Cook County Holidays

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    Save up to €185 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Cook County

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was €799, price is now €648 per person
€648
per person
21 May - 24 May
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (2,086 reviews)
Staff was extremely helpful. Rooms were clean and nearby lots of shopping and restaurants. Good continental breakfast in the morning too. Only negative was it was noisy at night with door clicking and noise when you turn on bathroom light at night. It wakes everyone with you up.

Reviewed on 13 Mar 2026

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

3 out of 5
Save 100% on your flight
Price was €3,307, price is now €2,573 per person
€2,573
per person
26 Apr - 4 May
found 1 day ago
Return direct flight included
Cork (ORK) to Chicago (ORD)
No reviews
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Price was €873, price is now €748 per person
€748
per person
21 May - 24 May
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
7/10 Good! (973 reviews)
Staff was really nice, amenities were great and the rooms were very clean.

Reviewed on 24 Feb 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was €868, price is now €770 per person
€770
per person
21 May - 24 May
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (3,713 reviews)
Excellent location-walkable to many restaurants, theatre, museums, and shopping. The room was very nice and valet parking was a convenient and easy.

Reviewed on 13 Mar 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,555, price is now €1,049 per person
€1,049
per person
14 Apr - 19 Apr
found 17 hours ago
Return direct flight included
Larnaca (LCA) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast

Reviewed on 13 Mar 2026

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 €166 per night from 27 Mar to 28 Mar
€166
27 Mar - 28 Mar
includes taxes & fees
8/10 Very Good! (9,922 reviews)
The location is amazing, right on Michigan Avenue, across the street from the park, a few blocks south of the river. The staff was friendly and efficient when I checked in, asked a few questions, and checked out. The room was great... nicer than I imagined. I would have liked daily room service. ...

Reviewed on 14 Mar 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 30 Mar to 31 Mar
€160
30 Mar - 31 Mar
includes taxes & fees
9.4/10 Exceptional! (3,527 reviews)
Clean, central and amazing breakfast

Reviewed on 13 Mar 2026

Hotel Riu Plaza Chicago
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 €128 per night from 15 Mar to 16 Mar
€128
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (5,736 reviews)
Great location. Good amenities. Nice breakfast. Comfy beds. Quiet.

Reviewed on 12 Mar 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,906 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 €648. 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.