Couples Itinerary: A Day Trip to Chicago


For all the love birds out there, we want to help you put together the perfect date. This itinerary is a great pick for a romantic day in Chicago. We’ve picked the most charming spots we could think of – check it out.

First on the list for the day: head over to the Riverwalk for an intimate stroll through the heart of Chicago’s skyscrapers. Look up at the city in awe and across at your partner with love. Along the Riverwalk, you’ll find a number of exciting activities to choose from. If you’re hungry, have a picnic with food you brought from home right by the river.

If picnicking isn’t your style, head over to City Winery Chicago for a tall glass of wine and a plate of delicious food.

Next up: Take a nice boat ride right on the Chicago River. Near the Riverwalk, you have your pick of numerous tours. Check out Chicago’s First Lady architecture boat tour, rated number one by Tripadvisor. Enjoy the nice weather and gorgeous Windy City views with your partner. Relax while contentedly riding the waves and learning about Chicago. Make sure to check their website for available times. At time of publishing, tours are only available on weekends.

Third up: head over to Wicker Park, a trendy and happening north-side neighborhood. Wicker Park is a fun spot with lots of stores with ornate, eclectic, and nice items. While you’re there, walk the blocks and stop in shops that catch your eye. Milwaukee Ave. is a center for these cool stores, so be sure to stop there. The street is home to a variety of vintage stores, like Kokorokoko. The happening vibe of Wicker Park is sure to feed the light-hearted energy of your date.

To complete the night: head over to Wicker Park’s Kennedy Rooftop. This brand-new bar and restaurant is the ideal way to top off date night. With a complete view of the Chicago Skyline, the city lights make the rooftop glow with energy. Enjoy craft cocktails while atop the rooftop. You and your partner are sure to love the intimate vibes that Kennedy provides.

Written By Emma McVady

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