Oak Lawn Trips (flight + hotel)

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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! (8,950 reviews)
"The room and bathroom were both spacious with high ceilings. Great view on the lake side."

Reviewed on Aug 3, 2025

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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 P9,947 per night from Aug 21 to Aug 22
P9,947
P13,111 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,824 reviews)
"could not use my Plat Amex, to upgrade bc of expedia."

Reviewed on Aug 3, 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 P8,375 per night from Aug 24 to Aug 25
P8,375
P9,832 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,330 reviews)
"Nice location"

Reviewed on Aug 1, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,702 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

McCormick Place

McCormick Place

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
Millennium Park showing modern architecture, autumn leaves and street scenes

Millennium Park

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

Millennium Park
Six Flags Great America which includes rides

Six Flags Great America

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

What to do in Oak Lawn

River tour boat in Chicago

Architecture River Tour

P2,350
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

P2,551
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

P1,698
per adult
92% of travellers recommend
Skyline Lake Tour
See all activities in Oak Lawn

Frequently asked questions

How much does an Oak Lawn vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 vacation package to Oak Lawn?
During your Oak Lawn vacation, 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 vacation package as early as possible.
Is it cheaper to book an Oak Lawn vacation as a package?
An Expedia vacation 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 vacation package to Oak Lawn?
If you're considering a spontaneous Oak Lawn vacation, 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 vacation 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 personalized Oak Lawn vacation package.

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