Cook County Vacations & Trips 2026 from CA $1,034

Your Cook County Vacation

Embark on your next adventure with a Cook County vacation package, and leave knowing the finer details have been taken care of. Plus with the ability to tailor your escape, you know it'll be one to remember. Want to know where to go on your trip to Cook County? Tinley Park is a popular city you won't want to miss. Whether you're planning to travel on a shoestring or want to splurge, Expedia are here to help you customize your next dream Cook County vacation.

Top Cook County Vacation Deals

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

The Whitehall Hotel, BW Premier Collection

Downtown Chicago

CA $1,034

per person

Aug 20 - Aug 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very good! (3,941 reviews)

Basic

Reviewed on Jul 5, 2026

Level Chicago - River North

Downtown Chicago

CA $1,064

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,013 reviews)

This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,263

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (512 reviews)

We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Level Chicago – Old Town

Downtown Chicago

CA $1,809

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (497 reviews)

Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,667

per person

Aug 20 - Aug 25

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,554 reviews)

Me encantó volveria mil veces a ese hotel

Reviewed on Jul 4, 2026

Cook County Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $244

CA $290 total

Jul 7 - Jul 8

includes taxes & fees

8.2/10 Very good! (1,689 reviews)

"We like our room, very clean and spacious"

Reviewed on Jul 4, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $172

CA $205 total

Jul 6 - Jul 7

includes taxes & fees

8/10 Very good! (10,157 reviews)

"Great location- good price for a holiday weekend"

Reviewed on Jul 4, 2026

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

CA $208

CA $294 total

Jul 8 - Jul 9

includes taxes & fees

9.2/10 Wonderful! (1,846 reviews)

"Great staff"

Reviewed on Jul 5, 2026

See all 4,591 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 CA $1,034. 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.