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Romantic Getaway in Chicago

From Local Experts

2 Days 52 Miles



from the local experts at Choose Chicago

Whether it’s for an anniversary or your first weekend getaway together, Chicago has tons of romantic spots for couples.

Start your staycation with an interactive cooking lesson, followed by cocktails with a view. Then get some culture and a taste of Chicago’s vibrant music scene. And don’t forget to book a hotel room for an overnight stay — there are great hotel packages and discounts all around the city right now.

Day 1:

Lincoln Square, Downtown, Wicker Park

  • People Walking

With heavily curated shelves of books, and a tasty menu of baked goods, Volumes Bookcafe in Wicker Park is a great spot to grab your morning Coffee.

The Chopping Block in Lincoln Square is offering in-person cooking classes on their outdoor patio, with plenty of space for social distancing. Choose from a variety of classes and demos, including wine tastings, a New Orleans-style brunch, and a German feast on the grill. You and your sweetheart can learn some new skills and enjoy generous tastings of each dish.

After class, enjoy cocktails with a view at one of the city’s many rooftop and patio bars. The Violet Hour, one of the city’s most famous cocktail bars, has recently opened a new outdoor space to sample their top-notch mixology. Near downtown, Three Dots and a Dash brings the tiki vibes to their new patio and The Laurel Room is a chic and airy rooftop space that feels like a California getaway. 

For an unforgettable experience at a Michelin 3-Star spot, Alinea in Lincoln Park should be booked well in advance.

Day 2:

Hyde Park, Chinatown, Humboldt Park, West Loop, Lincoln Park, River North, Old Town

  • A couple out for dinner

Grab some bites to go from a local restaurant and settle in for a scenic lunch at one of these top picnic spots. Check out spots like Ping Tom Memorial Park on the riverfront in Chinatown, near the historic boathouse at Humboldt Park, or Promontory Point with sweeping lake views in Hyde Park.

After lunch, visit the Art Institute of Chicago. Even if you’ve been before, the museum’s massive collection means there’s always something new to see. Wander through their famous Impressionist rooms (one of the largest collections outside of The Louvre in Paris) before checking out their recently extended special exhibit El Greco: Ambition and Defiance.

For dinner, cross one of Chicago’s most romantic restaurants off your bucket list. Dine in a hidden garden on the patio of Piccolo Sogno, or enjoy a Michelin-starred tasting menu at minimalist Elske (the name of the restaurant means “love” in Danish). And Geja’s Cafe in Lincoln Park is a classic for couples — the fondue spot bills itself as the most romantic restaurant in Chicago, with hundreds of proposals each year.

End your evening with a nightcap and some live entertainment at one of Chicago’s music and comedy venues. Catch local and national standup acts at Zanies in Old Town, outdoor concerts on the patio at City Winery’s West Loop location, or live jazz in River North at Andy’s Jazz Club.

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