Oak Lawn Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.

Top Oak Lawn Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
Jul. 2 - Jul. 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
This was a really nice hotel in a great area with tons of restaurants, well lit up streets and easy walking in the downtown River North area. The hotel itself was lively on the ground floor with its bar and restaurant and the room was clean and well laid out and quiet overall The bed/pillows were really, really comfortable. I would stay here again anytime.

Reviewed on May 18, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
7.8/10 Good! (1,743 reviews)
Just overall a really nice place

Reviewed on May 22, 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 2 - Jul. 6
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on May 21, 2024

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 14 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.2/10 Very Good! (1,509 reviews)
Balcony views were great! Staff was friendly and the room was a decent size. The only thing I would say needs improvement would be the cleanliness of the rooms and bathroom.

Reviewed on May 23, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.8/10 Excellent! (1,018 reviews)
Everything was awesome.

Reviewed on May 19, 2024

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
The price is CA $226 per night from May 27 to May 28
CA $226
CA $266 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,786 reviews)
"Nice old hotel with a lot of history, in a beautiful area in sight of Lake Michigan."

Reviewed on May 22, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from May 27 to May 28
CA $194
CA $228 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (2,886 reviews)
"Appreciated the easy of self serve check in and checkout. Did not have to stand in line. Only complaint is that the wait time for elevators is too long. Number iof elevators do not support number of guests"

Reviewed on May 22, 2024

River Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 27 to May 28
CA $172
CA $222 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,602 reviews)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many ..."

Reviewed on May 20, 2024

Warwick Allerton - Chicago
See all 4,206 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oak Lawn vacation package cost?
Cross off another part of the world with our Oak Lawn vacation packages, which start from a low CA $674. Choose the flights and hotels that fit your travel plans. Then, add on one or two experiences or tours to round off your unique escape.
How do I get a cheap travel package to Oak Lawn?
Track down flights that suit your busy schedule, add a hotel to your booking and see how much you save with an Oak Lawn vacation package. It’s as simple as that! From flights and hotels to rental cars and activities, Expedia is where your cheap getaway begins. And with more than 550 air carriers and 1,000,000 hotel options across the globe to select from, you’ll never be short of choice.
Where should I stay in Oak Lawn?
With so much to discover in Oak Lawn, it’d be convenient for you to book a room in a hotel close to its attractions. Chicago Ridge Shopping Mall, Advocate Christ Hospital and Medical Center and Little Company Of Mary Hospital are some good ones to add to your to-do list.
What are the top hotels in Oak Lawn?
If it’s your first time staying in Oak Lawn, book a room at Midway Inn & Suites or Hilton Chicago/Oak Lawn. Both offer friendly service and are top options with many savvy travelers.
How far in advance should I book my Oak Lawn vacation?
Savvy travelers often reserve their seats early. You can generally compare international fares on Expedia up to a year before your intended flight. If you’re late to book, don’t worry. Cheap prices sometimes become available in the last weeks before departure dates.
What does an Expedia Oak Lawn travel package include?
That depends on what type of trip you’re contemplating. Oak Lawn vacation deals can include hotels, car rentals and flights. You can mix and match to create the travel package that suits your budget and style. You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking an Oak Lawn travel package?
A travel package can be customized for your budget and is a fantastic way to make your money go further. How much you include is completely up to you. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
Can I choose my airline with an Oak Lawn Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Just choose the carrier you want and craft the perfect Oak Lawn vacation.
If I'm not able to travel, can I cancel my Oak Lawn vacation package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Oak Lawn vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, airline or hotel may impose a fee. Looking for more information? Take a look at our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Oak Lawn

Image for Wrigley Field

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

4.5/5(5 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(141 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Oak Lawn

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

CA $311
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Oak Lawn
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.