Expert Advice

Spring In Chicago: Where To Stay And Eat In The Windy City

Plus, how to earn Bonus Points just by eating out

Sheryl B
Chicago skyline on a clear, sunny day

March is a great time to visit Chicago. Watch the St. Patrick’s Day parade, witness the bright green Chicago River, enjoy Chicago’s excellent restaurants or time your visit with Chicagohenge. There are many reasons to visit my hometown, the Windy City.

The Chicago River dyed green for St. Patrick's Day festivities 

I registered for College Board’s A Dream Deferred™ and the Historically Black Colleges and Universities (HBCU) conferences in Chicago. While my employer paid for the conference registration fees, I had to cover my hotel stay.

I debated booking at the host hotel or Chicago Magnificent Mile, a Hilton Grand Vacations Club. There was a discount for conference attendees. However, Hilton Grand Vacations was a better deal overall. Additionally, March in Chicago means March Madness, the NCAA Big Ten Tournament. The host hotel was home to participating teams, hence the higher prices.

So, I booked with Hilton Grand Vacations and enjoyed a staycation in Sweet Home Chicago.

What’s It Like To Stay At Chicago Magnificent Mile, a Hilton Grand Vacations Club?

Chicago Magnificent Mile is the perfect Hilton Grand Vacations location. I could walk to the conference in less than ten minutes, and the property is near top attractions like Millennium Park, Chicago Theater, Navy Pier and — of course — Magnificent Mile.

The front desk agent was professional and greeted me with a smile. The property is located within DoubleTree by Hilton Hotel Chicago – Magnificent Mile, which means I received a DoubleTree chocolate chip cookie upon check in. The property is located on the hotel’s top floors.

A Hilton Grand Vacations Member at her laptop in her Suite at Chicago Magnificent Mile, a Hilton Grand Vacations Club 

The color scheme of the lobby, elevator, and hallways carried over into the well-designed Suite. I appreciated the large, wall-mounted TV and seating area near the window. There was also a desk where I could review materials from the conference.

Housekeeping service is only available in Chicago if you stay more than five days. Someone checked on me throughout my stay using the SMS concierge.

My schedule for the conference was tight, so I didn’t participate in a membership review. However, I recommend these presentations and learning how to maximize my ownership.

After settling in, I walked to Michigan Avenue to check in at the conference and attend the opening plenary. Because I knew I would be across the street from a Massage Envy, I booked an appointment for the evening and then turned in for the night. I slept so well that first night.

Where Can I Park?

While I didn’t drive to my staycation, I recommend planning your parking before arriving at the property.

Tiramisue and a cocktail from HotHouse, the on-site restaurant at Chicago Magnificent Mile, a Hilton Grand Vacations Club 

Parking with in-and-out privileges is available at the property for $62 per night. The PARK lot across the street is a less expensive option. However, once you leave, you must pay again. You’ll also need the ParkChicago app for most street parking around the city. Or download SpotHero to find discounted parking spaces in garages across Chicago.

Where Should I Eat In Chicago?

Breakfast and lunch were part of the conference package, so dinner was my chance to eat out. If you are looking for a late-night snack, stop by HotHouse on the ground floor of the DoubleTree for dinner.

My server greeted me with a smile. I ordered a cocktail, buffalo wings and tiramisu. Of course, I wanted dessert first and ordered the wings to go. The cocktail was well-crafted, and the Tiramisu cake melted in my mouth. The wings were flavorful and came with celery and carrot sticks.

Don’t forget to charge the meal to your room if you have a Hilton Honors™ card on file and keep earning Points. I recommend reading more about the additional benefits of the Hilton Honors card.

Burger from Timothy O'Toole, a restaurant in Chicago 

I also tried Timothy O'Toole. The food was delicious and worth the wait, even during Big Ten weekend in Chicago. The restaurant was full of fans watching the games on big-screen TVs. I ordered the burger with fries and a beer from the Happy Hour menu. Order the pretzel bread pudding to share — or enjoy by yourself. Again, bring your Hilton Honors card. I signed up for Hilton Honors Dining and collect Bonus Points when dining at participating restaurants. 

What Is The Hilton Honors Dining Program?

I’m always looking for ways to earn Points for things that are part of my routine, like dining. Stop reading and sign up for Hilton Honors Dining if you haven’t yet.

Although I enjoy the food and service at Timothy O'Toole, I also enjoy earning Bonus Points. After dining at each restaurant, you’ll need to write a short review for other members of Hilton Honors Dining.

Read “How To Spend 3 Fun Days In Chicago” for an itinerary that hits the Windy City’s top attractions.

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Sheryl B, a Hilton Grand Vacations Owner, poses for a selfie

Sheryl B

Sheryl has been an Owner for nine years and has shared several memorable vacations with her friends and family. Her favorite destination is Sunrise Lodge, a Hilton Grand Vacations Club, in Park City, Utah, where she celebrated her 60th birthday. You can find Sheryl vacationing year-round, relaxing by the pool, throwing snowballs with her family or sipping mimosas while playing board games.

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