Chicago is located on Lake Michigan and the Chicago River. Beach, imposing skyscrapers or historic buildings? You'll find it all right here in Chicago.

Combining city and beach is perfectly possible in Chicago

The Windy City has everything you need for the perfect city break. Nature, art, culture and above all very good food. Our recommendation? Pizza! Chicago is also a green city, brimming with parks.

And there is no shortage of fascinating museums and architectural buildings here. recovering from the countless impressions? You can do that on the 42 km long sandy beach on Lake Michigan. North Avenue Beach is the beach for the true Chicagoan.

“Chicago has a little bit of everything and is therefore really perfect for a City Break.“

City Breaks Chicago

Chicago, City of Cool

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.

Over 100 Travel Designers
all over Belgium are eager to assist you

Year after year Connections sends its Travel Designers to all corners of the world in order to be able to advise you even better when mapping out your trip.

No destination is too foreign or far. Find out who they are here and feel free to contact them!


Are you looking for cheap flights to Chicago?

The best fares to Chicago? Connections offers you the cheapest flights to Chicago all year round. Also for your last minute booking. This way you can keep the cost of your flight down and still have plenty of money available to enjoy your stay in Chicago. For more than 35 years, Connections has been the specialist in the lowest airfares to hundreds of destinations around the world.

But Connections offers much more than the cheapest tickets to Chicago. Whether it's a hotel stay, sightseeing tours or car rental in Chicago, we're here to assist you.

Want to know more about Chicago? Our Travel Designers in our travel shops are waiting to assist you. Of course you can also book your cheap tickets to Chicago through our website.

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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.