeat humor and culinary history expertise.
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Come hungry, as this fully inclusive tour features:
- An entire slice of deep-dish pizza
- An original chocolate brownie
- A craft beer
- A Chicago-style hotdog.
Chicago's Chinatown Food and Walking Tour
Get lovey-dovey over delicious dim sum and steaming hot pots on Chicago's Chinatown Food and Walking Tour.
Discover one of the most vibrant neighborhoods of the White City on this 2.5-hour culinary, cultural adventure. Walk and eat your way through the eclectic food scene of Chicago’s Chinatown with a nationally recognized tour company.
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Steal bites of authentic:
- Cantonese dim sum and tea
- Portuguese-Chinese bakery treats
- Xi’an cuisine
- Szechuan chicken
- Mongolian hot pot
Meanwhile, learning how this diverse array of Chinese cuisine made its way from Asia to the shores of Lake Michigan!
A distinctive dining experience like no other, this Chinatown Food and Walking Tour is not to be missed.
Underground Donut Tour: Chicago's First Donut Tour
Shower your sweetheart with some sugar when you book a delightfully delicious Underground Donut Tour: Chicago's First Donut Tour.
Donuts are the way to anyone’s heart, and there’s nothing sweeter than spending a day sampling the Windy City’s tastiest creations.
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Cleanse your palate and prepare your tastebuds for a sugar rush as you spend 2 hours visiting Chicago’s best donut purveyors. From chocolate sprinkled, to Boston cream, and jam-filled you can sample them all*.
Bring on the frosting, sprinkles, and creative fillings when you stop at:
- Doughnut Vault
- The Loop
- Firecakes Donuts
- Stan’s Donuts & Coffee
- Do-Rite Donuts & Chicken
**Vegan, gluten-free, and nut-free donut options are available.
Chicago Premier Dinner Cruise on Lake Michigan
Fire up the fancy when you and your ravishing date spend twilight cruising around Lake Michigan in your festive attire.
The Chicago Premier Dinner Cruise on Lake Michigan is a luxury affair that combines a gourmet three-course dinner, first-class sightseeing, and musical entertainment for one memorable night.
Anchors away when you board your high-end yacht for this 2.5-hour cruise. During your tour, you’ll witness the striking cityscape under cover of darkness.
Have your phone or camera nearby as you’ll be dying to document the stunning:
- Chicago Willis Tower (formerly Sears Tower)
- Navy Pier
- Shedd Aquarium
- and more
Your upscale maritime reprieve includes:
- Professional photo taken by the ship’s photographer
- A 3-course chef-inspired dinner complete with hors d’oeuvres, entrées, side dishes, and dessert
- And lively musical entertainment
There is a full-service bar on board your vessel offering a variety of craft beers, unique cocktails, and wine which can be purchased at your own expense.
Romantic Chicago Sunset Dinner Cruise on Lake Michigan
Dust off that dance card and get ready to boogie the night away on a Chicago Sunset Dinner Cruise on Lake Michigan.
Dazzle your dreamboat with a fanciful evening under the stars with this 3-hour buffet-style dinner cruise of Chi-town.
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While toasting to your romance, glimpse at renowned Chicago landmarks such as:
Tuck into a tantalizing buffet-style dinner with such sumptuous eats as honey sesame chicken, braised short ribs, and more. Savor sinful desserts like raspberry mousse and a red velvet and chocolate chip brownie. Then head to the dance floor to enjoy a live DJ and fun interactive games.
Blue Man Group
So you and your significant other have already painted the Chi-town red? Jump into the ‘blue’ when you reserve your Blue Man Group tickets today.
An idiosyncratic live spectacle like no other, Blue Man Group is a tour-de-force cultural sensation that should not be missed.
Hear the pulsating bass of PVC pipe drumming. Experience the explosive paint splatter. Meanwhile, giggle at the good-humored social commentary during this immersive, critically acclaimed show.
From giant GiPads to Drumbones, the Blue Man Group’s auto visual performance incorporates music, technology, and more to create a thought-provoking statement on our modern lives.
Private Speakeasy Pub Crawl in Chicago with Local Historian
Shaken, not stirred! Perfect that cocktail shake and transport you and your dollface to a bygone era on your Private Speakeasy Pub Crawl in Chicago with Local Historian.
Enter a decade of bank robbers, bootlegging, and gangsters on this 3 hour 1920s Prohibition-themed tour.
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Your tour is led by your professional historian guide (who will be dressed in costume).
Your intimate group will traverse speakeasies, secret passages, and historic hotels. Meanwhile, you will learn the fascinating and deadly history of Chicago:
- crime lords
- enjoy delicious cocktails
Squeeze through private supper clubs and sip on Prohibition-era drinks* as you visit:
- The Loop
- Palmer House Hilton Historic Lobby
- Untitled Supper Club
- And more!
**Drinks are not included in the price of the tour
Private Vacation Photography Session with Local Photographer in Chicago
Because every picture tells a story, tell your very own love story for years to come with a Private Vacation Photography Session with a Local Photographer in Chicago.
A romantic getaway deserves more than just selfies! So step up your photo game, and create lasting memories of your time in the Second City when you book a professional 1-hour private photoshoot.
Besides dealing in all the best tips on what to see, do, and eat, your local photographer knows the most photogenic locales for capturing captivating couples' pics.
Ideal for memorializing any honeymoon, engagement, anniversary, or babymoon walk away from your vacation with stunning snaps from:
- Chicago Riverwalk
- Millennium Park
- North Avenue Beach
- Lincoln Park
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Take home 15 - 60 high-resolution digital photographs (dependent on your photo package). Also, you'll be able to relive the magic of your romantic Chicago vacation whenever you like.
From the historic Wrigley Field to the colossal Sears Tower and true crime-filled after-dark tours, Chicago is just teeming with excitement, exhilaration, and urban energy.
From the fitness inclined to the finicky foodies, every couple will find something to enjoy in the Second City.
Feel the wind on your face as you bike through the Bean and Buckingham Fountain, or stare into each other’s eyes as you learn about speakeasy’s sexy past while sipping a Sidecar cocktail.
However, you choose to spend your romantic getaway, the "city in a garden" is just ripe for love.
What Romantic Things to Do in Chicago Did We Miss?
Any romantic things to do in Chicago for couples we missed? Let us know in the comments below!