Cook County Holiday Packages - Save on Cook County Flight & Hotel

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Top hotels in Cook County

River Hotel

75 East Wacker Drive Chicago IL

฿6,210

฿7,383 total

25 Oct - 26 Oct

includes taxes & fees

8.8/10 Excellent! (5,446 reviews)

"No view whatsoever, tried to get an upgrade, no luck …"

Reviewed on 26 Sept 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

฿5,364

฿6,377 total

26 Oct - 27 Oct

includes taxes & fees

8/10 Very good! (10,232 reviews)

"I booked a room with a bathtub, to find out that management allegedly is taking out all of the bathtubs. The room was tiny. It looked like they tried to maintain some of the early charm and details in the room but landlord special style. The entire place smelled old and musty. The bed was comfortable ..."

Reviewed on 26 Sept 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

฿5,975

฿7,104 total

25 Oct - 26 Oct

includes taxes & fees

See all 4,705 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 . 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.

Stay near popular Cook County attractions

An aerial view of a baseball stadium surrounded by urban buildings.

Wrigley Field

9.0/10 (11,704 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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A modern glass building with a curved roof, surrounded by a landscaped garden and a water feature.

McCormick Place

8.8/10 (9,822 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

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A large stadium surrounded by a cityscape with modern buildings.

Soldier Field

8.8/10 (7,063 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

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A large metallic sphere sculpture in a public square surrounded by tall buildings.

Millennium Park

9.4/10 (30,446 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

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A cityscape at night with illuminated buildings, a river, and a bridge.

Chicago Riverwalk

9.6/10 (13,574 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

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A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.

Michigan Avenue

9.4/10 (15,813 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

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