City Breaks - Chicago

Chicago,
City of Cool

The spirit of Chicago is like a club.
Once you’ve visited, you belong.

Discover Chicago, a cool city bursting with energy and style. From the chic boutiques of the Magnificent Mile to the trendy bars and restaurants of neighborhoods like Wicker Park, West Loop, Logan Square and the Fulton Market District. Discover the vibrant street art, diverse music scene and hip cultural events that make this city absolutely unique.

Whether you're looking for innovative dining, top-notch theater and comedy, or just a good time, Chicago has it all. With 77 neighborhoods each with its own character and charm, the Windy City will be forever etched in your memory, with its exciting mix of history, culture and urban ambience. What makes it so special is that you won't find the hustle and bustle of a metropolis, and you'll be blown away by its friendly atmosphere.

Our selection of
Chicago Breaks
Want to leave right away? No problem! Take your pick from our breaks, which include flights, hotel accommodation and exclusive experiences. Each program is different and focuses on different aspects, but the objective is the same: to let you experience Chicago like a true Chicagoan! Then choose one of our hand-picked hotels and combine the different breaks as you wish.

Chicago Untappd

Chicago is unique in many ways. There are over 160 breweries in and around the city! As part of this break, our Belgian guide will take you from one brewery to the next every Saturday. An experience you won't soon forget!

Included
  • Exclusive Brewery Tour (3 hours) with our guide Leentje De Leeuw

  • Overnight stay in one of our selected hotels (your choice)

  • Flights Brussels-Chicago-Brussels

Chicago On Fire

On Monday, climb aboard a century-old fireboat and follow the same waterways that firefighters once used to fight fires from the water. At the same time, you'll learn all about the beautiful architecture of many of the buildings that define Chicago's skyline today.

Included
  • Fireboat architecture tour (1 hour 30 min.) with English-speaking guide

  • Overnight stay in one of our selected hotels (your choice)

  • Flights Brussels-Chicago-Brussels

Chicago Like a Local

Exploring Chicago by bike is the best way to immerse yourself in the lives of real Chicagoans! Every Sunday, we'll take you exploring the city, from beautiful Streeterville to the historic Gold Coast.

Included
  • Neighborhoods bike tour (3 hours) with English-speaking guide

  • Overnight stay in one of our selected hotels (your choice)

  • Flights Brussels-Chicago-Brussels

Chicago All The Way

The complete experience! "Chicago All The Way" includes a brewery tour with our Belgian guide Leentje De Leeuw on Saturday, a bike ride along Lake Michigan on Sunday and a pump boat tour on Monday: an unforgettable experience!

Included
  • Exclusive Brewery Tour (3 hours) with our guide Leentje De Leeuw

  • Fireboat architecture tour (1 hour 30 min.) with English-speaking guide

  • Neighborhoods bike tour (3 hours) with English-speaking guide

  • Overnight stay in one of our selected hotels (your choice)

  • Flights Brussels-Chicago-Brussels

Chicago Goes Green

Chicago in the most sustainable way: you stay in a hotel that limits its carbon footprint (and yours) as much as possible, you participate primarily in activities that are respectful of people and society, and you contribute financially to a climate project that offsets 100% of the CO2 emissions of your flights!

Included
  • Exclusive Brewery Tour (3 hours) with our guide Leentje De Leeuw

  • Overnight stay in a sustainable establishment: CitizenM Hotel Downtown Chicago

  • Flights Brussels-Chicago-Brussels

  • Your contribution to a climate project equivalent to your CO2 emissions

Why choose Connections?

Because we are travellers, just like you. Always looking for exciting experiences, fascinating encounters and new horizons. Because we are 100% Belgian and can assist you in your own language. Because we make it our personal mission to lift your travels beyond your wildest imagination. Because life is more intense when you travel, really travel!

More about Connections

The twinkle in the eye

Do not expect conformity from us. We are always looking for those extra ingredients that make your trip truly special. We swear by intense experiences.

Over 100 Travel designers around the country

Meet the Connections crew in our Travel Shops located all over Belgium. All of our Travel Designers are looking forward to meeting you and welcome you with open arms.

+35 Years on the road

We've been paving our way for a while. Travelling with Connections means choosing 'peace of mind'. Everything perfectly arranged, excellent service, certainty and reliability.

Always by your side

We're here whenever you need us! Available via our website, our travel shops, our customer service center, at the airport and via our mobile travel agents.

Mondays to Saturdays 10 am - 6 pm

Connections, Luchthavenlaan 10, 1800 Vilvoorde, BE 0428 666 853

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