Oak Lawn Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Oak Lawn Vacation Packages

Oak Lawn Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is ₩186,457 per night from Sep 1 to Sep 2
₩186,457
₩218,873 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,965 reviews)
"Its location is the main reason why I chose to stay. The room has been updated; it is roomy and clean. Staffs are very friendly and helpful."

Reviewed on Aug 17, 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩209,588 per night from Sep 1 to Sep 2
₩209,588
₩246,035 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,194 reviews)
"Staff was kind and friendly."

Reviewed on Aug 17, 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is ₩223,124 per night from Sep 3 to Sep 4
₩223,124
₩261,927 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,717 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on Aug 17, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,629 properties in Oak Lawn
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.

Discover the most popular places to visit in Oak Lawn

Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Frequently asked questions

How much does an Oak Lawn vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 vacation package to Oak Lawn?
During your Oak Lawn vacation, 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 vacation package as early as possible.
Is it cheaper to book an Oak Lawn vacation as a package?
An Expedia vacation 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 vacation package to Oak Lawn?
If you're considering a spontaneous Oak Lawn vacation, 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?

  1. 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 vacation in Oak Lawn.
  2. 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.
  3. 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.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Oak Lawn vacation package.

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