Oak Lawn Vacations from $215

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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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $416, price is now $215 per person
$215
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Everything was excellent. Will definitely stay here again. I really liked the scent of the bath/shower products and the candles in the lobby

Reviewed on Nov 20, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,175, price is now $526 per person
$526
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Great location and staff was very accommodating. Rooms were on the small side.

Reviewed on Nov 19, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $858, price is now $463 per person
$463
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Leo handled our stay and made it seamless with first class service. Much appreciated!

Reviewed on Nov 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $443 per person
$443
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance. The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return. Mr. & Mrs.S

Reviewed on Nov 17, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $406, price is now $227 per person
$227
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.

Reviewed on Oct 28, 2025

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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

Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oak Lawn

Oak Lawn Hotel Deals

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
$87 nightly
The price is $102 total per night from Dec 8 to Dec 9
$102 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,274 reviews)
I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it.

Reviewed on Nov 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 21 to Dec 22
$145 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,072 reviews)
Staff could not have been more helpful. The venue was packed for an international rugby game, but everything was clean, well cared for and comfortable. Will defintiely stay here again!

Reviewed on Nov 18, 2025

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,337 reviews)
Thank you

Reviewed on Nov 20, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,676 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 $215 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.

Explore a world of travel with Expedia

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