Cook County Vacations & Trips from ￥176,416

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The Latest Cook County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥216,900, price is now ￥176,416 per person
￥176,416
per person
Nov 1 - Nov 4
found 7 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on Sep 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥316,864, price is now ￥229,480 per person
￥229,480
per person
Nov 1 - Nov 4
found 7 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Clean room. Great staff

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥252,514, price is now ￥185,212 per person
￥185,212
per person
Nov 1 - Nov 4
found 7 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Everything was amazing. From the room itself, the breakfast and the staff

Reviewed on Oct 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥259,048, price is now ￥198,999 per person
￥198,999
per person
Nov 1 - Nov 4
found 7 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Good location not far from all the big attractions. But it was noisy in the evening.

Reviewed on Sep 29, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥235,400, price is now ￥185,494 per person
￥185,494
per person
Nov 1 - Nov 4
found 7 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

Cook County Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ￥18,754 per night from Nov 2 to Nov 3
￥18,754
￥22,014 total
Nov 2 - Nov 3
includes taxes & fees
7.8/10 Good! (9,258 reviews)
"Love this place"

Reviewed on Oct 2, 2025

Congress Plaza Hotel
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 ￥28,267 per night from Nov 2 to Nov 3
￥28,267
￥33,184 total
Nov 2 - Nov 3
includes taxes & fees
8.4/10 Very Good! (5,023 reviews)
"Clean , a great location and the amenities are awesome"

Reviewed on Oct 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥22,018 per night from Nov 2 to Nov 3
￥22,018
￥25,848 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (3,002 reviews)
"The staff were super helpful. Great location, we were able to walk to the navy pier, the bean, and all the stores on Michigan Avenue! Only downside was the pool was closed but we were told that ahead of time!"

Reviewed on Oct 2, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,702 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 vacation package cost?
Explore the best of Cook County from as little as ￥176,416. 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 vacation.
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 travelers to Orland Park. If Tinley Park is on your itinerary, The Whitehall Hotel and Hyatt Regency Chicago are a couple of cozy options.
How far in advance should I book my Cook County vacation?
Savvy travelers 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 vacation 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 vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodations 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 vacation 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 vacation package?
We totally understand — unexpected stuff happens. If you've booked a Cook County vacation 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.