Oak Forest Vacations from $387

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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.

The Latest Oak Forest vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $387 per person
$387
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,371, price is now $741 per person
$741
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $659 per person
$659
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on Oct 15, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $737, price is now $443 per person
$443
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,306, price is now $788 per person
$788
per person
Dec 31 - Jan 3
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining.

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Oak Forest

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

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

Michigan Avenue

4.5/5(332 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 featuring a sunset and rides

Navy Pier

4.5/5(4,870 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

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Oak Forest

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
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,439 reviews)
Pleasant Stay for business
"Great location for downtown walking. The bar staff was friendly. I was here on business. The desk area didn't have any electrical outlets nearby for working but I get this isn't strictly a business hotel. If I was on vacation in CHI, this place would be ideal. Great value and the location was perfect. ..."

Reviewed on Oct 16, 2025

Congress Plaza Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
$176 nightly
The price is $207 total per night from Nov 16 to Nov 17
$207 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (2,138 reviews)
"Great place"

Reviewed on Oct 15, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
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
$122 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (1,601 reviews)
"Clean with great water pressure, plenty of hot water and excellent bedding. But most of all friendly and helpful staff."

Reviewed on Oct 16, 2025

Crowne Plaza Chicago West Loop by IHG
See all 2,189 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.

Oak Forest Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
28,100
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Midwest Carvers Museum, Bronzeville Childrens Museum and William W. Powers State Recreation Area

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Frequently asked questions

How much does an Oak Forest vacation package cost?
Offering excellent value package deals from $387 on Expedia, you'll be surprised at how little a vacation to Oak Forest costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Oak Forest?
You can typically find lower rates and greater availability in November, December and January. Browse our cheap Oak Forest vacation packages and you could score some great off-season discounts.
How many days is enough for Oak Forest?
The ideal duration for your Oak Forest vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you plenty of time to tick off all the major sights and explore some hidden treasures along the way.
How to find the best Oak Forest package deals?
Begin your search for an Oak Forest package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Oak Forest package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oak Forest escape underway.
Is it cheaper to book an Oak Forest vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Oak Forest escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Oak Forest?
If you're planning an impromptu Oak Forest getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oak Forest vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Oak Forest vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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