Book Exclusive Cook County Vacation Packages

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Search vacation packages deals in Cook County's top destinations

649-36 Hammel Creek Dusted in Snow

Tinley Park

Vacations
Tinley Park

Cook County flight + hotel packages

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,109, price is now CA $792 per person
CA $792
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,707, price is now CA $1,146 per person
CA $1,146
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,502, price is now CA $1,042 per person
CA $1,042
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,228, price is now CA $876 per person
CA $876
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff 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 $185 per night
CA $185
CA $219 total
May 25 - May 26
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $182 per night
CA $182
CA $256 total
May 25 - May 26
includes taxes & fees
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $184 total
May 25 - May 26
includes taxes & fees
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.
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 $168 per night
CA $168
CA $199 total
May 25 - May 26
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.
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 $175 per night
CA $175
CA $208 total
May 25 - May 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
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Free cancellation
The price is CA $218 per night
CA $218
CA $259 total
May 25 - May 26
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, 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.
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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.

Photos of local treasures

Browse Cook County vacation photos for more inspiration

Beautiful Sunsets behind Chicago
Stunning panorama of entire Navy Pier on Lake Michigan in Chicago with skyline during morning light
Skyline of Chicago at Grant Park in Illinois - United States
Sunset behind Chicago in the Winter
Chicago aerial view, river from a drone panorama

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 $792. 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.