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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,248, price is now CA $841 per person
CA $841
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.

Reviewed on Jul 1, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,393, price is now CA $1,698 per person
CA $1,698
per person
Sep 1 - Sep 6
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,644, price is now CA $1,172 per person
CA $1,172
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on Jul 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,612, price is now CA $1,188 per person
CA $1,188
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.

Reviewed on Jun 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,154, price is now CA $852 per person
CA $852
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
My husband and I and my daughter in law stayed at the omni because my son was having surgery at northwestern hospital. Is surgery was at 7:30 am and lasted almost 8 hours check in was not until 4, but they really understood our situation they were able to get into our room at noon. So we can rest. Everyone from the greeders at the door the front desk was tremendously helpful in our situation. A room was clean, check-up process with so easy.I highly recommend staying at this hotel.

Reviewed on Jul 1, 2026

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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 $211 per night from Jul 2 to Jul 3
CA $211
CA $251 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (10,185 reviews)
"This place was really horrible! The shower was cold as hell and the front desk didn't do anything to help. The room was not wiped down properly and I left first thing on the A.M. when I told the front desk about my stay, they did nothing to fix the issue or reimburse me a portion of my money. I came ..."

Reviewed on Jul 1, 2026

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 $346 per night from Jul 5 to Jul 6
CA $346
CA $454 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (2,508 reviews)
"The lobby looks great and impressive."

Reviewed on Jun 30, 2026

Palmer House a Hilton Hotel
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jul 5 to Jul 6
CA $172
CA $205 total
Jul 5 - Jul 6
includes taxes & fees
7.6/10 Good! (2,636 reviews)
"The room was older but very clean. TV didn’t work. Staff very very friendly and helpful. Would stay there again. Good price point."

Reviewed on Jun 30, 2026

Travelodge by Wyndham Downtown Chicago
See all 2,366 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.
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Stay near popular Oak Forest attractions

Gaelic Park

7.0/10 (12 reviews)
Learn about the events happening at Gaelic Park during your trip to Oak Forest. Experience the area's great live music or attend a sporting event.
See properties

What to do in Oak Forest

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 all activities in Oak Forest

Frequently asked questions

How much does an Oak Forest vacation package cost?
Offering great value package deals from CA $841 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.

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.