2 Day Chicago Itinerary for Couples


Attention lovebirds, couples, and soulmates, we are handpicking some seriously romantic activities for your next weekend trip to the Windy City. This list is full of romance-encouraging fun for you and your partner to enjoy — check it out!

Day One:

Coffee First

Before the romantic events begin, you’ll need some fuel. Stop by Fairgrounds Coffee & Tea, located in the heart of Chicago, just north of the stomach full of butterflies. This trendy spot is a great way to kick-start your weekend adventure together. Sip on some reviving coffee while strolling through the city with your significant other. Let the romance begin!

Bask in Lurie Garden

Flowers and dates go hand in hand. For your first romantic event, take a walk in Millennium Park’s Lurie Garden. The garden is beautiful and will surely spark a flame between you and your partner. With plants that change with the seasons, there is always something new to see. But, no picking flowers to give to your lover, even if it’s tempting!

Lunch Near Millennium

If you’ve worked up an appetite from all of the flower-sniffing, take a short walk over to Remington’s. This Classic American Grill is in a great spot and has some bold flavors. Try their French Dip sandwich with shaved prime rib and horseradish.

Share a Kiss Beneath “The Bean”

If you are at Millennium Park, you have to see The Bean — it’s a rite of passage! Check out Cloud Gate and snap a few photos in front of the popular sculpture. Something about seeing a famous landmark with your partner brings you closer.

Enlivening Drinks 

After all of the outdoor fun, meet the evening with a lovely cocktail from The Gage. The perfect way to foster a romantic evening is to get some spirits involved. This iconic spot is right in the center of the city and offers mood-lifting cocktails for your enjoyment. Finish day one of your romantic getaway at this upscale spot.

Day Two:

Coffee Again (Obviously)

For day two, head over to Stan’s, located right on the Magnificent Mile. You and your partner will be able to wake up with a nice shot of espresso and a sweet donut. Kick-start your romantic day with some wake-up food.

Take a Window-Shopping walk down Michigan Avenue

Along this famous street, there are iconic stores to shop at and plenty of sights to see. You and your partner can leisurely peruse the windows of famous stores like Nike, Burberry, Apple, Gucci and more. Discuss your likes and dislikes of the store goods along the way for an even better bonding experience. You can even utilize online ordering with in-store pick-up to make sure you are staying socially distanced. 

Grab Lunch at Labriola

This Italian cuisine screams Chicago, mostly because of their delectably-famous pizza! You and your partner will love getting a taste of Chicago cuisine together at this spot. After all, shopping makes you hungry.

Take a Boat Tour on the Chicago River

While you are close, you and your person have to stop by the river. Shoreline Sightseeing offers engaging boat tours that you and your partner will love. If you are interested in architecture, history, and more, these tours are perfect for you and your partner.  Learn more about the Second City and take in romantic Chicago views along the way.

Have a Sweet Treat

Chocolate inspires romance, so stop by Teuscher Chocolates of Switzerland and have some. Right on Michigan Ave, this sweets shop is the perfect way to make your night even more intimate. Grab some hand-dipped fruit for a romantic snack.

Finish Up Your Night at Lawry’s The Prime Rib

End the last day of your couple’s getaway with a high-end meal on the Magnificent Mile. This place is great for a date with delicious drinks for you and your partner to sip together. Order a delightful steak and a passion-inspiring red wine to end your night on a delicious note.

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