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Holiday rentals in Oak Brook

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Quick stats about holiday rentals in Oak Brook

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Brook

  • Nightly prices starting at

    Oak Brook holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Oak Brook holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Brook rentals

  • 4.8 Average rating

    Oak Brook stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Oak Brook

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Flat in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

ValueFamilyNearby

5.0 out of 5 average rating, 104 reviews
Guest favourite
An open living area features a comfortable sofa adorned with patterned pillows, set on light hardwood flooring. A dining space with a table and four chairs is visible. Natural light fills the room, enhancing the modern decor and inviting atmosphere.
Flat in Forest Park

Luxurious apartment in great central location!

Welcome to the Troost House. This property is newly remodeled with high end finishes including Quartz counters, hardwood floors and fully equipped with brand-new stainless appliances. This 2BR 1B offers its own laundry room as well as a 1 car garage parking space. Superb location with easy access to major highways, a 5-minute walk to Blue line train station, a 3-minute drive to Loyola Medical Center, a 10-minute drive to DT Chicago, and near the heart of DT Forest Park and historic Oak park.

LocationFamilyBack garden

4.93 out of 5 average rating, 108 reviews
Guest favourite
A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

ValueLocationQuiet

4.89 out of 5 average rating, 194 reviews
Guest favourite
Home in Villa Park

Cozy 5BD Home with Scandinavian Vibes

✨ Newly Renovated Spacious Scandinavian-Style Home Near Chicago Airport ☀️ Enjoy your stay in this beautiful, fully equipped 5-bd, 2-bath home featuring modern Scandinavian-style furniture, rattan details, thoughtful touches, and all the comforts you need for a relaxing getaway. This spacious and inviting house is just a short drive from Chicago O’Hare Airport and downtown, offering both convenience and comfort yet it remains peaceful and quiet, so you won’t hear the noise of passing planes.

LocationFamilySleep quality

4.91 out of 5 average rating, 46 reviews
Top guest favourite
A spacious living room features a large sectional sofa adorned with various cushions, complemented by a cozy throw. A sleek flat-screen television is mounted above a natural stone fireplace. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.
Home in Lombard

Spacious Home in Chicago Suburbs

Enjoy your stay in Chicagoland in this gorgeous, newly updated home. After a full day of sightseeing in the Windy City or hitting the local shops and attractions, this is a restful homebase to return to. The spacious fenced-in backyard and patio, a comfortable and tastefully furnished basement, and the full kitchen with amenities provide the perfect environment to unwind. You’ll find plenty of seating, sleeping accommodations for nearly a dozen, and an open layout that fosters connection.

LocationFamilyHospitality

4.97 out of 5 average rating, 62 reviews
Top guest favourite
A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.
Apartment in Clarendon Hills

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet​, private bathroom/shower.​ Bedroom 2 - queen bed​, closet.​ Bedroom 3 - size bed​, closet. Living room has a pull-out sofa bed​. Family room with gas fireplace, access to deck/outdoor area.​ Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

ValueFamilyHospitality

5.0 out of 5 average rating, 138 reviews
Superhost
Home in Elmhurst

A+: 4BR-3BTH Spacious Home w/ 2 Living Rooms

Welcome to your perfect home away from home! This spacious 4BR, 3BT home has been newly remodeled with a fresh, modern design and thoughtful finishes throughout. With plenty of room to spread out, it’s ideal for families, groups, or extended stays. Enjoy comfortable sleeping arrangements, updated bathrooms, a fully equipped kitchen you need for a relaxing and convenient stay. Whether you’re visiting for work or leisure, the home offers functionality to make your trip truly enjoyable.

FamilyValueKitchen

4.61 out of 5 average rating, 28 reviews
Guest favourite
A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.
Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

Feel at home at this cozy split-level ranch with separate spaces perfect for relaxing—whether you’re staying with family or traveling for work. Watch your favorite show in the basement while someone else is peacefully reading a book on the main level or taking a nap upstairs. Located on a quiet, dead-end street, but just 22 mins from O’Hare Airport, minutes from I-290 and 83rd, and 10 minutes from Oak Brook Mall. Our excellent guest-to-bathroom ratio ensures comfort for everyone!

