Holiday Rentals in Stickney

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Our top choices for Stickney holiday rentals

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1022)
"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 €143
includes taxes & fees
5 Jan - 6 Jan 2026
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
8.4 out of 10, Very good, (5)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is €108
includes taxes & fees
28 Dec - 29 Dec
Chicago luxury home suites

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is €144
includes taxes & fees
14 Jan - 15 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (5)
"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 €147
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is €147
includes taxes & fees
4 Jan - 5 Jan 2026
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
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 €147
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
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 €147
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is €147
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is €147
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
ENVITAE Hotel 4 Bedroom Luxury Apartments

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (405)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is €166
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is €147
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum
10.0 out of 10, Exceptional, (8)
"Very nice apartment close to downtown!"
United States
Dariana
The price is €172
includes taxes & fees
29 Dec - 30 Dec
Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Apartment in Hyde Park

Modern Studio Near UChicago
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is €132
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Studio Near UChicago
10.0 out of 10, Exceptional, (48)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is €222
includes taxes & fees
13 Jan - 14 Jan 2026
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
9.4 out of 10, Exceptional, (6)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
United States
Amer
The price is €132
includes taxes & fees
6 Jan - 7 Jan 2026
Sunny Studio in Heart of Ravenswood
9.4 out of 10, Exceptional, (10)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is €290
includes taxes & fees
26 Jan - 27 Jan 2026
Spacious 3-bedroom apartment near downtown, FREE PARKING

Apartment in Portage Park

Homey 2BR Apt w/ Parking
9.8 out of 10, Exceptional, (7)
"It was clean and well maintained unit. It’s next to grocery store and pharmacy which was very convenient. It’s not too far from downtown. I would stay again here in future if available."
United States
Jatin
The price is €171
includes taxes & fees
28 Dec - 29 Dec
Homey 2BR Apt w/ Parking
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 Stickney Hotel Reviews

Find out more about Stickney

Everything you need to know about Stickney 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 Stickney holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Stickney holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stickney holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stickney. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stickney 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 Stickney holiday rentals we have selected for you start as low as €73 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stickney rentals

At Expedia, we put the best Stickney 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 Stickney 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 Stickney 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 Stickney. 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 Stickney?

Yes, there are holiday rentals close to the most popular sights in Stickney, or you can select a more secluded option if you're looking for a relaxing stay.

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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Stickney offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Stickney?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. While in the area, you can also visit popular places such as Michigan Avenue and Wrigley Field.

What’s a holiday rental in Stickney like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stickney. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family trip.