Oak Forest Vacation Packages

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Your Oak Forest Vacation

Let our vacation packages to Oak Forest inspire your next getaway. There's loads to love about this lively city, starting with the neighborhood of South Deering, which is great for golfing and nature. If your trip to Oak Forest includes some sightseeing, don't miss well-known attractions like Hollywood Casino Amphitheatre, Odyssey Fun World and Coyote Run Golf Course. Check out Expedia's wide range of travel options and book your ideal vacation to Oak Forest today.

Top Oak Forest Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $976, price is now CA $604 per person
CA $604
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,863, price is now CA $1,113 per person
CA $1,113
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,022, price is now CA $654 per person
CA $654
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on Aug. 25, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,638, price is now CA $1,054 per person
CA $1,054
per person
Nov 10 - Nov 17
found 21 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug. 26, 2025

Ready to book your vacation to Oak Forest?

 

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Oak Forest 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 CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on Aug. 26, 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 CA $262 per night from Sep 4 to Sep 5
CA $262
CA $342 total
Sep 4 - Sep 5
includes taxes & fees
8.2/10 Very Good! (1,827 reviews)
"Hotel staff went above and beyond to make our stay great, even upgraded our room to a larger one for no extra charge!"

Reviewed on Aug. 26, 2025

Palmer House a Hilton Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
The price is CA $219 per night from Sep 2 to Sep 3
CA $219
CA $298 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (2,111 reviews)
"As a solo traveler, I felt safe the entire time I was here and in the areas surrounding the hotel. The staff were friendly and the interior of the hotel lobby is beautiful. The hotel was clean and centrally located to all the things you “have to see/do” when in Chicago!"

Reviewed on Aug. 25, 2025

Hilton Chicago
See all 2,252 properties in Oak Forest
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Oak Forest

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

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy 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

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Forest

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Oak Forest

Frequently asked questions

How much does an Oak Forest vacation package cost?
Offering great value package deals from CA $604 on Expedia, you'll be thrilled with how little a vacation to Oak Forest costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Oak Forest?
To pick up cheap Oak Forest vacation packages, organize your getaway outside of peak times like public holidays and major festivals. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Oak Forest?
To fully enjoy your Oak Forest vacation, we suggest booking for 2 days. Split your time between discovering Orland Square, Lake Katherine Nature Centre and other must-see attractions, on top of experiencing neighbourhoods like Orland Hills and Country Club Hills. If you've got some time to spare, add a tour or day trip to your Oak Forest vacation itinerary.
How to find the best Oak Forest package deals?
Bagging a cheap Oak Forest package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Oak Forest package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Oak Forest vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Oak Forest vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Oak Forest?
Score amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Oak Forest vacation.
How to plan a trip to Oak Forest?

  1. Choose your dates: What you want to do in Oak Forest and your favourite season can help you decide when to get away.
  2. Budget wisely: In addition to the cost of your accommodations, you should consider other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Oak Forest.
  3. Determine how many days away: Start by compiling a list of the sights and activities you'd like to experience in Oak Forest. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find an Oak Forest vacation package that brings all your bookings together.

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