Cook County Vacations & Trips from ￥263,796

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The Latest Cook County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Nice place, enjoyed the stay. Was close to Lollapalooza.

Reviewed on Aug 4, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 12 - Sep 17
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Excellent establishment great staff very clean and spacious

Reviewed on Aug 5, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
Sep 13 - Sep 20
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
First class property in every respect. Will stay again.

Reviewed on Aug 6, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
Sep 13 - Sep 20
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on Jul 27, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Sep 13 - Sep 20
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Communication was great. Offered upgrade immediately and also had gift at check in for my husband, it was his birthday. Very nice staff. Johnnie at front desk was excellent. Very kind.

Reviewed on Aug 6, 2025

Cook County Hotel Deals

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 ￥19,764 per night from Sep 1 to Sep 2
￥19,764
￥23,203 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,914 reviews)
"I love it"

Reviewed on Aug 5, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥25,528 per night from Aug 22 to Aug 23
￥25,528
￥33,648 total
Aug 22 - Aug 23
includes taxes & fees
8.2/10 Very Good! (1,832 reviews)
"Central location to everything"

Reviewed on Aug 6, 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is ￥21,494 per night from Aug 24 to Aug 25
￥21,494
￥25,231 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,351 reviews)
"I liked the in and out parking access for one rate per day."

Reviewed on Aug 6, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,804 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 ￥263,796. 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.