Book Exclusive Cook County Vacation Packages

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Search vacation packages deals in Cook County's top destinations

A wooden boardwalk over a river, surrounded by trees and greenery.

Tinley Park

Vacations
Tinley Park

Cook County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel 505 River North

Hotel 505 River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,695, price is now CA $1,216 per person
CA $1,216
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $2,641, price is now CA $1,699 per person
CA $1,699
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $4,316, price is now CA $2,787 per person
CA $2,787
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,746, price is now CA $1,230 per person
CA $1,230
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,692, price is now CA $1,226 per person
CA $1,226
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Cook County hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $170 total
Nov 11 - Nov 12
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $217 per night
CA $217
CA $258 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $204 per night
CA $204
CA $242 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $183 per night
CA $183
CA $218 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $181 per night
CA $181
CA $216 total
Nov 12 - Nov 13
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Pool
Pet-friendly
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $237 per night
CA $237
CA $323 total
Oct 30 - Oct 31
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Pool
Hot tub
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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.

Stay near popular Cook County attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
See properties

Photos of local treasures

Browse Cook County vacation photos for more inspiration

A city skyline with skyscrapers, a river, and a bridge.
A city skyline with a prominent mosque featuring a green dome, a waterfront promenade, and a large Ferris wheel.
A city skyline with modern skyscrapers and a large green park in the foreground.
A city skyline with a prominent skyscraper, a river, and a bridge.
A cityscape with a river, modern skyscrapers, and a sunset sky.

Frequently asked questions

How much are vacation packages to Cook County?
Exciting adventures await in Cook County, with Travelocity vacation packages from as low as CA $1,216. Including flights and hotels, these incredible deals make it a breeze to experience all corners of the globe.
Where can I get the best vacation package deals for Cook County?
It's hard to top Travelocity when it comes to finding your Cook County package deal. There are at least 400 air carriers and 1,000,000 worldwide properties to choose from. Lock in your trip now and get ready to cross another amazing place off your to-do list.
Why should I book my Cook County vacation bundle via Travelocity?
Whether you're planning a month-long vacation or a last-minute weekend trip, we have many attractive destinations to choose from at an affordable rate. What's more, we provide support 24/7, high-quality service and a Price Match Guarantee. Save yourself time and money and lock in your dream vacation now.
Can I save on my Cook County car rental if I book it with hotels and flights?
You sure can with our Cook County vacation packages. With one of these, there are plenty of ways to make your travel budget go further. Bundle any two or more car, hotel, flight and tour bookings and watch the savings pile up. With your own ride, all the attractions in and around Cook County are just a road trip away.
Which airport is best for Cook County?
O'Hare Intl. Airport (ORD) is where many travelers choose to touch down. Depending on your Cook County itinerary, Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are other choices for you to consider.
What is there to do in Cook County?
You'll be happy to know Cook County is full of fabulous things to see and do, however Hollywood Casino Amphitheatre and Odyssey Fun World are two you shouldn't miss.