Oak Lawn Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Oak Lawn Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 hour ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Convenient location. The hotel is quiet and staff are helpful and nice.

Reviewed on 14 Nov,2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Dec - 30 Dec
found 1 hour ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
They charge for upgrade.

Reviewed on 14 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 hour ago
Return flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 hour ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We thoroughly enjoyed our stay. The staff was courteous and attentive, the room was clean, modern, and comfortable.

Reviewed on 14 Nov,2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
27 Dec - 30 Dec
found 1 hour ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (3,559 reviews)
excellent staff, great lounge and location

Reviewed on 14 Nov,2024

Top hotels in Oak Lawn

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 S$135 per night from 26 Nov to 27 Nov
S$135
includes taxes & fees
26 Nov - 27 Nov
7.8/10 Good! (8,066 reviews)
"Every staff member we met greeted us with a smile and were at the ready to answer any questions we had. My son and I were so excited to stay here and we will definitely be back."

Reviewed on 13 Nov,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 S$153 per night from 16 Dec to 17 Dec
S$153
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (3,530 reviews)
"Nice"

Reviewed on 12 Nov,2024

River Hotel
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
The price is S$186 per night from 8 Dec to 9 Dec
S$186
includes taxes & fees
8 Dec - 9 Dec
8.2/10 Very Good! (3,184 reviews)
"Our family loved the breakfast buffet, reception every evening, and the pool."

Reviewed on 12 Nov,2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,164 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.

Frequently asked questions

How much does an Oak Lawn holiday package cost?
Cross off another part of the world with our Oak Lawn holiday packages, which start from a low S$707. 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 holiday 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 Centre 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 travellers.
How far in advance should I book my Oak Lawn holiday?
Savvy travellers 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 holiday 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 holiday 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 holiday.
If I'm not able to travel, can I cancel my Oak Lawn holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Oak Lawn holiday 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.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 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
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Oak Lawn

Flyover in Chicago

Flyover in Chicago

S$50
Per adult
94% of travellers recommend
Flyover in Chicago
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$71
Per adult
98% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Private Chicago Scavenger Hunt: Eastside Art Heist

Chicago Quest Experience: The Heist

S$14
Per adult
Chicago Quest Experience: The Heist
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.