Oak Lawn Vacations from $377

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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $599, price is now $377 per person
$377
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $652, price is now $396 per person
$396
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $728, price is now $453 per person
$453
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $824, price is now $520 per person
$520
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on Nov 5, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $625, price is now $403 per person
$403
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)
The room itself was pretty clean, it had a good shower which is sometimes rare to find. The staff was friendly and housekeeping was responsive. Close to things, but I wouldn’t necessarily say walking distance. It was pretty noisy but hard to get away from that in a city.

Reviewed on Nov 7, 2026

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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 Theater.
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What to do in Oak Lawn

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

$24
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
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
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,111 reviews)
"Great room, I hope the second elevator is fixed soon."

Reviewed on Nov 7, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 9 to Nov 10
$138 total
Nov 9 - Nov 10
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
$115 nightly
The price is $137 total per night from Dec 6 to Dec 7
$137 total
Dec 6 - Dec 7
Total with taxes and fees
8.8/10 Excellent! (5,591 reviews)
"The room was really clean and put together. The location is great, close to Michigan Ave and the river. Lots of restaurants and shops nearby, and Millennium Park is a quick 10 min walk!"

Reviewed on Nov 7, 2026

River Hotel
See all 4,498 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.

Find the Best Oak Lawn Vacation Packages

Oak Lawn Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
56,800
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
John G. Shedd Aquarium, Field Museum of Natural History and Brookfield Zoo

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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 $377 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.

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