LocationFamilyKitchen

4.78 out of 5 average rating, 160 reviews
Guest favourite
A light-filled living room features a spacious gray sectional sofa arranged around a simple coffee table. Large windows provide views of the outdoor space while soft curtains frame the light. A flat-screen TV is mounted on a textured wall, enhancing the room's modern design.
Home in Lombard

Grand Retreat/5Brs/Game Room

Welcome to the Grand 5-bedroom, 2-bath home in Lombard, IL – perfect for families or groups seeking comfort and entertainment! Inside, enjoy 5 TVs and a heated garage transformed into a gaming room with a pool table, PAC-Man, basketball, and board games for endless fun. Step outside to relax in the fully fenced yard with a grill, ideal for outdoor dining. The kitchen is fully stocked for all your cooking needs. Conveniently located near highways, shopping, and dining.

FamilyLocationCheckout

5.0 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Maywood

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

ValueLocationCheckout

4.93 out of 5 average rating, 272 reviews
Guest favourite
The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.
Guest house in Villa Park

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

LocationValueCondition

4.93 out of 5 average rating, 166 reviews
Guest favourite
The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.
Home in Westchester

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs, a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

ValueFamilyNearby

4.96 out of 5 average rating, 136 reviews

Popular amenities for Oak Brook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Oak Brook's top sights

Pappadeaux Seafood Kitchen

18 locals recommend

Go Ape Zipline & Adventure Park

13 locals recommend

Pinstripes

4 locals recommend

Other great holiday rentals in Oak Brook

Guest favourite
An open living area features a spacious, L-shaped sectional sofa with decorative pillows arranged around a wooden coffee table. A patterned area rug is beneath, and natural light filters in through large windows. A dining area with a table and chairs is visible in the background.
Home in Lombard

The Westmore Retreat

LocationValueBathroom

4.96 out of 5 average rating, 54 reviews
Superhost
Home in Bensenville

Fun and Cozy Family Home Near O’hare Airport

FamilyLocationDecor

4.88 out of 5 average rating, 24 reviews
Top guest favourite
Home in Lombard

Home in Lombard

ValueLocationHospitality

5.0 out of 5 average rating, 19 reviews
Guest favourite
A well-lit dining area features a rectangular table accompanied by four wooden chairs and a bench. Natural light filters through large windows, illuminating the space. A small potted plant is centered on the table, enhancing the clean and modern decor.
Home in Westmont

Cute & Cozy Westmont, IL House Near the Best Areas

ValueLocationAmenities

4.89 out of 5 average rating, 63 reviews
Guest favourite
A modern kitchen is showcased with dark cabinetry and a contrasting light countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, are featured. A patterned tile border adds visual interest to the space, while large windows provide natural light.
Home in Brookfield

Beautiful home near the Windy City!

ValueLocationCheck-in

4.86 out of 5 average rating, 66 reviews
Guest favourite
Home in Westmont

Sleeps 10 • Everyone Stays Together Pets too

FamilyLocationWalkability

4.93 out of 5 average rating, 27 reviews
Superhost
Home in Westmont

King beds, firepit, lake view

LocationValueCondition

4.87 out of 5 average rating, 46 reviews
Guest favourite
The living area features a spacious tan leather sofa positioned around a circular dining table. A large television is mounted on a pink accent wall, and natural light floods the room through expansive windows. A decorative plant sits on the floor, adding a touch of greenery.
Flat in Westmont

Harmony Haven - 2 Parking Spaces!, Sleeps 4!

LocationFamilyKitchen

4.86 out of 5 average rating, 78 reviews

When is the best time to visit Oak Brook?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$234 SGD$230 SGD$288 SGD$284 SGD$379 SGD$352 SGD$316 SGD$346 SGD$255 SGD$264 SGD$307 SGD$282 SGD
Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Oak Brook?

    Accommodations in Oak Brook include homes near shopping centers, tree-lined neighborhoods, or areas close to parks. Family-friendly rentals and suites are commonly available around Oakbrook Center.

