Oak Forest Vacations from $345

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Photo by Erik Rowley

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.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $840, price is now $345 per person
$345
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Hotel in great location, would stay again

Reviewed on Oct 19, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $724, price is now $368 per person
$368
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
this place is amazing

Reviewed on Oct 24, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $709, price is now $379 per person
$379
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,108, price is now $610 per person
$610
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $777, price is now $445 per person
$445
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!

Reviewed on Oct 22, 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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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
$116 nightly
The price is $136 total per night from Nov 24 to Nov 25
$136 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (9,567 reviews)
LOVED the room and the view was spectacular! The location could not have been any more convenient. Lobby was beautiful. Our room had a separate living room with bay windows looking out over Lake Michigan and the city. The bedroom was fantastic with a comfortable bed and pillows. We slept so well. ...

Reviewed on Oct 24, 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
$130 nightly
The price is $149 total per night from Nov 24 to Nov 25
$149 total
Nov 24 - Nov 25
Total with taxes and fees
8.4/10 Very Good! (2,029 reviews)
Empty shampoo bottle for days. Hotel rooms are not as clean being an old building. The common areas are beautiful and the vibe is amazing. Easy check in and out. Great location.

Reviewed on Oct 22, 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
$106 nightly
The price is $124 total per night from Nov 23 to Nov 24
$124 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,617 reviews)
The room was nice, clean, comfy bed. The front desk staff was super friendly and helpful, and the breakfast in the hotel was good.

Reviewed on Oct 23, 2025

Crowne Plaza Chicago West Loop by IHG
See all 2,218 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.

Find the Best Oak Forest Vacation Packages

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 $345 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.