Luxury Chicago Holidays

Offering the best view of across the city from 1000 feet above the magnificent mile, we love the TILT for it's jaw dropping experience of being tilted over the Chicago Skyline. This is an attraction you don't want to miss.

A year round attraction, if your travelling in winter head to the park for some ice skating. If you're travelling during the summer months, find dozens of free events to attended from films in the park to outdoor concerts. With so much to be explored make sure you head to the park.

Hit the shops on the Magnificent Mile for an adventure in itself, Michigan Avenue not only has some great shopping but also has great restaurants, entertainment and plenty of history. Along the Magnificent Mile you will find three malls and many high end shops. If you are looking for bargain we recommended heading to Nordstorm Rack.

Navy Pier is the place to go for rides, entertainment, shopping, dining and nightlife. Children will love a ride on the Ferris Wheel and musical carousel before visiting the Children museum. For the adults from the Pier you'll be able to join a tour boat or a dining cruise ship.

Take a guided river boat cruise, this is the best way not only to see the amazing architecture of Chicago but to learn about the history of the city. For something a little more thrilling join a guided kayak tour and paddle your way through the heart of downtown on the famous Chicago River.

Chicago is the place most people start the iconic Route 66 road trip. Almost 2,500 miles of stateside scenery, this journey should be on everyone's bucket list. There are many ways to take this journey from escorted tour in a coach to on the back of a Harley Davidson, to driving it yourself.

Taste of Chicago is an outdoor festival that’s been held in Grant Park every summer since 1980, usually in July. Visit the festival and you’ll get to sample some truly incredible food, bringing together all the tastes of the city, as well as amazing live music from local acts and some big-name artists. 

This is one you simply cannot miss on a trip to Chicago. It’s part pizza, part pie, and fully delicious. Though there are many imitations around the world, nowhere can make this iconic dish quite like Chicago. 

Chicago’s Italian immigrants first created this famous sandwich during the Great Depression and it’s been a Chicagan delicacy ever since. The classic Italian Beef Sandwich consists of thinly sliced and well seasoned roasted beef dipped in gravy, served on an Italian roll and topped with sweet peppers or spicy Giardiniera.

This slightly unusual take on pizza consists of a deep fried dough pocket, filled with everything and anything you’d expect to find on top of a pizza: cheese, tomato sauce, vegetables and meats. You’ll find pizza puffs at many fast food eateries and street food trucks in Chicago.

While many places all over the world serve hot dogs, like many of its cuisines, Chicago’s hot dog is made in a particular way. The sausage is an all-beef frankfurter and is served in a poppy seed bun and topped with yellow mustard, onion, dill pickle, pickle relish, tomato, pickled peppers and celery salt.