Best location for 3 nights in October

Question

Hi, I’m visiting Chicago for 3 nights in October with a friend. We will be doing the touristy stuff and some shopping, dining … 2 50 something women.

Good value hotel options seem to be Silversmith (downtown) or Stay Pineapple on the loop. Looking for suggestions as to best area to stay to help us pack the most in! Thank you ☺️

Answer

It sounds like you and your friend are going to have a wonderful time in Chicago! October is a fantastic time to visit, with beautiful fall weather and plenty of things to do. As for your accommodation options, both the Silversmith and Stay Pineapple are great choices, but let's dive into what would work best for your itinerary. Here's a breakdown of the best areas to stay to help you pack in the most sightseeing, shopping, and dining!

Best Area to Stay in Chicago for a 3-Night Trip:

Given that you’re looking to do the "touristy stuff," enjoy shopping, and experience some great dining, staying in or near downtown Chicago is definitely your best bet. Below are a few options to consider:

The Loop: The Loop is the heart of downtown Chicago and has great access to many attractions. It’s home to Millennium Park, the Art Institute of Chicago, and is also a central point for public transportation. You’ll also be close to famous shopping streets like State Street and the Magnificent Mile. Stay Pineapple on the Loop is in a perfect location for this type of sightseeing.
Grant Park and the South Loop: This area is near Millennium Park, the Field Museum, and the Shedd Aquarium. It’s a bit quieter than the Loop but still close to major tourist spots and shopping. If you're interested in museums and green spaces, this area is ideal. The Silversmith Hotel is in the heart of the Loop, making it a good central location if you want to be close to everything.
The Magnificent Mile: If shopping is a big part of your trip, the Magnificent Mile (Michigan Avenue) is where you’ll find all the high-end retailers and flagship stores. It’s also close to attractions like Navy Pier, the John Hancock Center, and the Chicago Riverwalk. Staying in this area would allow easy access to some of the best shopping in the city, plus plenty of dining options. Although it's a bit more upscale, it’s definitely a convenient base for tourists looking to shop and explore the city.
River North: This neighborhood is known for its trendy vibe, art galleries, great dining, and nightlife. It's a bit more lively and hip compared to the Loop, but still close to the Magnificent Mile, Millennium Park, and the Chicago Riverwalk. If you’re into contemporary dining and art, River North might be the perfect spot. It’s also just a short walk from the Loop and other downtown attractions.

What You Can Expect in Each Area:

Stay Pineapple (Loop): This hotel is in a great central location, perfect for exploring iconic Chicago landmarks like the Willis Tower, Millennium Park, and the Art Institute of Chicago. It’s ideal for first-time visitors who want to experience the heart of downtown. The Loop also has fantastic dining options, and you’ll be able to easily access public transit for further exploration.
Silversmith (Downtown/Loop): Located near the financial district, the Silversmith Hotel is also centrally located, making it convenient for shopping and sightseeing. The hotel’s historic charm adds to the experience, and its proximity to shopping, museums, and restaurants is perfect for a short stay. It's a very comfortable option if you're looking for luxury with a central location.

Things to Do in Chicago for Your Itinerary:

Shopping: Magnificent Mile is your go-to destination for high-end shops. If you're into unique and local finds, head to the trendy shops in River North or the Chicago French Market.
Sightseeing: Don’t miss iconic spots like Millennium Park (with Cloud Gate, aka "The Bean"), the Chicago Riverwalk, the Art Institute of Chicago, Navy Pier, and the Willis Tower Skydeck for amazing views. October is also perfect for a visit to the Chicago Botanic Garden or a boat tour on the Chicago River.
Dining: Chicago is a food lover's city! Try deep-dish pizza at places like Lou Malnati’s or Giordano’s, and don’t miss classic Chicago hot dogs. For something a little more upscale, head to the West Loop neighborhood for incredible restaurants like Girl & the Goat or Au Cheval.

Final Recommendation:

If you want to be right in the middle of the action, close to both shopping and sightseeing, I recommend staying at either Stay Pineapple on the Loop or Silversmith in the downtown area. Both options are centrally located, but if you want to be closer to more shopping options and a bustling atmosphere, the Loop or Magnificent Mile areas will serve you well. If you prefer something a little quieter but still close to everything, the South Loop or Grant Park areas offer a slightly more laid-back vibe.

Whichever option you choose, you're sure to have an amazing time in Chicago. Enjoy your trip!