Oak Forest Holiday Rentals

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Our top choices for Oak Forest holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is AU$253
includes taxes & fees
21 Dec - 22 Dec
Sentral Michigan Avenue

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is AU$256
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AU$256
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$256
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AU$256
includes taxes & fees
6 Jan - 7 Jan 2026
Sun-Drenched 1BR Apartment

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
Downtown Chicago
8.0 out of 10, Very good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AU$554
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 5

Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
2.0 star property
Downtown Chicago
The price is AU$526
includes taxes & fees
4 Jan - 5 Jan 2026
Downtown Chicago Stay with Free In & Out Parking 3

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is AU$485
includes taxes & fees
8 Jan - 9 Jan 2026
South Loop Rooftop With In & Out Parking 1

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
Stylish Apartment near Chicago Downtown

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AU$580
includes taxes & fees
17 Dec - 18 Dec
Your Chicago get Away

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is AU$554
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is AU$586
includes taxes & fees
30 Dec - 31 Dec
Modern West Loop Gem-City Views & Prime Location 3

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is AU$243
includes taxes & fees
1 Jan - 2 Jan 2026
Modern Studio Near UChicago

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
The price is AU$618
includes taxes & fees
30 Dec - 31 Dec
Modern West Loop Gem-City Views & Prime Location 2

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
2.0 star property
Lawndale
8.0 out of 10, Very good, (2)
"While it was a great price, you get what you pay for. "
United States
Deya R.
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Oak Park
8.8 out of 10, Excellent, (25)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is AU$318
includes taxes & fees
17 Dec - 18 Dec
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (1)
The price is AU$236
includes taxes & fees
16 Dec - 17 Dec
Cozy Charm Studio Apt in Chicago

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is AU$279
includes taxes & fees
16 Dec - 17 Dec
Sleek & Functional 2-Bedroom Apt

Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave
Hyde Park
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is AU$281
includes taxes & fees
16 Dec - 17 Dec
Explore Hyde Park: 2BR Apt on Blackstone Ave

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (3)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is AU$251
includes taxes & fees
16 Dec - 17 Dec
Bright & Cozy 1BR Near UChicago
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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Top Oak Forest Hotel Reviews

Find out more about Oak Forest

Everything you need to know about Oak Forest holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Forest holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Forest holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oak Forest holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Forest. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Forest holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Forest holiday rentals we have selected for you start as low as AU$144 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oak Forest rentals

At Expedia, we put the best Oak Forest holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Forest rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Forest holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Forest. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Oak Forest?

Yes, there are holiday rentals close to the most popular sights in Oak Forest, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Oak Forest. Make sure you have time to check out the forests and live music during your trip.

What are some of the best holiday rentals that Oak Forest has to offer?

NEW to the market! Relax with family in a super Lux Custom SFH. West town.: This holiday home rental outside of Oak Forest offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Oak Forest?

Expedia has 3 holiday rentals for your stay in Oak Forest.

What can I see and do in Oak Forest?

Explore the area and family-friendly sights such as Odyssey Fun World, or get out into nature at a spot like Lake Katherine Nature Center. Gaelic Park and George Dunne National Golf Club are other places to visit while you're in town.

What are holiday rentals like in Oak Forest?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Forest. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.