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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)
  • Flight + Hotel

    The Chicago Hotel Collection Ambassador Gold Coast

    rated as 4 out of 5 by 2,038 reviewers
    3 nightsFlights includedDublin
    421 m from beach
    from 966 € pp
  • Flight + Hotel

    Warwick Allerton Chicago

    rated as 3.5 out of 5 by 2,933 reviewers
    3 nightsFlights includedDublin
    748 m from beach
    from 1.083 € pp
  • Flight + Hotel

    Hilton Chicago

    rated as 4 out of 5 by 7,468 reviewers
    3 nightsFlights includedDublin
    766 m from city centre
    from 1.060 € pp
  • Flight + Hotel

    Arlo Chicago

    rated as 4.5 out of 5 by 1,055 reviewers
    3 nightsFlights includedDublin
    883 m from city centre
    from 1.130 € pp
  • Flight + Hotel

    Eurostars Magnificent Mile

    rated as 4.5 out of 5 by 5,279 reviewers
    3 nightsFlights includedDublin
    1.79 km from city centre
    from 1.074 € pp
  • Flight + Hotel

    Freehand Chicago

    rated as 3.5 out of 5 by 1,027 reviewers
    3 nightsFlights includedDublin
    1.6 km from city centre
    from 1.000 € pp
  • Flight + Hotel

    Silversmith Hotel Chicago Downtown

    rated as 4.5 out of 5 by 2,958 reviewers
    3 nightsFlights includedDublin
    495 m from city centre
    from 1.108 € pp
  • Flight + Hotel

    Hyatt Regency McCormick Place Chicago

    rated as 4 out of 5 by 7,433 reviewers
    3 nightsFlights includedDublin
    3.04 km from city centre
    from 1.098 € pp
  • Flight + Hotel

    ACME Hotel Chicago, Outset Collection by Hilton

    rated as 4.5 out of 5 by 4,959 reviewers
    3 nightsFlights includedDublin
    1.6 km from city centre
    from 1.136 € pp

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)
  • Flight + Hotel

    Livn Millennium Park Downtown Chicago

    rated as 3.5 out of 5 by 10 reviewers
    Flights included
    509 m from city centre
  • Flight + Hotel

    SpringHill Suites by Marriott Chicago Chinatown

    rated as 5 out of 5 by 250 reviewers
    3 nightsFlights includedDublinbreakfast included
    3.18 km from city centre
    from 1.011 € pp
  • Flight + Hotel

    Hampton Inn & Suites Chicago Medical District Uic

    rated as 4.5 out of 5 by 30 reviewers
    3 nightsFlights includedDublinbreakfast included
    4.06 km from city centre
    from 1.072 € pp
  • Flight + Hotel

    The Buckingham Hotel

    rated as 4.5 out of 5 by 60 reviewers
    3 nightsFlights includedDublin
    295 m from city centre
    from 1.159 € pp
  • Flight + Hotel

    Hampton Inn Majestic Chicago Theatre District

    rated as 4.5 out of 5 by 2,940 reviewers
    3 nightsFlights includedDublinbreakfast included
    313 m from city centre
    from 1.197 € pp
  • Flight + Hotel

    Residence Inn Chicago Midway Airport

    rated as 4.5 out of 5 by 323 reviewers
    3 nightsFlights includedDublinbreakfast included
    15.04 km from city centre
    from 1.057 € pp
  • Flight + Hotel

    Hilton Garden Inn- Chicago Central Loop

    rated as 4.5 out of 5 by 169 reviewers
    3 nightsFlights includedDublin
    427 m from city centre
    from 1.119 € pp
  • Flight + Hotel

    Hampton Inn & Suites Chicago-Downtown

    rated as 4.5 out of 5 by 3,610 reviewers
    3 nightsFlights includedDublinbreakfast included
    1.4 km from city centre
    from 1.198 € pp
  • Flight + Hotel

    Homewood Suites by Hilton Chicago Downtown

    rated as 4.5 out of 5 by 3,576 reviewers
    8 nightsFlights includedDublinbreakfast included
    1.53 km from city centre
    from 1.400 € pp

Our most popular holiday packages to Chicago

  • from Dublin, International (DUB)
  • from Cork, International (ORK)
  • Flight + Hotel

    Stay One Chicago

    rated as 5 out of 5 by 1 reviewers
    8 nightsFlights includedDublin
    775 m from beach
    from 3.053 € pp
  • Flight + Hotel

    LIVN - Millennium Park Downtown Chicago

    rated as 4.5 out of 5 by 8 reviewers
    3 nightsFlights includedDublin
    511 m from city centre
    from 1.272 € pp
  • Flight + Hotel

    The Guesthouse Hotel

    rated as 5 out of 5 by 534 reviewers
    Flights included
    10.8 km from city centre
  • Flight + Hotel

    L7 Chicago by LOTTE

    rated as 5 out of 5 by 301 reviewers
    3 nightsFlights includedDublin
    996 m from city centre
    from 1.191 € pp
  • Flight + Hotel

    Nobu Hotel Chicago

    rated as 5 out of 5 by 546 reviewers
    8 nightsFlights includedDublin
    1.78 km from city centre
    from 2.347 € pp
  • Flight + Hotel

    Sentral Michigan Avenue

    rated as 4.5 out of 5 by 62 reviewers
    3 nightsFlights includedDublin
    842 m from city centre
    from 1.084 € pp
  • Flight + Hotel

    Riu Plaza Chicago

    rated as 4.5 out of 5 by 1,143 reviewers
    8 nightsFlights includedDublinbreakfast included
    803 m from beach
    from 1.645 € pp
  • Flight + Hotel

    Le Meridien Essex Chicago

    rated as 4.5 out of 5 by 1,037 reviewers
    3 nightsFlights includedDublin
    857 m from city centre
    from 1.169 € pp
  • Flight + Hotel

    Hotel EMC2, Autograph Collection

    rated as 5 out of 5 by 1,644 reviewers
    3 nightsFlights includedDublin
    648 m from beach
    from 1.590 € pp

How does booking Flight + Hotel make travel even better?

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: Lincoln Park, Willis Tower, 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.