Oak Lawn Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Oak Lawn
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
€594
per person
24 Sept - 29 Sept
found 11 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,942 reviews)
This is a more affordable option for being right in the city within walking distance of tourist attractions. However this property is outdated (I don’t know if that is their style), the hallway have this weird attic smell, our room was dusty and the lighting is terrible in the room. The staff is okay nothing exceptional.
Reviewed on 18 Aug 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
€977
per person
24 Sept - 29 Sept
found 11 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Loved the location, cleanliness, staff and room for my family of 6. Could use an additional restaurant, but was still happy
With our experience.
Reviewed on 18 Aug 2026
Top hotels in Oak Lawn
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,247 reviews)
"Hotel needs to be renovated.. it’s in really rough shape. ..actual spider webs on the windows.. smells bad.. it’s wild.."
Reviewed on 17 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€147
31 Aug - 1 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€242
12 Sept - 13 Sept
includes taxes & fees
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 Oak Lawn attractions
Chicago Ridge Shopping Mall
7.8/10 (66 reviews)
This bustling retail hub features over 100 stores anchored by Dick's Sporting Goods and Kohl's with SEPHORA. Enjoy premium shopping complemented by diverse dining options and the latest blockbusters at AMC Theatre.
Childrens Museum of Oak Lawn
8.0/10 (32 reviews)
This interactive wonderland captivates young minds with hands-on exhibits like a firefighter station and supermarket. Children aged 0-8 can explore and learn through imaginative play in a vibrant space.
Centennial Park
You can take time to visit Centennial Park during your travels to Oak Lawn. While in this family-friendly area, you can savour the top-notch restaurants.
What to do in Oak Lawn
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
Frequently asked questions
How much does an Oak Lawn holiday package cost?
You can snap up a holiday package to this popular destination from €594 on Expedia. However, how much your holiday to Oak Lawn costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Oak Lawn?
November, December and January are the best times to search for cheap Oak Lawn holiday packages. Choosing to travel in less busy periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Oak Lawn?
Typically, a handful of days is enough to go to the top attractions during your Oak Lawn holiday. However, if you prefer to have more time to kick back or go on day trips, think about extending your itinerary.
Is it worth booking a holiday package to Oak Lawn?
During your Oak Lawn holiday, you can count on experiencing some excellent golfing and walking trails. Leave enough time in your itinerary to visit major attractions like Childrens Museum of Oak Lawn and Chicago Ridge Shopping Mall.
How to find the best Oak Lawn package deals?
Use Expedia's filters to find some of the best Oak Lawn package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Oak Lawn package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book an Oak Lawn holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can tailor your Oak Lawn getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Oak Lawn?
If you're considering a spontaneous Oak Lawn holiday, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Oak Lawn?
- Choose when to travel: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to holiday in Oak Lawn.
- Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Oak Lawn.
- Decide how long to go away for: Now that you're more familiar with Oak Lawn, you can figure out the perfect length of your break. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Oak Lawn holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
