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  • Writer's pictureCatherine

A Couples' Guide to a Romantic Chicago Weekend

If you’re from Wisconsin you know that Chicago is a great city adventure to travel to for a romantic weekend. It’s the perfect destination for couples who want to experience more city life and want to relax in style.


Drive down to the city and check into your Chicago Athletic Association Hotel, your accommodations for the weekend. This has been noted as ‘hottest hotels’ that has preserved the artifacts of the city's past. Select rooms feature views of Lake Michigan lakefront through original gothic traceries and arches. This hotel is very unique in the fact that it used to be a men’s only club. Now you can find a club room still there, of course anyone staying at the hotel can access it, with billiards, shuffleboard, and craft cocktails.

After you check-in, you can head down to the lower level to Shake Shack for a quick bite to eat. Or if you want to eat in style, have a delicious lunch at Summer House Santa Monica. The restaurant's West Coast vibe makes you feel like you’re on a tropical vacation.

Next, with your hotel in the center of downtown Chicago, you’re able to head right out onto the Magnificent Mile and walk along the streets of the city window shopping. Have dessert early by snagging a cupcake at Sprinkles Cupcake ATM.

As you walk back to your hotel, pay attention to when you arrive at the Chicago Riverwalk. Here you’ll find your next activity, a Chicago River Boat Architecture Tour. Chicago is a city known for their architecture because they reflect the city's history and multicultural heritage, featuring prominent buildings in a variety of styles.

Grab dinner at Brando’s Speakeasy and sing your heart out with their karaoke. Finish your first night taking a stroll through Millennium Park as you head back to your hotel.


Sleep in and take time to relax together before heading out for the day. After you’re done getting ready head outside and take a quick 19 minute walk towards Beatnik On the River for brunch. It’s the perfect place to grab gorgeous scenic views of the river, great vibes, and amazing food.

After, if your stomachs can handle it, head to SkyDeck at Willis Tower to experience the city up in the clouds. You know that infamous glass box that hangs off the end of the building, yep you guessed it, it’s here!

If you’re looking for something a little more calming, try the Color Factory. It’s an interactive art museum located on the lower level of Willis Tower. You can continue exploring more beautiful art at the Art Institute of Chicago.

For dinner try a giant deep dish pizza at Giordano’s, this is a must because Chicago is known for their deep dish pizzas! End your night with a drink at your hotel's rooftop restaurant Cindy’s. Here you’ll find amazing food paired with panoramic views of Millennium Park, glistening Lake Michigan, the Art Institute of Chicago and so much more!


You’ve made it to your last day and there’s so much more to do! First start your day, having breakfast at Somerset. Then head south towards the Museum of Science and Industry. This area is a perfect spot to lose track of time and spend all day there. After the museum, you can take a stroll through the Garden of the Phoenix and enjoy the beauty of the park.

On your way back up, stop at Chinatown and have lunch at Sushi Plus Rotary Sushi Bar. This place is amazing because they have a sushi conveyor belt. This place gets packed quickly so be prepared to wait a bit for a table.

Once you have finished lunch, head to Navy Pier and enjoy a ferris wheel ride while taking in breathtaking views of the city. If you’re wanting something a little less active try the Field Museum, which is close by. Then take a short walk and check out the stars at Adler Planetarium.

End your last night in Chicago on the rooftop restaurant, London House, one of the best rooftop bars in Chicago.

Want to experience Chicago differently?

Planning a special experience with your partner means getting to know what they like and dislike, having them involved in the planning process, even if it’s just a little bit, and working together to crank out all the loose ends. Of course this can be tricky to do and if you have a lot of moving parts things can get complicated quickly. That’s why our Love-Break package is the perfect way to plan a romantic weekend away. Let our team of expert planners take over and create a romantic Chicago experience unlike any other, unique to you and your partner.

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