Cook County Vacations & Trips from $428

Arlington Heights and Schiller Park offer some of the lowest typical prices for a weekend Cook County vacation package, while Chicago and Schaumburg are slightly higher. A weekend trip typically costs around $600 per adult in Arlington Heights and Schiller Park, around $650 per adult in Rosemont, and around $700 per adult in Chicago and Schaumburg.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

When you bundle, you can save up to 30%*. To save money on a Cook County package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

A Cook County vacation package lets you combine flights, hotel stays, and rental cars, based in destinations like Chicago, Rosemont, and Schaumburg. In Chicago, nearly all hotels offer airport shuttle service to and from Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), and most include free breakfast. Many hotels in Rosemont and Schaumburg also provide these amenities.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

Schiller Park, Arlington Heights, Chicago, Rosemont, and Evanston are some of the top destinations for cheap Cook County vacation package deals. For an affordable weekend getaway, Schiller Park is often among the most budget-friendly options, with package prices starting around $320 per adult. For notable bundle savings, Chicago is often among the best options, with flight-and-hotel bundles saving around $65 per adult.


Browse cheap vacation packages in Cook County on Expedia to compare current deals.


*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

The best time for a Cook County vacation package depends on which destination you choose.


Chicago is busiest in June and July, when highs are around 79°F and 73°F respectively; June also hosts the Chicago Pride Parade. If you'd prefer fewer crowds, from January to March are quieter, with highs around 30°F in January.


Schaumburg sees the most visitors in June and July, with highs reaching around 82°F in July and 78°F in June. For a quieter Cook County vacation, consider visiting from January to March, when highs are around 29°F in January.


Rosemont is busiest in June and July, with highs around 82°F in July and 77°F in June. If you prefer to avoid the largest crowds, from January to March are quieter, with highs around 30°F in January.

Cook County vacation packages offer a variety of travel styles across its popular cities like Chicago, Rosemont, and Schaumburg:

• Family: In Chicago, the 4-star Warwick Allerton - Chicago, rated 8.3 out of 10 by travelers, provides family rooms, with staff frequently praised for being fantastic.
• Budget: For value-focused trips, Chicago features the Ohio House Motel, rated 8.5 out of 10 by travelers, which offers free breakfast and is often highlighted for its super clean rooms.
• Pet-Friendly: In Chicago, the 4.5-star Omni Chicago Hotel, rated 8.9 out of 10 by travelers, welcomes pets and is praised for its fantastic location.
• Breakfast: Rosemont offers options like the 4.5-star Loews Chicago O'Hare Hotel, rated 9 out of 10 by travelers, which includes free breakfast and is noted for its super clean rooms.

For your Cook County vacation, consider these destinations based on your travel style:

• Chicago: A popular choice for those seeking a vibrant urban experience, offering a wide array of family-friendly attractions, cultural sights, and outdoor activities. Packages here are well-established.
• Schaumburg: Ideal for families and business travelers, this city is known for its entertainment options and urban attractions, making it a convenient base for exploring.
• Rosemont: This destination is excellent for business travel and entertainment, with many family-friendly attractions and city amenities, and is a well-established package base.
• Oak Park: A good lodging base for travelers interested in cultural attractions and outdoor activities, offering a quieter experience while still providing access to urban draws.

Cook County is primarily an urban and outdoor destination, known for its family-friendly attractions, city experiences, and scenic views. The city of Chicago, located within Cook County, sits on Lake Michigan, providing opportunities for lake views and waterfront activities.


The region offers a rich blend of cultural and urban attractions. Cities like Chicago and Evanston are hubs for city life and cultural experiences, with landmarks such as Millennium Park in Chicago. Oak Park is particularly known for its unique architecture, including the Frank Lloyd Wright Historic District. Schaumburg and Rosemont provide extensive entertainment options and are popular for business travel.


A Cook County vacation package is ideal for travelers seeking a dynamic mix of urban exploration, cultural discovery, and family-friendly entertainment, with plenty of outdoor activities to enjoy.

For a Cook County vacation, the region is primarily served by two major airports in Chicago: Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Both provide convenient access to the various cities and attractions within Cook County. Additionally, General Mitchell International Airport (MKE) in Milwaukee, Wisconsin, also serves the broader area and can be an option depending on your specific travel plans.

Cook County offers a diverse range of attractions across its many destinations, perfect for a varied Cook County vacation:


Browse and book things to do in Cook County on Expedia.

Family vacation packages in Cook County offer a range of options with kid-friendly amenities across its cities:

• Embassy Suites by Hilton Chicago Downtown Magnificent Mile: In Chicago, this 4-star property, rated 7.7 out of 10 by travelers, provides family rooms and a kitchen, with travelers often highlighting the ample space in the rooms.
• Embassy Suites by Hilton Chicago O'Hare Rosemont: In Rosemont, this 4-star hotel, rated 8.2 out of 10 by travelers, features family rooms and an indoor pool, and guests frequently praise the rooms.
• Country Inn & Suites by Radisson, Schaumburg, IL: In Schaumburg, this hotel, rated 8.3 out of 10 by travelers, offers family rooms and a hot tub, with its pool often noted as a nice feature.
• Fairfield Inn & Suites by Marriott Chicago O'Hare: In Des Plaines, this hotel, rated 8.6 out of 10 by travelers, includes family rooms and an indoor pool, and its comfortable facilities are frequently mentioned.

Luxury Cook County vacation packages can be found in its vibrant cities, particularly Chicago and Rosemont:


Most Cook County vacation packages pair the hotel with flights. Browse luxury vacation packages in Cook County on Expedia to compare options.

Booking times for a Cook County vacation package vary by destination, with most travelers booking around 2 to 5 weeks before departure.


Travelers tend to book trips to these destinations most often from April to May, from June to September, and in October. If you're planning a spontaneous getaway, Expedia also offers last-minute Cook County vacation packages.

Most Cook County vacation packages last around 2 to 3 days, but the ideal trip length depends on where you're going and what you'd like to experience.


Chicago, known for its family-friendly attractions and urban appeal, is well-suited for a trip of around 3 days. Most travelers choose weekend trips, with nearly a third also opting for week-long stays, allowing time to explore landmarks like Millennium Park.


Rosemont, a hub for business travel and entertainment, also typically sees trips of around 3 days. Weekend trips are most popular, though some travelers choose week-long stays, which is ample time to visit the Donald E. Stephens Convention Center.


Schaumburg, offering family-friendly attractions and entertainment options, is also a popular choice for trips of around 3 days. Most visitors choose weekend trips, and nearly a third also enjoy week-long stays, perfect for shopping at Woodfield Mall.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Cook County vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Cook County, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Cook County vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Cook County getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.