Cook County Vacations & Trips from $503

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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 destinations in Cook County

A river flowing through a forest with autumn-colored trees and fallen leaves.

Tinley Park

Tinley Park
A cityscape with a marina, river, and high-rise buildings.

Chicago Heights

Chicago Heights
A frozen river with snow-covered banks and trees in the background during sunset.

Matteson

Matteson
A park with autumn trees, fallen leaves, and picnic tables.

Park Forest

Park Forest

The Latest Cook County Vacation Packages

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

The Emily Hotel

Downtown Chicago
Save 100% on your flight
$503
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.

Reviewed on Sep 27, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$789
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$609
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Breakfast, clean room, Staff

Reviewed on Sep 27, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$976
per person
Nov 28 - Dec 4
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.

Reviewed on Sep 26, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$621
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.

Reviewed on Sep 26, 2026

Best Places to Vacation in Cook County

1. Book your ideal Schaumburg with a vacation package

Rosemont, Illinois offers a diverse range of activities and experiences for families on vacation. Whether you're into hockey, shopping, dining, or entertainment, Rosemont has something for everyone. Explore the local biking trails and enjoy outdoor recreation, or catch a live theater performance or live music show. The vibrant bar scene is perfect for adults looking to unwind. Rosemont is also known for its business opportunities, making it a great destination for both work and play. With a wide range of destination activities and things to do, Rosemont guarantees a memorable family vacation.

  • The peak season is from May to July
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Schaumburg

2. Find your perfect Rosemont vacation

Schaumburg, Illinois is a vibrant destination perfect for a family vacation. With its convenient location, there are plenty of opportunities for shopping, dining, and engaging in various sports activities like football. The friendly people of Schaumburg make it a welcoming place for visitors. Families can enjoy horseback riding, live music, and other entertainment options. The town offers a range of family-friendly activities and things to do, making it an ideal destination for a memorable vacation. Whether you're looking for a fun-filled adventure or a relaxing getaway, Schaumburg has something for everyone.

  • The peak season is from July to September
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Rosemont

3. Plan your dream getaway to Evanston

Evanston, Illinois is the perfect destination for a family vacation. This charming city offers a variety of experiences for all ages. Explore the vibrant downtown area with its abundance of shops, restaurants, and cafes. Take a leisurely stroll along the beautiful Lake Michigan shoreline or enjoy a picnic in one of the many parks. Evanston is also home to Northwestern University, providing a unique college town atmosphere. Catch a live music performance or visit one of the local theaters for a memorable evening. Sports enthusiasts can cheer on the Northwestern Wildcats football team. There is something for everyone in Evanston!

  • The peak season is from May to July
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Evanston

4. Experience Skokie with a travel package

Tinley Park, located in Illinois, offers a diverse range of experiences for a family vacation. The town is known for its friendly atmosphere and attractions suitable for all ages. Visitors can enjoy exploring the local aquarium, indulging in delicious seafood, and experiencing live music performances. There are also various tours available, showcasing the area's rich history and culture. Families can catch a show at the local theater, go shopping, and dine at family-friendly restaurants. Tinley Park is a great destination for those looking to have a fun and memorable vacation with their loved ones.

  • The peak season is from June to August
  • The off-peak season is from November to January
  • Travelers tend to stay 2 days in Skokie

6. Discover Tinley Park with our vacation deals

Schiller Park in Illinois offers a diverse range of experiences for a family vacation. The town is conveniently located near shopping centers, making it an ideal place for retail therapy. Visitors can also enjoy outdoor activities like running or exploring the local parks. Schiller Park is known for its family-friendly atmosphere, with friendly locals and plenty of entertainment options. There are numerous cafes and restaurants to dine at, offering a taste of local cuisine. Whether you're visiting for business or leisure, Schiller Park provides a welcoming and enjoyable experience for the whole family.

  • The peak season is from June to August
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Tinley Park

5. Explore Bridgeview with a vacation package

Skokie, Illinois offers a diverse and family-friendly atmosphere for vacationers. The city is known for its excellent shopping and dining options, as well as its beautiful gardens and nature areas. The friendly people and sunny weather make it a welcoming place to visit. Families can enjoy a variety of activities, including destination activities, theme parks, and water parks. Skokie has something for everyone, whether you're looking for outdoor adventures or indoor entertainment. Come and experience all that Skokie has to offer!

  • The peak season is from May to July
  • The off-peak season is from October to December
  • Travelers tend to stay 2 days in Bridgeview

Find the Best Cook County Vacation Packages

Cook County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Centennial Park and George Dunne National Golf Club

Cook County Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$186 nightly
$221 total
Oct 25 - Oct 26
Total with taxes and fees
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$157 nightly
$187 total
Oct 26 - Oct 27
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$170 nightly
$202 total
Sep 29 - Sep 30
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 4,699 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?
Handcraft your Cook County package from just $503. Pick from any combination of hotels, flights and rental cars to pull together the escape you've been dreaming about for ages. Be sure to add on some activities and experiences!
How do I get a cheap travel package to Cook County?
If you love bargains, bundle your bookings into a Cook County vacation package. Whether you're looking for flights, hotels, rental cars or activities, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 hotel options worldwide to pick from. Fly with who you want, stay wherever you like and save precious dollars — now that's the perfect vacation!
How far in advance should I book my Cook County vacation?
While prices do change, we generally advise booking your spot as early as possible. Most international airfares are found on Expedia up to 12 months in advance. If you're booking late, you might still be in luck. Cheap journeys to Cook County sometimes appear only weeks before departure.
What does an Expedia Cook County travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to create your perfect Cook County travel package. Once you've made your booking, you can add on all the fun stuff like day tours and activities. Remember, the more you bundle, the more dollars you'll save!
What should I know before booking a Cook County travel package?
We already have low prices. However, you'll pick up even more savings if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Cook County Expedia vacation package?
Yes, so take your pick! We offer more than 550 partner airlines throughout the world, so you can customize your Cook County adventure according to your budget and travel needs.
Does Expedia offer Book Now, Pay Later Cook County vacation packages?
Any trip away can become costly, so it's nice to know that Expedia is able to make things easier. Thanks to our partnership with online lender Affirm, you can now make the most out of your hard-earned dollars with a Book Now, Pay Later vacation package.
If I'm not able to travel, can I cancel my Cook County vacation package?
If your vacation plans in Cook County have changed, it's a relief to know that it's possible to cancel your booking. If you booked in the last 24 hours, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. For more information, visit our Customer Service Portal.

Stay near popular Cook County attractions

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

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.
See properties
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.
See properties
A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago

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.
See properties
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.
See properties
A large metallic sphere sculpture in a public square surrounded by tall buildings.
Photo by TM

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.
See properties
A cityscape at night with illuminated buildings, a river, and a bridge.
Photo by TM

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.
See properties
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 enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
See properties
A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
See properties

What to do in Cook County

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
See all activities in Cook County
Explore a world of travel with Expedia

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.