Chicago is one of our favorite cities for couples. It’s got everything from romantic adventures to exciting excursions, fine dining to fun snacks, and even great shopping.
Whether you prefer museums or love the great outdoors (and frankly, anything and everything in between), there’s something for both of you to love in Chicago.
If you’re looking for things to do in Chicago for couples, check out our list of the top attractions and activities, including…
- 360 CHICAGO
- Architecture River Cruise
- Shedd Aquarium
- Tall Ship Windy
- Art Institute of Chicago
- Field Museum
- Big Bus Chicago Tour
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Save on Admission to Popular Adult Attractions
Regular admission to a number of these attractions are included on the Go Chicago Card.
Choose as you go from dozens of Chicago activities and save up to 55% off combined admission vs paying at the gate.
See the city from above at one of two fantastic observation decks: SkyDeck Chicago at Willis Tower or 360 CHICAGO at the John Hancock building.
Both offer amazing views of the city below, but each have unique strengths.
You can see parts of four different states at SkyDeck Chicago! Or, if you prefer better views of Navy Pier and Lake Michigan, 360 CHICAGO and their exciting new TILT attraction is a good choice.
History & Natural History Museums
History fans, especially those with a taste for local history, will also get a lot out of a trip to Chicago. Visit the Chicago History Museum for a specific focus on the heritage and history of this marvelous city.
With its convenient location in the south part of Lincoln Park, the Chicago History Museum is also right near Old Town, a trend neighborhood with plenty of great food and drink options. We love Broken English (for tacos and margarita specials) or Old Town Pour House (for good apps and craft beer, plus sports tv).
Or, head to the Field Museum for a fascinating perspective on the natural history around the globe. Here you’ll find everything from SUE, the iconic T. Rex skeleton, to gorgeous gemstones of all varieties to Ancient Egyptian artifacts.
Do you both simply adore the sea? Then a visit to Shedd Aquarium is a must-do activity for almost any age. This world-class aquarium features hundreds of sea critters, great and small.
Encounter animals from fresh and saltwater, creatures who live near the water but are primarily terrestrial, and even seabirds.
From amusing penguins to intimidating sharks, you’ll find it all here. And with the Go Chicago Card, you’ll get priority entry!
Entrando: Shedd Aquarium admission is included on the Go Chicago Card.
Amazing Architecture Excursions
Chicago is famous for its eclectic and innovative architectural makeup — with iconic buildings designed by everyone from Frank Lloyd Wright to Mies van der Rohe.
If you’re a couple who loves art and architecture, or unique sightseeing in general, then an exploration of Chicago’s architectural scene is perfect for you.
One popular option is a tour of the Chicago River and the many beautiful and buildings visible from the water. This relaxing and informative cruise provides many opportunities for excellent photographs!
If you want to see more of the city’s architecture than can be seen from the shores of the Chicago River, then embark on a themed architecture walking tour run by the city’s more significant architectural organization.
Entrando: Chicago Architecture Boat Tour admission are both included on the Go Chicago Card.
Hop-on Hop-off Big Bus Chicago Tour
It can feel a little too touristy sometimes, but the trick to a good city tour is to find one that balances fun and information and convenience, all in one great package.
A hop-on hop-off Chicago bus tour is a great option here, as it provides the flexibility of boarding and disembarking wherever you please for maximum customizability.
See all the best sights of the city, from major landmarks like the Willis Tower and the Wrigley Building to top local attractions like the institutions at the Museum Campus and beyond.
Entrando: Hop On Hop Off Chicago Bus Tour admission is included on the Go Chicago Card.
Lake Michigan Cruises
If you are looking to get out on the water of Lake Michigan, we recommend taking a peaceful cruise offered by Shoreline Sightseeing — one of the best ways to see the city of Chicago.
This classic lake tour showcases the major sights along the shore – like Navy Pier and the beaches — and also the wild marine life found out on the lake.