  • What are the best things to do in Oak Brook with kids?

    Children often enjoy hands-on experiences at Fullersburg Woods Nature Center, playful afternoons at local parks, and browsing shops or sweet treats at Oakbrook Center. Family-friendly events and mini-golf are frequently suggested.

  • What are some of the best things to do in Oak Brook?

    Explore luxury shops and restaurants at Oakbrook Center, walk the scenic trails at Fullersburg Woods Nature Center, or visit the historic Mayslake Peabody Estate. Outdoor golf and family activities are frequently suggested.

  • How is the weather in Oak Brook?

    Oak Brook has cold winters near 19–32°F (-7–0°C), warming to mild springs and summers around 51–85°F (10–29°C). Rain is more frequent in the spring, so packing for wetter months is helpful.

  • When is the best time to visit Oak Brook?

    Late spring through early fall is often recommended for outdoor activities and milder temperatures around 50–80°F (10–27°C). Seasonal festivals and art shows add vibrant experiences during these months.

  • What are the best places to visit in Oak Brook?

    Explore the Oakbrook Center for shopping and dining, stroll the paths at Fullersburg Woods Nature Center, or visit the Mayslake Peabody Estate. The area also has parks and golf courses for outdoor activities.

  • What are some hiking trails in Oak Brook?

    Fullersburg Woods Nature Center has scenic trails winding through woodlands and along waterways. Mayslake Peabody Estate features quieter paths, and local parks offer walking and jogging routes for all ages.

  • What are some family activities we can do in Oak Brook?

    Families often explore Oakbrook Center, hike at Fullersburg Woods Nature Center, or visit local playgrounds and golf courses. Seasonal outdoor events and art programs are also popular with kids and adults.

  • What are some of the best day trip ideas from Oak Brook?

    Day trips from Oak Brook can include exploring nearby botanical gardens, visiting museums in surrounding cities, or discovering historic neighborhoods and lakefront parks. Seasonal outdoor festivals are also frequently suggested.

  • Are there any pet friendly accommodations available in Oak Brook?

    Many accommodations in Oak Brook welcome pets, making it easy to bring furry friends along for your stay. Green spaces around the area encourage walks and pet-friendly outings.

  • What are some local tips for visiting Oak Brook?

    Locals suggest arriving early for weekend shopping or special events and exploring nature trails for a quiet escape. Try locally owned restaurants for distinct flavors, and check for outdoor concerts during warmer months.

  • What is Oak Brook known for?

    Oak Brook is known for its upscale shopping at Oakbrook Center, expansive parks, and corporate offices. The community has well-maintained green spaces and historic sites, often drawing families and business travelers.

  • What are the best hidden gems to explore in Oak Brook?

    Discover tranquil trails in Fullersburg Woods, quiet garden spots at Mayslake Peabody Estate, or locally owned cafes tucked around Oakbrook Center. Small art galleries and historical sites often surprise visitors with unique stories.

  • What are the best foods to try in Oak Brook?

    Oak Brook is known for American classics, Italian fare, and contemporary cuisines often found in local restaurants. Families frequently enjoy hearty burgers, wood-fired pizzas, and seasonal salads.

  • What should I bring for a trip to Oak Brook?

    Pack comfortable clothing, a light jacket for cooler evenings, and a raincoat during wetter months. Shoes suitable for walking around shopping centers or nature trails are frequently recommended.

  • What is the nightlife in Oak Brook like?

    Nightlife in Oak Brook centers around laid-back lounges, lively bars, and late-night dining in and near Oakbrook Center. Those seeking entertainment can enjoy live music or gatherings in casual venues.

  • What are the most popular events or festivals in Oak Brook?

    Oak Brook has annual art fairs, local food festivals, and outdoor summer concerts that are often recommended. Seasonal celebrations and community gatherings around public spaces bring residents and visitors together throughout the year.

  • Are there family friendly vacation rentals in Oak Brook?

    Oak Brook has vacation rentals suitable for families, with spacious layouts and amenities like kitchens and multiple bedrooms. The area is known for parks and shopping centers that families often enjoy together.

Destinations to explore