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Our cheapest flights  to Chicago

All fares are per person, in Euro and ‘as from’. They are subject to availability and change without prior notice. All pre-payable taxes are included. File charges (from €12/p.p.) and cancellation and/or travel insurance are not included. Airport taxes may differ according to the departure date, booking class and flight route.
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Chicago is one of the top U.S. destinations. It has a vibrant town centre and a notorious past; upmarket, man-made architectural beauty with signature buildings by the greatest architects and a stunning natural setting along the clear waters of Lake Michigan. It is a university city which encourages sports and entertainment with miles and miles of jogging and cycle tracks, two inviting beaches and 2 large parks; with street and food fairs; with a buzzing theatre, second only to Broadway. Its billboards display the latest and the ageless musicals and theatre shows. Chicago has brilliant museums and a vibrant nightlife. It is home to the Chicago Blues, to the famous Route 66, to more than 40 Hollywood movies and to Oprah Winfrey and President Obama. Chicago is the place-to-be and to-be-seen and booking flight tickets to Chicago the in-thing to do.

Why Connections?


    28+ years of experience and trained travel experts

    Your one stop shop for travel: flights, hotels, excursions, rental cars and insurance

    No-nonsense: easily compare flight rates per destination

    +77.000 advantageous rates with 200+ airlines

Fly Brussels – Chicago from Zaventem

Brussels is definitely a convenient hub as flying direct from Zaventem, Brussels will save you on time, transport costs and effort. Delta, United and US Airways all serve the route. Online tickets are available and our Call Center or travel shops gladly assist you with your bookings. For last minute queries or extras the Connections airport travel shop inside Brussels airport terminal is open every day, Sundays and holidays included. It is nice to remember that Connections focuses on more than flights only and will gladly help you organise your getaway, be it solo, as a couple, with the family or in group, and to meet or exceed your travel expectations in order to turn your ideas into a journey of a lifetime, a travel experience you will look back upon with joy!

We are dedicated to go beyond praising Chicago as a travel destination and offering cheap flight tickets; we want you to have fun and make to most of your time abroad. By suggesting hotels we have stayed at and excursions we tried out for you, you will not undergo the city, but experience it in all its glamour and glory, even if you only have a short time and a tight budget. Take the smart way out and let us look after you, so all you need to concentrate on, is to savour each moment.

Citytrips to Chicago

Chicago has been amongst our flight toppers for years and many a cheap flight ticket has exchanged hands over our counters. WeekendSpecials to the ‘Windy City’ though are fairly new. Thanks to this formula you fly on a pre-set departure date for a clear-cut fare. Included in the price are your return flights Brussels-Chicago and a 3 nights’ stay. Our popular citytrips to Chicago include your flight, 2 nights’ stay and the Modern Skyscrapers tour and are an absolute topper. A Chicago citytrip can be easily combined with our Route 66 selfdrive which will lead you to California, where you could extend your stay with a few extra days in L.A. or San Francisco, or go on another selfdrive! Three birds with one stone!

Chicago Hot Spots

The historical Water Tower, one of the only remaining buildings after Chicago’s Great Fire; the Magnificent Mile and its extravagant shopping outlets, the Loop and its exquisite shopping and fun fairs, The Navy Pier, Lincoln Zoo, the J.Hancock Observatory and Michigan River and lake with it fun boat rides past all the different bridges and their unique opening systems and in front of Chicago’s skyline. Chicago is a university city with a long list of interesting museums from the Science and Industry with its modern IMAX theatre to the Hayden Planetarium, the Chicago Hall of Fame and the world’s largest (Shedd) Aquarium. And then there is the major feature Chicago is known for worldwide: its awesome skyscrapers and architecture, from the days of Frank Lloyd Wright in Oak Park to the present-day master architects who compete for attention.


Chicago: Essential info

Let us have a down to earth look at what is indispensable for your flight to the Windy City... 

Passport & Visa requirements: all traveller (children and babies included) must be in possession of a digital machine readable passport with a minimum validity of 6 months at your return from the U.S.A and a visa which can only be requested through the official website https://esta.cbp.dhs.gov. at the price of 14EUR/pers (subject to change). Please verify the latest updates on travel advice, documents and requirements on http://diplomatie.belgium.be/en.

Health requirements: there are no mandatory vaccinations. To verify the latest updates on health requirements, please surf to www.itg.be. 

Medical expenses and insurance: Medical bills can run sky high in the U.S. Come prepared and browse through our specifically designed temporary or year-long Protections insurances and compare! Tooth ache, ear ache, sprained ankle, those mishaps may befall anyone. Protections’ high covers and specific add-ons (fly-on-time, natural disaster and anti-terrorism cover) will give you maximum peace of mind.

Everyone knows that you pay in Dollars in Chicago, but a credit card on your own name is indispensable. Credit cards offer a guarantee and are often required to back-up your bookings. Do not forget to inform your bank you will be using your card overseas, as most cards today are protected against (internet) fraud and use abroad.

Chicago: Did you know that...

  1. Chicago’s motto is ‘Urbs in Horto’ which means as much as ‘City in a garden’, not surprising if you know Chicago still counts 552 parks today.
  2. The name Chicago would have originated from the Indian word ‘Shikaakwa’, meaning ‘stinking onion’. Onion fields were common in and around the present ay Chicago area at the time of the settlers.
  3. The John Hancock Observation Deck is home to the largest indoor ice-skating ring, so you do not need to wait for winter to come around to have some real cool fun.
  4. Michigan River flows backwards. Its flow was reversed to stop pollution to Lake Michigan and Lincoln Zoo one of the only Zoo’s worldwide with free access.
  5. The walls of the beautiful Chicago Tribune Tower includes building stones with originate from major hot spots worldwide, such as the Taj Mahal, The Arc de Triomphe, Westminster Abbey and the Great pyramid.
  6. People really do dance in the streets – in office clothes – at the State street annual Taste of Chicago food fair. 



* info and conditions in your travel shop or via our Customer Service Center
** Only valid upon reservation of an intercontinental flight + min. 3-night hotel stay or intercontinental flight + min. 1-week tour or intercontinental flight + min. 1-week car rental. Non combinable and while stock lasts. Info and conditions in your travel shop or via our Customer Service Center.
*** Only valid for a hotel stay on a Friday, Saturday, Sunday or during Belgian school holidays and upon reservation of an intercontinental flight + min. 3-night hotel stay or intercontinental flight + min. 1-week tour or intercontinental flight + min. 1-week car rental. Non combinable and while stock lasts. info and conditions in your travel shop or via our Customer Service Center.

Connections Travel shops

Brussels Airport

Brussels Airport

Departure Hall,
1930 Zaventem



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Why Connections?

  • 30 years of experience and skilled destination experts
  • Your one stop travel shop; flights, hotels, excursions, rental cars and insurance
  • 31 travel shops; in your neighbourhood and at the airport
  • Available 7/7 to answer all your questions
  • +77.000 affordable flight fares with 200+ airlines