Chicago holidays

Top offers for cheap holidays

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Holidays to Chicago

If you’re contemplating your next adventure, Chicago holidays present a vibrant mix of culture, cuisine, and iconic architecture that captivates every traveller. Known fondly as the Windy City, Chicago offers delightful experiences ranging from exploring world-class museums to indulging in deep-dish pizza. Wander along the scenic shores of Lake Michigan or take in the stunning skyline from Millennium Park – this city truly has something for everyone. Don’t miss the chance to uncover the charm of this bustling metropolis; be sure to check our exciting deals and offers to Chicago!

HOLIDAY TYPE:
City breaks
PEAK SEASON:
Dec - Jan
LANGUAGE:
English, Spanish
CURRENCY:
US Dollar ($)
NEAREST AIRPORT:
OBK
Northbrook Airport

Top holiday packages to Chicago

  • from Dublin, International (DUB)
  • from Cork, International (ORK)
  • 4 nightsFlights includedDublin
    748 m from beach
    from 810 € pp
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  • Hilton Chicago

    4 nightsFlights includedDublin
    766 m from city centre
    from 1.465 € pp
    1 of 5 slides
  • Freehand Chicago

    4 nightsFlights includedDublin
    1.6 km from city centre
    from 793 € pp
    1 of 5 slides
  • 4 nightsFlights includedDublin
    1.79 km from city centre
    from 977 € pp
    1 of 5 slides
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  • Kinzie Hotel

    4 nightsFlights includedDublin
    1.25 km from city centre
    from 1.024 € pp
    1 of 5 slides
  • Arlo Chicago

    4 nightsFlights includedDublin
    883 m from city centre
    from 1.079 € pp
    1 of 5 slides

Trusted by thousands of travellers

Cheap holidays to Chicago

Book the best deals on holidays to Chicago today!

  • from Dublin, International (DUB)
  • from Cork, International (ORK)

Our most popular holiday packages to Chicago

  • from Dublin, International (DUB)
  • from Cork, International (ORK)
  • 4 nightsFlights includedDublin
    775 m from beach
    from 1.437 € pp
    1 of 5 slides
  • 4 nightsFlights includedDublin
    2.92 km from city centre
    from 1.091 € pp
    1 of 5 slides
  • Flights included
    10.8 km from city centre
    1 of 5 slides
  • 4 nightsFlights includedDublin
    996 m from city centre
    from 1.313 € pp
    1 of 5 slides
  • 5 nightsFlights includedDublin
    1.78 km from city centre
    from 2.894 € pp
    1 of 5 slides
  • Riu Plaza Chicago

    4 nightsFlights includedDublinbreakfast included
    803 m from beach
    from 1.111 € pp
    1 of 5 slides
  • 4 nightsFlights includedDublin
    857 m from city centre
    from 1.311 € pp
    1 of 5 slides
  • 4 nightsFlights includedDublin
    648 m from beach
    from 1.497 € pp
    1 of 5 slides
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How does booking Flight + Hotel make travel even better?

Combine and Save

Enjoy access to special prices, only available on package deals.

Tailor-made trips

Choose from thousands of flights, hotels and stays.

Spread the cost

Book with a small deposit and pay the rest later.

Everything you need

Quickly add insurance, luggage, rental cars and more.

Travel tips for Chicago

Your Chicago questions answered

  • What are the most popular places to visit while in Chicago?

    The most popular places to visit in Chicago are: Willis Tower, Lincoln Park, United Center.

  • What kind of holidays does Chicago offer?

    Chicago is the ideal destination for city breaks.

  • Why should I book a flight & hotel package to Chicago on lastminute.com?

    Booking a flight + hotel package to Chicago with lastminute.com offers several advantages. By booking both services together, you can take advantage of exclusive deals and choose from thousands of flights and accommodations for the perfect combination. Additionally, you can secure your vacation with a deposit and pay the remaining amount later. You also have the flexibility to add other travel extras such as insurance, rental cars, and luggage to the flight + hotel package as per your preferences.