Chicago

Chicago holidays - Stylish, bustling and enticing

Chicago is a vibrant city brimming with opportunities to explore. Famed for exhilarating nightlife, passionate sporting events and breath-taking skylines, this is a thriving city set to a sensational Lake Michigan backdrop.

Why American Sky?
Award Winning
We're award winning Our awards reflect our dedication to delivering incredible tailor-made holidays
Why American Sky?
Protected
Your money is safe We safeguard your money with ATOL protection and have membership to codes of best conduct.
Why American Sky?
Award WinningExcellence in customer service
Award Winning Excellence in customer service Awarded 2024 Feefo Platinum Trusted Service Award for Tropical Sky's excellence in customer service.
Why American Sky?
Award Winning
We answer quickly On average, calls are answered within three rings. We also respond to emails quickly.
Why American Sky?
Award Winning
We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

A very cool city with trendy restaurants, museums, music and sports

Chicago will endeavour to surprise you – think beaches and you don’t immediately think of Chicago, yet this city has over 15 miles of beach within its reach. And while Memphis may be the home of blues, Chicago certainly puts in a grand effort with some amazing blues clubs dotted throughout the city. This year-round destination has an experience for everyone.

There’s a cultural draw to Chicago that keeps people coming back time and time again. It doesn’t matter what you’re interested in, from music and sport to art and food, this city does it all so well. Take food-lovers, for example, who will be spoiled for choice when it comes to fine dining, ethnic cuisines and local classics – don’t leave without trying a deep-dish pizza or exploring some of the city’s top restaurants.

Live performances, whether on a small scale in bars or massive festivals downtown, are regularly occurring somewhere within the city – Lollapalooza is one of the highlights for many visitors. And sport is a true passion for the locals – baseball, hockey, basketball, football…you name it, they play it. Of course, if you’re exploring, there are numerous ways to do this – why not take a self-drive tour of the city or visit as part of a multi-centre holiday with another destination of your choosing? Chicago moulds to fit whatever type of getaway you imagine, creating the type of holiday you reminisce about for years to come.

Five reasons to visit Chicago

  • The culture here is fantastic, with a rich selection of things to do from picnics in Millennium Park to hanging out in the authentic blues bars.
  • The ethnic neighbourhoods are diverse and interesting, providing pockets of vibrant communities and fantastic cuisine.
  • Love music? Chicago is brimming with festivals throughout the year, particularly in the summer when concerts, small and large, pop up throughout the city.
  • Food-lovers will be overwhelmed by the delicious selection of culinary delights on offer, from Greek, Middle Eastern and Mexican, to classic Chicagoan fare.
  • The art scene, nightlife and shopping opportunities are great here – head to Magnificent Mile for boutiques and malls, and to the Field Museum.
Chicago Quick facts
Flying Time: 8 hrs 30 mins

Inspired travel with our expertise

Recommended holidays

Alan  Facer
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun