Top Things to Do in Chicago for Couples

Chicago is one of the best places for couples to visit as it offers everything from romantic adventures to exciting excursions, fine dining to delicious snacks, and even some great shopping opportunities! Follow along as we count down our top things to do for couples when visiting Chicago - the Windy City.

Tripshepherd - Scenic Chicago Night Tour

Let’s face it one of the worst parts of a date is planning it, deciding where to go, how to schedule your time to fit in the best attractions, and waiting in line for tickets. Make your date night easier and reserve a spot with Tripshepherd on our small-group Scenic Chicago Night Tour.

This small-group Best of Chicago tour highlights the best ways to experience the Windy City's most prominent sites and attractions including the breathtaking Chicago architecture illuminated at night. You'll visit the former tallest building in the world, visit Adler viewpoint, and the famous Chicago Bean, and enjoy a relaxing boat tour on a Shoreline Sightseeing cruise.

You'll also experience a narrated drive through the Windy City passing by multiple points of interest including the remarkable Aqua Tower and stop at Buckingham Fountain to witness an outstanding night light show.

All our tours offer complimentary downtown Chicago hotel pick-up and drop-off, skip-the-ticket line entry, all attraction fees included (no hidden fees), and the comfort and style of a Mercedes Metris van.

If you are feeling extra romantic and want to enjoy the exclusive privacy of being the only people in the van and the opportunity to explore the city privately with one of our knowledgeable, fun, and friendly guides you can enjoy our Private Chicago Tour - a day tour of the city including spring water and a snack!

Shop Til You Drop!

Bond over shopping, or even go out to buy a new outfit for date night at any of the many shopping options Chicago has to offer. Whether you are looking to shop at any of the elite couture shops or fast fashion, Windy city has the best of both worlds.

Head over to the Magnificent Mile for the perfect mix for those looking for a bargain and those looking for something fancy or head to Water Tower Place Mall - offering everything from LEGO to lose tea. Either way, you will be able to find the perfect date night outfit or souvenir.

Marvel at the Beautiful Architecture of the City

The Windy City is infamous for its eclectic and innovative architecture and outdoor installations. You can marvel at the beautiful architecture and art from both land and sea! View the stunning architecture of the city on a shoreline architecture cruise on a relaxing Chicago River cruise where you can learn about the city’s architecture.

The city also features a large collection of outdoor public art including; the infamous Chicago Bean, also known as Cloud Gate and Crown Fountain in Millennium Park, the Chicago Picasso in Daley Plaza, Chagall’s Four Seasons a stunning mosaic, and Calder’s Flamingo in Federal Plaza, among many other unique sculptures positioned throughout the city.

Visit an Art Museum

Chicago is a beautiful city for anyone interested in the arts, not only does it offer unique architecture around the city but it is also home to some great art museums. Explore the world-renowned Art Institute of Chicago offering a wide array of unique and beautiful architecture and a wide selection of art pieces from various artists.

If you're looking for a smaller, more intimate museum visit the Museum of Contemporary Art with its focus on living artists and the most recent developments. These contemporary exhibits feature everything from graphic art to sculptures.

Take a Romantic Stroll through any of the city’s Beautiful Urban Parks

One of our favorite things about Chicago is its selection of stunning parks, ranging from the culture-filled Millenium Park to the lively, festival-friendly Grant Park there is a park for you to wander and photograph for hours!

Enjoy a picnic at Garfield Park with its beautiful conservatory home to 120,000 tropical plants and over 1.6 acres of glass-topped indoor space. You can also catch some sun at Jackson Park at the water's edge with beaches, marinas, lush green playing fields, and landscaped lagoons.

It is also an extraordinary bike-friendly city offering plenty of trails and pathways along the waterfront to enjoy a scenic ride. The city is flat making it perfect for a stress-free ride with a very limited amount of hill to pedal up.

Enjoy a Stunning Boat Cruise

Get to know the beauty of Lake Michigan while admiring the stunning architecture and cityscape on a peaceful cruise offered by Shoreline Sightseeing. The tour showcases many major sites along the shore including the Navy Pier and the Beaches, while also learning about the marine life found in and around the lake.

Explore History & Natural History Museums

Visit the Chicago History Museum to learn about the heritage and history of Chicago together. With its convenient location in a trendy neighborhood offering plenty of great food and drink options, the Museum is great for those hoping to make a day out of it.

For natural history around the globe, visit the Field Museum, featuring exhibits ranging from the iconic T. Rex Skeleton to Ancient Egyptian Artifacts and gorgeous gemstones!

Visit the Animals at Shedd Aquarium

Perfect for couples fascinated by the sea, this world-class aquarium features hundreds of both large and small sea creatures. From comedic penguins to intimidating sharks, to seabirds - you will find it all here at the museum!

Take in a Unique View of the City from an Observation Deck

Perfect for thrill-seekers, the city offers two great observation decks: Skydeck Chicago at Willis Tower and 360 Chicago at the John Hancock building.

Both offer unique and amazing views of the city below, at Skydeck Chicago view part of the four different states, or take in views of Lake Michigan and Navy Pier at 360 Chicago including their new and exciting TILT attraction!

As you can tell, Chicago offers couples a multitude of perfect date night experiences so what are you waiting for!? Plan your next trip to Chicago!