Chicago

Chicago, often referred to as the “Windy City,” is a hub of tourism and a popular destination for visitors from all over the world. One of the top reasons people come to Chicago is to experience the architecture, which is world-renowned for its variety and innovation. Visitors can take an architectural boat tour down the Chicago River, go on a walking tour, or even rent a bike and explore the city’s different neighborhoods to see some of the most iconic buildings in the world, such as the Willis Tower and the John Hancock Center. Chicago also boasts world-class museums, including the Art Institute of Chicago, the Field Museum, and the Museum of Science and Industry, which offer a glimpse into the history and culture of the city and its people.

Another attraction that draws visitors to Chicago is the food. The city is famous for its deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. Chicago is also known for its diverse food scene, offering a range of cuisine from around the world. Visitors can sample Mexican cuisine in Pilsen, taste authentic Polish food in Avondale, or try Chinese cuisine in Chinatown. The city also has many Michelin-starred restaurants, making it a foodie’s paradise. Some are overrated and others are worth the visit. 

Finally, Chicago is a sports town, and visitors can catch a game of one of the city’s professional sports teams, such as the Cubs, the White Sox, the Bears, the Bulls, or the Blackhawks. The atmosphere at a Chicago sports game is electric, and even those who aren’t big sports fans will enjoy the energy and excitement of the crowd. With so much to see and do, it’s no wonder Chicago is such a popular destination for tourists.

Chicago Luxury Itinerary

Recommended Stay: Long Weekend

Lodging Recommendation: Pendry Chicago (https://www.tripadvisor.com/Hotel_Review-g35805-d23228472-Reviews-Pendry_Chicago-Chicago_Illinois.html) or Hoxton Chicago (https://www.tripadvisor.com/Hotel_Review-g35805-d16735403-Reviews-The_Hoxton_Chicago-Chicago_Illinois.html)

Recommendation Mode of Transportation: Ride Share 

Arrive on Thursday Night

Do: Head to your hotel and drop your stuff off. 

Dinner: Au Chaval for the best burger in America (https://www.yelp.com/biz/au-cheval-chicago?osq=au+chuval) or head to Giordanos for Chicago deep dish pizza. 

Late Drinks: The Aviary – recognized as one of the best bars in the country (https://www.yelp.com/biz/the-aviary-chicago-2?osq=Aviary+Chicago) or Three Dots and a Dash. Another great bar 

Friday

Breakfast: Head to Wildberry Panckaes – expect to wait (https://www.yelp.com/biz/wildberry-pancakes-and-cafe-chicago-2?osq=Wildberry+Pancakes+And+Cafe)

Activity: Walk to Cloud gate Maggie Daley Park to get your pictures in before the swarm of other tourists arrive.

Activity: River Architecture Bout Tour (90 min Long but really interesting)

Lunch: Xoco for casual Mexican (https://www.yelp.com/biz/xoco-chicago) or the Purple Pig (https://www.yelp.com/biz/the-purple-pig-chicago)

Do: Walk to L.A. Burdick’s for Hot Chocolate and treats (https://www.yelp.com/biz/l-a-burdick-handmade-chocolates-chicago-2?osq=la+burdick)

Activity: Walk the Magnificent Mile along Michigan Ave.

Dinner: Alinea or Smyth (Do your best to get reservations ahead of time) – Cant get reservations? Head to Ramen Wasabi for great food (https://www.instagram.com/p/Btesx2enS16/) or Girl & the Goat (https://www.yelp.com/biz/girl-and-the-goat-chicago)

Saturday

Brunch: Junebug Cafe (https://www.yelp.com/biz/junebug-caf%C3%A9-chicago?osq=Breakfast+%26+Brunch) or Lucky’s Sandwich before Wrigley (https://www.yelp.com/biz/luckys-sandwich-company-chicago-2) 

Activity: Cubs Day Game at Wrigley Field

Dinner: Alinea or Smyth (Do your best to get reservations ahead of time) – Cant get reservations? Head to Ramen Wasabi for great food (https://www.instagram.com/p/Btesx2enS16/) or Girl & the Goat (https://www.yelp.com/biz/girl-and-the-goat-chicago)

Sunday

Breakfast: Head to brunch at Kasama for a great fusion breakfast (https://www.yelp.com/biz/kasama-chicago)

Activity: Observation desk at Willis Tower (get tickets ahead of time)

Lunch: Bonci for Roman Pizza (https://www.yelp.com/biz/bonci-chicago) or head to Carnitas Uruapan for amazing carnitas tacos (https://www.yelp.com/biz/carnitas-uruapan-chicago-2)  or if early flight out of Midway – head to Birrieria Zragoza for the best Birria in America (https://www.yelp.com/biz/birrieria-zaragoza-chicago)

Depart