Expert Advice

Need Last-Minute Plans? We Found Festive Fun In Chicago With Hilton Grand Vacations

HGV offers flexible vacations in our favorite destinations

Deanna and Mike O
Downtown Chicago skyscrapers along the Chicago River, dyed green as part of the St. Patrick's Day festival

Mike and I were staying in Branson, Missouri at The Suites at Fall Creek for the first time, when the weather shifted toward rain. We decided to head home to Michigan a few days early and use our Hilton Honors™ Points to stay overnight on the way.

The separate living area in a Suite at Chicago Magnificent Mile, a Hilton Grand Vacations Club 

But then we checked the HGV website and were pleasantly surprised to see that Chicago Magnificent Mile, a Hilton Grand Vacations Club was available. We booked it for that weekend, which coincided with the St. Patrick’s Day festivities.

We’ve traveled to Chicago before, but never during St. Patrick’s Day. We were excited to experience the festivities and try out Chicago Magnificent Mile.

The property is on the upper floors of the DoubleTree by Hilton Hotel Chicago — Magnificent Mile. When we arrived, we were greeted immediately and checked in by friendly front desk staff. Next, the concierge handed us our HGV Rewards Card, which gave us access to discounts on dining and other activities throughout Chicago.

Our 1-Bedroom Suite was spacious and modern. The room overlooked Columbus Avenue, where the St. Patrick’s Day parade took place. Although the parade was several blocks away, it was an easy, scenic walk through the city to the river. It was fun attending the parade and seeing the Chicago River dyed green.

Two Hilton Grand Vacations Owners pose for a selfie by the Chicago River, dyed green for St. Patrick's Day 

Restaurants are abundant near Chicago’s Magnificent Mile. We went for a fish fry at D4 Irish Pub & Cafe, just around the corner from the resort. It was busy and for good reason. The food was excellent, with large portions. As a bonus, the restaurant participates in HGV Rewards, so the discount made it even better.

We also tried some Chicago-style pizza at Gino’s East South Loop before the parade. Gino’s was a pleasant discovery with great food and service.

On Sunday, we had lunch at the Italian Village Restaurant, the oldest Italian restaurant in Chicago. It was cozy, with authentic Italian food and an attentive wait staff. It was also conveniently located near the Theatre District and the perfect stop before seeing a play at the CIBC Theatre.

After the play, we heard some awesome jazz music at Andy’s Jazz ClubFor a nightcap, we tried the restaurant at the property, HotHouse, which offers a 25% discount for Owners.

Chicago Magnificent Mile, a Hilton Grand Vacations Club is in a prime location with easy access to restaurants, the Theatre District, the Riverwalk, the Magnificent Mile, Navy Pier and comedy and jazz clubs. We were so happy with the room and location that we’ve already booked a trip to return in July.

Read “How To Spend 3 Fun Days In Chicago” for even more things to do on a long weekend in the Windy City. 

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Hilton Grand Vacations Owners Mike and Deanna pose at the beach

Deanna and Mike O

Mike and Deanna are Centum+ Owners who’ve owned with Hilton Grand Vacations since 2019. Their favorite vacation destinations include Barbados, Orlando, Arizona and Hilton Head Island, South Carolina. They enjoy golfing, seeing historical sites and attending HGV Ultimate Access events like the Hilton Grand Vacations Tournament of Champions. So far, they’ve visited 26 properties — with plans to visit more thanks to HGV Max.

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