Taking a friend from South Africa

Question

I will be taking a friend who is visiting from South Africa that would like to see Chicago on August 15 for one day and night. She is 36 years old. I’m driving from Holland Michigan. Where is a good place to stay that is a reasonable price. I figure that we will be having drinks so I don’t want to have to drive back to the place that we are staying. I’m also wondering where to show her in that amount of time.

Answer

For a one-day visit to Chicago with an overnight stay, the key is to pick a hotel that’s centrally located so you can easily walk or take short rides to main attractions, restaurants, and nightlife. Since you’re coming from Holland, Michigan, a downtown hotel near the Loop, River North, or Magnificent Mile areas will be most convenient.

Hotel options that balance reasonable price with good location:

Hampton Inn Chicago Downtown/N Loop/Michigan Ave: Affordable, modern, and within walking distance of the Magnificent Mile and Millennium Park. Good for short stays and easy access to restaurants and bars.
Hyatt Place Chicago/Downtown – The Loop: Centrally located, comfortable rooms, and within walking distance to major attractions and nightlife spots. Reasonable price for downtown Chicago.
Holiday Inn Express Chicago Downtown: Convenient location, straightforward amenities, and a solid value option for a night or two. Walking distance to bars and attractions.
Freehand Chicago: Trendy boutique hotel in River North, popular for younger travelers. Offers communal spaces and easy access to bars, restaurants, and public transit.

Since you plan to enjoy drinks without driving back, staying in River North, Loop, or Near North Side will allow you to walk or take a very short ride to bars and restaurants.

Suggested itinerary for one day and night:

Morning: Arrive, park, and start with Millennium Park to see Cloud Gate (“The Bean”) and enjoy a short stroll around the gardens and fountains.
Late Morning/Early Afternoon: Walk up Michigan Avenue for shopping or sightseeing. Stop for lunch at a classic Chicago spot such as Giordano’s (famous for deep-dish pizza) or Eataly for a variety of Italian foods.
Afternoon: Consider a river or lake architectural boat tour, which offers iconic skyline views and is perfect for first-time visitors.
Late Afternoon/Evening: Explore Navy Pier, Millennium Park, or the Chicago Riverwalk for a scenic walk. If time allows, a quick visit to the Art Institute of Chicago can be squeezed in.
Dinner & Drinks: Choose a spot in River North or the Loop. Popular options include RPM Italian, Cindy’s Rooftop (Millennium Park view), or any rooftop bar with skyline views. Afterwards, stroll to a nearby bar for cocktails or craft beers.

Parking tip: Consider a hotel with on-site parking or nearby parking garages. Downtown Chicago garages can be expensive, but many hotels offer discounted rates if you book in advance.

By staying downtown and focusing on walking or short rides, your friend will get a compact but memorable first-time Chicago experience without worrying about driving back after drinks.

Taking a friend from South Africa

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