Another excellent option is Tall Ship WINDY – which is Chicago’s renowned 150-foot four-masted schooner. This is a unique chance to sail the waters of Lake Michigan aboard one of these historic vessels.
Top Art Museums
Artistic couples and friends will find much to love about Chicago’s museum scene.
The world famous Art Institute of Chicago is the ideal artsy attraction, and boasts unique and beautiful architecture of its own. From the Renzo Piano-designed Modern Wing to the classic original structure, you’ll find a wide selection of pieces from Chagall’s American Windows to Georgia O’Keeffe’s “Black Cross New Mexico.”
The smaller Museum of Contemporary Art is no less fascinating with its focus on living artists and the most recent developments. They have fun and funky rotating exhibits that feature everything from installation art to graphic art to sculpture.
Plus, new for 2018 — a renovation and a new restaurant (the excellent Marisol) make this the hot spot to be.
Chicago is an extraordinarily bike-friendly city. From the many trails and pathways around the lakefront to the giant parks located throughout the city, there are plenty of low-stress places to pedal a bike.
If you’re a local or a real bike expert, you can even use a bike as transportation to get around the heart of the city itself.
So rent a couple of bikes and head off on your own outdoorsy adventure in lovely downtown Chicago!
Entrando: Bike and Roll Chicago bike rentals are included on the Go Chicago Card.
Chicago Theatre Tour
For the artsy couples or friends, the iconic Chicago Theatre is a must-visit attraction. Take a tour of this historic theatre and go behind the scenes of one of the art world’s most stories venues.
The beautiful French Baroque architecture is another testament to how important Chicago is to the history of design and architecture in America.
Plus, you’ll get to see the backstage walls autographed by the many, many celebrities who have performed on this stage, as well as a historic photo display. You’ll even get a chance to walk across the stage!
Entrando: Chicago Theatre Tour admission is included with the Go Chicago Card.
Beautiful Urban ParksOne of the most stunning things about downtown Chicago is its selection of gorgeous parks.
From the culture-filled Millennium Park to the festival-friendly Grant Park to the tiny but darling Lurie Garden, there is a park to wander and photograph for hours. Don’t forget to stop by the famous Cloud Gate sculpture, aka, the Bean.
Or, venture further out of the city center into Lincoln Park, which boasts a zoo and several beaches. It’s a great place to explore, ride bikes, run, play frisbee, etc.
Shopping, Shopping, Shopping
Whether you both love a good bargain or one of you is patiently accompanying the other, there’s oodles of shopping to be found in Chicago.
The Magnificent Mile is a particularly popular destination, featuring everything from elite couture shops to fast fashion favorites.
Or, head to Water Tower Place Mall for an excellent selection on everything from LEGOs to loose tea. A stroll along either locale is also just great sightseeing.
You’ll also be able to find souvenirs and more at many of the top attractions, too — the Art Institute of Chicago in particular has a stellar gift shop.
There’s more to Chicago than just the Mag Mile. In fact, some of the city’s best dining options are found in outlying neighborhoods.
Try the trendy neighborhood of Old Town for delicious cuisine and fun bars, or Wicker Park/Bucktown for boutique shopping.
If you’re craving Italian, try Little Italy & University Village, or if you want to embrace Chicago’s Polish heritage, scope out Portage Park.
Another fun neighborhood with great food and drink is Ukrainian Village, featuring a fun brewery, a top sushi restaurant, and some wonderful indie shops.
Remember to Save on Admission
As you can see from this brief list of some of the most fun things to do in Chicago for couples during your vacation, there are plenty of adult-friendly attractions in Chicago that appeal to a diversity of interests.
Whether you’re into bike-riding the lakefront trails or want to examine the many Monet paintings at the Art Institute, you’ll find that perfect attraction here.
Remember, many of these great activities are included on the Go Chicago Card, where you can save up to 55% on combined admission vs paying at the gate.
Consider adding a few of these fun options to your vacation itinerary. Enjoy!