A calm lake with reflections of trees and a sunset sky.

Oak Lawn Vacation Rentals

Q: What are some of the best vacation home rentals that Oak Lawn has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : Visitors like this Oak Lawn vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

Dates

November 2026

December 2026

Check prices for these dates

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Our top choices for Oak Lawn vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Downtown Chicago

Jeff

$191 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Downtown Chicago

Jair

$202 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Downtown Chicago

Robert Edward

$235 nightly

Nov 23 - Nov 24

Total with taxes and fees

A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

4. Cozy, Comfortable and Convenient apartment. Close to everything!

Oak Park

Alicia K.

$239 nightly

Nov 11 - Nov 12

Total with taxes and fees

A dining area with a table set for two, a black leather sofa, and a ceiling fan.

5. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Berwyn

Cynthia M.

$161 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

6. Wrigleyville Suites

Lakeview

Francisco

$149 nightly

Nov 11 - Nov 12

Total with taxes and fees

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

7. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park

rebecca

$143 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bathroom with a white sink, toilet, and a shower curtain with a cityscape design.

8. Serene 1-bedroom apartment in Berwyn perfect for a relaxing stay

Berwyn

$190 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern living room with a blue sofa, a patterned rug, and a television.

9. Great Area Logan Square Apt Games Pets - Sleeps 5

Avondale

Deborah J.

A rooftop terrace with a brick wall, large windows, and a metal railing.

10. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown

Michael S.

$258 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern living room with a sofa, a TV, and a dining area with stools.

11. 3BR Complete and Spacious Apartment in Ideal Spot

West Town

Francis

$183 nightly

Nov 11 - Nov 12

Total with taxes and fees

12. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Uptown

Paul J.

$210 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern living room with a grey sofa, white and patterned cushions, a round coffee table, and a ceiling fan.

13. Chic Suite/Mins to L Train /Laundry/Free Parking

Oak Park

Makenna

$180 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern living room with teal sofas, a coffee table, and a TV.

14. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Northlake

Kaitlyn W.

$158 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story house with a brick exterior, a sloped roof, and a front porch.

15. At Home in Oak Park

Oak Park

Melissa

$301 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

16. Chic Urban Retreat Near Wrigley Field w/Parking

Lakeview

Rachael

$405 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

17. Vibrant House, Walk to Train, Game Room

Brookfield

Chasity D.

$643 nightly

Nov 15 - Nov 16

Total with taxes and fees

18. ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago

Kenwood

Anonymous traveler

$577 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

19. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

$236 nightly

Nov 11 - Nov 12

Total with taxes and fees

A spacious lobby with high ceilings and a skylight, featuring marble columns and a central staircase.

20. LIVN West Loop Chicago Queen Superior Studio

Downtown Chicago

Tara H.

$155 nightly

Nov 11 - Nov 12

Total with taxes and fees

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Find vacation rentals that suit your style

Top Oak Lawn Hotel Reviews

A modern bar area with a marble countertop, bar stools, and a variety of liquor bottles.

Hilton Chicago/Oak Lawn

Oak Lawn

10/10 Excellent

Erick

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

Griffin

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Shatani

A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

ACME Hotel Chicago, Outset Collection by Hilton

Downtown Chicago

10/10 Excellent

Three day trip to Chicago. The hotel was a great central location in downtown and a 10 to 15 minute walk to most sites, Navy Pier, River walk, Michigan Avenue, all the great pizza places. The hotel was smaller compared to most which we loved. Room was updated, bathroom very nice and king sized bed very comfortable. We used the blue line to get to and from O’Hare via Clark station (a 12 minute walk from hotel.). We used the red line via Chicago station (10 min walk from hotel) to go see a Cubs...

Claudia

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

10/10 Excellent

Anne

A hotel with a classic facade, large windows, and flags.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two...

Joanna

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

Le Méridien Essex Chicago

Downtown Chicago

10/10 Excellent

Extremely easy check in, attentive and friendly staff, the attached restaurant and staff where great, we where given a credit to use at the restaurant upon check in at the hotel. The rooms are a bit small, but will do if your single or a couple, we feel the like shower design could be better as it causes water to get on the floor, the downside is parking, but it’s the cost of being in a prime location, I would stay again

Shamara

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

Fairfield Inn & Suites Chicago Downtown/River North

Downtown Chicago

10/10 Excellent

Claribeth

A hotel lobby with a bar area, seating, and a large window.

Hilton Garden Inn Chicago Central Loop

Downtown Chicago

10/10 Excellent

Laura

A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina

Find out more about Oak Lawn

Everything you need to know about Oak Lawn vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Lawn vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Lawn vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Lawn vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $83 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Lawn rentals

At Expedia, we put the best Oak Lawn vacation 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 Lawn 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 Lawn vacation.

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 Lawn. 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

Can I find a vacation rental in Oak Lawn?

Yes, you can find vacation rentals in Oak Lawn close to Childrens Museum of Oak Lawn, or you can go with a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Oak Lawn. While you're here, grab a bite or have a drink at the bars.

What are some of the best vacation home rentals that Oak Lawn has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Oak Lawn vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oak Lawn?

Expedia has 7 vacation rentals for your stay in Oak Lawn.

What’s there to see and do in Oak Lawn?

Explore the area and cultural attractions such as Moraine Valley Community College Fine and Performing Arts Center, or visit a family-friendly sight such as Childrens Museum of Oak Lawn. In the larger area, you’ll find popular places like Soldier Field and Navy Pier.

What’s a vacation rental in Oak Lawn like?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Oak Lawn. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip.

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