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Cook County Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Cook County

The Latest Cook County Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 6 Sept - 11 Sept

    Aloft by Marriott Chicago Downtown River North + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,256 reviews)
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWR1 stop
    €871
    €666
    per traveller
    found 20 hours ago
    Aloft by Marriott Chicago Downtown River North
  • 20 Sept - 25 Sept

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (543 reviews)
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWR1 stop
    €1,591
    €920
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • 6 Sept - 11 Sept

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (512 reviews)
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWR1 stop
    €1,436
    €886
    per traveller
    found 20 hours ago
    Level Chicago – Old Town
  • 20 Sept - 25 Sept

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (3,770 reviews)
    "Great location, clean and beautiful. Elevator from ground to level floor was out several nights and the rooftop was not open."
    Reviewed August 1, 2026
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWR1 stop
    €1,140
    €783
    per traveller
    found 1 day ago
    Eurostars Magnificent Mile
  • 20 Sept - 25 Sept

    Holiday Inn Express Chicago - Magnificent Mile by IHG + Flight

    Downtown Chicago
    5 nights
    2.5 star property
    8.4/10 - Very good (1,223 reviews)
    "I enjoyed the historic details of the building. The unique layout of our room worked really well for us. Perfect location for activities and eateries. Would definitely recommend."
    Reviewed August 2, 2026
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWR1 stop
    €919
    €667
    per traveller
    found 1 day ago
    Holiday Inn Express Chicago - Magnificent Mile by IHG

Discover the most popular places to visit in Cook County

Cook County Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does a Cook County holiday package cost?

Explore the best of Cook County from as little as €666. We offer a wonderful selection of flights, rental cars and hotels to suit every budget. Land even more discounts when you add a couple of sightseeing tours to your package.

How do I get a cheap travel package to Cook County?

One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got them all. Choose a combination that suits you and see your savings stack up. We know a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotel options across the globe, which lets you customize your Cook County holiday.

Where should I stay in Cook County?

Tinley Park is first up on many Cook County itineraries. Hollywood Casino Amphitheatre plays a big part in that.

What are the top hotels in Cook County?

Check out Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton. They're top picks for lots of travellers to Orland Park. If Tinley Park is on your itinerary, The Whitehall Hotel and Hyatt Regency Chicago are a couple of cosy options.

How far in advance should I book my Cook County holiday?

Savvy travellers book early. Air carriers typically advertise flights up to a year prior to departure, and this is your chance to land some rock-bottom prices. Boss just told you to use up all your holiday days next week? That's fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at an affordable price.

What does an Expedia Cook County travel package include?

Hotels, rental cars and flights — we have them well covered. With Expedia, you can create your Cook County package just the way you want. All you have to do is decide exactly what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the more you save!

What should I know before booking a Cook County travel package?

Whether it's adventure or relaxation you're craving, a Cook County holiday package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the more you'll save!

Can I choose my airline with a Cook County Expedia holiday package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.

If I'm not able to travel, can I cancel my Cook County holiday package?

We totally understand — unexpected stuff happens. If you've booked a Cook County holiday package and need to amend or cancel it, we're here to help. It's always worth browsing our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's more than 24 hours, your airline, hotel or car rental company may impose a fee.