Cook County Vacations & Trips from ￥300,644

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The Latest Cook County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥351,554, price is now ￥300,644 per person
￥300,644
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room Other than that the front desk and cleaning ladies was very nice.

Reviewed on May 29, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥414,738, price is now ￥327,358 per person
￥327,358
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
Staff was super nice and attentive.

Reviewed on May 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥365,475, price is now ￥301,248 per person
￥301,248
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Staff was so helpful

Reviewed on May 29, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥362,366, price is now ￥310,222 per person
￥310,222
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,579 reviews)
We didn’t love the room set up with the glass shower. And the elevators were very slow but the staff was great.

Reviewed on May 29, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥364,135, price is now ￥314,722 per person
￥314,722
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
I enjoyed our stay at LondonHouse Chicago, Curio Collection by Hilton. Staff members were friendly and helpful! Housekeeping staff were friendly and on point with cleaning! My next visit to Chicago, I plan on staying there.

Reviewed on May 27, 2026

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 ￥20,737 per night from Jun 29 to Jun 30
￥20,737
￥24,653 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"

Reviewed on May 29, 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 ￥30,104 per night from Jun 30 to Jul 1
￥30,104
￥40,329 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."

Reviewed on May 29, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ￥24,209 per night from Jun 28 to Jun 29
￥24,209
￥28,783 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,488 reviews)
"rooftop"

Reviewed on May 29, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,841 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 ￥300,644. 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.