Oak Lawn Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 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

Oak Lawn Holiday

Our pick of the best 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 NZ$373 per night from 14 Sept to 15 Sept
NZ$373
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,908 reviews)
Nice view
"We got a king room on the top floor overlooking Buckingham Fountain and Lake Michigan. So pretty. Last night we watched the fireworks show off of Navy Pier."

Reviewed on 14 Aug. 2025

Congress Plaza Hotel
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
The price is NZ$382 per night from 2 Sept to 3 Sept
NZ$382
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$285 per night from 4 Sept to 5 Sept
NZ$285
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (3,680 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
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.

Discover the most popular places to visit in Oak Lawn

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Navy Pier

Navy Pier

4.5/5(64 reviews)

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
McCormick Place

McCormick Place

4.5/5(21 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

River tour boat in Chicago

Architecture River Tour

NZ$69
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$75
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

NZ$67
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Oak Lawn

Frequently asked questions

How much does an Oak Lawn holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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?
November, December and January are the best times to search for cheap Oak Lawn holiday packages. Choosing to travel in less busy periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Oak Lawn?
Typically, a handful of days is enough to go to the top attractions during your Oak Lawn holiday. However, if you prefer to have more time to kick back or go on day trips, think about extending your itinerary.
Is it worth booking a holiday package to Oak Lawn?
During your Oak Lawn holiday, you can count on experiencing some excellent golfing and walking trails. Leave enough time in your itinerary to visit major attractions like Childrens Museum of Oak Lawn and Chicago Ridge Shopping Mall.
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 holiday package as early as possible.
Is it cheaper to book an Oak Lawn holiday as a package?
An Expedia holiday 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 holiday package to Oak Lawn?
If you're considering a spontaneous Oak Lawn holiday, 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 pack your bags. Your preferred season and the type of activities available will also help you decide when to holiday in Oak Lawn.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Oak Lawn.
  3. Decide how long to go away for: Now that you're more familiar with Oak Lawn, you can figure out the perfect length of your break. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Oak Lawn holiday package.

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