Oak Lawn Holidays

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Oak Lawn Holiday

Our pick of the best Oak Lawn Hotel Deals

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
The price is NZ$341 per night from 27 July to 28 July
NZ$341
27 July - 28 July
includes taxes & fees
8.2/10 Very good! (1,695 reviews)
"Tried to use the very small hair dryer only to find out it quite in a puff of black smoke and smelled up the whole room."

Reviewed on 5 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$410 per night from 9 July to 10 July
NZ$410
9 July - 10 July
includes taxes & fees
9.2/10 Wonderful! (1,857 reviews)
"This was a very clean and nice hotel. I enjoyed the room."

Reviewed on 6 July 2026

Omni Chicago Hotel
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$253 per night from 7 July to 8 July
NZ$253
7 July - 8 July
includes taxes & fees
8/10 Very good! (10,178 reviews)
"This will always be my go to place to stay in downtown Chicago. Fantastic location, clean and great staff."

Reviewed on 6 July 2026

Congress Plaza Hotel
See all 4,442 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.

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 Theatre.
See properties

What to do in Oak Lawn

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$48
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$70
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$43
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.

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.