Summer Staycation: Your Guide to a Chicago Getaway


Welcome summer with a special trip for you and your family! There are so many exciting things happening as the weather gets warmer, which means it’s time to start planning your summer staycation. As the pandemic continues, safety is still at utmost importance, so these places are working their hardest to ensure a safe environment. That being said, here is a possibility for what three days of your getaway could look like:

The Hilton Garden Inn Chicago Downtown Riverwalk is the perfect hotel to stay in for this excursion because it’s right in the bustle of everything, not to mention it also has great dining, a great bar, and it’s right near public transit!  

Day 1:

After a great night sleep in your cozy hotel room, wake up with a cup of joe and some fresh breakfast from Yolk to start your day with a full and happy stomach. Following your wonderful meal, make your way to the Art Institute for a celebration of art and culture from around the world made through the eyes of some incredible artists. We’re so proud to have one of the top art museums in the world right here in our city! Leave inspired, maybe even reflect a little as you find your way to Garrett Popcorn for a mouth-watering snack! 

Once you feel satisfied again, take a journey to the SkyDeck Experience and gaze out a glass box that’s 1,353 feet in the air! The new and improved SkyDeck Experience now houses an interactive journey that tells the history of Chicago before you head up to the Ledge to take in the views. 

With all the excitement from the day coming to a close, it’s time for a fantastic dinner! Just around the corner awaits a flavorsome menu full of Italian cuisine at The Florentine. Pair any of their amazing dishes with a wine or cocktail, and enjoy your evening in the windy city! 

Day 2:

Rise and shine to another beautiful day as you make your way to the hotel breakfast before your exploration begins. Once you’re ready to go, head on down to the Chicago Architecture Center to book a tour or explore their beautiful center. It’s a perfect way to learn about the city and decide what else you want to see during your visit. Don’t forget to make your reservations online for either an architecture walking tour, a Chicago River architecture cruise, or for some architecture and design exhibits before arriving on your chosen day! 

Time for a snack? Check out the Corner Bakery for some sweet treats, soups, salads, and more. Next, with a satisfied tummy, walk on over to the river for some urban kayaking fun! There are so many great options to choose from, and you really can’t go wrong with any of them.

Once you’ve had enough in the water, you can sit riverside at the Island Party Hut for a tiki drink and a tropical feel to relax and enjoy those vacation vibes. For a fancier dining experience, stop by Smith & Wollenskies for some delicious dishes such as steak or shellfish.

 Lastly, to end the night, make sure you make time to see Art on theMART, which is a 5-story-high installation of beautiful artwork that displays on the side of the Merchandise Mart. The show is truly extravagant, and you don’t want to miss a second of it. 

Day 3:

On your last day of activities, we recommend taking a bus to Navy Pier for some shopping, rides, and fabulous food options! From your hotel, the trip will only take about 20 minutes, so there’s no need to stress about too much travel time. 

This day can really go however you want it to since everything will be in one place. If you’re not sure where to start; though, here are some places and activities that we recommend: Billy Goat Tavern, Completely Nuts, Inc, The Original Rainbow Cone, Offshore Rooftop & Bar, all the outdoor rides, Chicago Sports & Novelty, and any of the brunch, lunch, & dinner cruises. 

There is a great deal of things to do in the city, and we hope you take advantage of all of it this summer. Let the memories begin!

Written By: Natalie Kokaska

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