Cook County Holidays

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    Save up to S$134 when you book a flight and hotel together*

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

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Top hotels in Cook County

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$184 per night from 26 Apr to 27 Apr
S$184
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,081 reviews)
Good in general

Reviewed on 11 Apr, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$205 per night from 26 Apr to 27 Apr
S$205
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,100 reviews)
Recommend packing light if you self-park and walk to the hotel!

Reviewed on 11 Apr, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$232 per night from 19 Apr to 20 Apr
S$232
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...

Reviewed on 9 Apr, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,909 properties in Cook County
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 . 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.