Explore Millennium Park and see Cloud Gate AKA The Bean
Explore Millennium Park and see Cloud Gate AKA The Bean
Bunckingham Fountain, Chicago
Bunckingham Fountain, Chicago
Lake Shore Trail, Chicago
Lake Shore Trail, Chicago
Grant Millennium Park, Chicago
Grant Millennium Park, Chicago
Navy Pier, Chicago
Navy Pier, Chicago

Chicago Short Break

3 nights from €799 per person Including Flights


Chicago offers an abundance of attractions catering to all tastes, from iconic sights to vibrant cultural experiences. Explore renowned museums like the Art Institute, housing masterpieces, and family-friendly spots like Navy Pier. Indulge in a shopping extravaganza along the Magnificent Mile, featuring an array of top brands and boutique finds. Delight in the city's diverse culinary scene in vibrant ethnic neighborhoods, and immerse yourself in live entertainment at theaters and jazz clubs. Navigating the city is made easy with a comprehensive public transport system.

Discover upscale shopping destinations such as Water Tower Place and The Shops at North Bridge, offering an extensive selection of high-end retailers and dining options. Chicago's nightlife is equally dynamic, with options ranging from cheering on sports teams at professional events to enjoying live music and boat cruises at Navy Pier. Theatre enthusiasts can catch captivating performances at renowned venues throughout the city.

Begin any shopping excursion on the iconic Magnificent Mile, a cosmopolitan hub brimming with luxury stores and historic landmarks. Explore the Loop's historic Macy's on State Street, a blend of retail mecca and history museum. Don't miss the unique boutiques lining the streets of Chicago's diverse neighborhoods, adding depth and character to the city's vibrant shopping scene. (TM)

With flights to Washington DC, Nashville and Toronto being under 1.5 hours or New York and New Orleans under 2 hours, this is a great city to pair with to extend your holiday!

Our holidays include
  • Flights & taxes
  • Accommodation
  • Checked baggage
  • CAR licensed & bonded
  • In resort assistance & 24 hour contact centre
Why Book with American Sky?
  • Hassle-free - book direct quickly and easily
  • Choice of airlines and the option to switch
  • A friendly, family run business with a wealth of experience.
  • Great deals on offer for multiple destinations
  • Low deposits
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We offer expert advice and great service Our luxury tailor-made holidays are created with impeccable service from start to finish.

Day 1

Fly into Chicago O'Hare international airport and hop on the CTA Blue Line to be in Downtown Chicago in 45 minutes with costs are around $5pp.

Start your day at the iconic Art Institute, where you'll marvel at world-class masterpieces. Afterward, stroll along the Magnificent Mile, indulging in upscale shopping and delectable dining options. In the afternoon, how about catching a matinee performance at one of Chicago's renowned theatres. As evening falls, head to Navy Pier for a leisurely dinner with stunning lakefront views. The start of Route 66 is here so look out for the discreet sign nearby!

Day 2 - 3

Begin your day with a visit to Millennium Park, home to the famous Cloud Gate sculpture, affectionately known as "The Bean." Explore the park's lush gardens and art installations before venturing to the historic Wrigley Field for a behind-the-scenes tour of this beloved baseball stadium, home of the Chicago Cubs. In the afternoon, delve into the city's rich history at the Chicago History Museum.

Venture off the beaten path today and explore Chicago's diverse neighborhoods. Start with breakfast in Pilsen, known for its vibrant street art and delicious Mexican cuisine. Next, head to the trendy neighbourhood of Wicker Park, where you can browse eclectic boutiques and artisanal shops. In the afternoon, take a leisurely stroll through the picturesque streets of Hyde Park, stopping to explore the University of Chicago campus. End your day with a sunset cruise along the Chicago River, admiring the city's iconic skyline from a unique perspective.

Day 4

Enjoy your morning at leisure as you take in the beautiful architecture. How about catching an internal flight to its nearby cities such as New York, Boston, Nashville or New Orleans? Or rent a car and experience Route 66!

  • Return international flights
  • Three nights hotel accommodation

What's not included

  • Airport transfers
  • Meals and optional excursions

Hotel Felix


Only a 10 minute walk from the lively Magnificent Mile, this sophisticated hotel is a trendy spot to rest your head in between exploring the city's best attractions. After a day of exploring, dine on delectable French cuisine or indulge in a relaxing massage.

Sheraton Grand Chicago


Stylish, relaxed and in the heart of Chicago, this is the perfect option for a stay in the Windy City. Make the most of the prime location, unwind in the spacious rooms and admire the views of the city and river from your room.

Omni Chicago Hotel


Located in the heart of the Magnificent Mile, the Omni Chicago Hotel is one of the area's best-loved hotels and home to Michigan Avenue's only all-suite luxury accommodations.

Fairmont Chicago Millennium Park


Conveniently located in the heart of downtown Chicago, near major cultural attractions, Navy Pier, the city’s business and financial district and the world renowned shopping along the Magnificent Mile

The Langham Chicago


This luxurious hotel sits close to the sophisticated centre of Chicago

Brendan White
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Talk to our travel experts for more information and to book or tailor-make your holiday

01 6649900 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun

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