Citytrips - Chicago
Chicago,
City of Cool
Chicago,
City of Cool
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.
Chicago Citytrips
Chicago Flex Citytrips: completely customized
Ideal for those who want to compose their citytrip in complete freedom, you leave when you want and stay as long as you want, in a hotel of your choice.
Choose your own flights: the day of departure and return is entirely up to you from our wide range of competitively priced flights, at the conditions of the moment.
Add a hotel of your choice: staying in a historic gem, an urban chic boutique hotel or a Japanese design hotel? An affordable three-star hotel or something more luxurious? Choose your own hotel from our fine selection of Chicago lodgings.
Complete your break with fun extras: with a Go City Explorer Pass you can visit a number of top attractions. Three attractions are already included in your Flex Citytrip. Belgian guide Leentje De Leeuw shares her passion for the city during an optional private tour.
New Year in Chicago
Chicago in winter? Absolutely! This city is a hidden gem during the colder months. Think warm cafés, iconic architecture draped in snow, and an urban vibe that’s full of life—even when the temperature drops. As winter settles outside, you’ll discover the magic indoors: world-class museums, festive markets, and signature eats.
From sky-high views and cultural highlights to sparkling celebrations, this city trip immerses you in everything that makes Chicago unforgettable. With your Go City Pass in hand and a spirit of discovery in your heart, you’ll end the year in style—and kick off the next with a bang.
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 ConnectionsThe 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.