Do you find yourself caught up in the shuffle of your everyday routine? Do you find yourself just going through the motions of the day? I have the perfect antidote for you. Staycation! Planes need not apply to experiencing one of the best cities in the world.

I did just that with a two night stay at LondonHouse in June booking their summer package “Experience Chicago*,” which, with an overnight stay, includes discounts at local attractions like Navy Pier’s Centennial Wheel, Second City, 360 Chicago, and much more. Chicago is unbeatable in the summer – I do my best to squeeze every last drop out of it. Summer’s when Chicago comes alive with street festivals, park events, and beautiful weather that makes you want to be outside all day. We take warm weather very seriously – outdoor seating for restaurants starts as early as April and continues until there’s snow on the ground. LondonHouse has one of the best rooftop patios in the city with sweeping views. Watching the boats cruise below is more entertaining than the latest binge on your streaming device (although you can do that too – hotel room TVs have Google Chromecast).

I checked into LH on a Friday evening in June on a mild, drizzly day. Before entering the hotel I was aware of its history and cultural contributions. A Chicago Landmark, it was originally built in 1923 for insurance company, London Guarantee. From the 1950s to the 1970s, London House Jazz Club, on the 1st floor, was one of the best spots to see jazz in Chicago. Famed jazz singer, Sarah Vaughan, even recorded a live album here in 1959. LondonHouse Hotel calls upon this past with its chic and elegant interior.

I headed to my king suite on the 15th floor, which had a full view of the river and all its grand architecture. I immediately put on the robe and slippers that LH provides to all its guests and got ready for dinner.

Friday dinner was at 5 Rabanitos in Pilsen, which is one of the best neighborhoods to get a glimpse of authentic Chicago – built upon working class immigrants and full of a diverse heritage. I ended the night in my LH robe, streaming a movie with Chromecast.

Saturday was my first local experience included in the “Experience Chicago” package: an 1893 World’s Fair walking tour with Chicago Detours. Kicking off at Congress Hotel, it showcased buildings around the Loop that remain from the 1893 World’s Fair. Amanda, our guide, and founder of Chicago Detours, led us to some pretty cool hidden gems, including one of Chicago’s last manually operated elevators –in the Fine Arts Building. I was particularly excited to learn about Pickwick Place having been there before. One of the Loop’s tiniest buildings, it’s located in a 9 foot wide alley at 22 E. Jackson. It was built in 1892 by an English couple who lived on the 3rd floor and ran a restaurant on the 1st floor called “Abson’s Chop House.” Now a coffee shop, this alley is often missed by passersby.

Post-walking tour, I was pretty hungry so I went over to Little Goat in West Loop for dinner. Stephanie Izard is a local treasure and experiencing her food is a must for anyone visiting Chicago. Little Goat is a great spot to try it out as it’s not as crowded as her other restaurants.

On Sunday morning, I dined at LH Rooftop. LH Rooftop gets very busy at night but in the morning, it’s much more relaxed and serene. It doesn’t get better than breakfast with this view.

My weekend was winding down but I had another local experience to catch –  a helicopter ride with Vertiport. This was an experience I won’t ever forget! Vertiport operates out of the southwest side of Chicago and makes helicopter tours accessible to everyone. The ride lasted 15 minutes and we flew in a circle north to Fullerton, east over the lake, south over Navy Pier, and then, my favorite part, we flew straight over the buildings downtown. Heading home after a fun weekend was hard, but luckily, I was home in 30 minutes after hopping on the Brown Line!

*The “Experience Chicago” package is no longer available but please feel free to book Honors Discount for guaranteed low rates. With 90+ Hilton hotels in the Chicagoland area, you’re guaranteed to find the perfect place for your next staycation.

Previous Article

Treat Yourself to a Break from the Hustle & Bustle at the Chicago Botanic Garden

Next Article

The Must-See Spots in Downtown Chicago

Related Guides