Are you looking for a staycation idea in Chicago? I chose Hyatt Place Chicago Medical/University as my first staycation idea and Hilton Grand Vacations Chicago Downtown Magnificent Mile for the next staycation. HGV will occupy the top floors of the DoubleTree at 300 E. Ohio. Do not forget your cookies.

Staycation Idea in Chicago

Even though I visited at least one property in almost every state in the Hilton Grand Vacations portfolio, I had not made a reservation in my hometown. I was excited to learn about the addition of Chicago to the HGV portfolio, but the property remained closed during the early phase of the pandemic. When the city began to open slowly, the Chicago property was unavailable. Because I was flying to Honolulu for my birthday, New York for Thanksgiving, and a Winter Break trip to Washington, D.C., I did not make a reservation until January. I had a choice of a studio or a one-bedroom. I chose the corner view one-bedroom premier. If you are not a timeshare owner, you can reserve a room at a different rate.

View from the 23^rd

I had Club Points, but I booked through Open Season. If you are looking for staycation ideas in Chicago, I found a location for you. The property is beautiful and well maintained. Of course, I received a welcome bag with two bottles of water and two DoubleTree cookies. I did not worry about a room on a high floor since HGV occupies the top floors. You know I love a great view. If you want to see Chicago architecture differently, reserve a room on a high floor. We had access to a kitchenette: table, four chairs, microwave, cooling unit, and glassware. The bedroom and living room are spacious, and there is a huge tv in each room. The curtains and sheers are motorized. Although it was 2:00PM, I checked in early. Yes, check-in is at 4:00PM. If a room is available, most hotels let you check in early.

Are you Driving to your Staycation?

If you drive to Streeterville, you may want to skip parking at the hotel garage for $59 per night. You can park across the street for $38 or search for additional savings using SpotHero. Therefore, the further away from the hotel, the more money you will save on parking. Keep in mind if you park in the hotel garage, you can go in and out, but the lot across the street does not allow in/out privileges. After taking the luggage to the room, we took a short drive to Barrio before parking the car for the night.

Barrio and Timothy O’Toole’s Pub

If you are looking for a Mexican restaurant with a twist, try Barrio. You can save a few dollars if you stop by during happy hour. I ordered the chipotle mango guacamole, chicken taco, skirt steak taco, elotes, and a Paloma. The serving of guacamole and elotes is shareable. I like the casual atmosphere and would come back again. However, I will not order the elotes. Timothy O’Toole Pub is across the street from the hotel. Although I was not hungry, the Bulls were playing. We tried the famous buffalo wings with a side of fries. The food is good, and there are plenty of TVs. If you want a late-night snack, try Timothy O’Toole.

Eataly and Pinched

Eataly is a 15-minute walk from the hotel. Even though it was chilly in Chicago, I enjoyed the walk. We ordered a charcuterie board and pizza at customer service and dined in the Birreria. The pizza, cheese, and meats were fresh, and I ate everything except the mozzarella ball. Before we left, I picked up a serving of tiramisu. For dinner, we took a five-minute walk to Pinched on the River. I tried one of the Special Creations with grilled salmon. The food was fresh and delicious. As we were leaving, I purchased a bag of spicy potato chips. You will not be disappointed. If you have never ventured out, this staycation idea is a perfect way to enjoy great restaurants without driving to Pilsen for Mexican, Taylor Street for Italian, and further north for Mediterranean.

Theory

Bear Down! I had to watch the last game of the season. I wanted the Bears to finish the season with a three-game winning streak. After all, the Bulls were on a nine-game winning streak. After we checked out, we headed to Theory to watch the Bears game. Every place we dined at checked your ID against your vaccination card. I enjoyed the mask melter (chicken sandwich), fries, and smoked Paloma. If you are looking for a place to catch a sporting event, this is the perfect environment.

The Key to your Staycation Idea is Location

The HGV Chicago Downtown Magnificent Mile is the perfect location for a staycation. You can walk to Michigan Avenue and Navy Pier if you want. We walked to every restaurant except for Barrio. I encourage you to join a hotel rewards program and use the benefits. By the way, I received 5,040 points. How? I upgraded to the Amex Hilton Surpass card. I earn 12X points for my stays. A new feature to Hilton Honors allows you to book connecting rooms and pool points. The cost for my weekend stay was $420.29, and the $6 tip tip for housekeeping. Are you looking for a staycation idea in Chicago?