Oak Lawn Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 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

Top Flight + Hotel Deals in Oak Lawn

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 17 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Communication was great. Offered upgrade immediately and also had gift at check in for my husband, it was his birthday. Very nice staff. Johnnie at front desk was excellent. Very kind.

Reviewed on 6 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 17 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Excellent establishment great staff very clean and spacious

Reviewed on 5 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 17 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
First class property in every respect. Will stay again.

Reviewed on 6 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 17 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,035 reviews)
I always recommend this hotel to my guests and book travel for other people here. Super friendly awesome staff, great place to stay downtown and very convenient location.

Reviewed on 30 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 17 Sept
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 2025

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
7.8/10 Good! (8,968 reviews)
"Everything was good except the bathtub it was licking water and Im pretty sure there was mold but also the water in the bathtub was getting stuck not draining!! But the room was clean and cold and the service was good! You can hear the neighbors like it was in your room lol but we only use the room ..."

Reviewed on 4 Aug 2025

Get rates
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 €197 per night from 22 Aug to 23 Aug
€197
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
"Great!"

Reviewed on 5 Aug 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is €148 per night from 24 Aug to 25 Aug
€148
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,338 reviews)
"-"

Reviewed on 3 Aug 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,699 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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 street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

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

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
94% 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

€35
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 from €965 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.