Oak Lawn Vacations from $288

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Your Oak Lawn Vacation

Experience the unique personality of Oak Lawn with a tailor-made Oak Lawn vacation package. From its welcoming locals to its diversity and beyond, you'll never have a dull moment in this city. Want to explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the leading places to visit during your trip to Oak Lawn. Whatever your travel plans or budget, organizing a tailored Oak Lawn vacation is a cinch with Expedia.

The Latest Oak Lawn vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
per person
Oct 22 - Oct 27
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
In a great neighborhood. Quiet, clean. Excellent room layout. Free laundry was very nice to have. Nice breakfast.

Reviewed on Aug 14, 2025

citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Very relaxing I'll be back for future visits

Reviewed on Aug 17, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on Aug 16, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (431 reviews)
This is my go to place in the south suburbs.

Reviewed on Jul 30, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug 10, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Oak Lawn

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

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.

Michigan Avenue
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

What to do in Oak Lawn

River tour boat in Chicago

Architecture River Tour

$41
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oak Lawn

Oak Lawn Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,939 reviews)
"Friendly staff, clean rooms, huge hotel. Good location"

Reviewed on Aug 16, 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
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (1,187 reviews)
"Everything was great. Thanks for an awesome experience."

Reviewed on Aug 15, 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
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $189 total per night from Aug 24 to Aug 25
$189 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (4,707 reviews)
"The Italian restaurant inside is delicious, we went twice! If you aren’t I. The mood for there are so many options that are walkable. The Taco spot around the corner is also a win for food Taco Maya. The only thing we didn’t like is having to wait so long for the elevator, 25 mins to get from the ..."

Reviewed on Aug 15, 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.

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Frequently asked questions

How much does an Oak Lawn vacation package cost?
You can snap up a vacation package to this popular destination from $288 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?
If you'd like to snag a cheap Oak Lawn vacation package, consider visiting in September, October and December. You'll typically find lower rates on flights and accommodations during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Oak Lawn?
The ideal duration for your Oak Lawn vacation depends on what you'd like to see. Generally, a few days to a week will give you time to check out all the main sights and explore some hidden treasures along the way.
Is it worth booking a vacation package to Oak Lawn?
Well known for its golfing, walking trails and plenty of other highlights, you can be assured Oak Lawn is a good vacation destination. Some of the top attractions to put on your to-do list? Don't miss Chicago Ridge Shopping Mall and Childrens Museum of Oak Lawn during your Oak Lawn vacation.
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 get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Oak Lawn.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Oak Lawn.
  3. Explore Oak Lawn using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Oak Lawn. You can also save your favorite locations, collaborate with family and friends and organize your plans in one place.
  4. Decide how many days away: Start by compiling a list of the attractions you want to get to in Oak Lawn. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the ideal Oak Lawn vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Oak Lawn. Find all the exciting things to do in Oak Lawn with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Oak Lawn vacation packages?
Your Oak Lawn trip should be an escape from your daily routine, not a source of money worries. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.